At some point your company gets big enough that you can’t know everyone anymore. You won’t recognize half the faces in the all-hands. But here’s the asymmetry that catches founders off guard: they all know exactly who you are. And most of them want to know you better — how you think, why you make the calls you make, where you’re taking the company. You’ve lost the ability to build that one conversation at a time, right as the demand for it goes up.
So your communication has to scale without going hollow. The participant leadership, the cadence, the V2MOM — those are part of it. The harder question is how you keep the directness you had as a founder when you can no longer walk the floor.
Transparency without chaos
Here’s the thing I’ve learned: the more people know about a problem, the more of them can help solve it. The failure mode is the opposite — a small circle of senior leaders who know the real challenges while everyone else gets the glossy version. People can feel that gap. The moment they sense they’re being handled, you start breeding the exact distrust and disengagement you were trying to avoid.
There’s a line, though. Transparency isn’t dumping your anxieties on the company. Your job is also to point at a way through. It’s not enough to say what’s wrong — people want to know there’s a path, and that you believe in it. So when I raise a hard thing, I do it in a specific order: here’s the challenge, here’s the fact that every business has them, here’s what we’re doing about it, and here’s what you specifically can do to help.
Naming the problem without those last three parts is just anxiety with a microphone.
That’s the tone I carry into all-hands, cross-functional meetings, hallway conversations — and into my weekly note.
The weekly note
The weekly note is the best tool I’ve found for staying connected to a whole company as it scales. Scott Dorsey did this at ExactTarget, and I always thought it was a hallmark of how grounded his leadership was. I stole it. Every Sunday night I spend about twenty minutes writing a short note to the entire team.
It is not a newsletter. It’s not a polished recap of everything happening in the business. It’s a direct message from me about what’s actually on my mind and what I’m focused on this week. Sometimes it’s tactical — I’m prepping for a board meeting, or chewing on customer visits from the week before. Sometimes it’s just a story, an interaction that stuck with me. The one rule is that I write it. Not my chief of staff, not comms. Twenty minutes, no jargon, no corporate BS. It sounds like me because it is me.
And it works better than anything more polished would. I get replies all week — questions, pushback, things I didn’t know, and sometimes just “thanks for sharing.” The replies keep me connected, but the bigger effect is on the other side: people tell me it means something to know what their CEO is actually thinking about, to get a glimpse of what the week looks like at that level. When you’re scaling fast, it’s easy for people to feel a mile from the top. Twenty minutes on a Sunday closes some of that distance.
It’s also where I create urgency without cranking up the pressure. If we’re closing a hard quarter, or there’s a release that has to land, I’ll use the note to put that front and center — not to lean on people, but to make sure the priority I care about is the one they’re carrying too.
Start one. It doesn’t need to be long or well-produced. It needs to be real, in your voice, and sent every week without fail. The consistency is the point: honest, regular contact is what builds the kind of trust that holds up in the quarters when the news is bad.
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