The Question

Almost every founder or new CEO asks me some version of the same thing: how do you know when to push and when to hold back with a leadership team that spans several countries?

It usually comes up after a bad meeting. Someone gave direct feedback in a way that landed fine in one office and badly in another. Nobody said anything at the time. Then it surfaces weeks later as resignation, or worse, quiet disengagement that nobody flags until the numbers show it.

I have sat in rooms across the US, the UK, Europe and Asia where the same sentence, said the same way, produced completely different reactions. That is not a communication failure. It is a signal that the question people are actually asking is bigger than it sounds.

Why The Answer Isn’t “Adapt Your Style”

The advice I hear most often is to adapt your leadership style to each market. I think that advice is too small for the problem.

Adapting style is surface work. You learn that direct feedback works in one office and indirect feedback works in another, and you switch accordingly. That helps, but it treats culture like a costume change.

The deeper issue is what people believe leadership is for in the first place. In some markets, a leader is there to protect the team from uncertainty. In others, a leader is there to name the uncertainty out loud so the team can plan around it. Those are not style differences. They are different jobs.

If you only adjust your tone, you will get the words right and still miss the job.

What I Actually Do

Before I say anything substantive to a team I am new to, I try to find out what they think a leader owes them. Not through a survey. Through conversation, usually one on one, usually informal.

I ask people what a good boss did for them before, and what a bad one did. The answers tell you more than any culture guide. Someone might say a good boss “made the hard calls so we didn’t have to.” Someone else might say a good boss “told us the truth even when it was uncomfortable.” Those are two different contracts, and you cannot run both at once without people noticing the gap.

Once I understand the contract a team expects, I decide how much of it I can honor and where I need to change it. I am honest about which is which. If I am going to run a market on more direct feedback than it is used to, I say so plainly, and I say why, rather than letting people discover it in a performance review.

The Mistake I Watch People Make

The mistake I see most is leaders who assume the market that trained them is the default, and every other market is the exception. It usually is not intentional. It is just how habits form. You run one region for a decade, then you inherit three more, and you bring your old playbook with you because it worked.

The fix is not to throw out the playbook. Some things travel well: clarity about what matters, respect for people’s time, honesty about mistakes. Those hold up almost everywhere I have worked. What does not travel is the assumption that everyone already agrees on how those things should be delivered.

The Trade-Off Nobody Names

Here is the part people don’t like to hear: building a leadership team across markets that think differently is slower than building one where everyone shares assumptions. You will spend real time on conversations that produce no immediate output. That time is not wasted, but it does not feel productive in the moment, and boards and investors sometimes read it as drift.

I have learned to say this out loud early, so nobody mistakes the slower start for a lack of urgency. Slowing down to understand what a team actually needs from you is not softness. It is the only way the faster stretch that follows actually holds.

What Good Looks Like

A good multi-market leadership team argues in meetings and still trusts each other after. A bad one is polite in meetings and re-litigates every decision privately afterward.

That single difference tells me more about whether the leadership approach is working than any engagement survey. If people feel safe enough to disagree with me directly, in whatever form disagreement takes in their market, I know the contract is working. If they only ever agree with me, something is being hidden, and it will surface eventually, usually at the worst time.

I would rather hear the hard thing in the room than read it later in an exit interview.