The second common starting / breaking point
When a founder asks me to look at their pitch deck, we usually end up talking about something else entirely.
What surfaces, ten minutes into the conversation, is something quieter: the founder can articulate the strategy clearly — for the investors. But the next week it is slightly different again. But when I ask what the team is actually working on this quarter and why, their answer is that there is no strategy anymore. Or it points to a plan from six months ago. Or different people on the team would give different answers.
As the team grew, what stopped working was the way of letting the team execute on, and feeel the strategy and the plan. It sounds easy, but it feels very counter intuitive to tell the same story twice a week, 100 times a year. It feels wrong. But that means that on a team of 30, people have still only heard the plan three times in a year.
This is one of three patterns I see over and over in how founders communicate strategy as their companies grow. They look different, but they share a root: the founder's communication style hasn't scaled with the company. What worked at 5 people quietly breaks at 25, and loudly breaks at 50.
Pattern 1: Strategy shifts every week, but no one is told
In the founder's head, the strategy is alive. Every customer call, every board nudge, every walk to the coffee shop refines it. Each shift is small. Internally it feels like consistent thinking — like the strategy is gradually getting sharper.
Externally, to the team, it looks completely different. They set priorities last week based on what the founder said. This week the founder is acting on a slightly different version, but no one announced the change. The team's priorities are quietly stale. They don't know it yet. They'll find out the next time the founder sees their work and reacts in a way that doesn't match what they thought they were optimising for.
What the team learns over time is to wait. They learn not to commit fully to a direction until the founder has confirmed it recently — because they've been burned by acting on a six-week-old version of the strategy. The most expensive form of this is when senior people start asking for "alignment conversations" before doing anything substantial. That isn't them being slow. That's them being smart about a shifting target.
The shift the company is asking for: if your strategy is going to keep evolving, the evolution itself needs to be visible. Not just the conclusions. The reasoning, the new inputs, what changed and why. Otherwise the team is acting on snapshots while you're operating on the live feed.
Concretely: when something in your thinking shifts, that's the moment to write or say one paragraph about it. I'm changing how I think about X because of Y. Here's what that means for what we're doing. It feels excessive when the company is small. It is exactly the right amount when the company is medium. By the time it feels normal, you're past the point where you needed it.
Pattern 2: The plan, told once a year
The mirror image of Pattern 1. The founder noticed that constant micro-shifts were confusing people, and corrected by going the other way: declaring the strategy formally, once a year, at an offsite or a kickoff. The deck is good. The plan is clear. Everyone nods.
Then nothing happens for eleven months.
What went wrong isn't that the plan was bad. It's that humans don't internalise strategy from a single telling. The founder remembers the plan because they wrote it, lived it, defended it, refined it. The team remembers the slide deck. By March, half the team is operating on a fuzzy memory of January. By July, the link between what they're doing and what was said is so attenuated that the founder starts feeling, again, that the team isn't executing.
This pattern often coexists with Pattern 1. The founder gives the annual plan, then quietly shifts inside their own head for the rest of the year, and is then frustrated that neither version of communication is working. Telling everyone everything at once in January and assuming the message will carry — that's a 5-person communication style applied to a 50-person company.
The shift the company is asking for: strategy isn't a thing you tell. It's a thing you transmit, repeatedly, in many contexts, until it becomes the air the team breathes. The annual plan is fine as an anchor. But it has to be referenced, recontextualised, applied to specific decisions throughout the year. Every priorities conversation, every hiring decision, every "should we do this" question is a chance to reconnect the action back to the plan. Without that, the plan is just a document.
Pattern 3: Strategy as painkiller instead of vaccine
This is the deepest of the three and the one most worth naming.
Painkiller-strategy is what most founders default to: you explain the strategy when someone shows up confused, or when a decision is heading the wrong way, or when a hire is misaligned. The strategy gets told reactively, in response to symptoms. It works in the moment. It feels efficient — you're only explaining when explaining is needed.
The problem is that by the time someone is confused, the cost has already been incurred. They've spent days or weeks heading in a wrong direction. They've made decisions, hired people, shaped expectations on a faulty model. The painkiller helps with the current headache but doesn't prevent the next one.
Vaccine-strategy is the opposite. You tell the story before it's needed. Proactively, repeatedly, in many forms, so that by the time someone has to make a decision, they already have the context. They're inoculated against the confusion before it shows up. The team can move faster because they're not waiting for you to clarify — they already know.
This is the shift from being the team's clarifier to being the team's transmitter. The work moves upstream. You spend more time talking about strategy when no one is asking, and less time correcting after the fact.
The shift the company is asking for: stop waiting for the moment when explaining is needed. The moment explaining is needed is the moment when explaining is already late. Build a rhythm of proactive transmission — written updates, all-hands narratives, manager cascades, repeated framings of the same core ideas in different contexts. Tell the same story so many times that you get bored of it. The team is not bored. The team is just starting to act on it.
What ties these together
All three patterns are the same underlying transition: the founder used to be the medium, and now the company needs a medium that doesn't depend on the founder being in the room.
At 5 people, strategy lives in conversations. People overhear each other. The founder is in every meeting. Communication happens by osmosis and proximity.
At 50, none of that works. People don't overhear. The founder isn't in every meeting. Osmosis is replaced by ambiguity. The communication style that won the early phase — informal, reactive, in-person, just-in-time — is now the thing creating the confusion the founder is trying to fix.
The hardest part is that this isn't a skills problem. The founder isn't bad at communicating. They were excellent at communicating in the way the early company needed. The work is to develop a different mode — deliberate, written, repeated, proactive — without giving up the qualities that made the early style work in the first place.
You'll know you've made the shift when team members can answer "what's the strategy" in a way that sounds like you, when you weren't in the room. Not because they memorised your deck, but because they've heard the reasoning often enough that it's become theirs too.