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Career passages

The four passages every leader has to cross

The climb is not one ladder. It is four crossings, and the hard half of each one is what you have to put down.

Bill Dickinson Bill Dickinson, D.Min., RCC 8 min read
The four passages every leader has to cross

Directors who want the VP role, and VPs who want a seat in the C-suite, rarely stall for lack of effort. They stall because they keep practicing the version of themselves that earned the last promotion. The effort is real. It is pointed at the wrong thing.

The gate you passed is not the gate ahead

Every promotion you have earned so far was granted on evidence. You did the work, the work was good, and the record was visible. Someone could point at a number, a launch or a saved quarter and make the case for you in one sentence.

The seat you want now is granted on judgment. Someone has to decide that you will handle scope you have not handled, with information you do not have, in rooms you are not yet in. What they are really doing is placing a bet. And in my experience they place that bet on how you think and how you carry yourself far more than on what you delivered last quarter.

This is why the feedback you get is so unsatisfying. Be more strategic. Work on your executive presence. Those phrases are not vague because your sponsor is lazy. They are vague because what your sponsor is weighing is whether you can be trusted with ambiguity, and there is no metric for that.

A promotion gives you potential. It does not give you permission.

Four passages, four identities

I find it more useful to think of the climb as four crossings rather than one ladder. Each crossing hands you a new source of value and asks you to set down the old one. That second half is the part nobody schedules time for.

PassageWhat you gainWhat you must put down
Self to othersValue shifts from doing to developingBeing the best individual contributor
Others to managersYou grow leaders, not just team membersThe technical work itself
Managers to functionYou own the vision for a whole function, and lead beyond your original expertiseThe assumption that your expertise is your authority
Function to enterpriseYou think in systems and your decisions shape cultureLoyalty to your own silo's numbers

Directors are usually somewhere inside passage three. VPs looking at the C-suite are inside passage four. Neither is a rank. They are descriptions of what your value is made of at that altitude.

You can hold the new title and still run the old habits

This is the most common way to look stuck without understanding why. The title arrives on a Monday. The identity takes a year. In between, a leader carries the authority of the passage ahead and the reflexes of the passage behind, and nobody names it because the results still look acceptable.

Behaviour is a better guide than a title here. Read these honestly against your last quarter.

Your calendar looks like your old job with more meetings stacked on top.You are the escalation point for problems your team should own.You feel most valuable on the days you did the work yourself.Your updates upward are task lists rather than insight.

If three or four of those are true, you are operating in the passage you have already left. That is not a character verdict. It is a diagnosis, and it points at specific work.

Why the crossing feels like a loss

Each passage asks you to abandon a proven source of value before the replacement has proved itself. For a stretch you will feel less useful, and you will be less visibly useful, because the only evidence that it is working is indirect. Other people getting better.

Most leaders retreat at exactly this point, back into the work they can measure. That retreat is what stalling looks like from the outside. And there is one more visitor at the threshold, arriving precisely when you are most capable. In Korn Ferry's 2024 survey of 400 chief executives, 71 percent reported experiencing imposter syndrome. Competence does not protect you from it.

So let me say plainly what I have come to believe after thirty-five years of walking alongside both parishioners and leaders. The discomfort of honest self-examination is not a problem to be solved. It is the doorway.

Where to start

Ask yourself two questions and answer them honestly. Which passage am I operating in? And what am I still holding onto that served me before and limits me now, in this moment?

Then take one action, not five. The passage you are in will tell you which one.

Four things to hold
01Earlier promotions were granted on evidence. This one is granted on judgment, which is why the feedback feels vague.
02Four passages, and each one asks you to put down the source of value that got you here.
03You can hold the title of the next passage while running the habits of the last one. Check your calendar, not your title.
04The stretch where you feel less useful is the crossing itself, not a sign you have failed.
Bill Dickinson Bill Dickinson, D.Min., RCC Founder and Managing Partner, C3 Leadership

Thirty-five years spent alongside leaders in hard moments, first as a pastor and now as an executive coach. Author of Optimizing Self, second edition, September 2026.

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