Latest / Lead With Clarity: Practical Insight for Senior Leaders / The Price of Good Judgement
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. It's not noise. Just clear thinking for the journey of leading well. Today's episode is entitled The Price of Good Judgment. Here we go. There's a quote that I really like, not because it's clever, but because it's uncomfortably accurate. Will Rogers said it best. He said good judgment comes from experience and a lot of that comes from bad judgment. He's not being cynical. He's being precise. We spend a lot of time in leadership circles talking about experience as a credential. Years in the seat, industries navigated, teams built, and yes, all of that matters. But Rogers is pointing at something most leaders quietly avoid. The experience that actually sharpens you is not the wins. It is the losses you were willing to sit with. Will Rogers, American humorist, actor, social commentator, a man who had a remarkable gift for cutting through pretense with that single sentence. Good judgment comes from experience and a lot of that comes from bad judgment. Simple, devastating, true. Think about the most consequential decisions you've made in your career. Not the ones you're proud of, but the ones that kept you up at night. The ones that you look back on and wince. Now ask yourself honestly. How much of your current judgment, your instinct for people, for timing, for risk, was forged in those moments? I've worked with executives who carry one bad hire from 15 years ago as a permanent lesson. Not a wound, but a reference point. They learned something in that failure that no training could have taught them. They learned what they tend to miss. They learned their own blind spots. And that knowledge made them sharper. Here's where leaders get this wrong. They think the lesson is to avoid bad judgment, to be more careful, more deliberate, more guarded. So they slow everything down. They overanalyze. They create committees where a call should be made. They mistake caution for wisdom. But Rogers is not saying be reckless. He's saying be honest. The misread is thinking the goal is fewer mistakes. The real goal is better learning from the ones that you make. Good judgment is not the absence of bad judgment. It is the accumulation of reflected upon bad judgment. There's a meaningful difference between a leader who has made 10 poor decisions and learned from all of them and a leader who has made two poor decisions and buried both. Years in the seat don't guarantee anything. Deliberate review does. The leaders who develop the sharpest instincts are not the ones who have been the most successful. They're the ones who have been the most honest. Honest about what went wrong. Honest about their role. in that failure, honest about what they would do differently. Most organizations and most leaders are far better at celebrating the win than studying the loss. We do after action reviews when something fails spectacularly. We almost never do them for the quiet decisions that drifted sideways over months. And that asymmetry can be quite expensive. So here's what I want you to carry into this week. Think of one decision from the past year that you have not fully examined. Not the most dramatic one, maybe a hiring call, a budget allocation, a conversation you avoided, a direction you held too long. Pick one and spend 20 minutes with it. Not to assign blame, not to replay what could have been, but to ask three questions. What did I know? What did I assume? And what would I do differently now? That exercise done consistently is the difference between experience that accumulates and experience that compounds. One just adds time, the other adds precision. Will Rogers was reminding us that wisdom is not given, it is earned through a specific kind of courage. The courage to look back without flinching, the courage to name what you got wrong, the courage to carry that into the next decision without letting it become fear. Good judgment is built, not bestowed. And most of the building happens in the moments that we would rather forget.