The anti-fragile culture

By lincolnq @ 2025-08-21T21:41 (+159)

How to prevent infighting, mitigate status races, and keep your people focused. Cross-posted from my Substack.

Organizational culture changes rapidly at scale. When you add new people to an org, they’ll bring in their own priors about how to operate, how to communicate, and what sort of behavior is looked-up to. Despite rapid changes, in this post I explain how you can implement anti-fragile cultural principles—principles that help your team fix their own problems, often arising from growth and scale, and help the org continue to do what made it successful in the first place.

This is based partially on my experience at Wave, which grew to 2000+ people, but also tons of other reading (top recommendations: Peopleware by DeMarco and Lister, Swarmwise by Rick Falkvinge, High Growth Handbook by Elad Gil, The Secret of Our Success by Henrich, Antifragile by Nassim Nicholas Taleb, as well as Brian Chesky’s essay “Don’t Fuck Up The Culture”). Thanks also to my friends and ex-colleagues who have read and given suggestions on drafts.

Common Problems

It’s quite common that orgs fail (or lose their magic) at scale. I think many such orgs started in a good place leading to early success leading to scale, but as they grew they hit cultural “mines” which blew up the org or made it fail to scale well.

Cohesive cultures are more resilient and can withstand shocks… Every single founder I know who has compromised on culture when hiring has regretted it due to the disruptions it has caused their company: having to fire bad actors, creating a crappy work environment, good people quitting, trust eroding between coworkers, product moving in the wrong direction, misaligned incentives emerging in the organization, etc.

– Elad Gil, High Growth Handbook

There’s a dense minefield of ways your culture can get into a bad equilibrium that’s hard to get out of:

• Putting self ahead of mission
  • Reinforced when: people see others behaving selfishly and getting away with it, they realize they are getting exploited and start behaving selfishly too.
  • Also, more insidiously: self-interested Machiavellian actors may view mission-oriented people as less controllable and seek to disempower them.
• Lack of trust in the team (micromanagement, bad policy)
  • Trust is empowering and self-reinforcing for the best people: when they’re trusted, they make better decisions and learn from their own mistakes, and want to stick around because it’s a lot more fun and rewarding to work in a trusting environment.
  • But there are a lot of ways for organizations to erode this trust (e.g. through bad policies or bad management); employees have a very sensitive “radar” for how much trust they’re receiving, and they will reflect the trust they perceive back to the org. When they reflect less trust, the org will naturally respond by extending less trust, and you have a race to the bottom.
• Internal races, e.g., competition for the best opportunities, status, or benefits/comp
  • Reinforced when: folks feel the reward is a fixed-size pie and that they need to compete with others for promotable/high-value work, they start intentionally hiding their methods, undercommunicating, and carving out fiefdoms, and set a really bad example for everyone else.
• Bad-seeming leadership decisions that go uncorrected
  • An example would be that leadership makes a mistake like over-focusing on proxy metrics, then employees notice and attempt to correct this but leadership is not interested.
  • This leads to a feedback loop where your team loses confidence in leadership to hear feedback or solve similar problems broadly. They stop bringing important things up because what’s the point? And if leadership is already out of touch, then it goes further off the rails.
• Tribal infighting
  • Productive disagreement is very often a good thing, but “infighting” refers to unproductive, often emotional, disagreements. The worst forms of infighting are those which are tribal: dragging others in by creating us-vs-them identity dynamics usually reinforced by external political/hotbutton/culture war issues.
  • Tribal infighting is self-reinforcing: it distracts individuals’ energy from the org’s unique problems, giving energy to hotbutton issues, pushing away the people who want to solve the unique problems and attracting those who are into culture wars.

There are more cultural mines than these. Hitting even one mine can blow up your org if not carefully managed, and hitting a mine during a fast-growth stage can easily be a major slowdown or severely limit the org potential, even if you react perfectly.

Write down your culture

Defining your culture explicitly and communicating your values can protect against cultural mines: either by helping to avoid specific mines, or by making it much easier to repair things when you do hit a mine.

Having a meaningful mission is critical to success. First, it’s critical to attracting like-minded people, who want to propagate the culture to achieve the same goal. Secondly, you can refer to it when reinforcing cultural points, as I’ll show below.

Some examples of questions that culture can help answer:

• What are the priorities? How do you manage and propagate those priorities? How are shared resources managed to achieve the mission?
• What words do you use (and avoid) to explain the company to outsiders?
• What’s taboo to talk about? What do you talk about which would shock outsiders?
• What happens if you criticize your boss? Does it matter if in public or private?
• What are the drivers of increasing status within the org? How do people get promoted? Do de jure and de facto power line up?

Writing down values is super useful when you’re trying to think about and plan for the culture you want, and whatever you write and share becomes citeable for moments where you need to teach an explicit lesson.

That said, you don’t have to write everything down

In the end, culture is too complicated to write down fully. It will be mostly picked up and converged on through words and acts every day—explicit and implicit prioritization, what’s shared and what’s hidden, word choice, and body language. Leaders’ words and actions play a huge role in defining the culture.

Here are a few common cultural values that are “in the water” of Silicon Valley tech companies. We usually don’t write them, or even really talk much explicitly about them:

• Product and marketing matters. The greatest technology advance is a waste of energy if you can’t get people excited to use it.
• Only write code and talk to users at the earliest stages. Everything else is downstream of having a great product, and these are the only two activities that help improve your product.
• Measure and do science. Hard data eats instincts for breakfast.
• People quality matters. People want to work with other great, motivated people and will work way harder and with greater output, compared to if they are surrounded by average-quality folks.
• Meritocracy. Rewards (attention, power, money) go to the ones who contribute the most to the outcome—and not to the best-connected, suck-ups, early adopters, the rich, etc.
• Nurture people and relationships. Make sure people feel respected and appreciated by the company and specifically their boss. Do 1:1s every week or two that are more than just status check-ins. Don’t let people be blocked.

If you’re in the same tech bubble I’m in, the above values seem like common knowledge—they’re not particularly distinct. They do avoid important mines, but we don’t really perceive them as mines because they’re so obvious (“of course the people are important!”). You don’t want or need to write this stuff down if people aren’t confused about it. But if your org is bringing on a lot of people who don’t have a lot of experience in similar orgs, maybe some of the above is worth being explicit about.

Anti-fragile values I recommend

In this post I’m highlighting some less-obvious values that I feel can be super helpful for fast growth orgs. I think we did this really well at Wave and so a lot of what I’ve written in this post is reflective of Wave’s culture, but I also have some different takes from what we settled on at Wave. (You can see the current iteration of Wave’s values on their website.)

Mission First

Herb Kelleher [the longest-serving CEO of Southwest] once told someone, “I can teach you the secret to running this airline in thirty seconds. This is it: We are THE low-fare airline. Once you understand that fact, you can make any decision about this company’s future as well as I can.

“Here’s an example,” he said. “Tracy from marketing comes into your office. She says her surveys indicate that the passengers might enjoy a light entrée on the Houston to Las Vegas flight. All we offer is peanuts, and she thinks a nice chicken Caesar salad would be popular. What do you say?”

The person stammered for a moment, so Kelleher responded: “You say, ‘Tracy, will adding that chicken Caesar salad make us THE low-fare airline from Houston to Las Vegas? Because if it doesn’t help us become the unchallenged low-fare airline, we’re not serving any damn chicken salad.’”

– Made to Stick by Chip and Dan Heath, who cite James Carville and Paul Begala.

In a mission first culture, every decision boils down to mission; every hiring and firing; every internal metric and every external communication.

• This is key to attract and retain great people for an ambitious project and to enable focus.
• Anti-fragile because it enables fixing problems, and doing so with greater buy-in, when you have a strong history of pointing to the mission as the driving reason for decisions.
• The above quote is a great example of how Southwest Airlines used this value.
• SpaceX has had the idea of a Mars mission as a goal that animated a lot of people. Google aims to “organize the world’s information.”

Focus

We’re all here to achieve a specific mission, and efforts not aimed at the mission are unwelcome.

• Helps attract people who want to work on the mission, and repel those who don’t.
• Anti-fragile because it helps prevent many problems but especially people bringing their external initiatives into the org (especially hot-button political issues that can trigger infighting).
• A sports example from the New England Patriots - “Do Your Job” was the mantra of the team during a historic win streak.
• Focus as a value really works if you also have a mission value (so you can point to the mission as the reason for focus) and a high level of buy-in for the mission.

Fire Fast

Maybe someone is not performing. Maybe they’re performing well but are still causing a distraction or making it harder for everyone else to perform. “If there’s any doubt there’s no doubt.”

• It’s a relief for everyone (often including the ex-employee!) when you fire people who are not a fit for whatever reason.
• Firing is a natural corollary of “people quality matters,” but is rarely made explicit, and I think it’s a shame.
• Anti-fragile because your team will certainly make hiring mistakes, and when you do, you need to be able to fix them. It works best if the managers at all levels have this affordance, not just the executives.
• It’s not yet clear to me how to apply this to grassroots/opt-in movements. One possible solution, from Swarmwise, related to “attention junkies” who don’t care about the mission: “As the swarm is open, you cannot and should not try to keep these people out — but you can deny them the space and spotlights they crave…they will eventually flush themselves out, sometimes in quite a bit of disruption.”
• Firing fast is a tough value to highlight because it makes people feel personally threatened. It will need other values to balance this out. (At Wave, we never made this explicit as part of the values doc but it was always a pretty clear part of Wave culture.)

Feedback for everything

Every decision you take should eventually generate some information about whether that decision was right or wrong; the value is to seek out and make use of such information.

• Anti-fragile because it enables course correction.
• The speed of the feedback matters immensely. The shorter you can observe the data and act on it, the more effective your org can operate in fast-changing environments (to the extent that you may not realize that you’re in a fast-changing environment until your feedback loop is short enough!) For more, read about OODA loops.
• Ask people for, and offer, explicit feedback. Don’t limit to quantitative; qualitative feedback is of great value; run postmortems constantly; shorten feedback loops.

Mutual Trust

The goal here is omnidirectional trust: the team trusts each other and boss/leads, and the company trusts individuals to make decisions, and individuals trust that the company’s values and principles are fairly applied.

• Anti-fragile because strong trust promotes strong interpersonal bonds, making people want to work together and communication simpler and quicker. When people are trusted, they feel more valued and can hear each other’s feedback.
• Ben Kuhn has a great post about trust as a bottleneck to collaboration.
• At Wave, the value of “embarrassing honesty” is focused on mutual trust, among other things.
• There are a ton of ways to build trust, the more radical the faster: radical vulnerability, radical transparency, radical responsibility delegation, radical mutual reliance.
• Trust can also be built over time, through slow relationship-building and consistency in principles and decision-making.
• This is one of the hardest cultural aspects to maintain as you grow for many reasons:
  • As the org grows, it naturally seems more and more alien and hard-to-trust (e.g., person you complain to is initially the CEO when small, but becomes a faceless HR department at scale). Similarly, individuals tend to have fewer social ties with people they have to work with in large orgs.
  • Legal departments tend to push back strongly against many forms of vulnerability and transparency. This is a difficult balancing act, because their reasons for pushing are valid (they want to protect the org from well-understood risks), but at the same time they don’t have a complete picture of the org’s strategy and they tend to under-index on culture since they have no accountability for it. Hiring culturally aligned folks for HR, legal, and compliance departments is one of the best things you can do to help preserve long-term culture.

Work sustainably and avoid burnout

Anti-fragile because it reduces the impact of status races and the risk of burnout—first, visibly over-working leaders can trigger a status race; unchecked this can escalate into toxic workaholism, creating suppressed resentment and risking mass quitting. And second, even without status races, people don’t always know how to set a sustainable pace, and may be borrowing energy from their future selves. They take on too much and become an unstable pillar.

• The blog post “Melting Gold and Organizational Capacity” by Ray Arnold is a good example of ways that leaders might not build a sustainable structure in volunteer organizing, and how burnout and abrupt quitting can destroy organizations.
• Surprisingly often, work output decreases with marginal increase in hours worked. Since Henry Ford, we have seen industry settle into 35-40 hour weeks. You may be able to get a bit more productivity from motivated employees, but probably not that much more. Doing 60-hour weeks for more than a few months is probably counterproductive to overall productivity (e.g., construction).
• That said, for a mission driven org, it doesn’t mean taking the norms of for-profit industry wholesale. Jeff Kaufman has a nice blog post about Prioritizing Work, where he argues that someone excited about and proud of their work will naturally choose to prioritize it in their lives. Your workers can be happy and sustainable in a mission-driven org when they and others around them prioritize their work within the context of their lives, and that may mean working longer or harder in some way.
• As a leader, you are a highly visible bearer of your org’s standard here; this standard needs to take into account the tradeoffs of long-term sustainability vs. showing deep commitment and excitement about the mission.

Write only what’s new & helpful

It’s great to start by writing everything you might care about down! But then aggressively cut it to what’s most likely to be new and/or helpful. New means the people don’t already know it; helpful means people know it but frequently need reminding. Because culture is transmitted mostly face-to-face, you don’t need to (or want to) write down everything that’s part of your culture. Your values doc needs to be short and sweet to be memorable. So, first think about the whole culture you’re aiming to promote, and then keep only the new and most-helpful items.

Feel free to take any/all of the above values wholesale, but realistically, your org’s culture needs to channel aspects of what makes it unique. That said, until anti-fragile values are as much a part of “default culture” as the Silicon Valley ones above, I think it can be very helpful to include aspects of them in your cultural design and values docs.

I’d also add that sometimes it’s enough to write a memo, e.g., Elon Musk’s “Acronyms seriously suck” was written to solve a specific cultural problem at a specific time. It’s still very useful as a reference even though it’s not part of an official values doc.

Go off and scale something great!