The Team That Tried to Kill Itself Before Anyone Else Could

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Ian Brand walked into his first standup and left with his jaw on the floor.

Twenty engineers. All of their bosses. Fuck you’s flying across the room. People not aligned, not talking, not even pretending to pretend, just openly at war.

He'd been brought in as the fixer—eight months into a high-visibility bet. A new product org built to move like a startup within a large corporation, funded to announce to investors, and supposed to launch in November. It was November. Nothing worked. The mobile app, the whole point of the thing, did nothing.

What did Ian just sign up for?

"I was like, what did I get myself into?" he told me.

There's a Y Combinator line Ian kept coming back to in our conversation:

Your startup is much more likely to die from suicide rather than murder. The thing that takes you out isn't the market, the tech, or the smarter team down the road. It's the dysfunction inside your own four walls.

You already know this. Everyone knows this. We all nod along on LinkedIn, then go back to the team we've been meaning to fix since Q2.

Ian walked into the version of this nobody wants to inherit. Not a team with some friction. A team that was actively trying to kill the product before anyone else could.

Before product management, Ian was a basketball coach. And somewhere in a Mike Krzyzewski book he'd picked up years earlier, he found the thing he now uses to diagnose every team he walks into.

Coach K calls it: The Fist.

Five fingers, poking around on their own, can annoy you. Maybe hurt a little. Bring them together, and you can land a punch. Five things have to be true for fingers to become a fist: communication, trust, collective responsibility, care, and pride.

Ian's first standup had zero of them.

No communication, or the wrong kind. 

No trust. 

Nobody is thinking about how their work affected anyone else. 

No empathy. 

No pride in what they were building, because there was nothing to be proud of yet.

You can have the smartest engineer on the planet, Ian said. But if the team's toxic, you net out at zero. It doesn't matter how talented that person is if the group can't move together.

So Ian started with himself.

He didn't call a meeting. He didn't announce a values initiative. He just changed how he showed up, how he communicated, how he wrote requirements, and how he reacted when something went wrong.

When engineers didn't understand a spec, he didn't think they were idiots. He thought, “What did I do wrong that they didn't understand, and how do I fix it?" That's the collective responsibility finger. Small internal shift. Huge external tell.

Then he broke up the 20-person standup. You can't build a fist with twenty people and their bosses glaring at each other every morning. He split it into smaller scrums where actual work could be discussed.

Then, once there was enough trust in the room to do it, he ran a values and culture workshop. Named the problem out loud. Told the team this was why they weren't shipping.

The proof that it was working wasn't dramatic. It was a Tuesday.

QA was behind on testing. The engineers whose work was being held up had a choice: complain or help. "My stuff's not that important for launch," one of them said. "I'll come help run test cases."

That sentence doesn't happen on a toxic team. On a toxic team, engineers don't run QA test cases. They don't even read QA test cases.

They launched in January. Two months late. Scope cut, but shipped. And over the next few months, they hit what Ian calls rhythm and flow, that thing where a team recognizes, discusses, plans, makes, and ships in one smooth string. The fist, swinging.

Ian got goosebumps describing it. "That's what I'm most proud of in my career."

Great. Fixed team. Product shipping. Roll credits.

Except…

A few months in, Ian started going to the business leadership's staff meeting. Marketing. Ops. Finance. The CEO.

It was the first standup all over again.

Marketing hated ops. 

Ops was trying to sabotage marketing. 

The CEO, who'd come from Wall Street finance, ran her team the way her old firm ran theirs. Pit people against each other, and reward whoever survives. A culture imported wholesale from a trading floor into a startup, quietly killing it.

Ian asked for the financial data. He wanted to see where the product was actually making or losing money.

He got told to fuck off.

So they grew. That was the mandate. Grow, get users on the platform, don't worry about the rest. Ian pushed back: " You don't pour water into a leaky bucket.” They grew anyway.

Then a new CFO arrived, looked at the numbers, and told the team to stop. They were losing money on every customer. Every signup made the hole deeper.

You already know where this is going. Because you've seen it. The engineering org gets its act together, and the business org is the one bleeding out. Or vice versa. One side of the house figures out how to be a team, and the other side is still running on politics.

The dysfunction doesn't care which room it's in.

The old CEO left. Ian got his chance. He flew to Detroit and ran a workshop. Ops, marketing, the new finance person, a few of his engineers, and designers. One room. Two days. The balance book open on the table.

Why are we losing money here? Ops would do some digging and come back with an answer. Why is this happening? Marketing would pull a number. What's driving this? Finance would surface something nobody had seen.

They found twelve issues that stopped making sense the moment you said them out loud. Ten of them had product fixes. Small, obvious software changes that nobody had built because nobody on the product team had ever seen the balance book.

Two months after they shipped those fixes, contribution margin was up 30%.

"Was I a Steve Jobs product genius?" Ian said. "No. These were things anyone could obviously see. What was missing was the communication. We weren't talking to each other. There wasn't transparency. We didn't trust."

The same five fingers. The same fist. Different room.

Then COVID hit. The company got nervous. The product wasn't profitable enough yet to ride out the uncertainty, so they pivoted, kept the one piece that was working, and shut the rest down.

Ian doesn't think the product failed. It got taken out by timing.

But his real lesson is about how close it came to dying the other way. Twice.

"What if we were working that way, from the beginning? If we were solving those business problems from day one? Not a few years in, after a new CFO forced the conversation?"

You already know which dependency in your org is the real risk. It's not the vendor. It's not the API. It's the two functions that aren't talking to each other. The standup that's become a hostage situation. The leadership meeting where people are sharpening knives.

Y Combinator says you're more likely to kill your startup than get killed.

Ian just watched his almost do it twice.

When Ian described what actually worked, it came back to the same thing: be the change you want, then make room for other people to be that change too.

Everything in this playbook is a version of that. The fist isn't a thing you build. It's a thing you model until other people start modeling it back.

Ian Brand borrowed The Fist from Coach K. Five fingers — communication, trust, collective responsibility, care, pride — bound into a fist. A team that has all five hits like a fist. A team missing two or more pokes and annoys and occasionally hurts itself.

The framework below is what Ian actually used. Not the theory. The moves.

Before you do anything, figure out whether you have a fist problem or something else. Five questions. Answer honestly.

If you're missing two or more, you have a Fist problem. If you're missing four or five, you have Ian's problem: a team that's more likely to kill the product than the market is.

The instinct when you inherit a toxic team is to call a meeting and announce that things will be different. Don't. You haven't earned the right to run that meeting yet, and the team has seen this movie before.

Start with yourself. Specifically:

When someone doesn't understand your spec, don't think they're an idiot. Think what did I do that didn't land, and how do I fix it? That single reframe covers more ground than any process change you could announce.

When you see something that needs doing, and nobody owns it, do it. If QA is behind and you know SQL, write the test cases. If the release notes are late and you can write, write them. The team is watching who jumps in.

When you disagree with someone in a meeting, disagree in the meeting. Not in the hallway after. Back channels are what toxic teams run on. Starve them.

This step takes two to four weeks before anyone notices. That's fine. You're not trying to be noticed yet. You're trying to earn trust later, which requires doing the work now.

If your standup has more than ten people in it, the standup is the problem. Ian walked into a 20-engineer standup with all the managers in the room. Nobody was going to say anything real in that room. Nobody was going to admit they were blocked, behind, or confused. The room was too big for honesty.

Break it. Rules of thumb:

The mechanical change is small. The cultural signal is big: we trust you to run your own work, and we're not going to sit in the back and watch.

Every toxic team has 2-3 people already aligned with how you want to work. They're not always the loudest. They're often the quieter ones who've stopped fighting because nobody was listening.

You find them in 1:1s. Specifically, you find them by listening for someone repeating back the values you've been modeling, in their own words, without you prompting them.

For Ian, it was an engineering lead. In a 1:1, the lead said something that was almost word-for-word what Ian had been saying in standups. Ian followed up. Turned out the lead had been on toxic teams before, had the same instincts about what was broken, and had been waiting for someone to do something about it.

From that point on, they partnered. Talked through issues 1:1. Backed each other in bigger meetings.

Here's the move that's worth stealing.

Sometimes the lead would say something sharp in a 1:1 that needed to be heard by the whole team. Ian would tell him: I'm going to ask exactly this question in the next standup. I want you to answer with exactly what you just said.

Why? Because it can't always be the new person saying it. If the only voice naming the problem is the outsider who just showed up, the team writes it off. When the engineering lead says it, in a meeting, in front of everyone, it lands differently. The fix isn't being imposed. It's being requested by someone the team already trusts.

The other thing the lead did, on his own, was run a moment that did more for trust than any team-building exercise Ian could have planned. Symptoms of distrust were showing up across the team. So in a meeting, the lead asked everyone to put in the chat: "Why are you here? What motivates you?

Once the answers were in, the dynamic shifted. When someone got short or said something off-putting later, the rest of the team had context. They knew where that person was coming from. The same comment that would've been a threat the week before was now just a frustrated person whose motivations everyone understood.

That meeting wasn't Ian's. It was the lead's. That's what an ambassador does.

One operating principle Ian stuck to with every ambassador conversation: don't be a know-it-all. When something was breaking down, he wouldn't show up with the answer. He'd ask: What can I or we do to put our team in a better position to succeed at these values? Then he'd iterate based on the answer.

The ambassador isn't a recruit. They're a partner. Treat them like one.

This is the step you can't do first. You have to have completed Steps 1 through 3 before you've earned the right to run this conversation.

Here's the thing nobody tells you: the conversation isn't a single workshop. If you walked in on day one and announced a values-offsite, it would come across as a lecture from an outsider and backfire. So instead, you wait for the right moments. And then you stack them.

This is another Coach K idea. When he took over Team USA Basketball after their bronze-medal embarrassment, the first thing he did was hold a values-and-standards workshop. He let the players voice the standards and organize them. He facilitated. From then on, every player held every other player accountable to standards they'd set themselves.

If you're there at the start of a team, do that. Forming, storming, norming. Take advantage.

If you joined late, like Ian did, you don't get that moment. So you watch for substitutes. Beginnings and endings are everywhere if you look. The end of a quarter. The end of a major project. The launch of something. The closing of a chapter. Each one is a window where it's natural to step back, look at the big picture, and talk about how the team is actually working.

Sprint retros are the smallest version of this. Use them. When something Fist-related comes up in retro, vocalize it. Don't make the retro your presentation, but don't let the moment pass either. Ian has a saying he learned at company: speak fearlessly. He gets recognized for it constantly, partly as a joke, mostly as a compliment. He's not afraid of tough conversations. You shouldn't be either.

Bigger windows take more planning. Ian had planned to run a real reflection meeting right after the January launch. Then the team got busy iterating post-launch, and he missed scheduling it. Realizing this, he booked an end-of-quarter meeting under the premise of reflecting on big-picture strategy and roadmap.

In that meeting, he latched on to the things they'd been touching on in retros. He named how far the team had come in the way they were working. He pointed out that this shift was a major factor in the turnaround. Then he went into the Fist directly.

That's the structure. Not let me give you a workshop on team values. Instead, we've already been doing this work. Here's what we've been doing. Here's what to call it. Here's how to keep doing it on purpose.

What people leave with isn't a doc. It's a vocabulary. Now the team can name what's happening as it happens. Someone can say we're not communicating in a planning meeting, and everyone knows what they mean. The thing becomes nameable, and once it's nameable, it's fixable.

You'll know it's working not because of a big moment but because of a small one. Ian's was an engineer saying: My stuff's not that important for launch. I'll come help run test cases.

That sentence doesn't happen on a toxic team. On a toxic team, engineers don't help QA. They don't even talk to QA.

When you see the Tuesday signal, don't call attention to it. Don't put it in a slide deck. Just notice. It's the first sign the fist is forming.

Other signals to watch for:

If you're three months in and not seeing any of these, something's wrong. Go back to Step 1 and ask honestly whether you've actually changed how you show up, or whether you've just redecorated your calendar.

Everything above is for a team. But the same dysfunction shows up between teams, and it's usually worse because nobody owns the fix.

The first thing to know is that you can't force this conversation. Ian tried, early on. He pitched leadership that they should understand the unit economics before scaling. The CEO told him to fuck off. Worse than the rejection itself was what it revealed: there was no strategy behind the growth mandate. If there had been, leadership could have explained it instead of shutting him down.

So the question becomes: when does the window open?

For Ian, two things had to change before it could.

First, the people blocking it had to leave. The CEO who'd said no was gone. Some of the most hostile leaders in marketing and ops had been replaced with deputies who'd been promoted into their roles. The new ones were sick of the toxic culture themselves and ready to talk.

Second, somebody from the previously-walled-off function had to want in. The new CFO had just sounded the alarm on profitability. Ian had a cross-functional strategy session already on the calendar. He reached out to ask if the CFO would join. Before he could finish the ask, the CFO jumped in: I heard you're running a product improvement workshop. Can I be a part of it?

That's the window. New leader, no precedent, actively looking for collaborators. When you see one of those, move fast.

Ian asked the CFO to open the session with a review of the balance sheet. Absolutely. Ian came in with a schedule. The schedule lasted about 15 minutes before the session took over. He threw it out.

Here's what worked in the room:

Of the twelve issues they identified, ten had product fixes Ian's team could ship. Two were legal matters already in progress. Two months later, the contribution margin was up 30%.

The pattern under all of it: when a function has been walled off, and the wall comes down, what you find on the other side is usually a person who's been wanting to talk this whole time. Your job isn't to break the wall. Your job is to recognize when it's already cracking and walk through.

None of this requires purchasing a tool. Here's the operational layer underneath:

Cadence. Weekly 1:1s with every direct report. Biweekly skip-levels. Monthly team retro. None of this is optional. The fist doesn't form in meetings you skip.

Room. Physical room, if you have one. Same video call link if you don't. Consistency of the room matters more than people think.

Documents. One shared doc where the team's values live, once you've run the workshop. One shared roadmap everyone can see. One shared definition of done. That's it. Don't add more documents than the team will actually read.

Time horizon. Two years. Ian's full arc was two years from the first toxic standup to the cross-functional workshop. You're not going to fix this in a quarter. Tell your boss that out loud so they don't expect otherwise.

To read more about this from Ian himself, check out his Substack post on the Fist.

Until next time,

Matt