When I Put My Team Somewhere They Had No Business Being

2021 was the year my best team almost quit. Not because the work was too hard. Because the work was the wrong kind of hard, and I had put them there deliberately, despite being told twice that I was making a mistake.

That detail matters. This wasn’t a miscalculation born of ignorance. Their manager came to me with specific concerns. I listened, acknowledged his point, and changed nothing. Which is either evidence of considered leadership or a fairly confident act of institutional recklessness, depending on which week you ask me about.

What happened next is the part I return to. Not the outcome, it went better than anyone, including me, expected, but the mechanics of what changed in those eight weeks, and why no training program I’ve ever seen could have produced the same result., –

The Situation

The context was a cross-border regulatory implementation. Five jurisdictions, compressed timelines, the usual chaos that attends anything involving multiple regulators who technically harmonized their frameworks but practically agree on very little.

I made the call in the commercial negotiation. Two compliance leads, genuinely excellent at their work, technically rigorous, professionally credible, were assigned to a room where the currency wasn’t regulatory precision but commercial positioning. Different instincts required. Different language spoken.

Their manager’s concern wasn’t unfounded. These were professionals whose careers had been built on structured frameworks, defined parameters, and the confidence that comes from knowing exactly what the rules say. I was handing them a situation where the rules were being written in real time by the people across the table.

By week four, they were struggling. Not failing, there’s an important difference, but clearly operating in a way that cost them more energy than the same effort would have in a familiar environment. They were translating. Converting commercial signals into regulatory logic and back again, in every meeting, in every conversation.

By week eight, they had stopped translating. They were reading the room directly., –

What Actually Happened

The first thing I noticed was how they handled ambiguity. In a regulatory environment, ambiguity is a problem to be resolved, you find the rule, apply the rule, document the application. In a commercial negotiation, ambiguity is often a tool. The other side uses it deliberately. Learning to recognize that distinction, and then to use it yourself, isn’t something you develop from a course on negotiation frameworks.

They developed it by being in the room without a script long enough that improvising became the only option.

The second thing, and this is the part that stayed with me, was how it changed the way they thought about risk. Compliance professionals are trained to see risk as something to be mitigated, disclosed, or avoided. Commercial negotiators see risk as something to be priced. Neither view is wrong. But someone who can hold both simultaneously is genuinely rare, genuinely valuable, and almost impossible to hire for because most hiring processes sort for one or the other.

These two had been forced to carry both, in the same meeting, across eight weeks. The cross-wiring that produced wasn’t visible on any CV. But I watched it happen.

The third observation, the one I keep coming back to in conversations about team development, is what happened to their confidence. Not the surface-level kind that comes from positive feedback, but the structural kind: the understanding that they could be wrong, correct in real time, and still keep moving. That specific resilience is what I mean when I say discomfort builds range rather than confidence. Confidence is a feeling. Range is a capability. You can fake the first. The second only exists if it has been tested., –

What This Means

I’ve written before about the connection between strategic clarity and team ownership, the idea that people move with more precision when they understand the *why* behind a decision, not just the *what*. What 2021 added to that is a harder truth: sometimes the *why* can’t be shared in advance, because the person receiving it isn’t yet equipped to trust it. You have to earn their retrospective agreement by being right. And that means accepting that you might be wrong, and that the cost of being wrong lands on them first.

That’s an uncomfortable position for any leader who takes responsibility seriously. It was uncomfortable for me. The reflection I offer in *Final Reflections from the Front Lines of Finance* is that the decisions I most regret aren’t the bold ones, they’re the ones where I defaulted to safety on behalf of people who, given the choice, would have chosen the climb.

The ceiling on familiar territory is real. Most people can’t see it from where they stand because they’ve never been high enough in unfamiliar territory to look back and notice the difference in the view.

The implication for any organization trying to develop the next layer of leadership is this: your internal talent pipeline is being constrained not by ability but by assignment. The people who will surprise you most are probably sitting in rooms where they’re too comfortable being excellent at the thing they already know.

Put them somewhere they don’t yet belong. Stay close enough to catch a fall. Far enough that the climb is genuinely theirs., –
Comfort produces competence. Only discomfort produces people who eventually stop needing the net, and quietly start building one for someone else.