Being a scaleup CEO is hard, but it should also be fun. You worked for years to get here — now the job is to lead the thing you built.
When people ask me what to do about a team that’s become misaligned, my honest first instinct is to want to rewind three or six months and stop it from happening at all. That’s the whole point of the cadence, the offsites, the metrics, the weekly notes: they exist to make small corrections continuously, so misalignment never gets the chance to harden.
Because misalignment doesn’t arrive overnight. It seeps in — a little missing clarity here, a conversation that didn’t happen there — until one day two of your leaders are quietly working at cross purposes. The processes are your tune-ups. Keep making the small adjustments and you never face the big crisis.
When a team is genuinely aligned, even brutal problems feel different: they’re something you solve shoulder to shoulder, in the foxhole together, instead of something tearing you apart. Some of the hardest stretches I’ve been through as an executive ended up bringing my teams closer, not breaking them.
Never let daylight show
Here’s the part founders get wrong most often, and it’s the one that matters most. Holding your exec team together means understanding that your job is not to commiserate with them about each other — especially about personality, style, or how someone runs their function.
The moment one of your execs senses daylight between you and another leader, that leader is done. They’re now vulnerable, sidelined, and a target for everyone’s politics.
So when conflict comes up between two people on your team, you have a choice, and it defines you as a leader. Say your CRO comes to you frustrated with your CMO. You can commiserate — nod along that the CMO is hard to work with, maybe agree they need to upgrade their team. Or you can represent the person who isn’t in the room:
“I hear you. But remember we’re trying to create a new category, and that takes some trial and error on the messaging. The new head of product marketing is still finding their footing — though I heard your last meeting with them actually went well. Let’s put the messaging issues on the agenda for the next GTM strategy meeting.”
A surprising number of leaders take the first path. It’s easier in the moment, especially when it lines up with your own frustrations. It’s also lethal. You set the tone: either your executives have your full backing or they don’t, and there is no middle ground.
None of that means you ignore real concerns. If someone raises a genuine issue about another exec — their fit, their style, whether they’re the right person for where you’re going — take it seriously. The feedback might be dead right. But you handle it directly with the executive in question, with a plan to fix it now, while they still have your support. You don’t handle it by leaking your doubt to the rest of the team.
Set the culture out loud
The other half of cohesion is culture, and it gets more deliberate as you scale. Every culture is different, but a growing one needs accountability and trust baked into not just how work gets done but how people treat each other.
For the last decade I’ve opened every offsite, company event, and gathering with the same simple slide. The message is plain: we’re here to do great work and have fun doing it, my expectations for how we treat each other are high, and bad behavior won’t be tolerated — zero tolerance for misconduct, full stop.
I’m always clear that it’s not there because we’ve had a problem; it’s there so we don’t. Setting the tone out loud helps. Living it every day is what actually makes it real.
Keep your ear to the ground
As you scale, layers of management form. You need them, but they also wall you off from what’s actually happening on the floor. Cutting through those layers to get direct, unfiltered feedback is one of your real jobs — and it’s harder than it sounds, because people want to please the CEO. They want you to hear the good news.
If wins are all you’re hearing, you’re missing half the picture.
So build the listening into your cadence:
- Talk to employees at every level. You don’t need a big survey or a formal process. Grab someone for 30 minutes about a project you’re curious about — a casual conversation surfaces things no structured update ever will. When I travel, I’ll see if a few local team members want to grab coffee or dinner. Low-pressure, and it tells you more about the real mood of the place than any dashboard.
- Stay close to customers. Sometimes that’s jumping into a live deal to help close it. Just as often it’s asking an existing customer for 15 minutes to hear how things are really going. People are more receptive than you’d expect — a CEO reaching out says the company cares, and it opens the door to honest feedback. The trick is to not always be in fix-it mode. Sometimes the most useful thing you can do is shut up and listen, good news and bad.
You can’t be everywhere. But if you keep making the effort to hear directly from the people doing the work and the people buying the product, you catch the problems while they’re still small — which is the whole game.
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