When we were developing Messenger in early 2011 it wasn’t uncommon for the app to crash or freeze. The product team didn’t worry too much about that because it was in our control to fix bugs like that. What the product team worried about was when a message we sent randomly failed to deliver. That kind of error might be hard to see on a dashboard but would subtly destroy people’s confidence in our service. If a message got dropped inexplicably while we were testing we would stop feature development and focus on the infrastructure until we understood why.

That story has two important lessons.

Consistency and reliability stem from stability. McDonalds doesn’t sell the most hamburgers because they are the best. They sell the most hamburgers because they are the most reliable. In exchange for higher certainty outcomes people are willing to reduce their expectations. Making a good enough burger isn’t that hard. But doing it consistently is and requires an impressive amount of infrastructure to achieve.

High value work tends to stop when the underlying infrastructure is unstable. I’m amazed how much energy our industry has spent asking regulators to tell us what we are allowed to build. Just like our consumers, we would gladly trade away option value and autonomy for certainty. Rather than build atop uncertainty our energy is spent trying to get to certainty or building in other lower value areas instead.

Today we are dealing with an entirely novel form of uncertainty in the face of a global pandemic. When will be allowed to go back to normal life? Will it be safe? What will the new normal look like? The change in our routine exacts a toll but I suspect the toll from the uncertainty is even larger.

As the cliché goes you don’t always know what you’ve got until it’s gone. I didn’t appreciate our new motto until the infrastructure we rely on got shaky.

But what happens when it doesn’t work? Things unravel pretty quickly. You may have to learn about fuses and amperage. You may have to learn how wires were run through your house to understand the load on each circuit. An abstraction that usually works for you has leaked and now you have to understand how things really work. Or at least hire someone who does. But of course hiring someone is its own kind of abstraction.

I first learned about leaky abstractions from Joel on Software. He explains that engineers often end up needing to understand how their abstractions work under the surface to deal with inevitable failures. More and more, however, I realize the advice in this article is relevant beyond engineering. The world is full of leaky abstractions.

While I am not writing much code anymore I find I still rely on a huge number of abstractions. I talk to one person as a proxy for an entire team. I communicate a decision and assume everyone will follow it. I sign a contract and expect all parties to fulfill their duties. These things work most of the time which allows us to scale. But each one also fails sometimes.

Avoiding abstractions entirely is impossible. It isn’t possible to build anything great without them. There isn’t enough time in a day to talk to every member of every team. I certainly can’t review the communication between all those people to ensure decisions are being executed appropriately. And I can’t even imagine the mechanism that would allow us to navigate complex topics like the law and finance without trusting third parties.

But just because we can’t avoid abstractions doesn’t mean we have to be victims to them. Whenever you use an abstraction you have to understand the ways that it will fail. I may spend most of my time talking to a team leader but I also periodically check in with individuals directly and the team as a whole. I generally trust people are following decisions but we have periodic reviews to verify.

In my job I am sometimes asked “what keeps you up at night?” People expect me to talk about the competition or perhaps technical risk. But my answer is always the same: I worry that something on my team is going wrong and I don’t know about it.

I see this in other industries as well. People hiring public relations firms to try to tell their story only to find out that firm has its own baggage. Political campaigns that accept contributions they didn’t intend to. Businesses hiring consultants to be more efficient but disenfranchising their own leadership in the process. When politicians ask leaders “how could you not know this was happening?” I just think to myself about leaky abstractions.

Furthermore less important topics tend to be accessible to more people. That leads to entrenched factions which protract the argument further. This is the Law of Triviality.

Consider how hard it is to pick a movie or a restaurant with a group of friends when nobody has an urgent preference. Consider how much easier it is when you are starving or have a strong preference for a film.

To maintain the proper sense of urgency it helps to decide in advance of a discussion how much time to spend on it.

You can also forego arguments entirely by designating a clear decision maker. That could be a manager in a workplace or a system like rotating who picks the movie. The most powerful line for the decision maker comes from Jim Barksdale: “If we have data, let’s look at data. If all we have are opinions, let’s go with mine.”

But even with a clear decision maker it can be hard to make a call when the choices aren’t very differentiated.” The harder it is to make a decision, the closer to equivalent your options are.” I propose three strategies to make those close calls easier:

1. The easiest choice. Which restaurant is closest? Which movie starts at the optimal time?

2. The best choice. Which restaurant is most expensive? Which movie has the highest rating?

3. The common choice. Which restaurant do you usually go to? Which movie has the most show times?

Sometimes there are hard choices that need a lot of discussion and we should make space for those. Sadly, that isn’t what we spend most of our time arguing over. The biggest opportunity for each of us is to realize when we are in such a trivial argument. We should bow out even if that means the decision goes in a different direction than we hoped.

Whether it be a manager or a reviewer or inspector, people in positions of authority feel a sense of responsibility. Like anyone else they have a job to do and they want to do it well. If work is presented to them and they make no changes they may fear they have shirked their responsibility. Too often they look for something – anything — to change so they can feel confident they did their jobs. I call this Value Add Disease.

I heard a story about a video game design team who had developed a character they really liked. But their manager suffered from Value Add Disease and never let them out of the room without making a change. They devised a solution. They added a duck that flew around the character. At the end of the review the manager approved the character on the condition they get rid of the duck. In some circles the term “duck” is used to describe features added specifically so they can be sacrificed later.

I am told a similar technique is often used by architects when they are reviewing their plans with planners or inspectors.

If you find yourself faced with someone infected with value add disease there are things you can do to help short of the subterfuge described here. Don’t accept changes you don’t believe in without returning to the first principles that led to the decision in the first place. Highlight ways in which your results were the consequence of guidance already provided to you. Whenever possible frame meetings in terms of getting advice rather than asking permission.

The most important thing you can do is inoculate yourself against contracting value add disease. Get comfortable with adding no value to the work you are responsible for. Consider instead that building teams that create good work without your help is precisely the kind of value you should be adding. In the times you do feel compelled to add value you should ask yourself whether something went wrong earlier that forced you to get involved at this point.

I recall my Junior year, a student asked him indignantly about how a university that accepted public funding could develop valuable medical technology and then sell it to a corporation in good conscience. Larry responded, that “I know it can be counterintuitive, but if your goal is to get medical care to the most people possible the right price isn’t always free.”

He went on to explain that if the University put the work into the public domain it would still require a lot of capital to bring it to market. But if every company knew the other companies were building the same device then they were unlikely to see a return on that capital. By licensing the technology to one company they could ensure that company built up capacity to mass produce it and even require as part of the agreement that they distribute it to lower income areas which might not otherwise be profitable.

“The best thing we can do to save lives is make these technologies cheap, but we cannot make them cheap if we make them free.”

I recognize that this is as much an critique of capitalism as it is an explanation but even outside of economics it always stuck with me as a poignant lesson about understanding incentives.

Free is a very unusual price point that introduces nonlinearity in human behavior. Sometimes that nonlinearity is to their benefit as in the case of services like Facebook and Google. However sometimes the opposite is true, for example as it relates to SPAM or abuse where creating some cost forces people to assess their true value for engaging in an activity.

I’m reminded of a clever trick scammers learned a long time ago which was to add more typos to their messages. Of course adding more typos dramatically reduced the number of people who responded which seems like it would be a bad thing. However the people who did respond were substantially less skeptical and more likely to actually fall for the scam. Creating a selection bias that worked in their favor increased the return on time spent for scammers, thus reducing the only marginal cost they had. Had people been charged even a fraction of a fraction of a cent for each email sent, most such campaigns would not be profitable.

There are many more examples. Adoption of Facebook Workplace went up after we started charging for it as it gave companies more confidence that we were accountable to them. People who received a GearVR for free engaged with it much less than those who paid even a small amount for it. There even exists an entire class of luxury goods whose demand increases along with price; people want them because they are expensive.

The unlimited free distribution provided by the internet is generally a good thing. But the right price isn’t always free.

One way to better understand very large or very small numbers is to put them in context. However we often fail at that too by focusing on the wrong details. My favorite new twitter account is “Relatively Risky” which demonstrates how often an article citing something like a “40% increase in risk,” for example, is often generating fearful clicks on what is a negligible increase in absolute risk.

As if those weren’t enough, we are also very bad at estimating trends. We tend to assume everything is linear which leads us to be constantly surprised by trends that are geometric or exponential. Indeed this has been a source of arbitrage for investors for decades. Savvy capitalists look for areas of nonlinear opportunity because they are often priced incorrectly.

The solution to all of these things is to be skeptical of ones own instincts as it relates to numbers, relationships, and trends. We must be especially cautious when those instincts confirm a narrative we already believe.

These observations have lead me to ponder a cliché we hear often in technology: “We sent a man to the moon but you can’t do this?!” It turns out the list of things that are harder than sending a human to the moon is dramatically bigger than people expected. Many of our fixed points of reference are secretly misleading, and rather than using them to contextualize new information we should be using new information to recalibrate our reference points.

Imagine I told you that your goal was to hike to the highest elevation possible. You look around and find the highest peak and scale it. When you get to the top you realize you can now see much higher mountains in the distance. You have two choices: set up camp on your hilltop and call it a day. Or climb down into the valley, to lower elevation, to get to higher ground over the long run.

When we were a college only social network we were at the top of a hill. Opening to all users to get to higher ground meant risking everything. Our college users might have abandoned us. We might never have gotten traction with a larger audience. As history has shown, that change was the right one.

It wasn’t a mistake to start at college. The path matters and you have to start somewhere. But “Move Fast, Break Things” was an exhortation to never get comfortable.

We believe we should never be afraid to risk sacrificing a good product in the search of a great one. If we never broke anything because we were afraid of what might happen then we would not survive in the long run. It is better to fail fast and learn how to push past your limitations than to have bounded success. The competition will be brave.

Most companies end up myopically focused on protecting what they have. They don’t see other companies providing more value to their users until it is too late. To quote Tyler Durden, they end up “polishing the brass on the Titanic. It’s all going down, man.” We believe we must be vigilant about the ways consumer expectations are changing. As Andy Grove said, “only the paranoid survive.”

None of this requires a sacrifice in product quality. The great chef Thomas Keller has a sign hanging in his kitchens that reads ”sense of urgency.” Few would accuse him of low quality output. In both cases it just means don’t get complacent. Every second you delay robs your consumers of a better experience. Every second you rest is a second your consumers look elsewhere. Never stop trying to do it faster, make it better, make us stronger. Our work is never over.

However there are instances when circumstances demand leadership be the focus. No matter how humbly we approach our positions, our teams are still deeply aware of our point of view. Demurring too much can leave people feeling disconnected from each other and from leadership. It isn’t always enough just to care; people have to see that you care.

Advocacy needs to be visible. The greatest value in advocacy comes when you tie your own reputation to that of a cause, team, or individual you believe in. You can do that behind closed doors but it won’t carry nearly the same weight as when you do it in plain view.

When I want to create a cultural shift I ask everyone to demonstrate visible leadership. I want them talking to their staff and setting expectations for them to do the same in turn.

People seeing action and investment is half the fix. (The other half is, you know, actually fixing things). If you spent your time fixing things but nobody saw the investment, they might believe things improved but still feel that you didn’t care. Both matter.

We all like it when our plans speak for themselves. But above a certain scale it just isn’t enough. We have to speak on their behalf. Conspicuous presence is what gives people confidence in a plan. It demonstrates that someone believes in it enough to be held accountable for it.

Authenticity has always been important. Humans are relatively allergic to bullshit. That allergy has only increased with the growth of capitalism where deceit bears a real cost. But I would argue the demand for performative authenticity has hit new highs in the last few years.

We are numb after decades of polished speeches, curated documents, and flawless visuals. We demand proof of life from those who wish to speak to us. We want to see their humanity on display.

When I give talks I work hard not to over rehearse. When I write I try not to over edit. Mistakes can make you relatable and recovering from them can get an audience on your side. Showing vulnerability ironically demonstrates that you are strong and confident.

Every week involved reducing three hours of lecture materials into a thirty minute summary. If I did a poor job, the students were relentless with questions. Together we would iterate to simpler framings of the material. When we were successful, the students were able to complete their assignments with much less help.

Whatever simple explanations lack in nuance, they make up for in power. People remember them. They become the basis for future knowledge. Complexity becomes a feature of something more fundamental rather than the subject itself.

I have seen the same thing play out in my professional career. A good team faced with a hard problem will produce a rigorous document. A great team faced with the same problem will produce a single page. People often aspire to explain the complexity they uncover. But the opposite is more valuable.

If you can’t explain something simply, then you don’t understand it.

I admit there are some issues that can not or should not be simplified. The interface between product and law, for example, is often irreducibly complex. Still, I have the pleasure to work on some of the most novel technologies on the planet. And I’m amazed at how often our conversations boil down to just a few simple ideas that really matter.

I often observe colleagues with long emotional memories. I see them burdened by the grievances they carry with them. Even when their project succeeds, it is hard for them to see past their own accounting of failures. It can also be hard for them to accept growth in their colleagues because they so acutely remember past mistakes. At some point the weight of history overwhelms them and they lose touch with the present reality.

Some of this is just loss aversion. People fear losing meaningfully more than they value winning. Much like overcoming sunk cost fallacy, moving forward requires a frank evaluation of the present without indulging the contrapositive scenarios.

Some of this is overfitting. If someone previously made a mistake, it sounds reasonable to expect them to make it again. In fact, the opposite is much more likely. After making a mistake, most people learn from it. In my experience, novel mistakes are much more common than repeated mistakes.

I’m not suggesting we ignore past mistakes. It is important to learn from them. But at some point the value derived from dwelling on a mistake runs in reverse.

This is also one of the most powerful tools in the toolkit of great leaders. When teams come and ask for decisions my first consideration is a whether I should weigh in at all. Often I am not in a position to provide better guidance. In such cases, I may refuse to rule.

I don’t send the team away empty handed. Sometimes I provide procedural feedback about how I might approach the problem. I may even provide the criteria I would use to evaluate possible solutions. But I try to be humble about my ability to help and respectful of their ability to help themselves.

Making decisions for teams can cause people to become dependent on you. Learned helplessness creates a bottleneck for execution. It also has insidious impact on how much teams feel responsible for their work.

Some teams have what they need, but are afraid to take responsibility for the outcome in the face of risk. They would prefer to get sign off from someone else in case things fail. One way to help is to create a culture that encourages risk taking. Another way to help is to refuse to indulge risk transfer. Over time teams learn to take responsibility for themselves.

Let me tell a personal story. Before Facebook had likes we had an internal tool called “ideas” that allowed for upvoting. Facebook was about to unify “the wall” and “minifeed.” I had concerns about the change as did many other employees. I wrote a heated post on the ideas tool criticizing the change that garnered massive support. The comments voiced rabid support for my critique. I felt vindicated by the reaction, as if the number of votes and comments was a measure of my rightness. I thought might made right so I rallied a mob.

I was wrong on all counts. First, Facebook isn’t a democracy so Mark Zuckerberg proceeded with the change in spite of the mob. Second, the product was an immediate success. There was no backlash and in retrospect it was an improvement on the user experience. At the end of it all I felt pretty foolish. Might doesn’t make right after all.

The saying we have at Facebook is that Code Wins Arguments. If you are truly confident you are right then you have to trust that the product will prove it. The market is good at weeding out bad products. We have lots of products that people don’t use as much as we want. That’s how we learn and improve over time. That’s the process.

This is a common occurrence in business. It is also grounds for one of the most common mistakes I see.

In this scenario, many leaders sell out their management and rally the team. They say management sucks, but don’t worry, we will make progress in spite of them. This approach is staggeringly effective.

Until it isn’t.

In the short term, the team galvanizes as underdogs against the common enemy. They survive the change more committed to one another and to their immediate manager. They are “us” and everyone else is “them.” It feels good. As long as this was the only change to the roadmap the team would be fine.

But this won’t be the only change. Under this oppositional framing each additional change hits the team hard. They start to see themselves as victims. They don’t trust company plans or rely on those plans to be stable. They don’t believe they can affect company direction. Success is now earned in spite of the company while failure comes because of it.

Over the long run, this conflict moves the team from a victim mentality to outright martyrdom. They quit or change teams because even their beloved manager is ineffective. This is clearly not the ending one would hope for. It could have gone better.

So let’s return to the opening scenario. How should a team leader proceed when management makes a decision they disagree with?

Assuming you don’t disagree enough to leave the team, you must commit to the new direction. It doesn’t mean pretending to agree and offering blind fealty. But it does mean demonstrating your intention to execute to the best of your ability on the new path. Driving a wedge between yourself and your management only sacrifices your own credibility. Instead enlist your management to help you execute.

It is important to acknowledge the frustration people may be feeling. You should even share your own. But you also can’t let people linger to the point that it becomes debilitating. Instead you can share the process that led to the decision. You retain agency by making your team the owner of the change.

Only when your team feels agency can they work effectively. Only once they trust you will the follow you. Only once you commit can you truly lead.

Facebook decouples teams whenever possible to remain agile. With a clear shared strategy such a division of labor reduces communication overhead. But it puts more pressure on the quality of that communication.

When two teams find themselves out of alignment, it is tempting to compromise. But teams working around one another will harbor animosity. Deferred conflict will become blocking conflict. The dispute may get resolved but at a real cost of time, thrash, and ill will.

The best way to collaborate is to escalate issues early on. When teams identify a fundamental disagreement, they need to escalate immediately. This means within hours, not days. Every day that passes without resolution only increases the cost of resolution. I’ve seen teams become entrenched in their views in as little as a week.

This is critical beyond the teams directly involved. Every strategy is incomplete and every roadmap has flaws. They only improve when we expose their weaknesses as we work. Escalation is one of the best ways to examine how our plans fall short. If we do this pairwise then we risk arriving at different solutions rather than improving the underlying strategy to the benefit of all.

Escalation needs to be easy. If teams see them as competitions or exercises in blame, they will remain unpopular. Instead, we must reward them for highlighting an area of uncertainty in the strategy. Forums for escalation should be widely accessible, frequently checked in on, and heavily promoted by leadership.

Escalating doesn’t have to be a big deal. But failing to escalate almost always is.

Meetings are seen as mechanisms to verbally exchange and modify information. That is certainly how they work but it misses what I think is a more fundamental purpose. I posit that if we held a meeting and everything that was said was already known by every individual, the meeting would still be immensely valuable. After such a meeting everyone now knows that everyone else knows the same thing that they do. This is what linguists call mutual knowledge and it is perhaps the most powerful concept I have come across to describe what is required for successful collaboration.

In a state of mutual knowledge, people can speak frankly to advance the state of that knowledge. It serves as a platform to build upon. They can also act with greater independence trusting that they know where their team stands on an issue. By contrast, without mutual knowledge the bulk of time spent in conversation is wasted either speaking indirectly or catching up on cursory details.

If you accept the importance of mutual knowledge, there are a few important implications:

Stable groups matter. I am conservative about varying the membership of meetings or groups because each person gained or lost resets the entire group’s confidence that they are on the same page. Attendance matters a great deal for the same reason. Other attendees can come and go but there must be some core group that identifies as such and shows up consistently. This is why I create a Workplace group (or named email distribution, or slack channel, or whatever) for any recurring meeting I have; to reinforce a sense of shared identity.

Pairwise discussions are costly. Sharing information in successive one on ones can be effective because it allows you to subtly adapt the message to each audience. However, in addition to the tremendous cost in time, it has the much more pernicious cost of denying participants a mental model of others. Information is much less useful when you don’t know who else has it. When people do finally connect around the information, entropy will cause subtle mismatches in their understanding which will undermine their confidence in the information itself and in the leadership they got it from.

Transparency is critical. One of the more dangerous things that can happen is for people to incorrectly believe they are in a state of mutual knowledge. Surprises are bad and information is naturally subject to entropy so keeping an active channel open allows people to maintain their confidence in the state of mutual knowledge. If I have something that I think is relevant to more than one person in the group I share it with everyone. If people recognize their own mental model has changed, it is critical they update the group.

Narratives are important. In many ways, sharing information so that everyone has a copy is not the biggest challenge. It is versioning that information. We must ensure that your copy and my copy are in sync when both are regularly changing. In my experience, maintaining mutual knowledge as the knowledge itself is changing requires us to create simple narratives. First I describe what the previous state of my knowledge was, then I describe what changed, and then I describe what the current state is.

Mutual Knowledge isn’t about agreement but rather a precursor to it. We cannot hope to agree if we don’t understand the mental model of those we wish to align with. The larger the organization, the more intentional we must be to ensure we will arrive at a state of mutual knowledge.

I have found the same to be true for groups of people.

Many managers do their best to protect their teams. They manage information carefully and they defend their teams aggressively against change. They expend their own energy to carefully maintain a consistent environment. Their focus is on precisely what needs to be done and how. These managers are often beloved by their teams as long as the protection holds. However when an unexpected failure occurs, as will invariably happen, these teams and their managers often struggle. Maybe the company strategy changed or the market isn’t reacting as expected, but the pressure is now on the manager alone to restore order by developing a new plan for the whole team. These teams are fragile.

The best managers I know don’t do any of that. They are transparent with information in real time, especially potentially disruptive information. They embrace change when appropriate even if it is painful. They expend their energy to ensure their team is as equipped as possible for whatever might come. Their focus is on clarity around the goals and the operational constraints of the team. And when an unexpected failure occurs, the burden of how to react is shared by the entire team. They all know the goals and the constraints, they all have all the information, and they may not even need their manager at all to coordinate and plot a new course. Instead of protecting people, these managers empower people. These teams are antifragile.

Things that are antifragile gain from chaos. These are systems that are able to capture upside without participating as fully in the downside. Just like bones strengthening when subjected to stress, antifragile systems flourish through failure.

When teams survive change together they are stronger for it. They understand their goals better. They have learned more about the world they operate in. They are better equipped to handle future changes. If you get really good at change management your team can harness the opportunity that comes with failure instead of being attached to the loss.

Stability is important for effective execution so providing stable environments is an admirable goal for leadership. But that only holds as long as the stability is genuine and not manufactured. In periods of heightened risk and uncertainty I find it much more effective to be earnest about the situation with the team and help them be robust to the changes.

Instead of protecting your teams from failure, prepare them for it.

I have found the same to be true for groups of people.

Many managers do their best to protect their teams. They manage information carefully and they defend their teams aggressively against change. They expend their own energy to carefully maintain a consistent environment. Their focus is on precisely what needs to be done and how. These managers are often beloved by their teams as long as the protection holds. However when an unexpected failure occurs, as will invariably happen, these teams and their managers often struggle. Maybe the company strategy changed or the market isn’t reacting as expected, but the pressure is now on the manager alone to restore order by developing a new plan for the whole team. These teams are fragile.

The best managers I know don’t do any of that. They are transparent with information in real time, especially potentially disruptive information. They embrace change when appropriate even if it is painful. They expend their energy to ensure their team is as equipped as possible for whatever might come. Their focus is on clarity around the goals and the operational constraints of the team. And when an unexpected failure occurs, the burden of how to react is shared by the entire team. They all know the goals and the constraints, they all have all the information, and they may not even need their manager at all to coordinate and plot a new course. Instead of protecting people, these managers empower people. These teams are antifragile.

Things that are antifragile gain from chaos. These are systems that are able to capture upside without participating as fully in the downside. Just like bones strengthening when subjected to stress, antifragile systems flourish through failure.

When teams survive change together they are stronger for it. They understand their goals better. They have learned more about the world they operate in. They are better equipped to handle future changes. If you get really good at change management your team can harness the opportunity that comes with failure instead of being attached to the loss.

Stability is important for effective execution so providing stable environments is an admirable goal for leadership. But that only holds as long as the stability is genuine and not manufactured. In periods of heightened risk and uncertainty I find it much more effective to be earnest about the situation with the team and help them be robust to the changes.

Instead of protecting your teams from failure, prepare them for it.

I believe in this concept so completely that I’ll take the importance of writing a step further: I find it valuable to write even if only for my own benefit. Writing is a linear process that forces a tangle of loose connections in your brain through a narrow aperture exposing them to much greater scrutiny. In my experience, discussion expands the space of possibilities while writing reduces it to its most essential components.

Of course even when I write for my own benefit, it is undoubtedly a bonus that at the end I have a document which I can easily share to invite critiques or enlist support. I know of no more scalable way to engage a large audience than the written word. Given that, I thought it might be helpful to share some of the things that have helped me in my journey to writing more.

When I was an undergraduate I took a seminar to help me write my senior thesis. It was led by a computer science professor, and I expected it to be about how to structure the document, how to make a strong argument, or maybe how to program LaTex. Instead, all he ever had us do was write. We had to write a lot. He didn’t care what we wrote as long as we produced pages.

It was only years later that I realized he was following the story of the pottery teacher. As the story goes, a pottery teacher divided her class into two groups. The first group would be judged on the quality of their finest pot. The second group would be judged by the number of pots they produced. At the end of the term both groups were invited to share their finest pots. By far the best pots were produced by the second group of students, whose assignment had been quantity rather than quality.

It is very rare that I publish something even to relatively small groups without having an editor review it. A good editor is anyone who tells you when something sucks. This is surprisingly hard to find so when I find someone who is unfailingly honest with me I value that person immensely. If you plan to write as much as I am suggesting, you’ll want to find several editors to spread out the load.

While great editors help you see your writing from another perspective they are not responsible for the final content. That means don’t take their notes unless you really believe them. Never abdicate responsibility for your content to your editors.

One thing that surprises some people is that I rarely take meetings on Wednesday. This is partly to ensure I support a Maker culture by not proliferating meetings every day of the week. A bigger part of this, however, is so that I have time to think, by which I mean write.

Writing, much like programming, illustrating, or any other creative pursuit, is best done without interruptions so you can occupy the entirety of your consciousness with the exploration at hand. My advice is to set aside dedicated time on your calendar, disable notifications, set your phone aside, and commit to your keyboard (or typewriter, or pen & paper, or whatever).

There are many software tools that can help you focus on a single application. In addition, when I’m writing for very large audiences I use an editor called Hemingway (targeting a fifth-grade reading level) as it helps me account for some of my bad habits where I prefer overly ornate sentence structure and word choice which makes my writing much more opaque. (← case in point)

I learned this phrase from my friend Carolyn Abram who was Facebook’s first Content Strategist. One of the most common problems I run into when I write is that I get very attached to some specific structure or turn of phrase and I find myself struggling as I unwittingly contort the rest of the content around it. When I hit a wall in my writing, the very likely cause is that I need to revisit some fundamental part of the document. More precisely, I need to revisit some fundamental part of my thinking.

All of the above is half the equation, the other half is actually putting your writing into the world and seeing the response. You don’t have to go find the biggest group in the world; just writing for your own team or even posting internally on your wall are enough. Writing with the intent to publish will improve your writing as it tricks your brain into applying greater scrutiny to the ideas.

Once you start writing it will be hard to stop. As much as I write, I still have around 150 outlines of ideas I want to write but haven’t found the time to get to “paper.” Well, 149 with this post out.

As organizations grow they run the risk of becoming hopelessly disjointed. Teams end up working on projects that overlap or conflict, individuals struggle to see how their work fits into the bigger picture, people fail to see meaning in what they do and overall progress grinds to a crawl. Our ability to fight this entropy determines our ultimate capacity, both in terms of bandwidth (how many things we can work on) and velocity (speed at which work gets done). Thankfully, we have many communication tools at our disposal to help us remain connected while we grow.

A long entanglement with corporate jargon has given mission statements a bad name but a dense statement of the goal you are working to achieve over the long run can be immensely valuable if you choose your words wisely.

Consider the mission of Facebook itself: “To give people the power to share and make the world more open and connected” These aren’t obviously good things. Does everyone want the world to be more open and connected? Taking a stance on those is no small part of what has enabled us to have tremendous focus even as we have grown, avoiding much of the random project investment that has bogged down so many of our competitors at different times.

A strategy prescribes a path to achieve the mission, answering the question how in the most minimal way possible. Effectively we are mapping out a path from where we are today to where we are trying to go in very broad strokes with diminishing granularity we look further into the future. The standard for something to be strategic is quite high; it means in order to succeed at our mission we must do it and we cannot succeed at our mission without doing it.

Strategy rarely describes a straight line path to the goal. We may have to take detours that appear to be orthogonal to our goal but are, in fact, the only way to ever arrive there. The ads organization is a great example; Facebook’s mission says nothing of revenue but we accept it would be impossible to accomplish it without any. Revenue is a strategic imperative.

Strategy is generally created assuming good (but not perfect) execution. As a consequence it is common to see a step in the strategy whose sole purpose is to ensure execution. For example, if your mission is to build a platform then it is common to include building an app on top of that platform as part of the strategy because it just isn’t believable that someone would build the right platform without this work.

Strategic risks are things that could cause you to fail you to achieve your mission despite perfect execution. External forces rarely invalidate the mission but they could have a dramatic impact on strategy in a very short period of time, for example a new competitor entering the marketplace, changes in geopolitics, shifting market conditions, or even changing priorities within the company. Thus, the strategy to achieve a mission changes over time.

Even without external forces, strategy may change as execution gets under way — if you aren’t executing well enough in an area you may re-evaluate the strategic assumptions you have made about what is possible.

Tactical concerns are those which aren’t likely to prevent us from achieving the mission or enable it, but relate instead to how quickly we are able to do so. If an ads team builds the wrong ad unit and nobody adopts it, that doesn’t necessarily mean they can’t later get those revenues, it just means it will take longer as they build something different. Developing a tactical approach involves setting roadmaps and creating tasks in order to realize the strategy. Teams establish goals and milestones along a timeline to track progress and measure how well they are executing relative to expectations.

Tactical decisions aren’t unimportant but there are many orders of magnitude more of them which is why it is critical that everyone involve agree on the strategy.

When the goals set are not being achieved, or are not being achieved in a timely manner, teams may have to revisit the strategy and develop new tactics. Execution risk exists in areas where if failing to execute has consequences to how soon teams can achieve our mission, but not necessarily jeopardize their ability to eventually achieve our mission.

The word vision is thrown around often can be easily confused with mission statements and strategy. I have come to see vision as any description of a desired future state. For Facebook, if I were to describe what the world would be like when we achieve our mission that is an example of vision. If I describe the state of the user experience after a given set of strategic work is done that is an example of vision. Well articulated and widely shared mission and strategy should create vision that is broadly shared.

When someone asks you a question of the form “what will it look like when…” or “how will it feel if…” or “how do you see this playing out after…” they are asking you about your vision. When you say “imagine a world where…” or “I think the way the market will react is…” or “I think it should feel like…” you are describing a vision.

Interestingly, this post is an example of something even more paramount than having a mission: providing a common language for the team to use that everyone understands. Ensuring people use terms consistently isn’t just pedantry, it is potentially critical to scaling execution.