I've had a lot of great bosses in my career.

People I respected. Learned from. Genuinely enjoyed working for.

If I'm honest, I've been unusually lucky on that front.

But if I ask a different question — not who was good, but who actually changed the trajectory of my career — the list gets very short.

It was two.
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What set them apart was not that they made work easier. It was that they moved me further, faster than I would have gone on my own.

The First Was Early

My first role out of McKinsey. I stepped into a job where I was suddenly responsible for functions I had no background in. IT. Marketing. Programming. Patient advocacy.

I remember thinking: I don't actually know how to do most of this.

She didn't try to close that gap for me. No slow ramp. No careful staging of what I was given.

It was more direct than that.

This is your job. You can do this. Figure it out.

And I did.

Not perfectly. Not without mistakes. I learned things the hard way, sometimes the very hard way.

But I always felt supported while I was doing it. My credibility wasn't on the line. My career wasn't hanging by a thread.

The stretch was real. And the growth didn't feel optional. It felt inevitable.

The Second Was Much Later

I was leading Medical Training for a biopharma company at the time. He wasn't my boss yet, but he had seen what I built and said, in effect:

You’ve made learning a competitive advantage for Medical. Now come do it for the entire company.

All therapeutic areas. All geographies. All employees.

Then he put me in a room with the executive team and made it my problem to solve.

I had never operated at that level before. These were not people I had worked closely with. Now they were my stakeholders, my sponsors, the people whose time, money, and credibility I needed to win over if this was going to work.

There was no playbook.

This is yours. Go figure it out.

And again, I did.

What They Had in Common.

Those two leaders could not have been more different in style and temperament. But both gave me work that exceeded my current self-concept — and expected me to grow into it.

They changed what I believed I was capable of.

Not in a motivational sense. In a practical one.

I had taken on work I was not fully ready for when I started. And I figured it out. I learned to operate with more scope, more ambiguity, more visibility, more consequence.

So later, when I stepped into C-level roles, the confidence wasn't something I had to manufacture.

It was built.

Not Every Good Leader Leads This Way

That does not mean every good leader should lead this way all the time.
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Some of the best leaders I worked for gave me something different. They trusted me. Backed me. Made the work better. Made the day-to-day more manageable.
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At certain points in my career, that was exactly what I needed.

By the time I reached my last CPO role, I was not looking to be stretched in the same way I had been earlier. I was already operating at an executive level.
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What I needed then was different: trust, authority, partnership, and room to do the job I had already grown into.

That mattered too.

So this is not a hierarchy.
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It isn't an argument that stretch is always better, or that every great leader should be pushing every person into discomfort all the time.

It's a more specific distinction than that.

And that is where leaders can get this wrong.

When Stretch Leadership Looks Like Bad Leadership

Part of the reason is that stretch leadership can look, from the outside, like a leader is not doing their job.

They hand someone a problem that is too big, too visible, too messy. There are no detailed instructions. No cleaned-up path. No guarantee it will go smoothly.

To a lot of leaders, that feels irresponsible. Am I setting them up to fail? Am I asking them to do something I should still be doing myself?

Sometimes, yes. But not always.

Sometimes the leadership move is to hand over the real problem before it has been simplified or solved halfway in advance.

Not because you are disappearing. Because you are leading differently.

You are still there — watching, coaching, helping them think, making sure they do not break trust or create avoidable damage. But you are no longer doing the hardest part for them.

That is what makes it leadership rather than abdication.

And when leaders do too much easing, absorbing, smoothing, and protecting, teams can perform well while people quietly stop growing.

You usually do not see the problem until later — when someone is asked to step into a bigger role and finds they have never had to build that muscle.

Some leaders make work better. Far fewer expand what their people believe they can do.

This Month's Experiment

Pick one person on your team who may be ready to operate at a bigger level than their current role requires. Someone capable. Trusted. Someone whose role may have become a little too comfortable.

Ask yourself:

• Where am I regularly resolving something this person could learn to work through themselves?
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• Where am I giving answers when I could give context instead?
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• What access—to a room, a decision, a harder problem—have I been holding back because it feels easier or safer if I handle it myself?

Then make one move.

Bring them into a conversation they wouldn’t normally be part of. Hand them a problem before you’ve shaped it into something neater. Let them wrestle with a question you would usually answer.

Then watch.

Not just what happens to the work.

What happens to them.

The Bottom Line

I've had a lot of bosses I was lucky to work for.
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Only two changed the trajectory of my career.

What they gave me wasn't comfort — though I felt supported. It wasn't autonomy alone — though I had room to operate.

They pushed me further, faster than I would have gone on my own.

That stayed with me long after I moved on.

The leaders who gave me something different mattered too — but for different reasons, at different stages.

Which is why the real question is not just whether you are a good boss.

It is what your leadership is making possible in the people who work for you.

Because people do not just remember what they did under your leadership.
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They remember who they became because of it — and what it made them believe was possible after you.

Warmly,
Angela
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👉 Had a boss who changed the trajectory of your career? Or know one who still could? Share this with them.
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​P.S. My recent BioSpace article looks at the other side of this dynamic: When a Good Boss Is Bad for Your Career.