What Got You Here Won’t Get You There

I once had vertigo. It started on a flight and didn't end until my ears finally repressurized on another flight a month later. Before I ever experienced it myself I didn't understand it, I figured a little dizziness was no big deal. What I didn't know was the 3am wake-ups, that sick feeling in your stomach, the deliberate staring at a fixed point on the wall just to cross a room.

There's another kind of vertigo that comes with a promotion.

One day you're the person who gets things done. The next day your job is to make sure other people get things done. It's thrilling, a bit unnerving, but nobody tells you the unsettled feelings. No one tells you these are different jobs. Nobody warns you that the skills that earned you the promotion are the same ones you'll need to set aside.

Marshall Goldsmith named this pattern in his book of the same title. What he observed in senior executives, I've watched play out in nonprofits and public sector organizations for more than twenty years: the transition isn't about adding new skills. It's about recognizing which old ones are now working against you.

The shift no one names

When you're a manager, your job is to know how to do the work. You master the process, model the standard, execute well. That speedy skillful competence is what is visible and rewarded.

When you become a director, your job changes. You're no longer responsible for knowing how to do everything. You're responsible for evaluating whether the people you lead know how to do it - and for creating the conditions that let them find out.

That's not a small shift. For most leaders, it's a complete reorientation. I've learned this lesson in both directions.

When you step in too fast

I was responsible for a leadership training school. We'd brought in a guest speaker for a session, and somewhere in the first twenty minutes, I started to feel the room going flat. People were disengaging. I could see it.

As a facilitator, I have a strong instinct to move when I see any sense of boredom. I wanted to reframe, redirect, try something different. My head was firing with great ideas. During the break, I went to my program manager and started throwing out options. How we could shift the session. What we could try in the afternoon. I kept going, kept offering new angles.

He paused. Then he said: Mark, I just need time here. This is just too much. I can't take everything that you're doing so quickly. I need some time to adapt.

I thought he didn't understand what I was offering. Looking back, I was the one who didn't understand. I had inserted myself into a situation that wasn't mine to solve. My program manager was smart, he had already seen the problem and needed to find his own footing. My job was to give him the conditions to find his own balance, not to flood him with my solutions before he'd had a chance to form his own.

When someone gives you a room

Years earlier, I was the one who needed the room. I was preparing to lead an experiential session for several hundred people at a seminar. The night before, I showed my director what I had. He looked at it. He said: I think it's okay. But I think you can do better.

That was all he said. No explanation. No suggestions. No examples of what better might look like. He left me with the question.

I stayed up most of the night working. I turned the problem over and over. And sometime in those hours, something shifted. I had a breakthrough. An insight about how to design an experience, something that I had never seen before. I built something new that night. I used that activity for the next ten years.

He could have told me what to do. He had the experience. He almost certainly saw a way through. Instead, he gave me a room and trusted me to find my way through to the audience.

When you try to solve someone's problem, you take away their opportunity for innovation and creation. It feels like kindness. But it's harming both of you. It shrinks the capacity of people to grow, and shrinks your role from leader to fixer.

Managers perfect themselves. Directors allow managers to perfect themselves.

Five shifts that matter

The manager-to-director transition isn't one change. It's a cluster of changes that happen at the same time, which is why it's disorienting.

From achieving to enabling. As a manager, you succeed by doing. As a director, you succeed by creating the conditions where others can do. This is the deepest shift. Many directors never make it fully. They keep running toward the technical fix because that's where they've always found their approval from others, it's where they feel confident. In doing so, they keep the people they lead from finding theirs.

From KPIs to North Star. A manager is responsible for the KPIs of their direct reports. They ensure that the targets are hit, the work is done on time, the budget is managed. A director is responsible for something upstream of that: setting the direction those KPIs are meant to serve, and making sure the work at every level is actually pointed at the right destination. The organization's energy can be fully engaged and still aimed at the wrong thing.

From internal to external. Managers focus inward goals, processes, and internal relationships. Directors have to hold the external view: how the work is perceived by stakeholders, partners, funders, and the communities you're trying to serve. That perspective doesn't diminish the internal work. It gives it a reference point.

From yes to no with judgment. Managers succeed by staying engaged with everything. Their job is to keep wheels turning, keep people moving, keep problems from piling up. Directors who try to do the same thing burn out, or worse, they make themselves the bottleneck in every decision. The transition to director requires learning to say no with judgment: to distinguish things that require your presence from things that require your trust.

From doing to directing. This one is hardest to name because it doesn't feel like leadership. It feels like stepping back. But a director who is constantly in the execution is a director who has no capacity left for the work that only a director can do: scanning the horizon, reading the pressure patterns, making the calls that require a different vantage point.

The particular pressure of mission-driven work

I want to say something honest about the nonprofit and public sector context, because the transition is harder here.

The CanadaHelps Giving Report 2026 found that more than two-thirds of Canadian charities reported increased demand for their services — even as the donor base funding them continued to narrow. Donors want measurable outcomes. Financial pressure is constant. The system asks for more with less, year after year.

In that context, the "step back and enable" instruction sounds like a luxury. It doesn't feel like leadership. It feels like watching things break.

I remember sitting at a team retreat early in my time as an executive director. I asked everyone to share what they were looking forward to in the months ahead. Program launches. End of a difficult cycle. When my turn came, I realized what I was actually hoping for: a nondescript Wednesday in the fall when I get to the office and there's no crisis in front of me. I'll just do a regular day's work and go home.

That was what I looked forward to. Not a win. A normal day.

The pressure we operate under comes out in different ways. Some leaders just work harder, believing that if they stay long enough and arrive early enough, eventually they'll find the answer. Some push their teams more. Some leave the sector entirely.

What I've seen in effective directors is something different: they recognize reality without pretending it doesn't exist. They identify the coping mechanisms they're using and make explicit trade-offs. If they hold excellence as a core value, and most of them do, they recognize there are moments when the system can't hold that value right now. That's not surrendering the value. That's choosing a pathway that keeps the team sane so the value can be expressed more fully later.

That kind of judgment doesn't come from doing more. It comes from seeing clearly.

The self-test

When something goes sideways on your team, what's your first instinct?

If the answer is to step in and solve it ... to take the problem into your own hands because you know you can fix it faster, cleaner, more reliably? You're still operating as a manager. That instinct served you well. It's not wrong. But it's not the director's job.

The director's job is to ask: what does this person need so they can find their own way through this? Sometimes that's a question. Sometimes it's a boundary. Sometimes it's what my director gave me the night before that seminar ... a short statement of confidence and the space to figure it out.

I think you can do better.

Not: here's how. Just: I believe you can.

That's the room. Learn to give it.

If you're in the middle of this transition and you want a clearer picture of where you're carrying the most pressure, the Stopover Leadership Check-In is a good place to start. It won't tell you what to do. But it will help you see the pattern.