Want to know what they had in common?

Every turnaround started with an admission:

Something pretty basic is not being done here as well as it should be.

See, most underperforming businesses aren’t underperforming because they’re being outmaneuvered. They’re not losing to some better-skilled opponent in some elaborate game of 4D business chess. Their business model isn’t being disrupted, they’re not being flanked, and they’re not losing a winner-take-all race to invent some groundbreaking new product that blows customers’ freaking minds.

Most underperforming businesses are just under-executing.

Your problem isn’t strategy

Look, I’m not saying long-term thinking and strategy aren’t important. They are important. They’re what you need to create the foundation for growth.

Every business needs to make a choice about where it should play and how it’s going to win. It needs to get clear about which customers it wants to serve, why those customers should buy from them, and what it needs to do differently to stand out from everyone else trying to win that business. It also needs a long-term vision and financial plan for how all of that is going to happen (and how the company is going to pay for it and create a worthwhile return for its investors and management).

But once those questions are answered, making a strategy work depends on whether the company actually does what the strategy requires.

And when things aren’t going well, that is often where the problem is. The problem is not a flawed vision or strategy or long-term plan. The problem is that the work that makes the strategy happen isn’t happening consistently enough.

The difficulty is not in knowing what to do, or even getting the right things started.

It is in continuing to do the right things.

Execution is about consistency

Strength coach Dan John has a line I’ve always liked:

“It worked so well, I stopped doing it.”

Anyone who has ever gotten themselves into better physical shape understands the joke. The basics work, but only when you do them and keep doing them. You lift weights, move more, drink less, eat better, and get enough sleep. As a result, you look, feel, and physically perform better.

But then life inevitably gets busy. You skip a few workouts. Your diet slips. The habits you had started to build begin to fade. Eventually you find yourself looking for a brand new program to jumpstart things even though the old one, consistently adhered to, worked perfectly well.

The same thing happens to companies.

The weekly process everyone used to inspect starts running on trust. The training program gets launched, but six months later new hires are learning through osmosis. Customer onboarding gets a little less consistent. The company moves on to a new area of focus before the last one fully takes hold.

Nobody decides to lower the standard on these things. The standard just kind of erodes naturally.

After all, hitting the standard as part of the everyday work is kind of… boring. It’s not about inventing anything new. It’s fixing broken windows and tightening loose screws.

And because the work feels so basic, it is easy to assume it is happening without looking too closely. That is where another problem starts.

Execution is about looking closer

Here’s the other reason, beyond the boredom, that execution is hard: improving it requires vulnerability. You have to be willing to look closely and honestly at how the work is actually getting done, even when what you observe reflects poorly on you as a leader.

Execution is a more uncomfortable and less fun topic than strategy because it’s basic. Are we paying attention? Are we consistent? Are we attuned to the quality of our work? Are we following through on the things we said mattered?

Well, of course we are. We’re adults, right?

Those questions, when they’re asked honestly, can feel personal in any setting. But in professional settings, where everyone is protecting their status at least a little bit all the time, they are harder to ask and harder to answer.

Strategy is easier to talk about. And because strategy discussions are often focused on the medium-to-long-term future (they don’t have to be, by the way), nobody really expects you to know the answer yet.

Execution eventually forces a different question:

Why are we not doing something right now that we know we should be doing?

That question isn’t fun. It’s uncomfortable. And that discomfort can affect how closely we’re willing to look for the answer.

And looking closer feels kinda bad

I call this dynamic the X-ray effect. The X-ray effect goes something like this: the more carefully you inspect what’s going on, the more likely you are to find things you wish you hadn’t. Processes you built are not being followed. Standards you assumed were being met are not being met. Work you assumed was happening isn’t happening.

Oh shit, you think. This doesn’t look so good for me.

That “oh shit” can nudge you to start avoiding looking quite so closely. This isn’t a conscious decision. It’s a natural human response to our status suddenly being a little more uncertain than it was before we started looking.

But the less you look, and the further you stay from the truth about what’s actually going on, the longer those execution problems survive. The longer they survive, the worse they get. And the worse they get, the less appealing it becomes to look.

And so the cycle continues.

Good leaders have to fight that natural human instinct. The point of looking closely is not to confirm that everything is working. It is to find the things that aren’t, even when you would rather not see them.

You cannot improve what people are unwilling to discuss. And the people who are willing to talk honestly about these problems without getting defensive or treating them like a personal attack usually discover an encouraging fact:

The business is not fundamentally broken.

Something basic is simply not being done the way it should be.

And basic things are usually fixable.

In Don’t Drop The Ball, I wrote about three execution problems we work on all the time inside our portfolio companies: stale opportunities filling the sales pipeline, inbound leads waiting too long for a response, and sales teams walking into demos without enough preparation.

If those seem like basic problems, they are. Are the changes that solve them hard to make stick? Sure they are. But they require nothing more than a little expectation-setting, a little training, and a lot of reinforcement.

When you’re willing to admit you have a problem, and you’re willing to do those things, performance gets better.

You don’t need a transformation program. You don’t need a fancy strategic offsite or a set of chartered initiatives to turn things around.

You just need to find a few things that matter and decide to start doing them better.

Executional DNA

I used to think that what mattered in hiring was finding the smartest person. I wanted the person who could solve the hardest problem, see around corners, run complicated analytics with ease, and invent a novel and better way of doing things.

Nearly a decade into doing this job, I care a lot less about all that now.

When I think about the executives inside the best-performing companies I’ve worked with, the quality that stands out isn’t intelligence.

It is reliability.

These people have high standards. They have ways of knowing whether those standards are being met. And they have both the guts to point out when things aren’t meeting their standard and the discipline to keep reinforcing the things that matter long after everyone else is ready to move on to something new.

More than anything, they care deeply about those basic things being done the right way under their watch.

These people have executional DNA.

Executional DNA is rare. And nearly a decade into this operating partner job, it’s now the #1 thing I test for in my interviews.

Most people are distractible. We like new problems, new ideas, new tools, and new initiatives. We get bored with work we already understand. Even experienced executives can be surprisingly inconsistent about the basic disciplines of their jobs despite having been “doing the job” for years.

Companies are collections of people, so they behave the same way.

That makes people who can stay attentive to the basics unusually valuable. They keep standards high, notice when they slip, and care enough to bring them back up again. They are also usually simplifiers, not complicators: when they find a problem, they don’t make it bigger or more complicated than it is.

That is also why execution problems are oddly encouraging. If the problem is that something basic is not being done well enough, you often don’t need anything else to break your way. You don’t need the market to improve, a competitor to stumble, or a brilliant new strategy to emerge from the next offsite. You just need to get a little better at the work.

And at a moment when AI and an endless supply of new technology make distraction easier (and make it tempting to outsource more of our attention and more of our thinking) executional DNA is only becoming more valuable.

There has probably never been a better time to be unusually good at the basic parts of your job.

Fix the basic thing

We can usually feel when things at work should be going better than they are.

We all know the feeling of, this is not what winning looks like.

My advice? Pay attention to that feeling.

Then ask yourself:

What basic discipline are we falling short on?

Don’t make the answer more complicated than it needs to be.

Then go look closely at what is actually happening.

Find the thing that isn’t being done the way it should.

And work on it.

Subscribe now

Start a #dumbsalesquestions channel in Slack.

What’s a #dumbsalesquestions channel? And why do you need one?

Let’s answer the second question first, with a bit of a hypothetical: Has something like this ever happened inside your company?

An AE is on a call when the prospect asks whether your product integrates with some obscure-but-business-critical system they can’t live without.

The rep isn’t sure, so they say they’ll follow up after the call. Then the call ends, and they realize they don’t know who to ask.

They’re a little embarrassed that they don’t know the answer. They’re also reluctant to bother the one person they know on the already-busy product team with a somewhat intimidating technical question.

So they ask around. They misfire with a few people. Those people refer them to a few other people. Eventually, after working up the courage to message someone in a different office and a different time zone, they find the person who knows.

By the time the answer gets back to the prospect, a week has passed.

What just happened here? Well, you just burned seven days answering a question someone else inside your company could have answered in 30 seconds.

The obvious problem here is speed. You added a week to your sales cycle for no good reason.

But the bigger problem is that the answer was sitting somewhere inside your company the entire time. Your AE just didn’t know who to ask (and didn’t want to look dumb asking the wrong person).

Look, there is always going to be a gap between what your company knows in aggregate and what any individual salesperson knows in isolation. You’re never going to eliminate the gap. But you do need to think about how you’re going to minimize it.

The way you minimize it is not to train every salesperson to know everything there is to know about what you sell and how it works and how to sell it. (That is impossible, especially if you sell multiple complicated products.)

The way you minimize the gap is to make the company’s collective knowledge easier to tap into.

That is what a #dumbsalesquestions channel does.

It gives your sellers (and everyone else) a dedicated place to ask the slightly-vulnerable-but-commercially-important questions that come up during winnable deals.

Questions about pricing. Integrations. Technical details. Partner relationships. Product terminology. Lead follow-up. Competitors. Roadmap items. Process. How things actually work.

All those questions now go in #dumbsalesquestions.

It is a low-tech way to reduce the two kinds of friction dragging your win-rates below where they should be.

The first friction is practical:

I don’t know who has the answer.

The second friction is social:

I don’t want to look dumb for asking.

Putting the right people in a dedicated channel helps you solve the first problem. How you introduce, frame, and operate the channel determines whether you solve the second.

Keep reading for the complete how-to guide.

Subscribe now

How To Implement Your Own #dumbsalesquestions Channel

1. Create the channel

#dumbsalesquestions is a dedicated channel where anyone (sales, marketing, product, customer success, support, etc.) posts the stuff they do not know or cannot answer with confidence.

No question is too small. No one is going to make fun of you or judge you for not already knowing the answer.

That is the whole point.

Note: Do not change the name. The name is already perfect. Calling it #dumbsalesquestions sends an important signal and gives people permission to ask before they hesitate and before they wonder whether their question is going to make them look dumb.

The questions are supposed to be dumb. That’s the whole point.

2. Invite the right people.

The knowledge you need to advance and close complex deals is spread unevenly across your company. The person who knows the honest answer on the integration question your customer just asked probably sits in product. The person who knows why you lost the last three deals to a competitor sits in marketing. Your engineering leader knows what’s on the roadmap, what isn’t, and what feature they’re considering adding next. Invite all those people into the channel. You’re doing two things at once here. You’re making that valuable-but-scattered knowledge reachable, and you’re giving your most helpful people on your team a place to be helpful.

A few more worth pulling in: customer success knows how people actually use what you sold them, implementation and support know where things tend to break, and finance knows which pricing structures you can really stand behind. You don’t need the whole company, just enough coverage that almost any question reaches someone who can answer it or point the asker to whoever can.

3. Frame things in a launch post.

This might be the most important step. It’s how you set the tone.

Once you set up the channel, you have to explicitly declare why you’re doing this and what this channel is for. This is what HBS professor Amy Edmondson (famous for her research on psychological safety) calls framing. Framing is a leadership technique you use to set up your work so people know what’s expected of them. Amy’s research uncovered that people in work settings speak up more (and perform better) when their work is framed as a learning problem instead of an execution problem.

Frame your work as execution-focused and every question sounds like an admission you can’t do that part of your job. Frame it as learning-focused and the same question turns into an opportunity to surface something that’s holding you back and improve your performance.

The key here is to explicitly frame what the channel is for with a “launch post” right when you set it up.

Say why you’re starting the thread, say explicitly that not knowing something (and needing to ask for help) is normal, and then (the part that matters) ask the first dumb question yourself. If the most senior person in the channel models it, everyone else will follow. If the most senior person only ever answers and never asks, the thread never unlocks its true power (because people are still a little unsure re: whether it’s safe to ask their question or not).

4. Praise people when they use it.

The first couple of weeks in #dumbsalesquestions are always a little slow. People are waiting to see what happens to the first couple people who stick their necks out and ask a real question. So when someone posts, thank them in the open, and mean it. You’re not being nice. You’re showing everyone watching that the person who asked (a) got help and (b) didn’t suffer any consequences. That makes it easier for everyone else to ask about what they don’t know without hesitation.

5. Remind people it’s there.

Like anything else, you have to remind people that the #dumbsalesquestions channel exists. Bring it up in your sales meeting. Drop a question in yourself every week or two. Point new hires at it on day one. A channel nobody remembers might as well not exist.

6. Turn good answers into reusable answers.

Slack is great at getting you a quick answer. It’s terrible at making that answer reference-able later on. A great reply to a common question scrolls out of sight in a day and gets asked again six weeks later. So when you know a question/answer deserves to be memorialized, move it somewhere permanent (e.g., your sales wiki, a battlecard, the integration list, the pricing guide, onboarding docs ) and drop the link back in the thread.

7. Mine the channel for ideas.

Every month or quarter, depending on traffic, pull the whole thread and run it through AI. Ask it to spot patterns and suggest process improvements you can formalize. What comes out: proposal templates, a formalized integration list, sales training topics, and marketing angles you would have never thought of otherwise. The questions your team is asking is the best hint you can get about how to grow faster.

Final Thoughts

Winning teams share a unique quality: their people are quick to admit what they don’t know, and quicker to help each other fill those gaps. You can’t buy that quality, and you can’t order people to have it. But you can help create it—and a #dumbsalesquestions channel is a sneaky-good way to get started.

For that to work, people have to feel safe. That’s the real magic underneath all of this: psychological safety. When Google went looking for what separated its best teams from the rest in Project Aristotle, psychological safety emerged as the strongest predictor, well ahead of who was on the team or even how smart they were. Psychological safety helps teams not only get their work done faster, but improve what they’re doing as they go. It’s the secret ingredient to higher performance.

I’ve written before about how our brains process uncertainty in much the same way they process physical pain. It’s why a buyer who doesn’t feel certain about a purchase will kick the tires for months and then vanish into “no decision.” That same wiring is running inside your team. Asking a dumb question in front of your peers is a status risk, and your brain treats an uncertain risk to your standing a lot like it treats a physical one. “Are you sure you want to do that?” it asks.

That matters because an unanswered question doesn’t stay in Slack. It follows the rep into the next sales call. When that thing they should have asked about comes back their way in the real world, they hedge, avoid the subject, or promise to follow up later because they still aren’t sure. The buyer may not know exactly what’s wrong, but they can feel the uncertainty. It’s contagious. And unless you give that seller a place to ask those kinds of questions, that uncertainty will infect your future pipeline for as long as you let it.

So yes, go start a #dumbsaleschannel. But you can’t just announce that the channel is safe. You have to prove it. Answer questions without judgment. Thank people for asking them. Have leaders ask the questions first.

Do that consistently, and you turn the things people are embarrassed to ask into a running record of where the company needs to get clearer, and a practical way to help everyone get better at their job.

Subscribe now

If you’re a VP of Finance or a CFO, you’re eventually going to get deputized to help one of your teammates with something analytical.

Sometimes it’s product. Sometimes it’s customer success.

But pretty often, it’s sales.

“Sales feels a little too hard to understand right now,” your CEO tells you. “Can you spend some time with the team and help us figure out what’s going on?”

You say yes. Then you pull some reports. You look at the forecast. You stare at the pipeline. You ask a few reasonable questions about coverage, conversion, win rate, sales cycle, average deal size, discounting, quotas, and comp plans.

And then you run into the first real problem: the numbers that you assumed would be easy to get are actually not that easy to get.

Some of the numbers live in the CRM, but the CRM is kind of a mess. Some of them live in a spreadsheet on a sharepoint drive that someone built last year and nobody has looked at since. Some of them are actually pretty easy to grab, but everyone defines them differently. (Ever asked about something simple like conversion rates and then gotten immediately sucked into a wormhole? I certainly have.)

It’s pretty easy to tell whether the team hit or missed the number. But you still cannot answer the more useful question: what, specifically, caused the result, and what do we need to do to get better?

This is when your job as finance leader gets delicate.

Because your questions are reasonable. But unless they’re framed appropriately, they can also be… a little annoying?

This isn’t because sales leaders are fragile or allergic to accountability (ok, sure, a few are). The issue is that the questions finance leaders like to ask usually land right on top of the high-pressure work the sales leader is already doing.

Why did this deal slip? Why did that rep miss? Why did conversion get worse YOY? Why does the forecast say one thing while the pipeline report suggests something else? Why do we keep discounting late? Why do we have 3.2x coverage and still feel nervous about the quarter? Why why why?

Look, those are fair questions. They are also questions that can make a sales leader feel like they are being audited by someone who does not have to carry the emotional weight of convincing a bunch of messy, complicated human beings to contractually agree to pay your company tens of thousands of dollars every 90 days.

This is the fundamental tension between finance and sales.

You want to understand the business well enough to help it grow faster. You also do not want to become the finance person who turns every conversation with sales into a deposition.

The ask from your CEO isn’t to whip sales into shape. It’s to help the person running sales make better decisions.

That distinction matters.

Finance can absolutely help sales. In fact, in a lot of growing companies, finance is one of the only functions with the analytical capacity to help sales see what is happening across the whole system. But the help only works if it feels like help to the person receiving it.

Dave Kellogg has a line I’ve always liked:

Help is defined in the mind of the recipient.

It does not matter that your question is reasonable if the sales leader experiences it as criticism. It does not matter that your analysis is right if nobody uses it to make a better decision. And it does not matter that you are trying to help if the person you are trying to help feels like they are being put on trial.

A better, healthier, more productive version of this relationship is possible. Finance can absolutely help sales understand the business more clearly, make the budget more useful, improve forecasting, clean up the data that matters, make selling easier, and ultimately build a more predictable, exit-ready business.

But to do that, you, my dear finance leader, have to pick your spots.

Subscribe now

So How Should Finance Work With Sales?

This is what my friend CJ Gustafson and I wanted to talk about a few months back. CJ writes Mostly Metrics and hosts Run the Numbers. (Finance leader or not, you should check out both if you haven’t already.)

We’ve done a few podcasts together now, including our last one where we flipped the format and I interviewed him about what it has been like to build a niche media business focused on CFOs.

After that episode, we started emailing about what we should record next. We started telling stories about finance and sales, and how those functions typically interact inside of growing companies.

This was the note I sent him after we kicked around a few ideas.

We more or less stuck to that agenda, but also hit on several angles of how to find that balance between rigor and support between finance and sales:

• Why the budget process is one of the few key alignment moments that sets up the entire year.

• Why forecasting is such a key opportunity for sales and finance leaders to team up.

• Why “more data” is usually not the answer, but making the right numbers easier to understand often is.

• The short list of specific RevOps problems where finance can be helpful

• And why none of this works if the person running sales does not believe you are actually there to help.

You can watch or listen to the full episode here:

Also available wherever you get your podcasts (Apple and Spotify links here).

A few of the best nuggets from our conversation below:

Make the Budget Mean Something

Most could be making a lot more of their budgeting process. Not making the budget more complicated, but using the budget as a tool to create agreement, alignment, and clarity.

Here’s what budget season typically looks like inside of a small, emerging company: Everyone wakes up in September and realizes they have a couple months to put the budget together. Revenue gets rolled into one top-line target. Expenses get negotiated. The leadership team agrees to something that feels achievable enough to defend and aggressive enough to satisfy the board. Then everyone moves on.

The problem is that a budget built that way does not tell you very much once the year starts.

If the whole revenue plan is one number, you have limited your ability to diagnose what happens once the inevitable chaos and lumpiness inside of every business starts to happen. Three months into the year, when the company is tracking behind plan (whether everywhere or within one product, region, or business unit), everyone starts asking the questions they could have started to explore when they built the plan.

Was new logo soft? Was expansion weak? Did one region miss? Did one product underperform? Was the core business fine, but the growth initiative failed? Was the sales team short on pipeline, or did they have enough pipeline and fail to convert it?

If you did not separate those things in the budget, you have to figure them out after the miss. That makes the operating conversation slower and less useful than it needed to be.

The better move is to decide how you are going to segment the business before you build the number. Maybe it is by product. Maybe it is by region. Maybe it is by segment. Maybe it is new logo versus expansion. Maybe it is the part of the business that is supposed to keep performing versus the part of the business you are trying to improve.

The way you break the business apart depends on the situation. The point is that you have to decide on how you’re going to do it before the year starts.

This is where finance can help a lot, because finance is usually the function with enough discipline and distance to force that conversation. You are not just asking, “What number do we need?” You are asking, “What has to be true for this number to happen, and which part of the business is responsible for making that happen?”

That question changes the budget process. It’s what turns the budget from a board document into an operating plan. It also gives the CEO, the sales leader, and the CFO a shared language they can use to talk about performance and what they should do next. That’s huge.

Here’s CJ and me on the simple segmentation move that can make your budget actually mean something.

Lend a Hand With Analysis and Metrics

In a lot of growing companies, finance is the only team with spare analytical capacity. But the best use of that spare capacity is usually not another report.

Sales leaders already have plenty of numbers around them. What they do not always have is someone helping them understand how those numbers connect to the business they are trying to run.

There is a big difference between knowing a metric and understanding it. A sales leader can say “NRR” in a meeting and still not really understand what moves it. They can know the bookings target and still not have a clear picture of how pipeline, win rate, sales cycle, average deal size, ramp time, churn, and expansion all work together. They can know the number and still not know which decision they are actually making when they hire another rep, change territory coverage, or push the team toward one type of customer instead of another.

CJ told a story I liked about this. He had been talking about NRR for a couple of quarters with his sales leader. The sales leader knew the metric mattered. He could repeat it back. He understood, at least generally, that the company cared about it. But it was not changing the way he made decisions.

Then CJ sat down with him and walked through the actual pieces underneath the number. What drives expansion. What drives contraction. What happens when churn improves. What happens when one customer segment grows faster than another. What happens to the P&L when the company hires ahead of demand or waits too long to add capacity.

Same metric. Different conversation.

After that, the sales leader started connecting his own decisions back to the number. Hiring decisions. Coverage decisions. Customer focus. The metric became useful because someone had done the work to make it understandable to him.

That is a much better, more useful job for finance than producing a cleaner version of the same dashboard.

Do not just tell the sales leader what the number is. Show them why it matters. Show them what changes it. Show them how the decision they are making this week shows up in the P&L this quarter and in the value of the company later.

As I’ve written before:

“Data is only as good as the conversation it creates.”

Once you start having a human conversation about the data with your sales leader, you put them in a position to use that data to improve their part of the business. That’s what real help is. That’s what you’re going for.

A little more from me and CJ on that topic below.

Get Involved in a Few Key Revops Spots

RevOps is another place where finance can help, but only in a few specific spots.

You do not need finance involved in every CRM field, workflow, dashboard, and process debate. That is how a potentially useful partnership turns annoying fast.

But there are places where finance should care because the RevOps problem eventually shows up in the numbers. I I think pricing and quoting is a fantastic place to start.

This is where a lot of sales momentum gets wasted. The discovery call goes well. The demo goes well. The buyer is interested. They ask the obvious next question: “What does this cost?”

And then the company makes that question hard to answer.

The rep needs approval. The package is unclear. The discount rules are not written down. Nobody is totally sure what the customer should buy. The quote takes too long. Legal gets involved too late. Two weeks go by. The buyer who was ready to talk pricing is now busy with something else.

That is not a sales mystery. The company made it too hard for the buyer to keep moving.

This is a good place for finance to get involved because it’s a complex area that sits at the intersection of sales, pricing, packaging, margin, approval rights, and risk. The goal is not to make quoting more controlled for the sake of control. The goal is to make the business easier to buy from.

What do we sell? How is it packaged? Where can reps negotiate? Where can they not? What requires approval? What should a rep be able to quote without asking anyone? What terms create problems for the business later?

Answer those questions and you remove a real source of friction from the sales process and meaningfully improve win-rates. The sales rep can respond faster with more certainty. The buyer gets a clearer picture of what they’re buying (which makes it easier to advocate for internally). The sales leader gets shorter sales cycles. Finance gets fewer strange end-of-quarter deals with big discounts, custom terms, and weak explanations for why “we had to do it this way.”

Here’s CJ and me with more on the revops problems that finance should be focused on.

Check out the full episode with CJ and I here on YouTube, Apple, and Spotify.

And if you’re a finance leader, go ahead and subscribe to Mostly Metrics. You’ll be glad you did.

Then they heard it.

Out of the darkness came a howling that stopped both men cold.

Wolves.

This didn’t sound like just one animal. This was a terrifying, overlapping chorus, rising from somewhere just ahead. Grant wrote in his Personal Memoirs that to his ear, there must have been enough of them to devour their party, horses and all.

His companion, equally terrified, leaned over and asked: “Grant, how many wolves do you think there are in that pack?”

Grant, not wanting to seem rattled, deliberately undersold his real estimate. “Twenty,” he lied.

They pressed on. But when they finally spotted the source of all that noise (and all that fear) they were pleasantly surprised. As Grant wrote:

“There were just TWO of them. Seated upon their haunches, with their mouths close together, they had made all the noise we had been hearing for the past ten minutes.”

Two wolves. Not twenty.

Something to be cautious of, sure.

But nowhere near the life-or-death threat they’d imagined from what they first heard.

Grant captured the lesson with one line:

“There are always more of them before they are counted.”

What Fear Is For

Picture yourself in that situation. You’re out in the dark. You’ve fallen behind your group. You’re moving through unsettled wilderness. And then a pack of wild animals starts announcing themselves a few feet in front of you.

Of course you’d be scared. I would be.

And guess what? In that situation, fear isn’t a bad thing. Fear is a rational thing. A useful thing. Fear gets your attention. It gets you ready to act.

But here’s the problem with fear.

Fear gets you ready. Fear does not tell you what to do.

When he first heard those wolves, Grant didn’t know how scared to be — or what to do next — because he hadn’t assessed what he was actually dealing with. He could hear the wolves. He couldn’t see them. So, faced with what might be a dangerous situation, his mind did what all of our minds do: it filled in the blanks.

And when fear fills in the blanks (when we guess at how big a problem is before we can really see it) fear rounds up. Every time. Whatever we’re only starting to understand, we assume is really bad. From a few seconds of howling, we get twenty wolves. Or more.

Here’s why that overreaction matters: when you misjudge the size or shape of a problem, you misjudge your options for dealing with it. Grant thought he might have to fight or outrun an entire pack. His eventual move (keep walking past two relatively disinterested wolves) never entered his mind, because he didn’t get what was actually going on.

It wasn’t until he saw the truth for himself that he could clear his head, assess his options, and make the obvious choice.

Thank god. Two wolves. Not twenty.

Let’s keep moving.

It’s tempting to read Grant’s wolf story as a parable about emotion getting in the way of good decisions. But Grant needed that fear. We all do.

That fear got him to stop, focus, take the situation seriously, and get ready to act.

That’s what fear is for. In life and at work.

That sick drop in your stomach when a piece of bad news lands (the customer’s cancellation notice, the unexpected product outage, the competitor’s threatening announcement, the star employee’s resignation) isn’t weakness. It’s your biology telling you that something meaningful is happening.

Pay attention, it says. This matters. Get ready to do something.

But way too often, that initially useful signal goes overboard. Grant’s fear alerted him. Then that same fear told him there were twenty wolves out there waiting to eat him alive. The emotion that told you “this matters” (thank you, fear) starts screaming “game over, man” (easy, fear).

Those are two very different messages coming from the same source. And learning to tell them apart (paying attention to the one that says this matters, and ignoring the one that says this is the end of the world) is what it’s all about.

That’s what the best leaders do. They stay alert enough to notice the problem the second it shows up. They allow themselves to get amped up. But then they just as quickly center themselves and take the first step they can towards learning the truth of the situation, instead of acting on their first, overly-emotional read.

Alert but Centered

There’s a certain emotional aliveness you need to notice there’s problem in the first place. And there’s a discipline in tempering that aliveness so you don’t blow it up bigger than it really is. That’s the fundamental tension in being a good strategist, a good businessperson, a good leader.

Noticing isn’t hard. We do this almost automatically, thanks to our five senses and the constant flow of communication we’re subjected to at work. The hard part is what comes next: when that same energy starts lying to you about how big the problem is.

That’s the part I want to get into.

Mindfulness is great, but the answer here isn’t learning to calm down. Telling yourself to relax in the middle of a crisis (real or imagined) never works. Centering yourself works. Getting objective is what works. And you get objective By replacing the size of the problem you’re feeling with the size of the problem that’s actually there.

Good strategy is mostly about forcing objectivity onto emotionally-overwhelming situations. The people who can force themselves to get objective when shit gets hard produce a better diagnosis. A better diagnosis tells you what the real challenge is inside the mess you’re looking at. And once you understand the real challenge, the options you have (and the winning option) tend to become rather obvious.

The reason you have to force it is that objectivity almost never comes from your gut. Under pressure, your gut doesn’t measure the problem. It guesses at it. And when it guesses, it always rounds up.

So how can you learn to force that kind of objectivity onto emotionally-challenging, downright scary situations?

It’s hard. But here’s three moves that work for me.

Move 1: Get closer to the problem

You could argue that Grant’s whole problem in that story was distance. He could hear the wolves. But he couldn’t see them. He was too far away.

And from that distance, out in the wilderness, out in the dark, that sound was all his imagination needed to build a monster. It wasn’t until he got close enough to lay eyes on them that the threat (and the magnitude of the threat) became clear. The closer he got, the better he understood what he was dealing with.

It’s the same thing with strategy. The higher you climb in any organization or team, the further you get from the truth. Customers get handled by your salespeople, not you. Products get built by your engineers, not you. You’re always a couple of degrees removed from what’s actually going on, and you have to be. You need that distance to do your job. It’s how you create your leverage.

But distance also distorts. Every layer between you and the truth is a kind of lens you’re forced to look through. Stack enough of those lenses up on top of one another, and the picture you see from your leadership perch looks quite different from the truth.

So when you find a problem worth solving, the first move is to collapse that distance. Get closer to the problem. Closer to the work. Closer to the customers you serve and the numbers your report on.

This is what weak leaders don’t do enough. They stay removed enough that they never build a real point of view on what’s actually happening. They accept the distortion instead of combatting it. And they end up misjudging the problem, their options, and ultimately, their decisions.

Don’t let that be you. When in doubt, just get closer.

Move 2: Find something to measure

This is the literal interpretation of Grant’s quote.

Count the wolves.

I’ve written about this in my What Data-Driven Leaders Do Differently series: If you only rely on your own five senses to tell you what’s going on, you’re going to miss things.

Your senses are built to detect threats, not measure them. Sure, they’ll tell you something’s wrong. But they’ll lie to you about how bad things really are.

Numbers don’t lie. Numbers are the same whether you’re panicking or calm. They’re a fixed point, immovable by human emotion. Grant’s gut told him there were twenty wolves out there. But his count told him there were only two. The count didn’t care that he was scared. The count told him the truth.

When you finally put a number against a thing, the thing is almost always smaller than it felt when you first encountered it. And smaller things are always easier to deal with.

Move 3: Borrow someone else’s objectivity

The trouble with your own read is that it’s yours. You’re standing inside the problem with your pride and your identity and your fears and insecurities wrapped up in the decision that created it, and the little movie running in your head about what this all says about you and what others think about it. Some problems are harder to get objective about. Some are impossible.

What do you do when you can’t get in touch with your own objectivity? Go get someone else’s.

If you’re panicking, find the person who isn’t.

If you’ve never seen this before, find the person who’s seen it twenty times.

If the problem is technical or complex or niche (and you’re not), find the person who speaks the language of the problem. You’re guessing at how big it is from the outside. They can open it up, pick it apart, and show you what’s actually going on.

And if your blind spot is you (and your habit of inflating, flinching, catastrophizing, or talking yourself out of the hard call) find the person who knows your tendencies well enough to check you.

This is what great coaches, friends, mentors, and teammates do. Use them.

Final Thoughts

When you hit the next big, ugly, emotionally loaded problem, try this:

Sit in the discomfort one beat longer. Get in touch with your objectivity. By getting closer to what’s going on, finding something to measure, or connecting with someone you trust who can look at the problem with fresh, less biased eyes.

Count the wolves.

Then work the problem.

Subscribe now

• How many high-intent inbound leads/hand-raisers did we create last month?

• What did we do (and spend) to get them?

• What are we going to try next to improve those numbers?

Why are those questions so important?

Well, unless you’re an extremely early-stage company in a category that’s literally being created right now, a CMO’s first job is to capture existing demand. As in, find the people who are actively trying to buy the thing you sell and make sure you’re on their radar.

And the easiest way to track how good you are at that is by measuring your count of high-intent inbound leads.

Yes, a good marketing leader should be doing much more than this, but this demand capture thing is a foundational layer of the growth machine you want to build. There’s people out there who have already decided (and secured the budget!) to buy what you sell in the very near-term.

So, do you have a mechanism for finding and converting at least some of them? And are you improving how that mechanism works over time by making little adjustments to it?

Are you paying attention to the overall quality of how demand capture works at your company?

Good marketing is about much more than just creating hand-raisers.

But great marketing leaders make sure this part of their lead creation and conversion process becomes and stays absolutely airtight.

A few of my best posts below on the topic below.

Subscribe now

My Best Stuff on Capturing Demand

I spent this past weekend manning a booth in Detroit with one of our portfolio companies. And during the show, I noticed a consistent pattern of behavior that I see way too often at events like these:

Salespeople sitting behind their table, checking their phones… just waiting.

Not scanning the room. Not noticing the person who slowed down for a half-second to look at their booth. Not making eye contact with the passersby who leaned in and considered their brochure or table or signage.

Just sitting there waiting for the next hot lead to walk up, introduce themselves, and elbow their way into their pipeline.

Those people are missing something important.

They’re missing an opportunity to make friends with their market.

Subscribe now

What Does It Mean To “Make Friends With Your Market?”

“Make friends with your market” is one of those powerful principles that has all kinds of applications.

At its most basic level, it’s about recognizing that sales and marketing and anything that gets and keeps customers is mostly about human relationships: Creating them, keeping them healthy, and using the fact that they matter to guide your behavior and strategy and in-the-moment choices re: how you do your work.

An illustrative LinkedIn post below:

The connections with the people who might eventually buy something from you don’t just happen. Nobody is going to randomly wander into a relationship with you or your company. You have to build that relationship intentionally, one small, proactive, thoughtful interaction at a time.

Too many sellers and marketers ignore this principle. They assume their prospects already know they exist. They assume some invisible relationship is developing in the background without anyone tending to it. They assume that simply by showing up and logging in, they are magnetically attracting attention and demand and dollars their way.

Spoiler: That is not how it works.

Forget about work for a second. We’re talking life now. What does it take to make friends? Mostly, it takes proactive effort. Think about what good friends actually do. They remember things about you. They send you stuff they saw that made them think of you. They check in without needing a reason. They don’t wait for you to reach out first. None of this is elaborate. It’s just consistent, low-key proof that sends a signal: You matter to me, and I’m paying attention.

It’s no different with work. The sellers and marketers who are easiest to buy from aren’t necessarily the ones with the best product or the slickest deck. They’re the ones who manage the balance in the relationship piggy-bank. They’re the ones who send you relevant stuff, who remember the thing you mentioned three months ago, who make you feel like a person and not a pipeline opportunity.

They’re easy to buy from, because you already know them, like them, and trust them. Not because of a single action, but because of the accumulation of all those little signals.

The reason I’m connecting this concept with trade shows and conferences is this: Trade shows and conferences are a hyper-concentrated opportunity to make friends with your market.

In the span of two or three days, you’re surrounded by more of the right people than you’ll encounter in a normal month of blindly firing off outbound sequences and LinkedIn DMs. And it’s not just about potential customers. It’s also about everyone else playing the same game you are: the vendors in the booths next to you, the competitors across the aisle, and the whole entire ecosystem of people who live and work in your market every day.

The more you know and connect with those people, the better you understand the market. And the better you understand the market, the easier everything gets.

Here’s my thoughts on how to make the most of that opportunity at your next event.

How to Make Friends With Your Market: The Trade Show + Conference Playbook

Look For Openings

Here’s what manning a booth looks like when you’re doing it wrong: you’re standing behind the table, arms crossed, waiting for someone to walk up and announce themselves as a lead. Maybe you’re checking your phone. Maybe you’re chatting with your colleague. Either way, you’re missing all the little opportunities happening five feet in front of you.

Here’s what it looks like when you’re doing it right: you’re not just watching the room, you’re paying attention to it. You notice the guy who slowed down for half a second to read your banner before moving on. You catch the person who made eye contact, held it a beat, and then looked away. You see the person who thought about picking up your brochure, but then hesitated.

Those are openings.

And what do you do with those openings? You create an invitation.

An invitation doesn’t mean a rehearsed opener or a mini sales pitch. It’s just a hello:

“Come and talk to us if you want.”

Some people will. Some won’t. That’s fine. The point is you noticed, you put yourself out there, and you made it easy for someone who was even a little curious to engage.

Every one of those hellos is a potential connection. Stack enough of them up and you’ve got a very different return on that expensive booth of yours — and a much more interesting two days.

Meet Your Neighbors

Here’s what most people do with the vendors next to them at a trade show: nothing. They set up their booth, they face forward, and they treat the people eighteen inches to their left and right like furniture. Polite nods if eye contact happens. Otherwise, strangers.

Which is a waste. Those people are away from their families, staying at the same hotel, doing the exact same thing you are. They know your market. They talk to your customers. They have relationships you don’t have and problems you might be able to solve — or vice versa. You just don’t know any of that yet because you never said hello.

So here’s my strategic recommendation: Say hello.

This past weekend, we spent 20 minutes talking to the software company next to us and walked away with a potential future intro into a customer segment we hadn’t even considered before. That doesn’t happen if we treat those people like strangers.

Yes, you’re there at the booth to meet customers. But you’re also there to create the surface area for luck. The people to the left and right of your booth are the easiest place to start to help make that happen.

Get To Know Your Competitors

Here’s what most salespeople do when they spot a competitor’s booth at a trade show: they avoid it.

This is a mistake. At every conference, you should try and meet at least a couple people from competitors.

These people are playing the same game as you. They understand your market, your buyers, and your problems better maybe even better than you do. They can teach you something.

Jason Lemkin said it plainly in a recent post: there are very few downsides to knowing your competitors. So get to know a few. They’re just people (like you).

Final Thoughts

It’s a lot more fun selling to friends.

So, at your next conference, trade show, or event, try a few of these techniques and go make some.

You’ll be glad you did.

Subscribe now

Questions you want me to answer? Ideas for future posts? Sponsorship or partnership idea for Hello Operator?

Email me at paul@hellooperator.com. I’d love to hear from you.

The underlying problem here is how the demo-er make that decision. It’s not based on what the prospect told them in discovery. It’s not based on the problem they described or what they said was most urgent or costly or annoying.

They decide based on muscle memory.

They decide based on what they always show.

They demo what they’re most comfortable with, not what’s most relevant to this particular prospect.

The real problem here isn’t that this paints the product in a bad light. If you demo this way, you’ll probably still (eventually) show this person (a) the most valuable parts of the product and (b) at least one thing they told you they care about.

The real problem is the experience this creates for the person you’re trying to sell this product to.

This person (who, at this point, is almost always still very much on the fence about whether they want to get serious about buying your product or not) sits there politely for 45 minutes watching a complete stranger navigate every click and every menu and every feature for a product they’ve never seen before, trying to translate silently to themselves whether any of it applies to them or the stuff they shared with you in discovery. While they do this, this is what they’re thinking:

“…Did these guys even listen to me?”

That’s not a demo.

That’s an in-depth user training session for a tool this person is nowhere close to using yet. And you are forcing them to do all the work to translate between what you’re training them on and the much more basic buying questions they still have.

Most prospects won’t do that work. Instead, they’ll just smile politely, slowly tune you out (watch for them checking their email on the other screen), and start thinking about who or what else might be out there that can solve their problem.

That’s not what you want, is it?

No, it isn’t.

What you want is to give this person is proof.

• Proof that you understand their problem.

• Proof that you can solve it for them.

• And proof that your solution is better than whatever else they might have tried or might be considering alongside you.

Subscribe now

Comprehensive vs. Compelling

See, good demos aren’t about being comprehensive. You don’t need to show them the whole entire product and how every part of it works. That’s not how you convince someone to buy. People buy things all the time without understanding every technical detail of how the thing functions. We don’t want to know how a watch works; we just want to know what time it is and how it looks on our wrist.

No, good demos are about being compelling. They’re about connecting the dots between life before your product and life after. And they’re about driving home that contrast as clearly as possible so the person watching your demo starts thinking about how badly and how quickly they want to get to that “after” version of life: where what you’re showing them removes the obstacle in their way and lets them get on with their work.

So how do you do that?

How do you run demos that are compelling instead of just comprehensive?

And how do you start to build this muscle inside a sales team so it becomes a repeatable competitive advantage that helps you win more deals?

Luckily, I answered all those questions for you in my article “How To Give A Demo That Doesn’t Suck.”

If you feel like your demos are holding you back from winning deals you deserve to win, give it a read.

Subscribe now

My Best Stuff on Building a Better Sales Process

Want more? Check out Hello Operator’s dedicated sales + marketing page.

Do you have questions about how you can build a better sales machine for your business?

Want to share a suggestion on what I should write about next?

Drop me a line at paul@hellooperator.com.

I’d love to hear from you.

And it reinforces a super-important idea re: what it takes to create more leads:

See, when you cold call someone, they aren't thinking about whether they want to buy the thing you're selling.

This is what they're thinking,

"This is probably a total waste of my time and I'm just waiting for this person to stop talking so I can say no."

And make no mistake: That's what will happen to you, unless you make it 1000% clear to them in about 30 seconds why taking a meeting with you would be both relevant and valuable to them.

Reflect on that for a second. When's the last time you spelled it out for someone why agreeing to speak with you for half-an-hour would be an absolute no-brainer for them?

To do this well you have to:

• Very quickly introduce who you are and why you're calling

• Tee up /get permission re: what you are going to ask them for

• Make a convincing argument why that ask/appointment you're trying to set with them is a GREAT give-to-get FOR THEM.

So what makes a good give-to-get?

• You're offering to tell them something about their business that is both interesting and useful (if they take the meeting).

• You're offering them something tangible and valuable as a result of meeting with you (No, not airpods or a theragun. I've been offered both. I'm good.)

• You're offering them some kind of proprietary data or insight that you can unpack for them on the call (making them literally SMARTER by meeting with you).

• You're offering them a compelling alternative way to solve a problem they are literally experiencing right now.

Notice the word I used in all three of those:

"Offer, offer, offer."

Creating a give-to-get is all about the offer.

And the offer has to be good FOR THEM.

Good Offer + Clear Communication = Meeting Booked.

It's that simple.

Subscribe now

My Best Stuff on Prospecting and How To Book More Meetings

Let me guess. It probably went something like this:

• You hopped on a Zoom call. You exchanged pleasantries and maybe talked about an agenda. The salesperson asked if you had any questions up front. You didn’t. Not yet, you just wanted to see the thing. So they shared their screen.

• What followed was 45 minutes of monologed clicking. Dashboards. Settings. Reports. Integrations. Every menu, every dropdown, every tab. They showed you all of it.

• The only question they asked you while all that clicking was happening was “Does that make sense?” You nodded politely, regardless of whether it did make sense. (You said “that’s interesting” a few times. At least one time because you were just trying to be polite.) But 15 minutes in you started checking your email, thinking about your next meeting, zoning out.

• The seller wrapped up with “Any questions?” You said you’d discuss with your team and get back to them. Everyone thanked everyone. Everyone was polite. Everyone hung up.

Let me guess. Here’s what happened next: You probably did not buy the software.

It wasn’t because the product was bad or didn’t work. It was because the demo felt like a training session for a tool you weren’t sure you needed yet. They showed you everything. They explained how it all works. It looked impressive. But they never convinced you it solved your problem.

So you didn’t buy.

This happens all the time. And if you work for a software or technology company, I guarantee it’s happening to you and your team.

And that’s a shame. Because it’s not only costing you customers. It’s making the experience of buying from you much less enjoyable than it needs to be.

Bad Demo vs. Good Demo

Here’s the difference between a bad demo and a good demo.

Why do so many companies struggle to move from the left side of the table to the right? Here’s my theory. When you build a software product (or spend a lot of time selling one) you fall in love with it. You know every feature, every capability, every clever thing it can do. That love is a real asset. But it creates a problem in demos.

When you love your product, you want everyone to see what you see. You want them to experience all of it. And because you’re so excited to show them everything, you never really stop to ask whether the part of the product you’re showing to them right now is even relevant to them.

This is what creates what I call the “decided” demo. You make up your mind about what to show before the call even starts. You decide what’s important, not the customer.

The assumption behind a decided demo is that if you show enough features and prove how much the product can do, your prospect will fall in love with it (just like you did). You assume that providing more evidence that it can do all the things is what will win people over. It’d be easier if this worked. It doesn’t.

The truth is, prospects don’t care how much your product can do. They’re not trying to learn every feature you’ve built. They just want to know whether you can solve their most painful problem, which ideally you uncover before you ever even thought about saying, “Can you see my screen?”

Show them you can solve that #1 problem, and you don’t need to show them much else.

So why don’t people do this?

Why are there still so many bad demos out there?

The Broken Handoff

A few months ago, I watched a deal die on a sales call recording.

The Account Exec had done everything right. She’d had a great discovery call. She’d learned that their team was spending 10 hours a week on a manual process. She’d gotten them to say, in their own words, why it was becoming urgent. She’d logged it all — pain points, use cases, specific workflows they hated. It was a roadmap for exactly what to show and exactly what to skip.

Then the demo started. The Sales Engineer opened with the dashboard overview. Then settings. Then the reporting module. Then integrations.

Ten minutes in, we hadn’t gone anywhere near the thing that they said was their biggest challenge. We were running the standard product tour.

I watched the prospect’s face. Nodding. Taking notes. But their eyes had gone glassy. The look you get when you’re being polite but you’ve already checked out.

When our demo ended, the prospect said “This is really comprehensive, thanks.”

Some sellers take that as a compliment. I heard it as code for: I’m not buying this thing.

The sad part was, the SE thought he’d crushed it. After all, he’d been thorough. He’d covered everything.

But he’d missed the point entirely. The AE had handed him a blueprint (here’s their pain, here’s what matters, here’s what needs to be fixed) and yet, he’d defaulted to his standard “harbor tour of the product” approach. Not because he didn’t care. Because he didn’t do the work to translate “they’re drowning in manual work” into “open with this feature, spend 20 minutes talking about life with it and life without it, and skip everything else.”

The AE did the hard work of discovery. She uncovered the pain. She got the prospect to articulate exactly what was broken and why it mattered. She created a real opportunity to prove we’d been listening. And the demo threw all of it away.

Not because the SE showed the wrong features. He probably did show the right ones somewhere in that 45-minute tour. But because he didn’t prioritize that feature, and (more importantly) he never connected what they told us to what he was showing them. He never said “Remember that manual process you described? Here’s how this changes it.” He never made the prospect feel heard.

So they didn’t buy. Not because we didn’t have what we needed to run a great demo. But because the transfer of that information never occurred.

Basically, the handoff broke. When this happens, everything you learned in discovery becomes wasted work. You find out exactly what it would take to win the deal, and then you demo like you found out nothing at all.

The Four Questions

Why does this happen? Why does the sales <> SE handoff break?

The handoff breaks because there’s no forcing function. The AE asks discovery questions, uncovers the important stuff, and takes down notes. The SE doesn’t read them, or reads them but doesn’t know what to do with “CFO is frustrated with manual reporting.” There’s no formal handoff and no transfer of context. So they default to the standard tour.

What you need is a repeatable mechanism that ensures (a) clean transfer of what you learned in discovery and (b) alignment around what you’re going to demo and how you’re going to connect it to what you learned. (A) isn’t enough by itself.

How do you do this? You use co-creation. More specifically, you ask sales and sales engineering to fill out a very simple “demo plan on a page” that summarizes what you learned in discovery, uses that information to prioritize and structure the demo, and creates an interlock between sales and sales engineering so everyone is on the same page.

One worksheet. Four questions. Sales and pre-sales sit down for 15 minutes before the demo and fill it out together. That’s it.

Here are the four questions I use to build my worksheet:

1. What problem did they describe?

Not what you think their problem is. What they actually said.

• “We’re spending 10 hours a week manually pulling data into Excel.”

• “Our CFO is frustrated with unclear reporting that takes weeks to produce.”

• “[This manual part of our workflow] takes 3 people to manage.”

• “We can’t get visibility into pipeline without asking three different people.”

You’re looking for direct quotes, word for word if you can get them. Most SEs walk into demos knowing the company name and the industry. They don’t know what the prospect said was broken, why they’re looking now instead of six months ago, or what they already tried that didn’t work. Once they have this context, it’s much easier to (a) look like you were actually listening and (b) plan a demo that shows them how we can help.

2. What will we show?

What is are the 3-5 specific features that address the specific problems they described? That’s what you should show them during the demo, ideally in the order of priority they expressed to you during discovery.

If they’re drowning in manual Excel work, show them your automated reporting firstest and most-est. Not API docs. Not user permissions. Not dashboard customization. Show them the thing that gets them out of Excel.

This is the shift from decided to discovered. You’re not showing them the whole product, you’re showing what they need to see. You’re taking the work off of their plate and framing the product so it’s immediately obvious how it solves their problem.

3. What should we emphasize and ask during each part of the demo?

Knowing their problem and knowing what to show is how you create a relevant demo. But answering this question beforehand is how you create a resonant demo.

Write down the small details from discovery that tell you how to make each chapter of the demo land — not just what to click, but what to say while you’re clicking it. A specific frustration they mentioned in passing. A technical requirement they flagged but didn’t dwell on. An integration you haven’t confirmed yet.

When you surface these during the demo, the prospect notices because you remembered something they told you. That’s what resonant feels like from the other side of the table. You’re not just showing them a relevant feature. You’re proving you were listening the whole time. (Having a couple questions like these for each feature you’re going to show is also the easiest way to make your demos more conversational - more notes on that later in the article).

4. What do we still need to learn, and what happens next?

What don’t you know yet? Budget? Timeline? Who else signs off? Technical constraints or necessary integrations you haven’t uncovered? Write them down ahead of time and surface them during the demo.

And decide before the demo starts what you want to happen next — technical validation with IT, building a business case, pricing, pilot. Don’t end with “Any questions?” Start the call with a mini-contract re: how you’ll cover next steps at the end. Something like:

“Assuming what we show you resonates today, I’m going to leave 10 minutes at the end of the demo to discuss next steps. I believe part of that ten minutes will include discussing how we can arm you to present a proposal to the rest of your team, but I want to get your feedback on (a) the questions or doubts you still have after the demo and (b) what else you see happening to advance the conversation and get those questions answered. Fair?”

Then actually do that at the end of the demo. Don’t leave the call without (a) asking if what you showed them makes them believe you can solve their most important problems and (b) understanding where they still have doubts, questions, or purchasing steps to cover.

It’s not enough to run a relevant, entertaining demo. You also have to know (after you provide them at least a bit of proof you can solve their problem) what they’re still curious or skeptical about, and what additional work would need to get done before they sign a contract. If you leave the demo without that knowledge, and if they say some version of “we’ll get back to you” when you ask about next steps, you might as well mark that opportunity as closed-lost right now.

You don’t have a winnable deal.

Three More Techniques of Winning Demos

Once you’re aligned, the demo itself needs to do a few things.

1. Prioritize Upfront: Start by confirming what you heard

Before you even get close to sharing your screen, prove to them you were listening and how you plan to prioritize your time:

“Based on what you told us, the most important thing we need to prove today is that we can help with [#1 problem you uncovered in discovery as expressed in their words]. If we focus most of our time there, what else would we be missing?”

This is a critical moment of confirmation and feedback. You’re confirming you heard them right before you start clicking. And you’re inviting them to correct you if you’re wrong. Most demos skip this and hope the prospect connects the dots on their own. Do not make them connect the dots on their own. No prospect wants to do that work.

2. Before vs. After: Show the contrast, not just the feature

Before you show something, remind them why they should care. The easiest way to do this is (you’re probably noticing a pattern by now) to use the exact words they used to talk about the problem they have.

“You said your sales reps are spending hours every week logging calls, and you’re using [competitive alternative] to do that, but despite adoption of the platform, you’re still running into [their articulation of the problem]. Here’s what how that would change with our product.”

Then show them what you’re going to show them. The goal here is not to display what the product does. The goal is to illustrate how different a day-in-the-life can be before vs. after working with you. One SE I know never shows a feature without this exact setup. “It takes five seconds,” he told me, “but it’s the difference between them thinking ‘cool feature’ and thinking ‘this fixes my problem.’” Cool features don’t close deals. Solved problems do.

3. Make It A Conversation: Use curiosity to surface feedback and objections throughout the demo

Here’s the #1 question that gets asked during mediocre demos:

“Does that make sense?”

That questions sucks. It’s closed-ended, which means it stops the conversation before it has a chance to get started. It sets up the prospect to lose face (what happens if something actually doesn’t make sense? Now you’re putting them on the spot and forcing them to admit that in a professional setting. Record-scratch moment). And it’s basically proof that you’re coming up for air after a deep monologue and realizing you have to say something, even if it isn’t that good.

What you should be doing instead of falling into the “does that make sense” trap is making your demo a conversation. How do you do that? You ask open-ended questions before, during, and after you show them each part of the product can do. Your mantra here is to get curious. Wanna know the best way to get curious? Literally start your question with the words, “I’m curious.” As in:

• Before showing them the feature: “I’m curious - you mentioned you’re using [other product] and are running into [challenge]? What does that look like at its absolute worst?”

• While showing them the feature: “I’m curious, you seemed to lean in there while I showed you [feature in your product]. What about that seemed most interesting or useful to you?”

• After showing them the feature: “I’m curious - I know we covered a couple aspects of that part of the product…what parts of what I showed you makes you think this can solve your problem, and what still seems unclear to you how you and your team would use it?”

Those questions invite reflection on what you just showed them, and they also provide evidence that you care about how what you’re showing them is landing. Leading with open-ended, “I’m curious” questions creates a fun, engaging conversation that surfaces what the prospect really thinks about what you’re showing them.

And until you know what they really think, you aren’t in a position to win the deal.

This Only Works If Your Discovery Does

One thing this worksheet doesn’t fix: bad discovery. If you haven’t read my checklist on what great discovery looks like, check out the link below to Discovery Done Right:

Here’s a quick summary: If you don’t know what the prospect is doing today, what’s painful about it, and what their top priority is, you can’t properly plan for a demo. You can only guess at what it makes sense to show them. And guessing means you’re already back to the scripted, product-tour, crappy, decided demo.

Good discovery is how you figure out what problem the prospect has, whether you can help, and how to prove it to them. Proper demo planning and execution ensures you deliver that proof.

Final Thoughts

Most demos are glorified product tours that make the customer do all the work of figuring out whether you can help them. So why do so many technology companies keep running them this way? It all comes down to a few avoidable behaviors:

• They fumble the handoff from sales, so they don’t seem like they were listening when they show the product for the first time

• They don’t prioritize the features that prove they can solve the prospect’s #1 problem, so they bore the prospect with irrelevant parts of the product

• They don’t use the demo to align on next steps, so they lose control of and momentum in the deal

• They don’t make the demo a conversation, so they never find out what the prospect is actually thinking while they’re evaluating

For a prospect sitting across from a company that has fixed these behaviors, the demo experience feels completely different.

Instead of sitting through a boring product training, they’re in an engaging conversation about how they can make their business better. Instead of doing the work of figuring out if the product applies to them, someone’s already done it. Instead of leaving feeling like they need to figure out how to evaluate what they just saw, they leave knowing exactly what happens next. The seller feels like a mind-reader. The prospect hangs up feeling heard and ready to move forward.

That’s what winning looks like.

And most of your competition isn’t doing it.

What an opportunity.

Subscribe now

• Interested in seeing the demo-plan-on-a-page template I use? Shoot me a note at paul@hellooperator.com and I’ll send it your way.

• Want to go deeper on what makes good demos good? Check out How To Demonstrate Software So People Buy It by Brian Geery, who inspired many of the ideas in this article.

On the one hand: the basic stuff that marketing teams should be doing to generate pipeline really aren’t that hard. On the other hand: a lot of businesses genuinely struggle with how to get started, or they get going but then fall out of rhythm after a month, or they agonize over what to talk about and how to measure the results and then sort of lose momentum and move onto a different marketing channel they read about over the weekend.

It’s a lot like fitness. Some people struggle to start working out. Some people struggle with going to the gym consistently. But everyone struggles with some part of building and keeping the habit, especially at the beginning. And we all make it harder by overthinking things and succumbing to training ADD. There’s always something else to try. (That’s both part of the fun and part of the problem.)

When I start to do lots of work within a topic like this (one where I feel like I understand “how to do the basics well” but notice lots of conflicting opinions and unnecessarily-confusing jargon related to it) my instinct is to (a) try and write down what I believe and (b) see how simple I can make it.

So the other day, I ripped a notecard off the pile on my desk and wrote down the four coaching points I keep repeating with my companies during these marketing projects.

Then I took a picture, wrote a short LinkedIn post, and hit publish.

The response was immediate.

I wouldn’t exactly call these numbers “blowing up”, but the level of engagement relative to other recent posts of mine was hard to ignore. This thing struck a chord. People saw themselves in it. If I had to put into words what resonated with them, I think it was something like:

Oh right, I already know what I’m supposed to do. It’s just that we tend to overcomplicate this and I needed someone to say the simple version of what we’re actually going for here out loud.

There’s a lot of marketing/content/demand generation stuff you can do to create leads for your business. Paid ads, retargeting, content, intent signals, influencer programs, SEO, answer engine optimization, and a couple dozen other tactics and channels that genuinely work when you do them well.

But if you’re just getting started, especially if you’re building marketing out from scratch, and if you’re looking for the highest ROI on a simple way to start talking to your potential customers and generating pipeline, here’s where I think you should start.

Subscribe now

1. Make Good Content

There’s a lot of bad content marketing out there. Especially in my world of B2B. You should strive to create good content. Good content stands out.

But what makes good content good?

I believe good B2B content has two qualities:

1. It answers questions people care about.

2. It’s enjoyable to consume.

1. Answer Questions People Care About

Quality #1 (answering the right questions) is all about research and understanding your customer. You gotta get to know the people you’re selling to. How do you do this? You listen. You talk to your best customers. You read your company support tickets. You sit in on sales calls.

The questions these people are asking are already there. You just have to recognize the pattern.

Here’s the kinds of customer questions you should listen for and think about answering in your content.

“Do we have a problem?”

This is where customers realize they have a problem. They’re trying to understand what’s going wrong and why it keeps happening.

• “Why does our [process] always break down at [specific step]?”

• “What are the signs we actually need to fix this?”

• “What is this problem costing us?”

• “Is this problem just us, or is everyone dealing with this?”

• “Why is this so hard? Why can’t we get [outcome] no matter what we try?”

“What are my options?”

Once the problem is clear, they want to know what solutions exist and understand the real tradeoffs between them.

• “Should we build this ourselves, buy [product], or just hire more people?”

• “What are the 3-4 ways people like me solve this problem?”

• “What’s the real difference between [your category] and [adjacent solution]?”

• “Which approach makes sense for a team our size/shape?”

“Why you?”

They’re narrowing their options. Now they want to understand what makes each approach different and why they’d pick one over another.

• “Why would I use [your product] instead of just using [adjacent tool] better?”

• “What’s the actual tradeoff between [your approach] and [common alternative]?”

• “How is this different from what [competitor] does?”

• “Why did you build it this way instead of [other way]?”

“What happens if I buy?”

Further down the path, now they’re close to deciding. These questions are all about seeking proof that this actually works and clarity on what success looks like.

• “Can this actually eliminate [time-consuming process] or just make it faster?”

• “What kind of improvement should we realistically expect?”

• “Who has already tried this and what results have they gotten?”

• “How long until we’d see [specific result]?”

• “What does success actually look like with this?”

• “How much work is this going to be to implement?”

“What’s changing?”

This one doesn’t neatly fit into the buying journey, but great content isn’t always about shepherding someone through a purchase decision. Sometimes it’s about “bringing the outside in” and helping people understand what’s going on and how they should think about it. Not directly related to any one part of the buying journey, but a fantastic way to build trust and establish authority.

• “Is [regulation/trend] going to force us to change how we do this?”

• “Should we be worried about [competitive threat/market shift]?”

• “What are companies like us doing about [industry change]?”

• “How should we be thinking about [trend]?”

If you sit down and start to think about this question-based approach to content, you’ll soon realize that there are infinite questions you could be answering for your customers. Learning to think in questions (and answer them one at a time) is the #1 thing that will help you create better content. Because, as HBS professor Clayton Christensen once said:

“Without a good question, a good answer has nowhere to go.”

If you like this question-and-answer approach to content creation, I highly recommend the book They Ask, You Answer by Marcus Sheridan. It’s the book for learning this approach to customer obsession—and there are tons of great examples inside re: how you can apply this philosophy to any business. Marcus and I also did a podcast episode together a while back and had a lot of fun doing it.

2. Make It Enjoyable To Consume

The second quality (making your content enjoyable to consume) is a little harder to teach. How do you make stuff people want to read, watch, or share with others? What does enjoyable even mean?

My take: Enjoyable content (especially in B2B) respects people’s time. It’s clear. It’s linear. It builds. It pulls you in, hand-over-hand, using good structure and by opening and closing loops in a satisfying way. It feels finished. The rough edges and distracting bits and jarring transitions have all been sanded off.

A good editing trick: read the thing you’re writing out loud (or watch the video you’re making) and notice where you start to get bored. That’s where the problem is. That’s where you’re not respecting people’s time. Fix that part.

An even better trick: Whenever possible, take a written piece of content and turn it into video. Record the answer instead of writing it. There’s all kinds of reasons to do this. One: Most people literally do not read anything anymore. Two: It humanizes you. They can see that this is a real person who actually knows what they’re talking about, who’s putting themself out there in a way that written content just doesn’t demand. A three-minute video explaining how your product works will almost always get watched more than a 1,500-word blog post saying the exact same thing.

And yes - AI can be a HUGE help for creating high-quality content, if you use it in the right way. Here’s three prompts I use all the time (and a lot more here) to take something that’s nearly done and turn it into something polished. Something I’m proud to publish.

1. AI Prompt #1 - Find The Waste: I want you to go through this like an editor with a red pen—cut filler, redundant points, weak transitions, or anything that doesn’t move the argument forward. Highlight where I’m repeating myself, where I could say something in half the words, or where the energy drops. Then rewrite a tighter version without losing clarity or personality.

2. AI Prompt #2 - Turn The Dial: I want you to go through this and identify which sections need the volume turned up (more vivid, more confident, more emotionally resonant) and which ones should be turned down (quieter, tighter, less try-hard). Then show me what that calibrated version looks like, with pacing, tone, and emphasis adjusted for maximum impact without losing the voice.

3. AI Prompt #3 - The Tough Critic: Imagine you’re a [insert target audience] who is busy, skeptical, and has seen a hundred versions of this before. Rewrite the message to grab their attention fast. Cut anything that sounds generic or fluffy, avoid trying too hard to persuade, and frame it in a way that speaks directly to what they care about.

If you’re looking for more thinking on what makes good content good, I highly recommend Nobody Wants To Read Your Sh!t by Steven Pressfield. It’s the wakeup call you need to find the boring parts in your content and kill them with fire.

2. Send It To Your Customers and Prospects

If you’re reading this, I want you to take an oath with me. Ready?

I will stop just posting the stuff I create to my company Linkedin page and then calling that marketing.

Good job. You’re better than that.

Here, I'll prove it to you. Go check your LinkedIn impressions on the latest post from your company account right now. (I'll wait.)

If you're an emerging tech business—call it $50M ARR or under—I'll bet you're seeing a couple thousand impressions per post, maybe less. Let's think about what that number actually means. Of those 1-2K people that saw your post, a lot of them aren't your ideal customer profile at all. Let's say 50% aren't. They're just randos that happen to see you pop up in their feed. If you got 1K impressions, and 50% are in your market, that means maybe only a few hundred relevant people catch a glimpse of your post while speed-scrolling their feed, get counted as an impression, and keep going about their day.

Should you still post stuff to LinkedIn?

Sure. Don't not do that. Every impression counts.

But you need more than that. You need insurance that the people who matter actually see your stuff.

Email is the simplest form of that insurance. We all use it. We all check it a billion times a day. And it’s the cheapest, simplest way to amplify the good stuff you’re creating and give it a fighting chance of being read by someone who might actually buy something from you someday.

To do this well, you need to build some lists. Start with two lists:

• For customers: Start with knowing who pays you money and making sure those people are in a system of record you can send from. Sounds basic. Surprising number of companies don’t have this buttoned up.

• For prospects: Align on your ICP, build a list of the right people/titles inside those companies, use a data provider to get contact information, load it into your system, and send responsibly.

That last part matters more than people realize. Cold email at any volume puts your domain reputation at risk. Here’s the short version of how to protect yourself: never cold email from your primary domain. Set up a subdomain (yourcompany-mail.com works fine), warm it up over 3-4 weeks by gradually increasing send volume, and rotate between a couple of mailboxes so no single address takes the full hit. There are plenty of tools out there that can handle this automatically for you.

Think of this like breaking in new running shoes. You don’t wear them for a marathon on day one. You need to put some miles on them first.

3. Pay Attention To Who Consumes It

This is where you need a little help from RevOps. Not a lot, just enough to make sure you’re noticing the right signals.

I’ll use myself as an example. After every Substack post, I go into my stats and check who read it. If I see a cluster of reads from one person, I know one of two things: either they have a giant crush on my writing, or they probably sent it to someone else. Either way, that’s a signal. Something I wrote resonated with them. My message landed.

My newsletter is a bad example in one sense—it’s free, and I don’t really have anything to sell off the back of it (not yet anyway). But here’s a very basic thing I do with those signals: if I’m not connected with that person, I send them a connection request. “Thanks for reading today’s post on [X], just putting a face to the name.” I want them seeing more of my stuff, telling their friends, maybe introducing me to someone useful down the road. It happens one person at a time.

That’s the workflow: Create. Ship. Notice. Connect.

And that’s what this should feel like if you’re a business. And even with basic sales and marketing tools, you have far more signals to work with (and far more potential connections to create) than I do on Substack. When marketers talk about lead scoring, this is what they mean. Building a list of signals you can track, then deciding how much weight to give each one.

Here are the signals worth paying attention to, roughly in order of how seriously to take them:

• Filled out a form — someone completed a contact or demo request. Obvious one, but it’s the ceiling, not the floor.

• Forwarded your email — a prospect shared a marketing or sales email with someone else in their org. This is a big deal. It means internal conversation is happening.

• Multiple page views in a short window — someone visited your site several times in a few days. That’s research behavior, not browsing.

• Opened a sales email 3+ times without replying — they’re reading it, probably sharing it, and haven’t said no.

• Visited your scheduling/demo page but didn’t book — got close, got cold feet, still interested.

• Opened marketing nurture emails repeatedly — not a hot signal on its own, but a pattern worth noting.

• Connected with you on LinkedIn — low intent but warm. They know who you are now.

• Found you through an AI tool — if someone discovered you via ChatGPT or another LLM, they were doing specific research. Worth paying attention to.

If your RevOps person is good, they will have opinions about how much weight to give each signal. Let them. It’s a fun and productive argument to have.

4. When It Feels Like Someone Is Interested, Call Them On The Phone

I chose those words (”call them on the phone”) very carefully.

Email is a great way to make sure people see your content. But in my world of B2B, it is increasingly not a great way to convert those people into meetings or paying customers. We’ve become numb to it, and the AI-generated spam cannon we’ve built for ourselves over the last decade has made the problem worse. Your prospects are drowning in “just wanted to circle back” and “can you at least point me to the right person” and they are hate-not-replying to all of it.

Here’s the fix: Call them, and don’t be weird about it. Reference what they’ve been engaging with without being a creep. You don’t need to open with “I noticed you visited our pricing page at 2pm on a Tuesday.” Ask permission to take two minutes. Make those two minutes good. And if the answer is “not now,” let them know you’ll plan to hang around the hoop (again, without being weird about it) so when the problem you solve becomes real for them, they know who to call.

What does “don’t be weird about it” actually mean? It means you acknowledge you can see what they’ve been looking at without making it sound like surveillance. Something casual like: “Our fancy tech stack tipped me off that you might be doing some research on our category—figured it was worth a quick call to see if I could answer any questions and maybe share an educated guess on how we might be able to help?”

That’s interruptive but at least kinda normal. “I noticed you spent 47 seconds on our integrations page last Thursday, can we now book a demo?” is not.

Final Thoughts

The goal of content marketing or demand generation or whatever term marketers decide to invent next week for this thing we’re talking about isn’t to generate immediate pipeline. Most people in your market aren’t ready right now. The goal is to become the most familiar, most trusted voice in your category so that when they are ready, they call you first.

How do you do that? You make good content, get it in front of the right people, notice who’s paying attention, and pick up the phone and say hello when you see your opening.

Are there technical details you need to figure out and processes you need to build to do this well? Sure there are. And yes, there are a few bits that are a little complicated that you have to get right.

But don’t lose sight of what you’re actually going for here.

Have something to say. Then make sure people hear you.

That’s it.

Subscribe now

Spoiler: We won 2-1, thanks to an electric transition goal in overtime from Jack Hughes, whose legend will only grow this week thanks to his missing two front teeth, knocked out by Canada’s Sam Bennett with a high stick in the third period.

If you haven’t seen it yet, his postgame interview (Bloody lip, gap-toothed smile, and pure joy) is a must-watch.

After my wife and I stopped scream-high-fiving and sat watching Team USA accept their gold medals, I started wondering how they put this team together.

It turns out, that’s a hell of a story.

How You Build a Gold-Medal Team

Deep down, I think Team USA coach Mike Sullivan and GM Bill Guerin knew that Team USA wasn’t going to out-Canada Canada.

Canada had Connor McDavid, Nathan MacKinnon, Sidney Crosby, and a deep roster of NHL stars, with 22 combined Stanley Cups on the roster and still-fresh international momentum after beating the US 3-2 in overtime last February in the 4 Nations Face-Off.

If Team USA’s leaders tried to win a goal-scoring contest against this group, they were likely to lose. So Sullivan and Guerin decided not to try.

Starting well before the final roster was announced in January 2026, the two leaders of Team USA built their team by asking themselves a counterintuitive question: not who the best players were, but what kind of team it would take to actually beat a roster like Canada’s. Their answer wasn’t about offense firepower. It was about accountability, defensive discipline, and the willingness to do the unglamorous but necessary work that wins close games against elite competition.

Guerin laid out his philosophy plainly when Team USA’s roster dropped in January. Eight of the top fifteen American NHL forwards in points didn’t make the team. Reporters wanted to know why. His answer:

“If you can’t check, you can’t play in the Olympics. This is about building a team, not an All-Star team.”

Sullivan had said something similar at the orientation camp he ran in Michigan the previous August, months before the final roster was even set. He told his players he wanted to build a team “emblematic of the values we hold dear.” He described those values using words like “work ethic,” “commitment,” and “care for teammates.” When Guerin was asked around that time about the qualities most important to him on his defense, he led with “the ability to defend, and the willingness to defend” before mentioning anything flashy or offensively-minded.

Guerin and Sullivan decided early on the kind of team culture they wanted to build. And they were going to be uncompromising about who would help them build that culture.

The Most Telling Roster Decision

The clearest proof-point of their level of cultural commitment was their decision to leave a player named Adam Fox off the roster.

Fox is a Norris Trophy winner — the award given annually to the best defenseman in the NHL. He was healthy. He was playing well. By any conventional measure, he’s one of the best defensemen in the world. And get this, Sullivan is even his coach in NHL.

But Sullivan and Guerin were assessing players on more than just talent. Fox was outstanding at the aspects of hockey that show up on highlight reels and Norris Trophy ballots: the breakout pass, the power play, and the offensive zone read. But what Sullivan and Guerin decided together they needed were players who were great at the things that don’t make the highlight reel. The more defensive aspects of hockey like checking, shot blocking, and penalty kills.

And when you consider that lens on their teambuilding strategy, you can start to understand their decision. Fox had gone scoreless and had been on the ice when McDavid scored the overtime winner in the 4 Nations tournament the year before. Despite his accolades, the questions about the less-visible, more defensive game at the highest levels of international competition outnumbered the answers.

They’d been saying out loud for months exactly what kind of team they were building and the basic techniques they were going to build their culture around. And while Sullivan initially advocated for Fox to make the roster, as the coach and GM weighed Fox against the philosophy they'd committed to together since August, the decision became clear.

They left him home.

Leaving talent on the sidelines because it doesn't fit what you're building is never easy. But Team USA’s commitment to unsexy, winning disciplines over star power, even though it may not have been the obviously right call at the time, delivered.

One specific example of how Team USA’s strategy, focus, and approach to talent helped us win?

It’s how amazingly well this team handled penalty kills in this Olympics.

18 for 18

Penalty killing is the most thankless job in hockey. You’re on the ice for two minutes at a time, a man down, structurally disadvantaged and exhausted while you defend against the other team’s best offensive players, who have the time and space they need to pick you apart. A good penalty kill seldom makes the highlight reel. Executing one requires a particular mindset more than elite skill: guys who are willing to sprint back, clog a shooting lane, and throw their body in front of a one-timer without thinking twice. You can’t coach someone into wanting that.

When you successfully kill a penalty, you don’t just neutralize the other team’s advantage. You take something from them. A team that fails to convert a power play doesn’t just reset and keep playing. They come off the ice deflated, the game’s momentum visibly shifted. The penalty kill is one of those beautiful moments in sports where doing your job correctly is also actively demoralizing for the other side. It’s a little unflashy thing that, when executed well, makes a huge difference.

Team USA finished the Olympics 18 for 18 on the penalty kill. That is a ridiculous stat. In the gold medal game, the U.S. killed a 93-second 5-on-3 (at a huge disadvantage with two of their players in the penalty box simultaneously) against Canada’s #1 power play unit. This was one of the most dangerous offensive lines in international hockey history, with a two-man advantage, and all the time they needed to put Canada ahead. And they still couldn’t score.

That’s what tough decisions like leaving Fox home bought Team USA. Not a flashy highlight. A perfectly-disciplined penalty kill at a moment and in the game that mattered most.

ESPN, in their preview of the gold medal game this morning, turned out to be pretty damn prophetic:

“The U.S. left some dynamic scoring at home because it wasn’t looking for the best players or an All-Star team; it wanted the right players for any situation. And many of those glue guys show up here on the penalty-kill.”

Yep. That’s right.

What’s Your Penalty Kill?

Mike Sullivan and Bill Guerin had a special kind of conviction when they assembled their roster. They decided early on the kind of culture they wanted to build and the basic disciplines that would underpin it. They made the hard calls to build a team committed to those disciplines, and they didn’t apologize for leaving otherwise-great talent on the sidelines when it didn’t quite fit.

The result: a workmanlike team identity, a group of players with a uniquely close connection, and the first Olympic gold medal in men’s hockey in 46 years.

If you’re reading this and thinking about how this applies to your work, I’m willing to bet you already know what your version of the penalty kill is. You know the basic, unglamorous discipline that (if you tightened it up, focused on it, and if you only hired and developed people who were committed to running that part of your business the way it’s meant to be run) could meaningfully change things for you.

The hard part isn’t identifying what that is for your business. The hard part is committing to it. The hard part is making it the thing you build everything else around. It’s about declaring that even though it’s not the most exciting part of what you do, it’s what matters to your team. It’s about making the tough personnel calls when someone can’t commit to it or just doesn’t fit. And it’s about staying focused on it when the people around you start chasing something flashier or more exciting.

Sullivan and Guerin did that. And it worked.

When you do that, good stuff happens.

When you do that, you win.

I wrote more about what it takes to win and how to make it happen for your business last year.

If this article resonates, I hope you’ll check out “What It Takes To Win” at the link below.

Oh yeah, and one more thing: U-S-A, baby.

Subscribe now

Missing on a senior hire hurts, no matter the position. But there’s one executive hiring mistake that’s uniquely expensive and uniquely painful: getting your head of sales wrong.

The miss rate on sales leaders is surprisingly high. You don’t have to look hard to find stats on how short the average CRO’s tenure is. The reason isn’t hard to figure out: these people get other people to say yes for a living. They’re good at it. The longer you’ve been in the working world, the more likely it is that you’ve run into a sales leader who talks a great game but can’t remotely back it up. The kind who probably sounds great in the interview and then quietly wastes everyone’s time for a year while doing everything but delivering the results they were hired to produce.

In Part I, I laid out the three go-to-market situations I run into most often in my work as a PE operating partner (Figuring It Out, Fixing It Up, and Scaling It Up) and argued that what you need from a sales leader depends on which situation you’re in. Hire for the wrong stage and you’ll pay for it — in time, money, and opportunity cost.

What Part I didn’t cover is the other side of the coin: the traits that matter regardless of which phase you’re in. Every stage has its own demands, but there are four qualities I look for in every sales leader evaluation (new hire or incumbent) that always matter.

The Four Universal Traits of Effective Sales Leaders

Here are the four traits that actually predict whether a sales leader will drive growth in your business. Every strong one I’ve worked with has them. Almost every bad hire was missing a few.

1. They Learn From Customers

In my world of B2B technology, there’s almost always an opportunity to position your product more clearly in the mind of the customer. Most sales organizations never fully nail that opportunity. The ones that do seem to grow faster than everyone else.

If your sales leader isn’t hunting for the most clear and relatable way to talk about what you do (and is instead blasting people with product specs and hoping they just buy the thing) they’re just a brochure with legs. A very expensive brochure with legs.

The best sales leaders are bloodhounds. They’re customer-obsessed. They’re like Tom Cruise in that famous scene from A Few Good Men: They want the truth.

They make it their responsibility to go find out what customers are struggling with, what it’s costing them, what they think is so valuable about their product, and what caused them to finally say yes. Because they know that once they know that, they have what they need to give every future prospect what competitors won’t: Expert perspective on the market, and credible help navigating their options.

That’s what earns trust. And trust is what closes deals.

What separates customer-obsessed sales leader from everyone else isn’t that they listen. It’s that they change things because of what they hear. They rewrite the messaging. They kill the talk track that isn’t landing. They shift who they’re targeting when the evidence points somewhere new. They use what they learn to make intelligent changes to how they and their team do their job.

The quality underneath all of this is curiosity. My best sales leaders are all genuinely, almost restlessly curious about customers. Not because someone told them to be. But because they know that truly understanding their customer gives them everything they need to win.

How to test for this: Ask them to tell you about a time they heard something from a customer that surprised them. Then ask them what they changed because of that surprise. What you’re listening for is the second half of that story. If the surprise didn’t lead to action, you’re talking to someone who listens politely and then keeps doing what they were doing. That’s not who you need.

2. They Have a Nose for Value

Some sales leaders will tell you they need six months of assessment and a full consultant-led diagnostic before they can tell you what needs to happen with your go-to-market strategy. Others stick their nose into what’s going on and know within a week where the biggest challenges or opportunities are (and have probably already started doing something about it).

I want to hire the second person. Don’t you?

I call this having “a nose for value.” It’s an almost involuntary ability to walk into any sales situation and immediately pick up on what matters. These people aren’t processing everything equally. They’re pattern-matching against a deep library of what an effective sales process looks like, what solid deal management feels like, and what the absence of those things looks like in the numbers and in the field.

You can’t fake it. It comes from years of paying close attention to the small things that actually create results — enough pipelines, enough customer calls, and enough sales motions that the patterns become second nature.

What separates this from simple experience are opinions, speed, and specificity. A lot of sales leaders have seen enough to have opinions. The ones with a real nose for value have seen enough that the read is fast, precise, and almost always pointed instinctually at the right thing first.

How to test for this: Send them something real before the interview. A pipeline export. A sample call recording. A look at your recent numbers. Ask what stands out, what they’d want to fix first, and why. The candidates who don’t have a nose for value will try to spin you around with a brainstorm: “here’s everything I noticed.” The ones who have it won’t be afraid to prioritize. They may give you a list, but they’ll also take a stance - on what the biggest challenge, opportunity, or insight is, and what they would do next to address it. That stance and that prioritization (and the instincts behind it) are what you’re looking for.

Subscribe now

3. They Build Systems That Outlast Them

Go-to-market strategy can get endlessly complicated. The best sales leaders resist that pull. They know that building a sales team is mostly about teaching people, and that complexity is the enemy of teaching. You can’t hand something to someone else and expect them to use it if you can’t explain it simply.

What I look for here is a bias toward simplicity. Specifically, I’m looking for the ability to throw a lasso around the business and get it under control. To identify two, three, maybe four moments of truth in the sales process and organize everything around those. What they teach. What they coach. What they measure. What they’re listening for when they join a rep on a call or review a recording on their own. The system doesn’t have to be complicated. It just has to be clear enough that other people can carry it out when they’re not in the room. And to believe in it enough to want to.

That’s the real proof of a system. It’s about full transference to the team and commitment from the team. Not that the sales process exists, but that it lives in other people. Pulling that off requires simplicity. You can’t transfer something complicated. You can only transfer something someone else can understand, repeat, and internalize.

The failure mode shows up in two places. The first is documentation (or the absence of it). If nothing about how your team should sell ever gets written down, that’s a tell. Writing it down forces you to simplify it. It forces you to take a stance on what actually matters. A sales leader who never documents never has to commit to a standard, which usually means they don’t have one.

The second shows up at the executive level, in the language they use to explain what’s happening in their part of the business in board decks and operational reviews. If the slides look different every quarter (e.g., different or unclear definitions, different metrics or methods of displaying them, or different framing for why the number is what it is) that’s not a reporting problem. That’s a systems problem. It’s evidence of a sales leader who’s thrashing reactively to whatever comes their way instead of building something stable and consistent enough to talk about the same way over time.

How to test it: A question I’ll sometimes use: “Tell me about a process you built at a job you left a while ago that’s still running.” The ones who built something real can tell you exactly what they built, how they adjusted it and made it stick, and why it survived. The ones who skirted building systems by playing the hero will tell you a bunch of basic “isn’t that just doing your job?” day-to-day management stories while avoiding talking about process, documentation, or reinforcement.

4. They Know How to Teach

A sales leader doesn’t have to be the best presenter or the sharpest closer on the team. But they have to be able to make other people better. Those are different skills, and confusing them is one of the most common mistakes I see in sales leadership hiring.

Here’s why teaching matters so much in this role: the basics of a great sales organization (e.g., curiosity-driven discovery, demos that focus on what the customer actually cares about, instincts for finding new opportunities inside existing accounts or finding the angle that drives a deal forward) are never really fully installed. They decay over time. Reps who were doing great discovery six months ago start slipping back into pitch mode. Demos that used to be tight start bloating back up to product tours that bore your prospects. The hunting instinct fades and reps start sitting back and waiting for leads to come to them.

Someone has to care enough to keep reinforcing the same things, over and over, long after it stops feeling interesting. That’s the job. And it takes a special kind of teacher to do it well — someone who understands that getting a team of people to master the ordinary things, and to take pride in mastering them, requires patience, high standards, and a willingness to repeat yourself indefinitely without losing conviction.

The best sales leaders I’ve worked with are all great teachers. They don’t dump feedback on people. They translate hard things into simple, teachable standards that sales reps can use in front of customers. And their standards transfer. You can see it when they’re not in the room. The team is running the same plays, using the same language, and holding themselves to the same bar.

How to test for this: Ask the candidate to tell you about an average rep on their team. Not their best. Not their worst. Someone in the middle. (Ask them for their first name. Not because you’re going to call that person, but because it tells you the story is real.)

Then ask: “If I called that person right now and asked them what you’re an absolute stickler about — something you reinforce over and over and over again with your team — what would they tell me?”

What you’re listening for isn’t the technique itself. Which technique or standard they name is less important than (a) whether they have one and (b) can talk viscerally about the time they’ve spent making sure it sticks. The best answers describe something specific (e.g., a moment in a discovery call, a habit in a demo, a discipline around follow-up) and then share stories about the repetition, reinforcement, and individual conversations they had to have to make sure even the average sales rep on the team could meet their standard.

How To Assess The Sales Leader You’ve Already Got

So now you know what to ask to assess for the qualities that matter no matter which stage your business is in. But what if you’ve already hired your sales leader and you’re trying to honestly assess whether they’re the right person to take you into the next chapter?

In theory this should be easier. You’re not relying on interview questions and rehearsed answers — you’re observing what they actually do every day. But assessing someone already on your team can be harder than evaluating a stranger. You have a relationship. You’ve made a bet on this person. And sales is the one function where the results are always visible and the excuses are always plentiful — some you’ll come up with yourself, some they’ll hand to you.

There’s always a deal that slipped, a macro headwind, a rep who left at the wrong moment. The question isn’t whether those things are real. They usually are. The question is whether you’re letting them explain away something that’s actually a leadership problem.

The most common pattern I see in underperforming sales leaders is a focus on activity instead of results. These people will tell you exactly how busy they are, how hard they’re working, how complicated the deals they’re managing have become. They are, in almost every case, complicators rather than simplifiers. They make the business feel harder to understand over time, not easier. If you find yourself getting less clarity on your sales performance every quarter rather than more — if the definitions keep shifting, if the pipeline math never quite adds up the same way twice — that’s not a reporting problem. That’s a leadership problem.

The earlier warning sign, the one CEOs most often talk themselves out of, is reactivity. These sales leaders are trying like hell to bring deals in. Nobody’s questioning their effort or their intent. But they never add anything to how their team performs. They invest in building systems or teaching their people only when that pressure comes from somewhere else — from you, from the board, from a consultant you brought in. Left to their own devices, they don’t view that as the job. They view their job as bringing in deals. Not building the machine, process, and culture that brings in deals at scale.

That distinction matters enormously. Because a sales leader who’s personally closing deals but not making their team better puts a ceiling on your business. And the longer they’re in the seat, the lower that ceiling gets.

So here’s a simple test. Look at the four traits above and ask yourself:

• Are they learning from customers and changing things because of what they hear — or are they relying on the same old pitch and process they brought through the door?

• Do they have a nose for value (can they walk into a situation and know within a week where the challenges/opportunities are) or do they need months of runway before they’ll commit to a point of view?

• Have they built anything that runs without them — or are they barely keeping things together by playing the hero?

• And can average people on their team do an impression of their standards — or is all that knowledge still locked inside the leader’s head?

If the honest answers to those questions are making you uncomfortable, trust that feeling. Sales is too important, and the feedback loops are too slow, to spend another quarter hoping things will turn around on their own.

Subscribe now

Have questions you’d like to hear me answer on the Hello Operator podcast? I’d love to hear from you. Shoot me a note at podcast@hellooperator.com, and I’ll answer them on a future episode.

See, the biggest barrier to growth for an investor-backed business typically isn’t competition. It’s confusion.

Think of it like this: There’s a bunch of people out there with the business model, money, and problem that makes them a fit for what you sell. (You wouldn’t have attracted investment in your business if that wasn’t true.) For most B2B businesses, there’s literally thousands of potential customers out there you could work with someday. Add all those people (and what the value of what they could potentially pay you) up, and that’s your total addressable market. That’s your TAM.

But you hold yourself back from accessing the full potential value of your TAM when your unclear messaging requires you to explain or unpack what it is you actually do to all those customers. This lack of clarity adds an unnecessary and wasteful step to the process of getting to know you. It makes your buyer work harder to understand if you’re even worth their time. And lots of otherwise-enthusiastic and willing buyers will just give up and look elsewhere if you make them do that work.

Clear positioning clears a path for your market to your door. It creates a more direct route to all those buyer relationships you’re trying to build. It lightens their load and makes it less intimidating for them to introduce themselves to you.

And especially in more technical categories, it’s a powerful and underrated way to build trust. “I like those guys,” people say about companies with clear positioning. “I can tell they’ve done some work to make it easier for me to understand what they do. I appreciate that.”

The more people that understand what you do and why it’s valuable, the more people you can successfully sell to, and the more people will proactively ask for your help (or at least take your call when you reach out).

Your TAM doesn’t change that much over time. Even if you analyzed and sized your market years ago, all those potential customers you talked about with your investors during diligence are probably still there, waiting.

And clear positioning is how you make it obvious to them why it’s worth meeting (and working with) you.

Subscribe now

My Best Stuff on Positioning

If you’re rethinking your positioning or you’re just curious about what makes good positioning good, here’s my three best resources on the topic:

By The Way… There’s a Podcast Now

Good news: The Hello Operator podcast is now live on all major podcast platforms. If you like my writing, you’ll love my audio essays.

Check it out on Spotify and Apple podcasts (and remember to subscribe and leave me a review). I’ll also be hosting the occasional AMA episode, so if you have questions you’d like answered on the pod, drop me a line at podcast@hellooperator.com.

Not “almost nobody does it well.” Almost nobody does it AT ALL. Like, zero. No checklist for what a good discovery call sounds like. No certification. Just vibes and hope and the occasional “let’s all listen to this call recording” before they move on to thinking about the next deal they need to land.

On some level, I get it. There’s a good reason training takes a back seat on the long list of sales leader agendas. Sales training seems complicated. It’s always less urgent than closing deals. Your best rep has a million bucks of in-quarter pipeline to bring in and you’re supposed to pull them off calls to... what, roleplay? With a fake customer? While real customers are waiting to throw money at you?

Isn’t that nuts?

Well, no.

Training is always going to seem less important than closing the next deal. That’s life as a sales leader. But I’m here to convince you why it makes so much sense to make the time to do it, how it’s going to help you beat your number, and how much simpler it can be than what you might have assumed.

Let’s go.

How Training Actually Moves The Needle

Here’s what private equity firms see when they look at a sales organization with no training system (and where the value comes from when you invest in training):

• Bookings growth: “Shouldn’t this business be growing faster? The product seems pretty good, and there’s a decent size sales team here already.”

• Revenue per rep: Capped at whatever your best natural salesperson can do, because everyone else is winging it with their own made-up process.

• Ramp time: Ramp time is approximately forever. New reps take 6-18+ months to productivity because they’re reverse-engineering “how we sell” from their own past experiences and very expensive trial-and-error with real potential customers.

• Win rate: All over the map. Some reps crush it, most don’t, and you can’t explain why or fix it because there’s no standard to measure against.

• Customer acquisition cost (CAC): Higher than it should be because a good chunk of your sales capacity is effectively wasted on reps who have never been taught why what you sell is so valuable and how to talk about it.

• Sales cycle length: Longer than necessary because reps don’t know how to run discovery, so they book extra calls to ask the questions they should’ve asked in meeting one.

By now, you get my point. The leverage here is enormous. If you can get your average rep to perform like your 75th percentile rep, you just increased revenue by 20-30% with the same headcount budget.

That math works. It always works.

The Minimum Effective Training Checklist

The good news is this doesn’t require an expensive training consultant or a six-month curriculum-building project or whatever other excuse you’ve been using to not do it.

It requires picking 2-3 moments that matter, writing down what good looks like, making people prove they can do it before you let them do it with real customers, and then finding creative ways to make the training stick.

That’s it. That’s the system.

That video above walks you through the four-step framework I use with my portfolio companies to build simple, effective training programs. Training will always be extra work, but it’s not complicated. You can get this going yourself in a few weeks.

The hard part isn’t the building, It’s the commitment to actually use the training instead of letting it become another “nice to have” that slowly wastes away stuffed in a Google Drive somewhere.

Subscribe now

The AI Unlock and How It Can Make Your Training Stick

Here’s the really cool thing that just recently changed: you can now automate the part of training that nobody seems to have time for.

This year, we’re building AI systems in several portfolio companies that grade discovery calls against that company’s certification scorecard. Our AI agent pulls the call recording, sorts it, checks whether the rep asked the right questions, scores their positioning against our value prop framework, and delivers specific feedback via Slack and Google Docs.

This isn’t designed to replace coaching or rub the sales team’s nose in how they sound in front of customers. It’s helping create more surface area for coaching and feedback. It’s helping coaching happen at scale.

• Before: Sales manager has 8 reps, can maybe listen to 2-3 calls per week, gives feedback to whoever’s struggling most or whoever asked the loudest. Most calls never get reviewed. Most reps never get feedback. The training you did in month one is forgotten by month three because nobody’s reinforcing it.

• After: AI grades every discovery call. Manager gets an easily-reviewable thread showing which reps are using what they learned in training and which ones are winging it. Instead of spending hours playing “find the coaching moment” across 40 random calls, the manager spends 30 minutes coaching the specific gaps that matter based on the discovery scorecard (e.g., the rep who keeps skipping discovery questions, the rep who’s pitching features instead of value, the rep who still can’t seem to remember to set a next step, etc.)

This solves the “I don’t have time to coach” problem that kills most training programs. You’re not asking managers to do more work. You’re automating the part that prevents them from coaching in the first place.

And the reps get better faster because they’re getting feedback on every call instead of the two calls per month their manager happened to listen to.

Why Training is a Competitive Advantage

Another reason training is so important: Your competitors probably are not doing it.

They’re running discovery calls with no standard for what questions to ask. They’re giving product tours for demos instead of tailoring how they show their software to the pain points this customer cares about. They’re hoping their reps figure it out through osmosis and natural talent, which means they’re effectively running a sales team where half the capacity is wasted on people who haven’t figured it out yet (and might not ever).

You can just... not do that. You can build a system where every rep executes the same basic selling techniques (and then makes them their own), where new hires ramp in three months instead of twelve, and where your average performer looks a lot like your 75th percentile performer used to look.

Not that hard. Almost nobody does it. And it’ll help you win.

(I think they call that a “competitive advantage.”)

Subscribe now

The week between Christmas and New Year’s.

Or, as I like to call it, the haze.

The normal rules of time and nutrition do not apply in the haze. Nobody knows for certain what day it is. Lunch is a combination plate of leftovers from three different meals, supplemented with leftover cookies from a holiday gift basket that has sat on your kitchen counter since before thanksgiving. An unbroken stream of bowl games and Christmas movies plays on the living room TV. Work feels like a distant fever-dream. And we all oscillate between thinking deeply about the year ahead and wondering if anyone has eaten that last piece of pie in the fridge yet.

For me, that deep thinking includes looking back at my writing and analyzing what performed the best. So this week, I pulled my Substack stats and looked at what you read, liked, and shared most in 2025.

Here are the articles that rose to the top of that list, how I feel about them, and why they might be worth another read (even if you caught them the first time around).

Thanks for reading, and happy holidays.

Subscribe now

Most Liked: What My Dad Taught Me About Work

We all have role models in our life. And if all we did was actually use the lessons they taught us, we’d probably be better off than we are with any framework, playbook, or modern-day tip we picked up from some self-proclaimed expert we’ve never met. I’m lucky to have a great role model in my Dad. And his approach to his work and career has deeply shaped how I think about my own. This article took me the longest to write of anything I’ve ever published. It’s also the one I’m most proud of. If you only read one thing from this annual recap, make it this one.

—> Read it here

Most Shared: How To Make ChatGPT Sound Like You

This was my practical guide showing people how I’ve trained AI to write in my voice.

I think one of the biggest barriers to people using AI more frequently is they get frustrated that it doesn’t sound like them. But with a little structural setup, you can solve this problem in about 20 minutes. Not only does it make any AI tool more satisfying to use, it also opens your eyes to all the possibilities for applying AI in your work and everyday life. It’s my tactical, step-by-step guide for removing one of the most important frictions to putting AI to work.

—> Read it here

Most Read: AI, SEO, and How To Simplify Your Content Strategy

I wrote this when everybody was panicking about the impact of AI-generated content flooding search results.

I think people wanted a bit of a technical explanation re: how SEO works, how AI is changing the SEO game, and some pointers for how to use AI to enrich their content strategy. I wanted to cover all three in this article, and that’s why I think it landed. It also includes some of my philosophy on “what you need to know first” before getting going with a new content marketing strategy (hint: focus on the questions your customers are already asking you in sales calls).

—> Read it here

Honorable Mention: How To Hire A Simplifier

This was the only post that showed up in the top three across all three metrics: likes, shares, and views. It’s about the most important quality that all A-players share: They’re simplifiers, not complicators.

Every time I hire an executive into one of our portfolio companies, this is the most important quality I assess for. This article covers not only why being a simplifier is so valuable, but also the specific questions you can ask in your next interview to uncover whether someone can help you simplify your business.

—> Read it here

Thanks for reading and subscribing. If you have questions or topics you’d like me to cover in 2026, reply to this email and let me know. I’m building my content calendar for next year as we speak, and I’d love to hear from you.

Subscribe now

But despite all the chatter out there, we’re still in this weird in-between phase with AI. Lots of people out there are playing with AI, but not enough are putting it to work.

This year, I spent a bunch of time trying to figure out the most practical ways to use AI to get stuff done.

And while I’m still figuring out all the ways I can put AI to work, I’m discovering a bunch of really useful prompts, tactics, and workflows that are making my life (and the lives of my companies) a lot easier.

So many, in fact, that I decided to create a dedicated page on Hello Operator that I’m calling “AI 101.”

There’s plenty already written on what we can expect from AI in the future, how much the biggest AI companies are investing behind their infrastructure, and the AI features the world’s most valuable tech companies are building next. This isn’t that. This is about the basic, everyday, non-obvious stuff you should be trying with AI. It’s about how you can start prompting more creatively. It’s about the work you should be teaching your team to outsource to AI. And, most importantly, it’s about what I think is worth experimenting with when it comes to this amazingly cool but occasionally mysterious and intimidating technology.

Here’s what I want for you: I want you to become someone who not only keeps up with what’s going on with AI, but also someone who develops their own POV on how AI can help you and your team get your work done.

I’ll be writing a lot more on this topic in the future, so if you have questions you’d like me to answer or ideas you’d like me to explore, send me a message. I’d love to hear from you.

For now, here’s my best and most-read stuff on the topic of AI from the past year.

Subscribe now

Basic Prompting and Setup:

• How To Make ChatGPT Sound Like You - How to tune your settings so your AI sounds a little less like AI (and takes way less time to give you what you want).

• Boss Your Robot Around - The #1 obstacle keeping you and your team from getting more out of AI? You’re not prompting it creatively enough. Here’s how to fix that.

• How To Put AI To Work - Applying Jobs-To-Be-Done theory to basic AI prompting strategy (and the workshop I use to teach my teams to get going with AI).

Advanced Prompting and Workflows:

• An AI Roasted My Writing - Here’s what it told me and what I changed.

• Building Trust In The Age of AI Slop - How to stand out with AI when everyone sounds like a bot.

• How To Analyze Your Call Recordings With AI - My #1 use case for AI with sales and marketing teams? Mining your call recordings for customer gold.

• How To Figure Out What Customers Care About - AI can help you stop talking about features and start connecting more deeply with your customers. Here’s the prompts to help you make it happen.

• Fake It While You Make It - How to use simple AI simulations to build a better go-to-market motion.

POV on the Evolution of AI:

• AI’s Impact on Sales and Marketing - I wrote this in 2023 before the AI boom. Always fun to check up on your predictions a few years later. (Mine weren’t bad).

• AI, SEO, and How To Simplify Your Content Strategy - AI isn’t rewriting the fundamentals of digital marketing. It’s just making the basics matter more.

• Your Next Executive Coach Might Be An AI - AI won’t replace your executive coach. (But it sure can do a lot of the stuff a good executive coach does.)

…And if you’d like to see real live walkthroughs on how I use AI (and what I’m teaching my companies), I hope you’ll think about subscribing here and on YouTube.

Subscribe now

And almost every salesperson I work with forgets to ask it.

Want to know what it is?

Here you go:

“Which of those challenges is costing you the most time, money, or sanity? Like, of all those problems you mentioned, which is your #1 problem?”

I want you to notice something about that question: It can’t be the first question you ask someone. Why? Well, to state the obvious, it’s a follow-up question. It presupposes that you’ve already gotten the prospect to spill their guts a bit about what’s going on with them and their work. More specifically:

1. It presupposes that you’ve gotten them to share what’s challenging about their work (i.e., naming the obstacles/problems standing between them and the results they’re paid to create).

2. It presupposes that you’ve uncovered the personal impact of those challenges (i.e., what’s painful for them about all the stuff they shared in #1).

Most salespeople are actually decent at doing #1 and #2. Every sales methodology ever created has beaten this stuff into us. We know we’re supposed to ask questions about what people are dealing with. We know those questions are supposed to help us find pain.

But the step that most salespeople skip is prioritizing that pain. And that’s a mistake.

A mistake that’s keeping you and your team from winning deals you deserve to win.

Subscribe now

Why Prioritizing Pain is So Important

You see, finding something painful about someone’s job is not that hard. Literally every human being does their work in under-optimized conditions. All of us have a vision of what an ideal state of work would look like if our job were frictionless. There’s a big gap between the reality of our work and that ideal, perfect-world state. That gap is where the pain we look for as salespeople lives. Most of us are pretty good at creating a conversation about that gap. We have to get talk about that gap if we want to make our sales pitch relevant to the person in front of us. Otherwise we’re just brochures with legs.

However, as my friend likes to say:

“Life is a series of pain points we mostly do nothing about.”

This is true for all of us. We’re all working around a million little sources of friction that we’ve decided we can live with. We feel a little pain, but we just keep soldiering on. Despite the fact that almost everyone out there has a long list of things they’d change about their job if they could, there are very few of those changes we’re willing to commit to doing something about.

Let me say that again more succinctly.

All of us have pain. But not all of that pain is worth doing something about. Not even close.

And that tension is absolutely critical for salespeople to accept, understand, and use.

You see, sales happen when pain rises to the level that someone is willing to do the work to secure resources to alleviate said pain. Resources in the form of money, yes. But also resources in the form of attention from their boss, political capital to champion a vendor selection process, cycles spent teaching people how to use a new tool, and credibility risked on a bet that this thing will actually make things better.

But how many of the little challenges rise to the level of “I need to fix this now”? How many of those million little pain-points are big and costly and annoying enough to will you to ask for budget, convince your team, and do the work of implementing some kind of solution?

Not many. And just like you, at any given time, there might only be one or two real problems this person you’re trying to sell is genuinely committed to solving. And if you only know the list of problems, and not their relative priority, you have no idea how committed your prospect really is to securing the resources you need as a salesperson to win the deal. You’re guessing when you should be sure.

Think about it mathematically. If someone has ten problems and you solve their seventh-most-painful one, they might like you. They might even agree that your product is cool and would probably help (how many times have you heard this from a prospect who ghosts you later?). But “cool” and “would probably help” doesn’t get you a signed contract. It gets you stuck on someone’s “nice to have” list while they silently de-prioritize you in favor of the two or three other vendors who can provide proof that they can solve problems one, two, and three.

You need to know where you rank. You need to know not only what hurts, but what hurts the most.

Because if you’re not near the top of their list, you’re not going to win the deal.

What This Unlocks

A while back, one of my portfolio companies was struggling with demo conversion rates. We were getting better at discovery, but when we got to the demo, we kept losing deals.

The problem? Our demos were still generic product tours. We’d uncover five or six pain points in discovery, then show up to the demo and walk through every feature in the product from beginning to end. We covered everything, but we never clearly proved we could solve the #1 problem the prospect cared most about.

Once we started asking the “which of those is your #1 problem” question in discovery and using the answer to plan our demos, everything changed. Not just because we learned what mattered most to the prospect. But because now we had permission to build the entire demo around the #1 problem they cared about.

We stopped trying to be comprehensive and started trying to be compelling. We started spending 70% of the demo proving we could solve their #1 problem, and left room in the rest of the agenda to show them we could handle their other problems (and answer any questions that arose naturally from our new, more-relevant, more conversational demo).

And, just as you might imagine, our close rates went up.

Because we now knew what their #1 pain-point was.

And their #1 pain-point became our pitch.

When you know what’s costing someone the most time, money, or sanity, you don’t have to guess anymore about what will resonate with them or what will drive urgency. You know what hurts the most. You know the problem they care most about solving. And you know exactly what you need to prove as a salesperson.

And knowing that is what allows you to make the natural shift to the most powerful moment in any sales conversation.

The moment when you can credibly say:

“I get it. And I think we can help.”

Subscribe now

In Part 1 of this series, I wrote about how most business problems aren’t strategic. They’re executional.

A lead goes cold. A ticket for an important customer sits undealt with. An important renewal slips by or gets mishandled. These aren’t issues of market selection, effects of macro-economic headwinds, or evidence of a deeper lack of product-market fit. They’re dropped balls. They’re small, preventable mistakes. Mistakes that kill your momentum, chip away at customer trust, and make it harder for you and your team to win.

I also touched on how these mistakes don’t happen on purpose. Nobody on your team is intentionally dropping the ball. They know what they should be doing. The problem isn’t lack of knowledge. This is the problem: personal vigilance is a finite resource. We all get distracted. We all get busy. Yesterday’s important thing gets buried under today’s newer, fresher, more urgent thing.

So, yeah. Balls get dropped. And that’s understandable, as long as it doesn’t happen too frequently.

What’s less understandable (and less forgivable) is when these silly little misses keep happening. What’s even less understandable is when people refuse to acknowledge or investigate the misses.

Why does this happen? Usually, it’s because we’re too embarrassed. It feels a little insulting to stand in front of a room of professionals and ask, “Did we prepare for that customer meeting?” or “How long did it take us to respond to that lead from yesterday?” Of course, the answer should always be some version of “We did what we’re supposed to.” So even though we know, deep down, that balls are getting dropped, we go ahead and choose to assume things are basically fine. Because assuming otherwise would mean admitting we’re not running things as well as we think we are.

It’s that assumption (and the dangerous combination of pride and ignorance that powers it) that’s killing you and your team.

High-performing teams don’t let that kind of pride in the door. They rip it out and replace it with a kind of workmanlike paranoia. They look at their business the way Toyota looks at a production line. Instead of assuming that the work is being done the right way, they obsessively hunt for the waste that they know will always be hiding somewhere. They assume the natural state of any system is not that it’s humming along, but that it’s quietly drifting off-course. They assume that if you aren’t actively applying energy to keep things tight, they will loosen. Slowly, but oh-so-predictably.

And because of their belief in and respect for this unavoidable drift, they adopt a more honest, powerful, and somehow-still-optimistic way to think about their business.

They assume that, even when things are going well, small opportunities to improve are hiding literally everywhere.

There’s a big benefit to adopting that mindset. When a leadership team believes that things will loosen unless they’re actively kept tight, they stop waiting for mistakes to reveal there’s a problem. They go looking for weak spots before those weak spots turn into dropped balls. That kind of vigilance creates a working environment where pointing out an executional gap isn’t seen as an accusation, but as an act of service. It’s the kind of environment where someone can say, “I think we’re dropping the ball here,” and the response isn’t defensiveness or finger-pointing, but an immediate, open, and thoughtful discussion about where the weak spot in the system might be and how to fix it.

That’s the kind of environment I want to work in.

And it’s the environment I try to help create when in my work with my portfolio companies.

Subscribe now

Three Kinds of Dropped Balls

Here are the three kinds of dropped balls (messy, slow, and unprepared) I see most often in my work, the invisible damage they cause, and the systems I build with my companies to catch, fix, and prevent them.

1. MESSY: Your Pipeline Is Full of Junk

A while back, one of my portfolio companies found itself stuck in a familiar pattern. We would start each quarter with strong pipeline coverage, often five times (or more) vs. our bookings plan for the quarter. On paper, it looked like plenty of cushion. The forecast felt reassuring. Look at all those deals!

But then, by the end of the quarter, we would inevitably end up on the same white-knuckle ride. We would either just make the number or just miss it.

Despite the seemingly strong coverage, we were just squeaking by.

In the first few weeks of one particular quarter, I can remember the headline coverage number looked great. There were lots of late-stage deals and plenty of volume. But when we slowed down and analyzed the pipeline opportunity-by-opportunity, a different picture emerged. A meaningful number of those late-stage opportunities hadn’t seen any activity in weeks. Many of them had no next step captured. And too many of the newer deals had what I would call “placeholder vibes.” In other words, they didn’t yet have the information attached to them that would indicate a believable close date or a customer with clear urgency to buy.

In other words, the headline pipeline coverage number was a complete head-fake.

When I asked the sales leader about it, they said something to the effect of, “Yeah, we probably need to clean that up.”

I actually think that’s a very human response. No one was trying to mislead anyone here. We weren’t stuffing the pipeline with fake deals. The system was simply allowing comforting but misleading data to accumulate faster than we could reality-check it.

And we needed to fix that.

The Impact

Here’s a dirty little secret of B2B sales: No one’s pipeline is ever perfect. There’s always going to be a lag between what’s really going on with the deals sales is working and the data in the CRM. But when that lag grows too large, you get several harmful effects that can really hurt your business.

• The Leadership Head-fake: See above. An inflated pipeline gives the management team a dangerous false sense of security. You think you have coverage for the quarter, so you don’t make necessary pivots or inspect your key deals’ probability to close until it’s too late.

• Cognitive Overload: Reps feel more stretched than they actually are because they’re subconsciously managing 50 zombie deals instead of the 10 that actually have a chance to close this quarter.

• Hiding the Gap: When the pipeline looks full but isn’t, it hides the urgent need to prospect or think of new ways to build pipeline. It lets reps off the hook from generating new business because “look how busy I already am with all these opportunities” (even though half of their pipeline should have already been closed out).

The System: The “Clean Your Room” Report

To fix the problem, we started running a “clean your room” CRM report every few weeks that surfaced open deals with three key markers:

1. Old: Deals open 150%+ of our average sales cycle (e.g., if you typically close a deal in 4 months, anything older than 6 months is flagged as part of the report).

2. Stale: Opportunities stuck in the same stage for ~X days with no movement. (X is often equal to ~20% of our sales cycle, so if you have a 6 month sales cycle, a deal would be considered stale when it sits in a single stage for ~40 days or so).

3. Sloppy: Deals missing critical, basic details like next steps, last activity, or a primary contact.

This report provided several helpful nudges for our teams. First, it acted as a forcing function for reps to update the details of their pipeline ahead of the report being published. Since “always scrubbing the pipeline means never scrubbing the pipeline,” it created a public deadline that encouraged hygiene without making CRM updates a pedantic, always-on expectation.

Second, it forced conversations at the ELT level about the key deals in the pipe and how solid our pipeline coverage actually was. While it can be painful at first to realize there’s a lot of junk in your CRM, it’s a necessary wake-up call for teams that want to get better at forecasting. It’s also the catalyst companies typically need to start acknowledging anemic lead-flow and focusing on building their top of the funnel more aggressively. As one of my former CRO puts it:

“Hunger is the best sauce.”

Once we put this report in place, our headline pipeline number went down. We started the quarter with less coverage and a little less comfort. At first, this felt worse. But we drew confidence from the fact that the pipeline we did have was real. And that started a clearer, more honest conversation about what we needed to do to win the deals that were actually in play.

With a pipeline we could actually trust, we started hitting our bookings numbers quarter-after-quarter. The forecast became more reliable. The end-of-quarter scramble eased. And we learned what it felt like to operate with less, but better, pipeline. (Spoiler: It feels good.)

2. SLOW: Your Leads Are Getting Cold

Another one of my portfolio companies had been making real progress on inbound. Every month, somewhere between 30 and 40 prospects were filling out a demo request form to learn more about what they did. That number was growing quarter over quarter. On the surface, this was exactly the kind of marketing momentum you want to see.

And yet, their conversion rates told a different story. Only 20–30% of those hand-raisers were turning into pipeline — far lower than you’d expect for a high-intent “give me a demo” form fill. Something wasn’t lining up.

So we dug in.

After a bit of analysis, the root cause became hard to ignore. On average, the team was getting back to these inbound leads in three to four days. Not hours. Days. Long enough for a motivated buyer to move on, get distracted, or (worst of all) take a meeting with a competitor.

By the time we followed up, many prospects had either lost urgency or forgotten they had raised their hand at all. The low conversion rate wasn’t a mystery anymore.

It was the predictable outcome of a systemically slow response.

The Impact

The most obvious cost here is wasted marketing spend. You pay to generate demand and then fail to capture it while it’s still warm.

But the invisible cost is trust. When a customer raises their hand and you wait three or four days to respond, they don’t experience that as you being busy. They experience it as indifference. Before you’ve even spoken to them, you’ve already signaled that they aren’t a priority to you.

You also kill momentum. You force the prospect to restart their buying journey from zero instead of meeting them at the peak of their intent — the exact moment they decided to signal that they’re ready to talk.

Everyone already knows that speed-to-lead is important. The data is unambiguous: contact a lead within a few minutes and you’re dramatically more likely to connect with them than if you wait even 30 minutes. Wait until the next day and your odds fall off a cliff.

The problem isn’t knowledge. The problem is that there’s no system to measure and expose your slow response times.

The System: Speed-to-Lead

To improve our conversion rates, we decided to implement a speed-to-lead initiative. We set up our CRM to timestamp when leads were created and when they were first contacted. Then we started reporting the difference between those timestamps as a shared metric across sales and marketing.

Just making the number visible completely changed the conversation. What had previously lived in the background as “something we should probably be faster at” suddenly became a concrete operating KPI that everyone could see.

From there, the fixes were straightforward:

• We started routing leads to the right reps

• We alerted sales leadership when a lead sat longer than expected

• We started reporting speed-to-lead at the board level on its own slide, alongside metrics like pipeline coverage and win rates

With only a few small changes, we sent an unignorable signal that response times mattered, and we created a compelling, visual scoreboard that showed the team, in real time, whether we were actually getting better at handling what should be our most important source of leads.

Today, our speed-to-lead at that company is consistently under an hour. And by driving down that one simple metric, our conversion rates (and the amount of marketing-sourced pipeline we have to work with) have gone way up.

What fixed this? It wasn’t making the argument that speed-to-lead matters. Everyone already knew that. What fixed it was measuring the behavior, creating a scoreboard for it, and making it a thing.

3. UNPREPARED: Your Demos Are Losing You Deals

At another of my portfolio companies, we spent months refining our discovery process. We trained the sales team on better pain-finding questions. We simplified our pitch deck. We got really good at uncovering the specific pain points prospects were dealing with in their workflows.

And then, after a really good discovery call, we’d get to the demo and we’d lose the deal.

It wasn’t obvious at first why this kept happening. Discovery was going well. We had gotten genuinely better at uncovering pain, capturing genuine interest, and nailing down solid next steps. But quarter after quarter, our opportunity-to-close rate sat below 20%. We were still converting less than one-in-five demos into closed business.

When we dug into what was actually happening in those demos, the problem became clear. Despite learning exactly what was challenging about our prospects’ workflows in discovery, our demos hadn’t changed much at all. They were still generic product tours. Instead of focusing on what the prospect said they cared about, our sales engineers would walk the prospect through every feature in the product from beginning to end. They covered everything, but never clearly showed how we could solve the specific problem the prospect had told us they cared most about. The problem that, if we proved to them we could solve, would have probably convinced them to buy.

The Impact

Our problem here wasn’t our product. The product worked fine. The problem was that we were treating demos as training sessions instead of proof sessions. We were teaching prospects how to use the tool before we’d convinced them it could solve their problem.

Prospects don’t want to learn your product. They want to know if you can make their pain go away. When you make them sit through a comprehensive product tour before they’ve decided you can solve their problem, you force them to do the work to translate what your product can do and guess at whether it will work for them. Most won’t do that work. They’ll just space out and move on.

Worse, by treating your demos as a product tour, you validate your prospect’s biggest fear: that they’re about to buy software that won’t get used. A demo that spends lots of time on features unrelated to what they told you they cared about doesn’t build confidence. It manufactures doubt.

The result is polite interest during the demo, followed by silence, a complete loss of commercial momentum, and an anemic win-rate.

The win-rate you can see in the numbers. But the loss of momentum you can feel. (It feels bad.)

The System: The 15-Minute Demo Prep Meeting

The solution here wasn’t improving our demo presentation. It was improving our demo preparation.

We started requiring a 15-minute demo prep meeting before every demo with a prospect, using a one-page worksheet. Sales and the sales engineer were required to fill it out together.

The worksheet has four sections:

1. Executive Summary: Sales summarizes the key points from discovery—who they are, what they’re dealing with, and what they shared on the first call.

2. Demo Agenda: The salesperson and the sales engineer filled out a table with three columns:

   • The problem the prospect described (from discovery)

   • What we’ll show in the demo (that solves their specific problem)

   • Key points/questions to focus on during that chapter of the demo

3. Questions We Still Need Answers To: Sales summarizes “what we still don’t know” that will help us move the deal forward (e.g., buying process, competitors involved, budget details, key integrations, etc.)

4. Desired Next Steps: Sales + sales engineering agree on what we want to ask for at the end of the demo (both emphasizing next steps and reminding them to save time at the end to ask about them)

At first, this felt a little bureaucratic. Another meeting, and another form to fill out. But after piloting the prep meeting during certification and asking a few “guinea pig” early adopters to use it in real calls with customers, the overwhelmingly positive feedback made it easy to roll it out to the rest of the team.

The Outcome

The immediate benefit from our pre-demo prep meetings? It gave our teams permission to rethink how our demos help us win deals.

We had given them a powerful sort of permission. Permission to not show everything in the product. They now had license to skip features that didn’t map to a prospect’s stated pain. Basically, they had permission to be compelling with their demos instead of comprehensive. (More on this framework in a future article.)

And here’s what our leadership team learned with this new approach: while our prospect’s workflows varied widely, most of them had the same three to five pain-points. Pain-points like finding their files quickly, automating manual work that was sucking up their time, or integrating with other tools in their stack.

Once the team had permission to focus the demo on just that shortlist of things the prospect actually cared about, everything changed. Demos got shorter. More focused. More conversational. Prospects stopped putting us on our back foot with questions like “But can it do X?” and started validating us, saying things like “This is exactly what we’ve been struggling to figure out how to fix.”

And our sales engineers felt more confident because the knowledge transfer was complete. They knew what the prospect cared about before the demo began. They had a plan. They weren’t being forced to wing it anymore.

Close rates started to improve not because our product or pitch changed, but because we learned how to make our demos relevant. All of that came from a simple 15-minute alignment worksheet. A worksheet that gave our team a framework for what it meant to be prepared.

Final Thoughts

The gap between knowing what needs to happen and making sure it actually happens every single time? That’s where most companies live and lose.

You already know you should respond to leads fast. You know your pipeline needs scrubbing. You know demos should be personalized. But knowing doesn’t matter if there’s no system forcing it to happen when your team is distracted, underwater, or moving on to the next fire.

High-performing teams don’t rely on people remembering to do the right thing. They build simple, repeatable forcing functions that make the right thing the easy thing. A weekly report that surfaces stale deals. A timestamp that exposes slow follow-up. A 15-minute prep meeting that prevents generic demos.

I’ll leave you with an encouraging fact. Your competitors are dropping balls right now. They’re letting leads go cold, accumulating garbage in their pipeline, and running demos that don’t land.

What does that mean? It means you don’t need to be perfect.

You just need systems that help you drop fewer balls than they do.

So… where are you going to start?

Subscribe now

“What’s the scariest thing a CEO can hear in a board meeting?

‘The marketing section is up next.’”

It’s funny, because it’s often true.

When this part of the board meeting goes wrong, you can feel it in the room. The CFO suddenly gets very interested in what’s on their laptop. The VP of Sales starts checking their phone. Everyone’s body language says “I’m about to hear a lot of jargon and acronyms that don’t mean a whole lot to me.”

It doesn’t have to be this way.

Marketing isn’t a mystical dark art. Marketing is a functional discipline - just like sales, finance, engineering, and all the rest. This means (even though it can seem complicated) it has fundamental rules and principles that you can adhere to, twist, measure, pin down, and drive.

But if that’s true, then why does marketing still seem like the squishiest section in your board deck?

Here’s the bad news: It’s probably (at least in part) because your CMO is making their job seem more complicated than it needs to be.

The good news: Simplifying the job isn’t that hard.

Your CMO Has Three Jobs

Your marketing leader (at least in my world of B2B) has three jobs to do. That’s it. Three.

Job 1: Capture demand

There are people out there right now with budget actively looking to buy something that solves the problem you solve. They’re comparing options. They’re googling “[your competitor] alternatives” or “best [solution] for [their problem].” They have a literal OKR due this quarter and it is to buy one of what you sell.

These kinds of prospects are gold. They close faster and more predictably than any other because they’re already in buying mode. They have timeline, budget, and urgency. Your competitors are already fighting for these deals.

The question is: are you even in the fight?

Your CMO’s first job is to make sure that you are. That’s what it means to capture existing demand. It means showing up when these “buying mode” people are doing their research. It means being in the consideration set when they start making their list of who they’re going to talk to. And it means making it easy for them to start a conversation with you.

To do this, your CMO needs to have a point of view on where high-intent buyers are looking for what you sell, and then they need to get a little obsessive about showing up there. For some companies that’s Google search. For others it’s G2 or Capterra or industry review sites. It could be paid ads, SEO, or a presence on comparison sites. The specific tactics matter less than the discipline: your CMO needs to take a stance on where people shop when they’re ready to buy, and then they need to make damn sure you show up when they do. The goal here is hand-raisers—people who want to talk to you and your sales team today, not six months from now.

The way to measure this: demo requests from your website. Your CMO should be able to tell you how many came in last month, how many became qualified opportunities, what you spent to get them, and what they’re testing next to improve those numbers. If demo requests are going up and the cost per demo is staying flat or going down, you’re capturing more of the existing demand that’s out there. If not, you’re probably losing deals to more visible, more trusted competitors who are finding a way to get in front of the existing demand that’s out there.

Job 2: Generate signals

Most people who will eventually buy one of what you sell aren’t ready to buy right now. They might be thinking about the problem. They might be trying to figure out if what you do is even relevant to them. They might be ready in three months. They might be ready in eighteen months. You don’t know yet, and neither do they.

But here’s what you do know: when they ARE ready, you want to be the first call they make. That means staying visible, staying relevant, and staying top of mind while they figure things out.

Your CMO’s second job is to generate signals from these “not yet but maybe someday” people. That means putting thinking and perspective out into the world (content, events, webinars, whatever) and then paying very close attention to who pays attention back. Who downloads the guide. Who shows up to the webinar. Who reads three articles in a week. Who visits your pricing page twice. These are buying signals. Little breadcrumbs that tell you someone is getting a little closer to being ready to buy.

Doing this well means having a system for creating content that actually resonates with people in research mode, and then tracking who engages with it. Blog posts that explain the problem you solve. Guides that help people evaluate solutions. Webinars that teach them something useful. The specific formats matter less than the discipline: your CMO needs to put helpful, relevant content in front of prospects, make it easy for them to engage, and then track who leans in.

And then, when someone generates enough signals, your CMO needs to create a process (maybe with some help from sales) about how you follow up and offer up a conversation. And for the people who aren’t ready yet? Marketing hangs around. That’s what nurture means—hanging around in a helpful, non-annoying way so someday, when they are ready, you’re the obvious call.

The way to measure this: leads generated and their conversion rates. But first, your CMO needs to define what the hell a lead actually is. This is critical. A lead isn’t just anyone who downloaded one piece of content. It’s someone who generated enough signals (enough engagement, enough behavior) to indicate real interest. Your CMO should be able to tell you: here’s what qualifies someone as a lead, here’s how many we generated last month, here’s how many turned into opportunities, and here’s what content or channels are producing the best signals. If leads are going up and their conversion rate to opportunities is staying strong, you’re building real relationships with future buyers that will slowly turn into pipeline and closed-won deals. If not, either your lead definition is wrong or you’re wasting your time on marketing activities that don’t effectively create signals.

Job 3: Make selling easier

Your CMO’s third job is to make selling easier. That means giving your sales team the clarity, tools, and supporting materials they need to have better conversations and close more deals.

Doing this well means two things. First, it means being the interpreter. It means your CMO needs to feel responsible for knowing what customers actually care about and translating that into what your sales team needs to say. To do this, your CMO should be spending lots of time talking to customers and prospects (not just listening to sales call recordings, but actually having conversations with these people) to understand what job they’re trying to get done, what they care about, what confuses them, and what they need to hear to feel confident in a buying decision. Then it means translating what they learn into stuff sales can actually use: positioning that resonates with prospects, a standardized pitch deck that gives structure to first sales calls, clear answers to the objections that come up repeatedly, and messaging that makes sense to the people you’re trying to sell to.

Second, it means listening to what sales needs and then building it for them. What would make their job easier right now? A simpler, better pitch deck? Battle cards for competitive deals? Case studies that help demonstrate ROI? Calculators that help quantify value? Your CMO should be asking sales what they need, building it, and then following up to see if it actually helped. This creates a feedback loop where marketing is constantly improving the assets and materials that sales relies on, and creating a healthy tension between themselves and the sales team by debating the answer to this question: “What, if we built it for you, would most help you close a few more deals this quarter?”

The way to measure this: win rates and sales team engagement. Your CMO should be able to tell you: here’s our win rate in competitive deals, here’s how it’s trending over time, here’s what sales has been asking for to help them close more deals, and here’s what we’ve built in response. If win rates are going up, it usually means sales and marketing are working well together. It means marketing is creating strong positioning and supporting materials, and sales is executing well on calls. If win rates are flat or declining, you need to figure out where the breakdown is happening. Is the positioning unclear? Is the pitch not resonating with prospects? Is the competitive differentiation weak? That’s on marketing to fix. Or is the issue that call execution is inconsistent? Are reps going off-script or not handling objections well even when they have good materials? That’s on sales leadership to address through coaching and enforcement of standards. Most sales leaders need marketing’s help to create that standard and the supporting materials in the first place—but once the standard exists, it’s on sales leadership to make sure their team is actually performing up to code.

Wait… That’s It?

When you look at marketing through this three-job lens, everything gets clearer fast. A thousand tactics collapse into a few simple responsibilities. The noise dies down. The job (both doing it and talking about how well it’s being done) suddenly feels manageable.

But wait, you’re probably thinking. What about account-based marketing and dark social and content strategy and brand awareness and SEO (or is it AEO now?) and all the other marketing terms I’ve been told are best practices?

Yeah… about those. I don’t want to hurt anyone’s feelings, but those are just fancy words for different parts of the three jobs.

“Demand generation?” That’s creating content that generates buying signals. Job 2.

“ABM?” That’s identifying the companies you want hand-raisers from, then doing Jobs #1 and #2 to those companies until they turn into hand-raisers or leads.

“Content marketing?” Again, Job #2 — putting useful thinking out into the world and paying attention to who pays attention.

“Brand awareness?” That’s what happens when you do all three jobs well.

And while we’re here: let’s talk about “demand generation” for a second. I don’t like that term. It’s misleading. You can’t actually create demand. It’s impossible to manufacture it out of thin air. You can’t hypnotize someone into wanting something they don’t need. What you can do is help people recognize a problem they already have. Give them language for it. Help them understand why it matters and what it’s costing them and what they can do next to start fixing it. That’s not creating demand; that’s surfacing it.

The demand was already there; latent, unarticulated, and waiting for clarity.
Marketing’s job is to provide that clarity.

Where This Goes Wrong

Most CMOs don’t fail because they don’t know these jobs exist. They fail because the jargon/complexity monster sinks their claws into them and they get stuck in a reactive cycle of doing random marketing things without having a grounding philosophy behind the work. In other words, they're doing a lot, but they don’t have a basic standard or framework that they’re building towards. As a result, they stir up a lot of unintended muck in a clumsy attempt to get the three jobs done in an indirect, roundabout way.

What do I mean by “stirring up muck”?

Launching random campaigns. Redesigning the website for the fourth time. (Somehow the website is always “not quite right.” It’s never fast enough or modern enough or conversion-optimized enough. This will always be true and that’s mostly ok but don’t let it be the reason that marketing isn’t working for you.) Chasing the hot new channel (”We should make a company tiktok.”) without a real hypothesis. Rebranding when nobody was confused about your brand in the first place. Writing “thought leadership” that nobody asked for and nobody will read.

It’s a lot of activity. It’s a lot of work. But it doesn’t move the business forward.

What you want is a CMO who shows up and says:

“Here’s our system for capturing demand. Here’s how many hand-raisers we created last month. Here’s how many of those turned into qualified opportunities. Here’s what we’re testing and tweaking next to make things better.”

“Here’s our system for tracking buying signals. Here’s how many people created enough signals for us to call them a “lead” last month. Here’s how we’re following up with those leads and how many turned into qualified opportunities and closed-won deals. Here’s what we’re doing to tighten that system up, and here’s what we’re putting out there next to keep the stream of leads flowing.”

“Here’s how our win-rates are trending and what sales asked for this month. Here’s what we built for them. Here’s what they’re saying about it, how we think adoption is going, and what we think they need next.”

How good does that sound?

How different does that sound than the marketing conversation you’re used to having?

How much better would your business be performing if you had that conversation every month?

Yeah. Exactly.

If you’re a CEO, that’s the conversation you deserve to be having.

And that’s the CMO you should hire.

Subscribe now

Author’s Note: Thanks to for the original inspiration for the “three jobs” framework used in this article. Sidney writes a fantastic Substack focused on B2B GTM strategy - you can check it out here.

In my follow-up to this article, I’ll be sharing the interview framework I use to test for these three qualities in CMO interviews. Until then, I’d love it if you subscribed to the newsletter. It’s free and it always will be.