Boring, yes. Effective, yes.

The routine is a decade old. The post I wrote about it is three years old, and I still run it. So do a lot of my team members. I used to require it. I stopped, because it turns out not everyone wants to work the same way, and a system forced on someone rarely works.

But I will admit, how I do it has changed. Half the steps are automated now with Claude Cowork. The other half you will have to pry out of my hands.

To bring you up to speed: every weekday morning I update my journal, do a two-day look ahead, write in an open letter to my kids, review the previous day’s meetings, process my inbox, respond to social media messages, process voicemails, and process texts. Eight things. It is simple, it is consistent, and it reduces anxiety more than anything else I do.

Claude does four of them better than I did.

Claude works in my Google Calendar, pulling my upcoming meetings, writing agendas, doing the preparatory research, and handing me a synopsis I can scan in a minute. “Looks like you only have 30 minutes to make a 45-minute drive between meetings, Scott.”

Claude combines my calendar with the previous day’s Fireflies transcripts to extract to-dos and add context to ongoing projects. I am in the middle of a rewrite of our company handbook right now. When yesterday’s leadership meeting touched on it, Claude grabbed the decision and fed it back into that project, so it cannot fall out of the final rewrite.

Claude processes my email. Removes the spam, files to the right labels, and bubbles up anything that needs me or is due that day.

Claude handles our companies’ social accounts, mostly the messages. Sometimes it responds. Sometimes it flags where I can jump in and add something. Either way the friction is gone.

The rote part of my Daily Start-up used to take 20 to 60 minutes. It now takes closer to 10.

The Four I Kept

Here is the part I did not hand over, and the reason is not sentimentality.

I still update my journal by hand. The point of that was never the record. It was clearing off my desk in my head before the day starts. A machine can produce the entry and skip the entire effect.

I still write the open letter to my kids. I started it in November 2007, when Hudson was one. A week ago I moved him into his new house. Thursday morning I got on a plane to move Taylor to Spokane. Nineteen years of entries, and not one of them was about capturing information.

I still review the previous day’s meetings myself, even though Claude already pulled the to-dos out. Because the to-dos were never the only thing in there.

And I still thank people myself. Could Claude draft the message? Yes. But it would never be able to replicate the intention behind it.

What Claude Actually Left Me

Claude did not make my morning easier. But not in the traditional sense of the word.

What it did was clear away the moving of information from one place to another, and hand me back the pile that is only mine.

Deciding whether to cancel that upcoming meeting, knowing it is going to disappoint the people who cleared their calendar for it.

Really considering whether what happened in that huddle yesterday was as concerning as I thought it was, and how I am going to approach it.

Formulating a real response to the email Claude flagged as urgent, which is urgent precisely because it needs a person.

That is not easier. That is a heavier morning with less noise.

The two-day look ahead is a good example. Same three minutes it always was. It costs more now, because two weeks ago I cleared my schedule and went back to work on sales and marketing, and I am actually going to do something about what I see in there.

The Line

Automate the review. Automate the processing. Automate the extraction.

Never automate the personal attention.

You are who you are, and where you are, because of the effect you have on your work and on the people around you. Do not rob the world of that. We need you to show up in that way.

So here is my challenge. Pick one thing you do every morning and ask a single question about it: is this output, or is this effect?

If it is output, for the love of Pete, automate it.

If it is effect, hold it closely. Guard it. Add your own flair to it. Do not let it go.

I used to close this newsletter with an offer to chat about the topic. But now is not the time to chat. Now is the time to get back to work.

A fortuitous turn of events put me in contact with the owner of a very large company in the same exact niche as kitchen & bath CRATE. I expected a brush-off. Instead, I got a hearty “Let’s get together and talk shop.”

So I walked into the cafe knowing exactly how this conversation was going to go.

We’d sit down, wade through the awkward small talk that comes with meeting someone new, give each other the obligatory rundown on family and career, then commiserate about a very sluggish residential remodel market.

Ah, yes. A chance to affirm that things are tough right now.

You know how this story goes.

That’s not what I got.

There was no awkwardness. This guy and I got each other from moment one. It was like talking to Bizarro Scott, a Scott from another, more successful dimension.

Here’s what I mean.

I came in expecting commiseration. Instead I learned they’re beating their 2026 forecast by a wide margin.

I came in expecting a guy frustrated with the market like I am. Instead I got a guy overflowing with optimism and energy.

I came in expecting a fellow operator scratching and clawing like the rest of us. Instead I sat before someone who knows exactly which jobs he wants and turns down the rest.

And here was the main takeaway: his business is better.

He has a better territory. He has 36 years on us. He’s stayed focused on a specific niche of kitchen remodeling that we’ve moved away from. He’s disciplined about the region he serves and doesn’t stray beyond it. He’s generating more qualified leads than he can serve. He has a healthy backlog. I could go on.

I was Eli Manning to his Tom Brady.

As I processed it over the next few days, it dawned on me. At some point in the last few years, I’ve taken my eye off the ball.

Don’t get me wrong. I have great people who are very good at what they do. But I’ve been robbing kitchen & bath CRATE of the unique skills and abilities I bring to the table. I’ve been asking my team to run a marathon on a prosthetic leg. Is it possible? Yes. Is it optimal? No.

So on Thursday of last week, I went back to work.

I cleared my schedule. I changed my working hours. I cut my personal brand content calendar back to a few things. (This one stays, because writing it is cathartic.) I put a few daily habits on hold, because they were nice-to-haves that didn’t move the ball forward.

And most importantly, I started asking a lot of questions, and I’m working on listening better. Because I’ve been disconnected and out of touch.

No more.

Now, some of you have watched me write the opposite of this for two years.

The plan was to step out. Get the businesses running without me, hand the day-to-day to people who are better at it than I am, and move into the seat where I’m most useful. That plan is real, and it hasn’t changed. Jake is stepping into the Integrator seat at Trinity Builder Solutions; he’s earned it, and he keeps it.

This is a different thing. This is me back in at kitchen & bath CRATE, heading up marketing and sales.

Here’s how I tell the difference between an owner making a call and an owner relapsing. A call is scoped, it’s said out loud to the team, and it has an end date. A relapse is none of those. It just quietly becomes the way things are again.

So I’ll say it out loud. I’m in through Q1 2027.

Here’s the thing. As an owner, sometimes you have to get back in the weeds. You have to prune back to the essence of what got you here. You have to rally the team and return to your roots. And no one, no one, can do that like an owner.

So here’s my question. Have you lost focus in the last six years, and is it time to get back in and start rowing?

Normally I’d end with an offer to chat about this. I’m not going to do that. Now isn’t the time to chat. Now is the time to work on my own business. There will be time to chat later, once I’ve cleared the weeds.

But that time is not now.

The one who knows where everything is. The one who can fix the thing nobody else can fix. The one who, at the slightest sniffle, has you asking: “You feeling okay? Getting sick? Anything I can do for you? Can I start a vitamin C IV right now so you’re here tomorrow?”

At Trinity Builder Solutions, that person was Jose. For years.

Jose ran our saw. Not “was on the saw team.” Ran it. Programmed it, maintained it, knew every quirk of the machine and every quirk of the material. If a job needed something cut, it went through Jose. And at TBS, if you can’t cut, you’re done. You’re a donut shop without oil, a laundromat with the water turned off.

I filed that under strengths. We had a guy. Not everybody has a guy. And he’s great.

Then I looked at what it was doing to him.

Jose couldn’t take a vacation without the shop slowing down. He couldn’t be sick. Every rush job landed on his shoulders, because there were no other shoulders. The pressure never let up. It had nowhere else to go.

He was carrying weight we never intended for him to carry, and we let it build, month after month.

Here’s what should have worried me a lot sooner: if Jose had taken another job, we wouldn’t have been inconvenienced. We would have been in real trouble.

What “Thank God for Jose” Actually Means

That phrase is more confession than compliment.

When you say “thank God for” somebody, you’re admitting that a piece of your company only works because one specific human keeps showing up. And honestly, if you’re saying that, or if I’m saying that, we’re putting lipstick on a pig. We’re covering up a weakness, key-person risk, with a compliment: “they’re irreplaceable.”

Concentration of knowledge feels like an asset right up until the day it becomes a liability. And it isn’t only a company problem. It’s unfair to the person holding it.

I’m working with an owner right now who has one of these. His guy holds most of the operation in his head. Pricing history, customer preferences, vendor quirks, the reasons behind decisions made five years ago. None of it is written down.

The owner talks about him with real gratitude. He should. But that man is one resignation letter, one health scare, or one better offer away from walking. Meanwhile, he’s fielding calls on the weekend and putting out fires left and right, tension building day after day.

Two people at risk. One root cause.

What We Did About Jose

We cross-trained Ray.

That’s it. No software purchase. No reorg. We picked one other person and taught him to run the saw.

It cost us time we didn’t feel like we had. Jose slowed down to teach, so we gave up throughput for a few weeks. Ray was slow at first, so we gave up a little more.

Then something happened I didn’t fully expect. Jose got better. The weight came off, and he started thinking about the operation instead of just surviving his day. He had room to improve the process because he wasn’t the entire process anymore.

Two people who could run the job beat one person who ran it perfectly. And as I write this, it sounds silly. “Why didn’t you do it earlier, Scott?”

I know. I don’t have a good answer. It just crept up on me, until one day I realized how vulnerable we were.

The Question

Here’s your one question before you close this.

If your best person didn’t come in on Monday, what stops?

Be specific. Not “things would be hard.” What actually stops? Which customer doesn’t get called? Which machine doesn’t run? Which decision doesn’t get made?

Write down that one person and that one thing. Then pick one other human on your team and start teaching them this quarter. Not documenting it someday. Teaching it now, with a name and a date on it.

You’ll give up some speed for a few weeks. You’ll get back a person who can finally take a vacation, and a company that keeps running while they do.

That’s a trade I’d make every time.

As always, if you’d like to chat about topics like this, I’m here for you: scott@scottmonday.com.

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One more thing. Nobody walks into your office and announces they’re carrying too much. You find it in the quarterly check-in, or you don’t find it at all. Here’s the exact framework I use with my team: Stop Doing Performance Reviews. Do This Quarterly Check-In Instead.

Things I’ve Enjoyed Lately: I just finished Inside Camp David by Michael Giorgione, and it was fascinating. I knew almost nothing about the history of the presidential retreat, and it was so interesting to read about how our leaders spent their downtime and how different the last handful of presidents have been from each other. It’s a quick, entertaining read, and perfect for anyone who enjoys a little presidential history.

If you’ve been reading this newsletter for a while, you’ve probably heard me fanboy him plenty of times. I met him once in 2019. Haven’t washed my hand since.

Greg arms readers with dozens of tools in his books, *Simple Numbers* and *Simple Numbers 2.0*. Among my favorites: the Thinking Model.

What Is It?

The Thinking Model is a very simple P&L model that forecasts your upcoming financial performance in three states:

• Minimum: What would it look like if you keep doing what you’re doing?

• Target: What would it look like if you execute on your growth goals and the market is average?

• Stretch: What would it look like if you pushed your team and your growth goals to the max and got a nice assist from the economy?

Here’s what it looks like.

Why It’s Powerful

It answers the question owners and operators ask all the time: “What happens if...?”

• What happens if I hire this person?

• What happens if the economy does this?

• What happens if I “fire” this customer?

In those moments, owners and operators wish they could see the future. With a Thinking Model, you get really close.

Once it’s built, you adjust any of the variables and look at the results. It’s really that simple.

How to Build It

1. Get your chart of accounts (inside your accounting software) in order like this: (1 hour)

• Income

• Cost of Goods Sold (COGS)

• Direct Labor (Labor that “faces” the customer more than 50% of the time)

• Management Labor

• Marketing

• Facilities

• Payroll Taxes & Benefits

• Other OPEX

• Other Income & Expenses

2. Download the template (2 minutes)

• Google Sheets

• Excel

• PDF

3. Run a P&L report from your accounting software (2 minutes)

4. Plug in the variables (the blue cells on the template) (30 minutes)

How to Use It

When you have a question, an opportunity, or a crisis, copy the tab, play with the numbers, then look at the results.

That’s it.

Example: what would happen if I “fire” a customer who represents 15% of my revenue?

1. Adjust revenue (row 4) down 15%.

2. Reduce any expenses you could cut if you no longer had to service that customer. Maybe you’d be able to pull back labor in a certain way. (Rows 8 and/or 14) Make those adjustments.

3. Now look at the new model. What’s the impact on the bottom line?

You have a clear picture of what that decision will actually cost you. Or maybe, what it will make you.

Wrap Up

My team and I use our Thinking Model often. It’s provided financial clarity for dozens of potential decisions.

Of course, the financial impact of a decision is only one factor to consider.

What I’ve found is that once I check this analysis off my list, my mind is free to focus on the softer factors: alignment with our overall goals, impact on people (team and customers), and my general “do I want to do this?” gut feeling.

So go ahead, give it a whirl. And let me know if the Thinking Model brings you some financial clarity.

As always, if you’d like to chat about topics like this, I’m here for you: scott@scottmonday.com.

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I recently shared my Audacious Guarantee talk with a local Rotary Club. I think it went well. I didn’t curse, which was a win. Check it out!

(Note to readers: For years I’ve ended the weekly newsletter by sharing a product, tool, or gadget I’ve been enjoying. Well, after 146 published newsletters, I’ve run out of things to recommend. So I thought I’d weave in an alternate ending section on occasion: Recent AI Impacts. In this snippet, I’ll share cool ways I’ve seen AI show up for my team or for me over the last few weeks. Newsletter nerd coefficient increasing by the week!)

Recent AI Impacts: Our newer business, Trinity Builder Solutions, is an accounts receivable generator. We do the work, bill for it, and then wait 30 to 90 days to get paid. That sucks up cash; thus, staying on top of A/R is critical. It’s also annoying. So I trained Claude Cowork to read my A/R report, generate follow-up emails to the accounting contacts at our customers’ offices, then build a weekly receivables forecast based on historic payment timelines and the replies that come back in. What used to take me two hours a week now takes 10 minutes. And it’s shortened how long our receivables sit out there. Cash is king!

Want to mill flour? Something had to turn a wheel. Maybe a human. Maybe an animal. Maybe a river.

It was clunky. If you and I looked back at it now, it would be wholly unimpressive.

Then, in the 1700s, a funny thing happened. Steam power arrived. Thomas Newcomen built the first working engine in 1712. James Watt made it genuinely useful in 1765.

Over the course of a few generations, we learned to burn coal, boil water, and turn that into far more power than muscle could ever produce. We could turn wheels, then gears, faster. Production no longer had to sit next to a river. And this little thing called the Industrial Revolution was upon us.

Here’s the part I find most interesting: nothing “new” was happening. The physics was always there. We just figured out how to reach it.

Friends, we’re in the same spot right now with AI.

Six Parallels

I was prepping for a talk on AI and faith a couple of weeks back, and it hit me how closely the AI revolution tracks the Industrial Revolution.

Both start with a hard constraint on output.

• Steam: physical work, limited by muscle.

• AI: knowledge work, limited by cognition.

Both sit on top of a massive reserve of stored potential.

• Steam: coal.

• AI: the accumulated body of human knowledge.

Both needed a tool to convert the reserve into work.

• Steam: the engine.

• AI: the models.

Both create leverage instead of headcount.

• Steam: not more people, better engineering.

• AI: not more people, better workflows.

Both reward the early adopter.

• Steam: the mill with steam beats the mill without it.

• AI: the AI-forward company pulls away from the competition.

Both move you from doing to directing.

• Steam: from doing the work to running the machine.

• AI: from doing the work to directing the tool.

The Danger

There’s one more parallel, and I’ve been feeling this one myself.

Pre-steam work was capped by physical capacity. Pre-AI work was capped by hours. I used to run out of day, and that was that. I was done.

Not anymore.

The work is accelerated enough now that I can finish in a few hours what used to take a day.

So what do I do with that? I do two or three days of work in a single day.

Cool, right?

But is it?

What I’ve lost is the time I used to spend marinating on an idea. Wrestling with it. Turning it over on a walk or in the shower or on the drive home.

When I can ship a deliverable in minutes, is it actually my most developed thought?

That, friends, is what I’m wrestling with. Ironically.

Wrap Up

Steam took decades to work its way through manufacturing. AI is moving faster. Years, not decades.

The way knowledge workers worked on 1/1/22 will look nothing like 1/1/28. Six years. Wild.

So the challenge before all of us is discernment: when to deploy this tool and when to leave it alone. I’m certain the answer isn’t “deploy it 100% of the time.”

What’s at risk is a kind of mental exhaustion most of us have never had to manage. Just because we can move faster doesn’t mean we always should.

Hold both of these at once with me: The AI revolution is the biggest opportunity of our careers, and it’s also the fastest path to burnout we’ve ever built.

Here’s your one question before you close this: what did you used to think about that you no longer make time to think about?

Protect that this week. Put it on the calendar if you have to.

As always, if you’d like to chat about topics like this, I’m here for you: scott@scottmonday.com.

Subscribe now

I recently shared my Audacious Guarantee talk with a local Rotary Club. I think it went well. I didn’t curse, which was a win. Check it out!

Things I've Enjoyed Lately: This year marked my family’s 18th year at family camp at Redwood Christian Park in the Santa Cruz Mountains. This year had its share of distractions back home, but our family, along with hundreds of others, treasures that place. Fair warning: take your kids once, and they’ll never let you not go again.

It’s one word, and it’s rooted in science: entropy.

In thermodynamics, entropy is a measure of disorder in a system. The Second Law says the same thing every time: left on its own, a system always moves toward more disorder, never less. Heat spreads out. Structure breaks down. Things come apart unless energy is put back in.

That’s a physics lesson. It’s also a business lesson, a marriage lesson, and a health lesson.

Entropy in human institutions is a slow, sometimes imperceptible degradation of quality, service, and the pursuit of the mission. Nobody announces it. No single day breaks anything. It just erodes a little at a time, while you’re busy doing everything else.

And we see it everywhere, don’t we? Our physical health. Our marriages. Our homes. Our communities. It’s a colossal game of whack-a-mole to keep it all at bay.

So what do we do? How do you fight something that’s written into the laws of the universe?

You can’t stop it. But you can fight it. Here’s how I do it, in three steps.

Step 1: See It Before You’re Far Off Course

You can’t fix what you refuse to look at.

Entropy is dangerous precisely because it’s gradual. You pop your head up one day and realize you’re a long way off course, further than you ever would have let yourself drift if you’d been watching.

So watch. Some of it lives in the numbers, and you should know your KPIs (Key Performance Indicators) cold. But some of it never shows up on a report.

Learn to listen for the quiet signs. The gut feeling. The small incongruity. The body language that doesn’t match the words. You know the one. You run into a customer at the grocery store, you ask how the project’s going, and they smile and tell you it’s all great, but something in you says they’re not telling you everything.

I’ll give you a personal one. Right now, I’m losing ground on my weight. It’s as high as it’s been in a while. I only know that because I’m actually looking, logging my food, tracking it, staying honest about the scoreboard even when the scoreboard is uncomfortable. You can’t fight what you won’t measure.

Step 2: Grab the Wheel Yourself

Here’s where I have to be honest about a mistake.

Our organic marketing had been sliding. The engine that used to work stopped working. And when I finally looked hard at why, the answer was uncomfortable, and it pointed right back at me.

Some of our best marketing has always been founder-led. It comes from me, in my voice, and it works because it’s mine. That’s not a task you can hand to someone else. Nobody else can be the founder. And somewhere along the way I got lazy and stopped doing the one thing that had always proven to matter.

That’s on me. Not my team. It was never theirs to carry.

So I took the bull by the horns. I said we’re going to fix this, and I turned it into a quarterly Rock. I started showing up for it again, and the numbers started climbing.

Fighting entropy is an act of ownership. When something’s decaying on your watch, it’s yours. Not the market’s. Not your team’s. Yours.

Step 3: Build the Small, Boring Habits

Bad news, folks: You don’t beat entropy once, then walk away, arms raised, singing “We Are the Champions” at full volume. Instead, you make small deposits, often. Obnoxiously often.

Order is expensive. Disorder is free. So the systems, the body, and the relationships all have to be re-energized on a schedule, not rescued in a crisis.

I’ll use my marriage as an example. What keeps it strong isn’t the big anniversary trip. It’s the small, intentional, repeated things. A monthly date night. Two to four trips a year. The TV off when we sit down together on a weeknight. Dinner as a family whenever we can get everyone in one place, which gets harder every year with two of our kids mostly out of the house now.

Nobody schedules a rescue mission for a strong marriage. You just keep making the small deposits so it never gets to the point of needing one.

Same with my health. Even while I’m losing on the scale, I’ve held a routine that’s working: stretching and mobility work, weightlifting, and pickleball. It’s kept me limber and (mostly) injury-free. The habits hold the line even when the scoreboard has me down in the 4th quarter.

Same with the business. The marketing fix didn’t stay a one-time push. It became a Rock, a recurring commitment, so the attention is scheduled instead of heroic.

Wrap Up

Entropy is constant, and it’s free. It never takes a day off, and it’s always calling you with the sweet siren song of “set it and forget it.”

Order costs something. It always has. The intention should have never been to build the thing once. The work is to fight the decay, over and over, on purpose.

So here’s your one question before you close this: Where is entropy winning right now? In your business, your body, or the relationships that matter most?

Be honest about it. Then pick one small habit, the boring, repeatable kind, and start re-paying the bill this week.

As always, if you’d like to chat about topics like this, I’m here for you: scott@scottmonday.com.

Subscribe now

I recently shared my Audacious Guarantee talk with a local Rotary Club. I think it went well. I didn’t curse, which was a win. Check it out!

Things I've Enjoyed Lately: I’m always surprised when I learn of a business on the Google Workspace platform that has never used Google Chat/Spaces. It’s a game-changer, folks! We use it as our primary form of communication across both companies. Text, images, videos, shared drives, all in one place. If you’re a Google business user, give it a try!

The video touched a nerve. In summary, my daughter and I had a terrible experience with a salesperson at our local Toyota dealership.

Clearly, this man was unmotivated, untrained, and unwilling to provide anything close to service.

No getting to know us. No uncovering our needs. No asking what we’d already seen and liked. No question about our timeline.

Heck, he had us waiting in the sun for 20 minutes while he tried to find a set of keys.

But that’s not the story.

What surprised me most was how many comments on social media, about half, defended the sales guy.

What? Am I living in an alternate universe?

Here are a few excerpts of the comments:

Now, I understand Instagram and TikTok are not a great source of customer sentiment. Most people who comment do it because they have polarizing personalities and love to spew “hot takes.”

But still, this got me thinking…

The Bar Is Forever Lowered

What came through in these comments is this: most business owners/operators have reluctantly accepted poor service as the “new normal,” and the consuming population has accepted it.

Why is this?

Because it’s hard to provide good service, and we have stopped doing hard things in the last 10 years.

It’s hard to find good people: “No one wants to work anymore.”

It’s hard to train well: “They’re just going to leave.”

It’s hard to build SOPs: “Who reads a manual anymore?”

It’s hard to hold people accountable: “If I’m too hard on them, they’ll sue me.”

So instead we hire poorly, don’t train, reinvent the wheel every day, and let our customers suffer at the hands of our team.

That’s where we are today.

The Opportunity

If you made it this far, congrats. Here’s the payoff:

There’s never been a better time for a company to win by simply doing the basics well.

Your competition has essentially given up.

Over at kitchen & bath CRATE, we often meet with customers shortly after they’ve met with a competitor. And oh, the stories we hear: the six-hour meetings, the high pressure, the false promises, the plain, offensive unprofessionalism. It’s an opportunity.

Wrap Up

The tools are available. Fixing what’s broken in your business has never been easy, but where do you start?

Ask this: Where has your customer lost hope in your industry, and how can you stand in that gap?

Because if you do, the game is yours to win.

As always, if you’d like to chat about topics like this, I’m here for you: scott@scottmonday.com.

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Last week's YouTube video is the fascinating story of the rise and fall of Napster. You 70s and 80s kids remember Napster, right? Check it out!

Things I've Enjoyed Lately: I’ve had the DJI Osmo Mobile Gimbal for about a year now, and I love it. I have zero videography experience or skill, and it makes even me look good. So if you need to make content and want a cost-effective, fully functional gimbal, this is one to consider.

I’ve been working with my coach, Greg, for about 15 years now.

Fifteen years.

It’s only an hour. It used to be every week. These days it’s every two weeks. And here’s the thing about an hour every two weeks: you don’t really notice it while it’s happening.

You just talk. You walk through whatever’s in front of you that day. You hang up. You get back to work.

But over time, something happens that you don’t see coming.

You look up one day and realize you’ve formed this amazing sandcastle of support. A whole library of situations, challenges, and victories the two of you have walked through together. And it’s astounding when you finally see the size of it.

That’s what hit me recently. An overwhelming sense of gratitude that I have a fellow soldier in the foxhole of life with me.

The Hours That Mattered Most

If I had to point to the time it mattered most, it was 2021, when I purchased AAI Tile & Stone.

I’d never done an acquisition. It was a very stretching experience for me, professionally. The deal itself was challenging, and Greg and I walked through all of it.

But the deal wasn’t the hardest part.

The hardest part came after. For six to nine months, it just felt like things were crazy. Everything was new. Everything was uncomfortable.

And Greg helped me walk through that window. He’s great at one thing in particular: reminding me of “the why.” The reason I do the things I do. Because in the moment, it’s easy for me to forget.

That stretch is probably the most helpful window I can recall.

What a (Good) Coach Actually Does

Here’s what I’ve figured out about why this works.

First and foremost, it’s the ability to verbally process. To talk through things out loud. For me, that’s perhaps the best form of counseling I can get.

And it’s all about the questions he asks, not the answers he gives.

I can’t recall Greg ever telling me what to do. Not once in 15 years. He asks great questions. He uses experience sharing. He lets me get there myself.

There are even times I make a decision he probably thinks is the wrong one. And he still supports it. It’s that old adage: we might disagree on the front end, but once the decision is made, we’re all in together on implementing it.

That’s the relationship. There’s a brutal honesty to it. There’s reciprocity in it. But be cautioned: those things don’t show up on day one. They build over time.

The Power Is in the Cadence

The other piece people miss is the consistency.

It’s that time on the calendar that doesn’t get scheduled over and doesn’t get missed, except in very rare circumstances.

Sometimes we get on the call and there’s nothing to talk about. And somehow those turn into the most amazing conversations. Other times there’s a real, pressing event we have to work through. Either way, the consistency of the moment is what matters.

There’s real power in the cadence. It’s not the intensity, it’s the rhythm.

The Other Side

I’ve started coaching now, myself.

And I’m watching the same thing start to happen. The early layers of a sandcastle, stacking up one conversation at a time.

Funny how that works.

A Warning for You, My Fellow Operators

So here’s the deal.

If you own or operate a business, you need someone in your life who fills this role. Maybe it’s a professional coach. Maybe it’s someone you pay. Maybe it’s neither. But you need someone to talk with on a regular basis to process through this very difficult job.

Because this is not for the faint of heart.

You are lonely at times. You’re at the top. You’re dealing with hard issues. And if you keep that struggle bundled up inside, it’s going to manifest. It’s going to come out as a monster you don’t understand and don’t want to look in the eye.

We have to process these things. We can’t bottle them up.

Call it “entrepreneurial hygiene.” It’s completely necessary. And if you don’t address it, you’re going to be in a bad spot down the road.

I don’t want that for you.

As always, if you’d like to chat about topics like this, I’m here for you: scott@scottmonday.com.

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This week's YouTube video is the fascinating story of the rise and fall of Napster. You 70s and 80s kids remember Napster, right? Check it out!

Things I've Enjoyed Lately: My brother-in-law knew I was considering the Oura ring, so when he spotted it for a huge discount, he called me, and I acted! After a few weeks, I like it. For me, the biggest advantage is sleep tracking without my Apple Watch on. I think sleep is about the most important health metric, and it’s nice not to worry about a watch being on all night. The Oura 4 is being replaced by the Oura 5, which is why the 4 I secured was such a good deal. But at the end of the day, the old model is just fine.

So, if you write a Substack, you MUST theme it around the day. It’s in the Substack rules. I promise. I checked.

But I thought to myself, “Scott, you have a ton of new subscribers in the last year. Like, double. There’s a lot of content they’ve likely never seen.”

And who am I to keep you from such pearls, right?

So, here are some of the highest-rated past posts from, well, the past. All themed around the holiday, of course. I’m a rule follower at heart. Enjoy!

I highly encourage you to:

• Declare Independence from a Disorganized Personal Life

• Declare Independence from the Cultural Constraints of Gen Z

• Declare Independence from Doing Tasks AI Can Automate

• Declare Independence from a Business that Lacks a Guarantee

• Declare Independence from a Terrible Company Culture

• Declare Independence from a Household that is Falling Apart

As always, if you’d like to chat about topics like this, I’m here for you: scott@scottmonday.com.

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If you grew up during the turn of the century, pirated music was a way of life. And the brand that represented free music downloads was Napster. A venerable institution! For 2 years… Here’s the story of this business “one hit wonder.” Check it out!

Things I've Enjoyed Lately: Kaustubh Deo writes a fascinating Substack for small business owners and operators. His approach is unique: he went from the world of private equity to small-business acquisition and ownership, and chronicles the journey along the way. This post demonstrates how well it works, and I found it engrossing and thought-provoking.

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She was frustrated. I was frustrated. On paper, everything was fine. We had a job description. We talked all the time. But we could not figure out how to make progress together.

Then one day, in the middle of a tense conversation, it hit me. What I thought was the most important part of her job and what she thought was the most important part of her job were two different things.

Here’s the kicker. The thing she thought was most important was a good thing. She just didn’t have the full context of the company to know it wasn’t the right thing to focus on. And that was on me. I had never given her a way to find out.

We had no consistent way of checking in with each other. We were two people rowing in different directions. That does not create alignment, and it does not create momentum.

Around that same time, I was sitting in my EO forum and a good friend of mine, Craig Hettrich, was presenting. Craig is a sharp Traction implementer. He helps business owners roll this stuff out every day. He walked us through a quarterly check-in system, and it hit me like Moses coming down the mountain with the tablets. That dramatic. I knew right away it was the thing we were missing.

We took it back to my companies, made a few changes, and we’ve run it ever since.

I first wrote about this system back in 2023. Two things have changed since then. I just recorded a full video on the framework and the why behind it. And we’ve added a layer of AI that automates almost all of the busywork. So this is the updated playbook: the how-to, plus how we actually run these today.

First, the Format

Here is the template, free. Excel, Google Sheets

It’s a simple spreadsheet. Each tab is one check-in session, which means you build an easy record of every past check-in without trying.

Each session has three columns:

- The elements being evaluated.

- The team member’s self-rating.

- The manager’s rating.

Every rating is on a one to three scale. One means rarely or substandard. Three means all the time or exceptional. Two is more often than not. No giant matrix. No complicated math.

The Order Matters

There’s a right order to fill this out, and it’s intentional.

Before the check-in, the team member rates themselves first. Always first. This process is about their development, not about you and not about the company.

Then the manager rates each element. Best practice: hide the team member’s column before you fill in yours, so their answers don’t sway you.

Now here’s the whole game. The gap between those two columns is the entire conversation. If they rated themselves a three and you put a one, that’s a conversation. A two against a one, that’s a conversation. Two ones lining up, that’s probably a conversation too. You’re hunting for the misalignment between how they see their performance and how you see it.

The Three Sections

The rows break into three sections.

Section One: Core Values

At TBS, our core values are: we’re good humans, we’re relentless, we’re self-aware, we’re exacting, and we’re process-driven. Your company needs its own. (I wrote a separate piece on building core values if you want it.)

Here, both of you rate how well the team member lives those values day to day. Three is all the time. One is rarely.

This is the part I love. It drags core values off the poster on the wall and turns them into a real assessment every 90 days. If you see anything less than threes here, treat it as a smoke signal. A values problem needs to be addressed right away, not filed away.

Section Two: Key Job Elements

These come straight from the job description. Any good job description answers one question: what does success in this role actually look like? The best ones list those answers in priority order.

Pull those same elements into the check-in. The team member rates their performance on a scale of one to three. You do the same. Again, you’re looking for the gap.

Here’s what makes this powerful over time. A job description is a statue. It sits there. But jobs change as the company changes course. The check-in happens every 90 days, so those elements get discussed, adjusted, and tweaked as you go. Over time, the check-in becomes a more honest North Star for the role than the original job description, and it back-feeds an update to that description every year or two.

For one of my key leaders, the four elements are: hit our rolling 12-month net profit number, lead and manage and hold the team accountable, execute the annual company playbook, and resolve cross-functional issues between departments. That’s what he rates himself on, and what I rate him on, every quarter.

Section Three: The Four Questions

This is the section that the original version of this newsletter was missing, and it might be the most important one. Four questions the team member answers about themselves. Not about you. Not about the company. About them.

1. What do you want for your future here, and how can I help you get there?

Employment should help a person reach their own goals through a professional setting. You can’t support that if you don’t know what it is.

2. What is your biggest frustration at work? What makes you want to pull your hair out on the drive in?

Smoke it out so you can fix it together.

3. What keeps you motivated to stay?

This one is sneaky. It usually reveals the opposite too, the thing that would make them leave. You want to know those lines in the sand.

4. Start, stop. Is there anything you want me to start doing, or stop doing?

Sometimes we drive our people nuts and they don’t feel safe saying so. Your job is to build the kind of relationship where they can be brutally honest.

Every one of these serves the team member. If your people feel heard and cared for, they execute. The business side takes care of itself.

Leading Up to the Check-In

A few days out, the manager creates the new tab and asks the team member to fill in their ratings and comments. The team member goes first. The manager then hides that column, adds their own ratings, and leaves comments where needed. Prep is light. Maybe five to 10 minutes for the team member, five for the manager.

The Day of the Check-In

The check-in should never be a surprise. Your team member should already know how they’re doing, because good managers bring things up as they happen. They don’t save them for a meeting.

That frees the check-in to be about three things:

- Alignment. Walk through each value and role together. Talk through the comments. Dig into any item you rated differently and work to understand each other.

- Support. Listen for the roadblocks in the team member’s way, then commit to specific to-dos to clear them.

- Development. The team member sets specific action items for the next 90 days.

The meeting runs about 45 to 90 minutes. Add it up. Roughly two hours every quarter buys you complete alignment with a person. That’s the whole pitch.

The Day After: Where the AI Comes In

In the original system, the day after the check-in the manager wrote a brief email to memorialize the meeting. A short summary, the list of what each side agreed to do, and the next meeting date. It worked. But it was one more thing on a busy manager’s plate, so it was the step that slipped.

So we automated it. Here’s how we actually run check-ins now.

We record the meeting with Fireflies.ai. And before anyone hits record, the team member knows and agrees to it. Full permission, every time. No secret recording, ever. That consent is not a formality. This entire system runs on trust, and you don’t get to keep trust by hiding a microphone.

From that one transcript, AI does the rest:

- It writes a brief summary document for the team member. We hand it to them the next day. Same memo as before, none of the manual work.

- It writes a separate file note for the team member’s HR file. That uploads on its own and becomes a permanent record of the check-in.

- It updates the tracking spreadsheet we use to see who’s been checked in with and when.

One conversation goes in. A team member summary, an HR record, and an updated tracker come out. The manager doesn’t touch a keyboard. We took the most valuable management ritual we have and removed the one excuse people used to skip the follow-through.

Why This Works

Craig’s format is clean, simple, and collaborative. Everything a standard performance review is not.

It keeps your core values front and center, because values are not a list on a wall. They’re a living set of principles you measure yourselves against every quarter.

It catches responsibility drift. It’s common for our first couple of check-ins with a new hire to include an “oh, I totally forgot I was supposed to be doing that” moment. That’s fine. Drift is natural. You just have to fight it on a regular schedule.

And here’s what happened with the team member I told you about at the top. This system changed how we worked together. It was like two lanes of traffic merging into one. We both started to look forward to the meetings. It went from critique to collaboration.

She’s moved on to other things now. But when she left, she told me the check-ins were one of the most impactful parts of her time with us. She said she stopped feeling like two people pulling in different directions. That’s the whole point.

Wrap Up

Pick the person on your team you most need to get aligned with. Put a check-in on the calendar. Start there.

The framework is free. The template is free. And the AI layer is something you can build yourself now, which is a sentence I couldn’t have written when I first published this in 2023.

A shout-out to my friend Craig Hetrich for the format, and for teaching it to me and my EO forum. The man knows what he’s doing.

You and I are both fighting the war on mediocre business. Go run one check-in.

As always, if you’d like to chat about topics like this, I’m here for you: scott@scottmonday.com.

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Last week’s YouTube video walks through a quarterly check-in strategy with my team that has completely changed the way we do performance reviews. Check it out!

Things I've Enjoyed Lately: If you’re a Costco member like 99% of North Americans, I’d encourage you to pick up one of these cantilever umbrellas. Fantastic quality and a great value. My wife and I put it together in just a few hours. (Including a trip to Home Depot to get the 350 lbs. of sand we realized it required… 😒) We love it. You’ll love it.

Welcome to Week 6. The final week.

If you’ve been with me since Week 1, look at what you’ve got. Claude knows who you are. It’s connected to your tools. It builds your morning briefing before you sit down, and last week you killed your worst workflow and turned it into a skill that runs on command.

Up to now, all of that has been for you.

This week, we hand it to your team. This is where Cowork stops being a personal tool and starts moving your whole company.

Below is this week’s video, about 13 minutes. I walk through the Team and Enterprise setup, show you how plugins work, and build a real skill live, the monthly financial synopsis I now run for both brands. That one took a 30 to 45 minute conversation and zero code.

Week 6, step by step:

1. Explor Team and Enterprise options. In Settings (click on your name in the bottom left side of Cowork), click Billing, then Adjust Plan. Your default account is an Individual account. Click the Team and Enterprise button under the headline. Consider your potential number of users and decide if migrating to a Team or Enterprise account is right for you.

2. Install a plugin. In Cowork, open the plugin marketplace. Plugins are packaged sets of skills built for specific kinds of work: marketing, sales, brand voice, project management, and design. Pick one that fits a team or function in your company. Install it. Suddenly, Cowork knows how to run a brand review, generate a competitive analysis, draft an email sequence, or whatever the plugin does. Out of the box, no skill-building required.

3. Build a team skill. Last week, you built a skill for a workflow that only you do. This week, build one for a workflow your team does. Examples: “qualify a new lead,” “kick off a project,” “review a quote before it goes out.” Same pattern as Week 5, but the trigger phrase and instructions should make sense for anyone on your team to use, not just you.

4. Train one teammate. Pick one person on your team who’ll get the most leverage from this. Block an hour on the calendar. Sit with them. Walk them through Weeks 1 through 4: install Pro, set up Cowork, build their Personal Preferences, connect their tools, and stand up their morning briefing. They won’t be at your level by the end of the session. They’ll be a few weeks ahead of where most of their peers ever get.

5. Make it institutional. Add “Set up Cowork, first 30 days” to your new hire onboarding checklist. Document your team’s skill from step 2 in a shared doc so anyone can find and use it. Pick a recurring slot (monthly works) for a 15-minute “what’s new in Cowork” share at your leadership meeting.

How we used Cowork at our office this week: I built the financial synopsis skill I mentioned above. I used to generate the spreadsheets and then build that report by hand every month, for both brands. Now it’s a conversation and a saved skill. We’ve also got a new team member starting next week, and we’re showing her Cowork from day one. That sets the precedent early: this is how we work here, and we’re handing you the tools from the start.

What I’m expecting from you this week: Pick one person on your team. Share one skill with them, or sit down and solve one of their pain points together. Just one. That’s the whole game now, moving this past yourself.

This week’s homework, in one line: Hand one thing you’ve built to one person on your team, then reply and tell me what you handed off.

That’s a wrap on Cowork Mondays. Six weeks ago, this was a blank Claude account. Now you’ve got a setup that knows you, runs your workflows, and is ready for your whole team. Nearly 1,000 of you followed along, and that means a lot to me.

This was never about replacing your people. It’s about letting them focus on what humans are great at while the AI handles the rest. Coworkers, side by side.

Thank you for being here. The full playbook stays free and public, so send it to anyone you want to bring along.

AI will never replace the need to communicate well with your team, and this week's YouTube video is all about the Quarterly Check-in Process that changed the way we do performance reviews at a tour company. Check it out!

Can I share something with you?

It’s a bit embarrassing.

I believe in the monster under the bed.

You know the one:

You’re a kid, you’re tucked in, you’ve got your stuffed animal underneath your arm and the sheets pulled up to your neck. Your parent flips off the lights and gently shuts the door. Then the thoughts surface. Yep, that’s definitely a monster under the bed.

But there’s an adult version.

We are, after all, just a slightly more mature (hopefully), wiser (hopefully), and bigger (surely) version of our childhood selves, right?

I call them imaginary enemies.

I’ve used them my entire life to spark motivation, to give me an edge, to make sure I’m running, running, running.

What Is an Imaginary Enemy?

An imaginary enemy is a person I trick myself into believing is against me.

It could be a real person I know. It could be someone I’ve just heard of. And sometimes, it’s an ephemeral archetype I make up.

Regardless, I think of them and project the single most powerful negative thought I believe a person could have about me: doubt that I will succeed.

That’s it.

An imaginary enemy is a person who I imagine doubts me.

That’s all I need.

How to Use Imaginary Enemies

Now, my version of an imaginary enemy is very personal.

But we can all harness this motivating effect in our own businesses and organizations.

There’s something powerful about a competitor you rally your team around.

When your team has a healthy dose of us versus them coursing through their veins, it does a few things:

1. It brings people together around a common goal of defeating the imaginary enemy.

2. It sharpens what makes you better, because your team is constantly contrasting what you do well against what the competition fails at.

3. It reduces your team’s desire to go work for the competitor. “Who would want to work there?” Coke people don’t want to be Pepsi people, and vice versa.

The Danger of the Imaginary Enemy

The motivating effect of imaginary enemies has to be used with caution. You can take it too far, to a toxic level.

Awareness of your imaginary enemy is powerful. Obsession is harmful.

At the office, us versus them can curdle into disrespecting and bad-mouthing the competition, even wishing them harm. No bueno.

How do you counteract this?

Use the tool with a little levity. Don’t take it too seriously. Make it “spirited competition,” not a fight to the death.

Wrap-Up

Sometimes when I write this newsletter, I imagine a reader thinking, “Man, this guy is NUTS. He over-shares and writes about stuff no one really relates to. He should quit and do something else. No one needs it. I just don’t think he has much to offer.”

Nothing motivates me like thinking of that reader.

See what I did there?

As always, if you’d like to chat about topics like this, I’m here for you: scott@scottmonday.com.

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This week's YouTube video walks through a quarterly check-in strategy with my team that has completely changed the way we do performance reviews. Check it out!

Things I've Enjoyed Lately: There’s got to be a few of you out there who are walking cliches like me, and therefore play pickleball. If you are, my newest paddle might be of interest. The Friday Aura Pro is fantastic. Highly recommend. Exceptional bang for the buck. (You can needlessly spend like $350 on a paddle if you want...)

Welcome to Week 5!

If you finished Week 4, you’ve got a morning briefing that builds itself before you sit down. Claude knows you, it’s connected to your tools, and it’s already saving you time every morning.

This week, we go after the workflow you dread.

Here’s the shift. The first four weeks, you told Claude what to do. This week, we flip the script. Instead of dictating the steps, you ask Claude to help figure out which of your most frustrating workflows it can actually take off your plate. Then we turn that workflow into a skill: a multi-step process Claude memorizes once and runs on command, forever.

Below is this week’s video, about 26 minutes. I build a real skill live, the one my team uses to create product spec sheets, from a blank chat to a saved, repeatable skill.

The moment to watch for: during its own test run, Claude grabbed the wrong image. It pulled the Kohler logo instead of the sink. Then it caught the mistake on its own, decided the selection wasn’t good enough, and fixed it before I said a word. That self-correction is the whole reason this works.

Week 5, step by step:

1. Pick the task. Make a quick list of everything that drains you week to week: bid responses, proposal drafts, expense reports, customer follow-ups, meeting notes, weekly team updates, vendor reviews. Pick one. Just one. (You can come back for the others.)

2. Let Cowork interview you about your current process. Paste this prompt:

> “I want to map out a workflow I do regularly so we can rebuild it together. Interview me one question at a time. Don’t bundle questions. Cover these areas: what task we’re mapping (name and trigger); the inputs I start with; the steps I currently take in order, with rough time estimates; the decisions I make along the way that need my judgment; the final output and where it goes. After the interview, output a clean workflow map titled ‘[Task Name] - Current Process’ with sections for trigger, inputs, steps, decision points, and output. Save it as a markdown file in my Cowork folder. Ask me question 1 now.”

Answer one question at a time. By the end, your current-state workflow is documented and saved.

3. Now ask Cowork to rebuild it. Type: “Read the workflow we just mapped. Tell me which steps you can do, which need my judgment, and how we’d run this together.” Read the response. Then push back: “Now propose a redesigned workflow where you handle as much as possible, and I make decisions on the things only I can decide.”

4. Run the redesigned workflow on a real example. The next bid. The next proposal. The next set of meeting notes. Don’t pre-clean anything. Use the actual messy input you’d normally start with.

5. Turn the workflow into a Cowork skill. Quick context: a skill is a reusable workflow that Claude can invoke automatically. Think of it as a saved playbook with a name. Once you build one, Cowork can run it any time you trigger it. We’ll do more with skills next week.

In Cowork, type: “Take this refined workflow and turn it into a Cowork skill called ‘[skill name like bid-response or proposal-draft]’. Build it so that when I say ‘[your trigger phrase, like let’s do a bid response]’, you run the skill automatically.”

Cowork’s skill creator handles the packaging. From now on, the workflow is a permanent capability you can call by name.

How we used Cowork at our office this week: I built a skill that assembles our entire proposal packet start to finish. It begins with a simple PDF of the cover letter and the project breakdown. From there, Cowork reads the breakdown, pulls the right sheets from our spec library, builds any that are missing, and merges everything into a complete 30 to 40 page proposal, ready to send. A process that used to eat hours now runs from one trigger.

What I’m expecting from you this week: Pick one workflow you hate. Just one. Run the interview prompt and let Claude map it. Don’t even build the skill yet if you’re not ready. The point is to see your own process laid out and watch Claude tell you how much of it it can carry.

This week’s homework, in one line: Map your worst workflow with Claude, then reply and tell me how much of it Claude said it could handle.

See you next Monday for Week 6, our final week, where we take everything you’ve built and hand it to the rest of your team. This is where Cowork stops being a personal tool and starts moving your whole company.

Ready to dive into Week 6? Here’s the post!

AI can help eliminate human error. And speaking of human error, last week’s From the Trenches video has me falling on my sword over a very costly mistake I made in the midst of an “entrepreneurial sezier.” I hope my learning the hard way helps you avoid similar pain!

At 30,000 feet over Mexico, I got a text.

Urgent. Call me.

It was from Jake, who runs kitchen & bath CRATE and covers for me at TBS while I’m on vacation.

I can’t. On a plane. What’s going on?

He broke the news:

There’s been an accident on a job. A slab fell on a homeowner and two of our guys. Injuries. Everyone’s alive, thankfully.

My stomach turned.

And there I sat for the next two hours, my only information coming in bits and pieces via text.

I got off the plane and called from the airport.

I got the full, gruesome story: Our TBS guys were installing a 500-pound wall slab in a massive custom master suite. In a freak occurrence, one of my guys got distracted by commotion behind him and, at the same moment, the slab cracked. Half of it came off the wall. Another of my team members went to help stop the fall, which sent his half off the wall too. Both halves came down on my two installers and the female homeowner standing behind them. All were injured, none severely. The female homeowner went straight to the ER.

As more information came in and I realized no one was critically injured, the secondary problems started to sink in.

• The homeowners were an affluent family we were trying to win future apartment work with.

• This was our first project with a GC we were trying to impress.

• This was literally day one on a job that would keep us on site for the next four weeks. The worst possible way to start the relationship.

Long story short: a terrible accident on the worst possible job.

So what do we do when our company does something harmful? How do we recover?

As I write this today, eight months later, the situation turned out better than I could ever imagine:

• We’re now a consistent subcontractor for that general contractor, including work on the owner’s private residence.

• We’re slated to work on the family’s next apartment development.

• We’re about to start work for their relative who lives across the street.

How do we go from almost killing a customer to being a chosen repeat vendor?

It all comes down to how the aftermath was handled.

Here’s how to recover from a mistake of this magnitude.

Step 1: Stabilize the Situation

The first step is to get through the immediate emergency.

Your mind wants to go into “solve” mode, but you’re not ready yet.

You have to slow down. Get to the scene and focus solely on caring for the victims.

You care for your team. You care for your clients. Live in this for as long as you need until the situation stabilizes.

Step 2: Apologize

Next, you apologize to everyone harmed, even if they were part of the cause.

Apologizing is hard for some people. Why? It requires humility and taking responsibility, both at a premium these days.

“Isn’t an apology an admission of guilt? Can’t that be used against you in litigation?”

Listen, if damage control in the face of potential litigation is your moral North Star, you can stop reading here.

Good humans apologize when they cause harm.

And the apology can’t be “I’m sorry this happened to you,” or even worse, the insulting “I’m sorry you feel this way.” Ugh. Just stop.

Those are not genuine apologies. If that’s the best you can do, skip it.

An effective apology is immediate and genuine. Do that.

Step 3: Ownership Steps In

Once the situation is stable and the apology is made, the business owner steps in to manage the aftermath.

This could take days, weeks, months, or years.

It cannot be handed off. This is the owner’s job.

(Think your business is too big for the owner to run point? Read how Disney CEO Bob Iger handled the Disney World alligator fatality in 2016.)

The owner’s role in this phase:

• Continue to care for the people harmed. Check in. Follow up. Don’t let them feel like you walked away after the apology.

• Conduct a post-mortem at the appropriate time. Ownership should lead the charge in identifying, defining, and solving the root cause of the situation.

• See the solution through. Make sure a permanent fix is in place.

Step 4: Making Things Right

Finally, it’s on the owner to make things right with the people harmed.

Often this is costly.

Fixing the damage, paying medical bills, going the extra mile to make recovery as easy as possible.

Leave no stone unturned. Show the people harmed that you’re taking full responsibility for making things right.

Wrap-Up

The homeowner reached out to me the other day, many months after the accident. This is the man who, the first time I spoke to him, was sitting in the ER with his wife. Needless to say, he didn’t exude warmth at the time.

He asked if I’d be willing to reimburse a small medical bill that came through late. The bill was tiny, probably close to a nice dinner out for this very affluent family. I agreed, of course.

Then it occurred to me: this request wasn’t about the money. This was his need to be sure we were still willing to take full responsibility. This was about what’s fair and what’s right.

That’s the essence of how we should handle our mistakes: be fair and make things right. We can’t control the accident. We can control our response. That’s the job.

Here’s to living above reproach.

As always, if you’d like to chat about topics like this, I’m here for you: scott@scottmonday.com.

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Last week’s YouTube video is a story about how I personally set one of our companies back by 9 months through poor leadership. Ugh. That’s hard to write. But it’s true… Check it out!

Things I've Enjoyed Lately: James Clear wrote an amazing book called Atomic Habits. Definitely worth checking out. But his newsletter, which comes out every week or two, is one of my favorites. Rarely does an issue go by without my pausing to reflect on something he said. I only subscribe to a handful of newsletters, but this is a must-read for me.

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Welcome to Week 4!

If you finished Week 3, Claude now has access to your tools. It can read your calendar, search your inbox, and pull files from your storage. That’s a big shift. You went from an AI that knows you to one that can actually see what’s happening in your business.

This week, we put all of that to work.

We’re building a morning briefing: a single daily prompt that pulls from your email, your calendar, and your task list and returns everything you need to start the day. The goal is simple: you open Claude Cowork in the morning, and it tells you exactly what deserves your attention. No tab-switching. No hunting. Just clarity.

Below is this week’s video: about 14 minutes walking you through how to build the brief, test it, and dial it in before turning it into a scheduled task that runs every weekday automatically.

The moment to watch for: Claude doesn’t have a native connector for my Trello board. So instead of stopping there, I train it to open Chrome, navigate to my board, and read my to-do list on its own. That’s Claude in Chrome doing something we never explicitly set up, and it worked on the first try. If your task platform isn’t in the connector marketplace, that moment will show you exactly how to work around it.

Week 4, step by step:

1. Decide what goes in your briefing. Pick three or four sources you check every morning. Some examples:

• Unread emails from the last 24 hours, prioritized

• Today’s calendar with prep notes for each meeting

• Your task list, sorted by what’s due today

• New leads, open opportunities, or whatever your business pipeline looks like

2. Open Cowork and type a starter prompt:

> “Every weekday morning, I want a one-page briefing. Pull from [your sources from step 1]. Format it with a short intro paragraph, then a section for each source. Keep it under 500 words. Do not yet create the scheduled task. Just show me the results here.”

3. Read what comes back. Tell Claude what to add, cut, or reformat. (“Skip the newsletter promotional emails.” “Pull only meetings before noon.” “Sort by priority instead of time.”) Iterate until the briefing feels right.

4. Run it again the next morning. Refine. Run it again. Most people lock the format by day 3 or 4. (Easiest way to do this: just “pin” the task in Cowork, and come back to the same task each day until it’s ready for step 5.)

5. Once the briefing is dialed, turn it into a scheduled task. In Cowork, type: “Take this morning briefing workflow and create a scheduled task that runs it every weekday at 6:30 AM (or your time). Save each day’s briefing as a dated file in my Cowork folder.” Cowork handles the scheduling. From now on, the briefing builds itself before you sit down. You walk in and the day’s briefing is waiting.

How we used Cowork at our office this week: The team at kitchen & bath CRATE has been manually assembling elaborate PDF proposals for years. This week, we turned this task over to Claude Cowork, and it expertly identified the appropriate specification sheets for each proposal and assembled them into complete packets. Hundreds of hours per year saved!

What I’m expecting from you this week: Run the daily brief prompt at least once and see what it returns. Don’t rush to turn it into a scheduled task yet. The whole point of this week is to test the output, figure out what’s missing, and tell Claude what you’d change. You’ll spend a few mornings refining it before it’s ready to run on autopilot. That’s by design.

This week’s homework, in one line: Run your daily brief prompt, see what shows up, and reply to tell me the one thing that surprised you.

See you next Monday for Week 5: we’re flipping the script. Instead of telling Claude which workflow to fix, we’re going to ask Claude to help us figure out which of our most frustrating workflows it can actually handle. That shift (from directing the AI to asking the AI) is where things start to get really interesting.

Ready to dive into Week 5? Here’s the post!

AI can help eliminate human error. And speaking of human error, this week’s From the Trenches video has me falling on my sword over a very costly mistake I made in the midst of an “entrepreneurial sezier.” I hope my learning the hard way helps you avoid similar pain!

Two vignettes:

Vignette 1

This is an email we received at kitchen & bath CRATE last month.

This customer wrote a 554-word email naming nearly 30 team members.

She did that because those 30 people had an impact. They created a human connection.

It was more than a remodel.

Vignette 2

A few months back, we completed a bathroom remodel.

During the initial meeting, our customer brought up how sad her adult daughters would be to see their dated 1990s shower tile go.

The tile was out of date, but it held meaning for those women. It was a memorable part of their childhood home.

I have similar memories of foil and felt wallpaper, no joke, in my own childhood home.

Daniel, the sales professional working with them, remembered that aside weeks later at the Design Meeting. “What if we harvest a few of these old tiles and work them discreetly into the design?”

The homeowner loved it.

Fast forward. Job done. The daughters come home for a visit.

On the back of a return wall in the shower, where no one would see them unless they were standing right there, two tiles from the original shower were expertly worked into the new design.

The daughters teared up when they saw them.

Part of their childhood home didn’t have to live in memory alone.

That is human connection; making a magic moment.

Losing Connection

The “invisible hand of capitalism” is moving us away from human connection in commerce:

• Online shopping

• Self-checkout

• Driverless taxis

• AI answering systems

• Phone support that makes you press an endless series of numbers

It makes sense on paper. Human interaction requires humans. And humans require a paycheck, can be difficult to manage, get sick, and sue you.

It is easier and more profitable to move away from humans.

And herein lies the opportunity: human connection with the AI in the background.

I think the most successful companies of the next 10 years will operate on this premise:

Fantastic human connection on the front end, facing the customer. Sophisticated AI behind the scenes, running the machine.

I liken it to cars.

The F1 car: all performance, nothing else. Miserable to sit in, impossible to get in and out of, and terrible on a regular road. This is the AI-replacing-humans company.

The old beater: basically technology-free. Pleasant, but always breaking down. Comfortable yet unreliable. This is the anti-AI, we-just-don’t-understand-it company.

The luxury sedan: beautiful, smooth, the satisfying “clunk” of the door shutting, whisper quiet at 80 miles per hour. Real comfort built on engineering perfection. This is the human-forward, AI-in-the-background company.

Which car do you want your business to be?

Taking Action

Three steps to building human connection on top of an AI foundation:

1. Define your ideal customer profile. Get embarrassingly specific about the one customer you are building for. (At kbCRATE, our ideal customer is a female homeowner between 40 and 70 with disposable income, a household income between $150,000 and $250,000, who is not a DIYer and not overly frugal, who values organization and delegation, and who holds high but reasonable standards. See: quite specific!)

2. Find the moment that is slipping away. Where should a human be showing up for your customer, and is not, usually because your people are buried in friction?

3. Point the AI machine at that exact friction. Not to replace the human moment. To protect it. Free your people up to show up.

It is not hard to think of these moments. It is hard to execute them consistently. Consistency is the machine’s job.

Wrap Up

When everyone is heading toward fewer connections, maybe that is the time to be different with more.

The companies that win will figure out how to free their people up to create magic moments.

The future will be turbulent, so buckle up.

But first, decide what car you are getting into.

As always, if you’d like to chat about topics like this, I’m here for you: scott@scottmonday.com.

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This week’s YouTube video is a story about how I personally set one of our companies back by 9 months through poor leadership. Ugh. That’s hard to write. But it’s true… Check it out!

Things I've Enjoyed Lately: When we start a new project at TBS, we bring the field and management staff a gift box. Hands down, the favorite item within has been a customized Yeti tumbler. Shout out to my friend Kacie for showing me this. The tumblers have the logo laser-etched, and they look great. Everybody loves swag they’ll actually use. Check out Yeti customizations if you want something like this.

Welcome to Week 3!

If you finished Week 2, you’ve got a Personal Preferences doc loaded into Claude’s settings. Claude now knows your name, your business, your people, and how you like to communicate. That’s a big deal. You went from a generic AI assistant to one that actually knows who it’s working with.

This week, we go one step further. We’re giving Claude access to your tools.

Right now, Claude knows you. But it can’t see your calendar, search your inbox, or pull up that email from a vendor last week. It’s doing everything from memory. This week, we fix that by connecting Claude Cowork to your email, calendar, and file storage; Google Workspace or Microsoft 365. When those connections are live, Claude stops being a smart assistant and becomes an action-oriented one.

Below is this week’s video: about 16 minutes walking you through the entire setup, plus four live demos showing what happens the moment Claude has access.

The moment to watch for: Demo 4. I ask Claude Cowork to create a calendar event on my behalf. Watch what happens when it asks for my permission before doing it. That’s the approval system in action, and it’s exactly the kind of control you want when you’re letting AI work inside your real accounts.

Week 3, step by step:

1. In the Claude desktop app, within Cowork, at the top of the sidebar menu, click Customize.

2. Click Connect your apps.

3. Connect your email. Gmail or Outlook, whichever you use.

4. Connect your calendar. Google Calendar or Outlook.

5. Connect your file storage. Google Drive, OneDrive, SharePoint, Box, Dropbox, whatever holds your documents.

6. Connect one more tool you live in. Common picks for operators: HubSpot, Asana, ClickUp, Monday.com, Notion, Slack, Teams.

7. Test the “read” abilities. Try these three prompts:

- “What’s on my calendar tomorrow?”

- “Find the last proposal I sent to [client name].”

- “Summarize the last five emails from [team member].”

8. Now test the “write” abilities. This one needs a quick setup first. Go back to Settings > Connectors, find your calendar connector, and turn on write permissions. Most calendar connectors default to read-only, so you have to explicitly enable Cowork to create events on your behalf. Once write access is on, head back to the Cowork chat and type: “Create a calendar event on my calendar for next Tuesday at 2:00 pm called ‘Test Cowork Event’ for 30 minutes.” Now open your calendar. There it is. That’s the difference between Claude reading your world and Claude working in your world.

9. Download and activate the Claude extension in Google Chrome.

• Open Google Chrome.

• Click the Extensions button on the top right (it looks like a puzzle piece).

• Click Manage extensions at the bottom of the window.

• Search “Claude.”

• Add the Claude extension.

How we used Cowork at our office this week: The team at TBS is working hard to find commercial cabinet vendors to partner with. This week, we used Claude Cowork to run a deep research task: identify companies that fit a specific profile, scrape their email addresses from their websites, and then write personalized email drafts for each one. A few minutes of quick review, and the emails were sent!

What I’m expecting from you this week: Connect at least one platform and run at least one of the four demos. Don’t try to do everything perfectly. The goal is to see Claude working inside your real accounts for the first time. Once that clicks, you’ll naturally start finding your own use cases. They’ll just appear as you work.

This week’s homework, in one line: Connect your email and calendar, run Demo 1 (the calendar overview), and reply to tell me what showed up.

See you next Monday for Week 4: we’re building your custom daily brief, a morning routine prompt that pulls your calendar, your email, and your priorities into a single snapshot at the start of every day.

Ready to dive into Week 4? Here’s the post!

When you hear the story of why Toys R Us failed, you’ll agree: not even Claude Cowork could have saved it! Last week’s Whatever Happened To… video is here, and it’s rather nostalgic for us 70s, 80s, and 90s kids…

Readers will have three reactions to this newsletter:

1. For some, this will be a completely foreign concept.

2. Some of you will think, “Check out the ego on this guy.”

3. For a few of you, it’ll land, and you’ll think, “Yes. He gets me.”

If you study anything about growing a Substack, it’ll tell you to absolutely not write a post like this. Keep it broad. Keep it accessible. Keep it targeted at your audience.

Alas, I am what I am. Here goes.

Introducing the “HC”

There’s a certain subset of people who are highly capable. HCs, let’s call them.

Now, most people will raise their hand and say, “That’s me.” But I’m sorry, it’s not most people.

I’m talking about people who will stop at nothing short of death to fulfill a commitment, keep a promise, and accomplish a goal. They may not be fast, but they are unstoppable.

They’re also crazy good at most things.

Not “jack-of-all-trades, master of none.” No. I’m talking broad and deep knowledge. Skilled and capable across the board.

You wouldn’t call them “unicorns,” exactly, but you’re also not passing them on every block down Main Street.

Here’s the irony: HCs often have one glaring weakness. They resent when others expect them to be highly capable.

I know. Completely illogical. Exceptionally annoying. All of it wrapped up into a lousy predicament for the people closest to them.

To know an HC is useful. They jump into action before most people even notice there’s a problem. They think three steps ahead. They identify and solve things quietly, without making a whole thing of it.

They’re also exhausted most of the time. There’s no such thing as being an HC and being “off.”

So what do people around HCs do? They step back and let them handle it. Why wouldn’t they? It works!

The problem is, HCs also resent having to “handle it.” Even the things they “gladly” volunteered for. They get stuck in a loop: “Why am I always the one to solve, fix, and do everything?”

Handling an HC

What’s the point here?

If you’re an HC, know this about yourself: You’re not alone.

Also, know that you’re being a little unfair to the people around you. You can’t blame them for expecting you to behave exactly as you’ve always behaved.

Sometimes just being aware of the pattern is enough to start working through it.

And if you’re a normal, well-adjusted non-HC, and you have an HC in your life, do them a favor: release them from duty once in a while.

Even if they volunteer to handle something, give them a pass. “That’s kind of you, but I’ve got this.” It doesn’t sound like much. It helps more than you’d think. It gives them permission to take themselves off the hook for a minute.

Wrap Up

It’s impossible to write a post like this without coming off like a jerk. But some of you needed to hear it. And I needed to hear it.

You’re not alone, and yes, you’re a little crazy.

But we love you.

As always, if you’d like to chat about topics like this, I’m here for you: scott@scottmonday.com.

Subscribe now

Last week’s YouTube video is a fascinating look at why Toys R Us, that merchandise mecca for so many of us 70s, 80s, and 90s kids, went from toy powerhouse to liquidation in just a few short years. Check it out!

Things I've Enjoyed Lately: Google’s Notebook LM is, in my opinion, an under-the-radar AI tool. Probably because it’s really hard to describe. I’ll put it like this: it takes large volumes of data (PDFs, documents, website links, etc.) and turns them into a searchable, interactive dataset. But for me, my favorite use case is having Notebook LM create custom informational “podcasts” from the information I give it. Load it up with a 100-page PDF, then click “Audio Overview.” A few minutes later, you have an audio synopsis built just for you. It’s magic!