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., –