What Happens to Teams When You Force Them Outside Their Comfort Zone
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.
The Leadership Trap: Encouraging Without Holding Accountable
The Most Expensive Kindness in Leadership There is a particular kind of management failure that never shows up on a project dashboard. It does not trigger a red RAG status. Nobody logs it as a risk. It accumulates quietly, the way damp accumulates behind a wall, invisible until the structural damage is already done. We call it encouragement. And sometimes, that is exactly what it is. But sometimes it is something else: the comfortable avoidance of a necessary conversation, dressed up in the language of belief. I have been guilty of this. Most leaders I respect have been guilty of this. The instinct to protect someone’s confidence, especially someone with real potential, is not wrong. It becomes wrong when it outlasts the moment that required honesty., – The Situation Eighteen months into a critical data migration programme, this was 2022, mid-execution, the kind of phase where every slipped dependency costs you three downstream, we had a senior analyst who was, on paper, exactly what a programme manager wants. Sharp. Fast. Energetic. The kind of person who volunteers for the hard problems and makes the rest of the team feel that progress is possible. Her delivery estimates were also consistently optimistic. Consistently, measurably wrong. Not by catastrophic margins, no single miss looked disqualifying, but with a reliability that, in retrospect, was its own kind of pattern. A ten-day task would land in fourteen. A two-week dependency would take three. Each time, the explanation was credible. Each time, the team absorbed it with grace. What nobody did, and I include myself here, was name the pattern out loud. We celebrated her energy. We noted the delays privately. We did not connect the two in any conversation she was part of. By the time we did, three downstream teams had quietly stopped building her timelines into their plans. They had worked around her. Built in their own buffer, recalculated their dependencies, and said nothing, because naming it felt unkind, or risky, or above their pay grade to raise. She found out the way people always find out in these situations. Late, and from a direction she did not expect. When we finally had the direct conversation, her response stopped me. She said: *”I didn’t know it had that effect. Nobody told me.”* She was not defensive. She was genuinely surprised. And she was right to be, because we had collectively chosen comfort over clarity for eighteen months, and the cost of that choice had been charged to her account, not ours., – What This Actually Means The first insight is the uncomfortable one: the teams that worked around her were not protecting the programme. They were protecting themselves from an awkward conversation, and in doing so, they removed her ability to course-correct. When you route around someone without telling them, you are not managing risk. You are manufacturing a blindspot and handing it to a colleague as a gift. The second insight inverts what most people assume about accountability. We tend to treat correction as the opposite of belief in someone. The working assumption, rarely stated, frequently operative, is that raising a hard truth signals reduced confidence. In practice, the opposite is closer to true. Leaders who only affirm eventually build people who cannot process critical feedback when it finally arrives. And it always arrives. The longer it is deferred, the more it arrives not as a conversation but as a consequence. Accountability is not the withdrawal of belief in someone. It is the proof of it. The colleague you correct early is the one you still think can change. The one you quietly work around has already been written off, they just have not been told. The third insight is about timing, and it is the one I find most useful now. Encouragement and correction are not opposing forces on a spectrum that leaders must balance. They are the same act, performed at different moments. Telling someone they are doing excellent work and telling someone their estimation pattern is creating downstream risk are both forms of investment in that person’s future. The problem is that we have built a professional culture where the first feels natural and the second feels like a performance review conversation that needs to be scheduled, prepared for, and survived. That friction is artificial. We created it by treating directness as a special occasion rather than a baseline expectation., – What This Means for Your Organisation Most enterprise programmes have at least one version of this dynamic running silently in the background. Someone whose work is being quietly compensated for. A pattern that the immediate team has accepted as a fixed variable. A gap between what is said in one-to-ones and what is said in dependency planning sessions. The question worth sitting with is not whether this is happening on your team, it almost certainly is, but what it is costing the person at the centre of it. They are operating without accurate information about their own impact. They are being managed around rather than managed. And when the moment of reckoning arrives, as it will, they will have been deprived of the eighteen months of feedback that might have changed the outcome. The most generous thing you can do for someone with genuine potential is make the invisible visible, before the damage compounds quietly into distance., – Closing Encourage loudly. Correct early. Not because the second makes the first more credible, though it does, but because both are expressions of the same underlying belief: that the person in front of you is capable of more than the version of them you are currently protecting. The kindness that costs nothing to give is usually the kindness that costs the most to receive., –