Latest / Lead With Clarity: Practical Insight for Senior Leaders / Let Them Fail, Not Be a Failure
Transcript
- Blake Holman: Welcome to Lead with Clarity. This is a space for leaders who want to grow without losing themselves in the process. Each episode is a short reflection on leadership, influence, and the inner work that shapes how we show up for others. It's not hype, not noise, just clear thinking for the journey of leading well. Today's episode is entitled Let Them Fail, Not Be a Failure. Here we go. There's a sentence from General Stanley McChrystal that I come back to periodically. He said, Leaders can let you fail and yet not let you be a failure. There are two different verbs doing very different work let you fail and not let you be a failure. Those are not the same permission. The first is about outcomes, the second is about identity. And the gap between those two things is where a lot of leadership either succeeds quietly or it fails loudly. Think about the moment right after something goes wrong on your team. Project misses its number, or Client call goes sideways. A decision that seemed reasonable in the room turns out to be wrong once it meets reality. What happens in the ninety seconds after that moment is often more important than anything that happened before it. In those ninety seconds, a leader is either separating the failure from the person or fusing them together. Here's the common misread. A lot of leaders think that letting people fail is itself the hard part. That the courage is in stepping back, giving some rope and Resisting the urge to swoop in and fix it. And that is real. That is hard. But it's only half of McChrystal's sentence. The harder half, the half that gets skipped, is what you do with the person once the failure has already happened. There's a version of letting people fail that quietly turns into letting people be defined by their worst outcome. You stop inviting them to the next big thing. You start hedging when their name comes up. You never say it out loud, but the message lands anyway. That mistake is now who you are around here. The reframe McChrystal is pointing at is that failure and failure as identity are two separate events, and a leader's job is to make sure the first one never quietly becomes the second. That does not mean lowering the bar, it does not mean pretending the miss didn't matter, or skipping the honest conversation about what went wrong. Real accountability and real dignity are not in tension with each other. In fact, the leaders who are best at holding people accountable are usually the same ones who are best at making sure accountability never slides into shame. They can look someone in the eye and say, This didn't work. We need to talk about why, and in the very next breath make it unmistakably clear that this one outcome does not change how they see that person's future here. That's a harder skill than it sounds like. Because our instinct under pressure runs the other way. When something breaks, the fastest emotional shortcut is to attach the failure to the person who was closest to it. It's faster to say he's not cutting it than to sit with this was a hard situation, he made a reasonable call, and it didn't land. The first resolves the discomfort quickly. The second requires you to hold complexity, and complexity is uncomfortable. That's exactly the discipline McChrystal is describing. Leadership and At its best, is the willingness to hold that complexity so your people don't have to carry it alone. Now, there's a place where this gets even more relevant as decision-making tools keep getting smarter and faster. It's easier than ever to run the numbers, model the scenario, and know in hindsight exactly where a call went wrong. That kind of clarity is genuinely useful. But clarity about what happened is not the same as judgment about what someone deserves because of what happened. No system tells you whether a mistake was a lapse in judgment or a reasonable bet that didn't land. No dashboard tells you whether someone needs a hard conversation or a vote of confidence. That reading, that judgment about a person's character and trajectory, still belongs entirely to the leader in the room. So here's what I'd carry forward from this one. The next time someone on your team fails at something, notice which sentence you reach for first. Is it about the outcome or is it about them? The leaders that people remember, the ones they'd run through a wall for, are almost never the ones who never let anyone fail. They're the ones who made failures survivable, who made it clear that a bad quarter, a blow call, a project that didn't land, was information about a moment, not a verdict on a person. Let people fail, that's how they grow. Just don't let them walk away believing the failure is who they are. Yeah.