Every executive walking into a new role is, for a while, stupid. Not incapable. Not unqualified. Stupid in the specific, unavoidable sense that they do not yet know what they don’t know about the organization they’ve just joined. Their track record, pattern recognition, and instincts were built somewhere else, in someone else’s organization and culture. None of that transfers automatically. Until they learn the local rules, they are operating on assumptions that are as likely to be wrong as right.
The Ethiopia-Kenya problem
Picture crossing the border from Ethiopia into Kenya by car. You clear customs and pull back onto the highway. What must you do next? If you don’t get this right, you’ll be dead in thirty seconds. What must you do? You must change lanes — Ethiopians drive on the right, Kenyans on the left. Miss that adjustment and the consequences arrive fast and hard.
Organizations are exactly this treacherous, except the “sides of the road” are invisible. One company drives on trust-first relationships; the next drives on documented process. One rewards speaking up in the room; the next punishes it. Nobody paints lane markers on culture. So, every new executive is, in effect, re-entering traffic in a place whose rules they’ve only half-learned — confident, capable, and one wrong lane change from a collision.
Not all wrong turns are equal
Here’s the part that matters for how you actually behave: these mistakes aren’t uniform. Some are fender-benders — a slightly awkward first meeting, a misjudged joke, an email cc’d to the wrong distribution list. Annoying, forgettable, recoverable by lunchtime. Others are the kind that total the car. Alienate the wrong stakeholder in week one, misread the true decision-maker, or move on a reorganization before you understand the political terrain, and you can spend the rest of your tenure digging out of a hole you dug on day three.
Since you can’t eliminate the stupidity — you genuinely don’t have the local knowledge yet — the best approach is deliberately choosing which flavor of stupid you’re willing to risk. That requires a simple, almost uncomfortable gut check before every ambiguous call: how stupid would I feel if I’m wrong?
Not “what’s the smart move” — you don’t have enough information to know that yet. Just: which wrong guess leaves me looking merely human, and which one torches my own credibility?
Applying the test
Take the classic onboarding trap of misjudging where someone sits relative to you. If you treat a colleague as a peer and it turns out they’re an indirect subordinate, you’ve been generous and collegial — mildly stupid, easily corrected with a warmer, more inclusive relationship than you might otherwise have built. Flip it: treat someone as a subordinate who turns out to be a peer, or worse, someone with real influence over your fate, and you’ve insulted them on the way in. One mistake heals itself; the other festers. Default toward the version that costs you less dignity if you’re wrong.
The same logic applies to timing your shift from converging to evolving. You must converge into a new team — earn trust, learn the terrain — before you evolve it. But nobody hands you a stopwatch telling you exactly when convergence ends. Pivot to evolving a little too late, and you look cautious, maybe overly deferential — a stupidity of patience. Pivot a little too early, and you look presumptuous, changing things you don’t yet understand — a stupidity that can define you as the leader who didn’t listen. Given ambiguity, lean toward the error that reads as humility rather than arrogance.
Or consider the question of pace on people decisions. Move too fast sorting your team and you risk cutting someone who simply hadn’t been given a fair shot — a mistake you can often repair with a genuine apology and restored trust. Move too slow, and underperformance compounds, credibility erodes, and your own boss starts quietly wondering if you can make hard calls at all. Here the slower error is usually the more expensive one — which flips the “feel less stupid” calculus compared with the peer example above. At the same time, remember the #1 regret experienced leaders have looking back on their careers is “not moving fast enough on people.”
The best approach isn’t avoiding stupid
It’s triaging it. You will misjudge relationships, mistime your evolution, and misjudge your pace on people — guaranteed. The executives who onboard well aren’t the ones who dodge every wrong lane change. They’re the ones who, before merging, pause long enough to ask which side of the road costs less to be wrong about — and then drive accordingly, eyes open, ready to correct the moment they see the oncoming traffic.
