The Leadership Mistake I Didn’t See Until I Became CEO

I want to tell you about a decision I got almost catastrophically wrong. Not a strategy decision. Not a financial one. A people decision. The kind that looks obvious in hindsight and anything but obvious when you're in it. I was the— because I was the MD, I'd done this before. I trusted my judgment and I was wrong. Here's what happened. And more importantly, here's what it taught me about the thing that actually separates good leaders from great ones. I was a managing director at Kolari. It was my first CEO role, and I was building the leadership team. We had a gap in the senior sales function, and we'd had it for a while. If you've ever been in that position, carrying a vacancy at the senior level while the business keeps moving, you know the pressure that builds. Then a candidate came through who looked on paper like exactly what we needed. He was a brilliant salesperson, had strong credentials, proven track record in precisely the area we're trying to grow. He'd done it before, what we're trying to do. Built from the ground up, hit significant numbers, and had the methodology to show for it. I interviewed him and I thought, this is the person. Everything I was looking for on the page, he had. Everything I asked him in the room, he He answered exceptionally well. So I sent him to Georgia. Georgia was our People and Cultural Manager. Sharp, experienced, exceptional with people. And she had something I didn't have at the time. She had a psychology degree. Georgia came back to me and said no. Not maybe. Not I have some concerns. Just no. She said he wasn't a cultural fit. That he was too brash, too out there, too cocky, and that he would clash with the rest of the senior team. And I pushed back. I'll be honest, I challenged her because everything I'd seen told me this person was the answer to a problem we'd been carrying for months. So I asked her to make the case. Give me the reasons. Walk me through it. And she did. Methodically. Factually. She went through exactly what she had observed. Not opinions, not feelings, specific observable behaviors and what they would mean inside our team. How he would land with this person, how he would conflict with that one, the specific dynamic he would create in the room. And she wasn't guessing, she was reading him accurately, precisely, with a kind of clarity that comes from generally understanding how people work. I sat there and I realized something. She could see something I couldn't see. Not because she was smarter than me, but because she had a framework for reading people that I didn't have. And in that moment, I had a choice. I could override her because I was the boss. The decision was mine, and I've been waiting to fill this role for too long. Or trust her, even though everything on paper pointed the other way. In the end, we didn't hire him. It wasn't easy. We kept carrying the vacancy, and for a period I wondered whether I'd made the right call. But then the right person came along. Different profile, not as immediately impressive on paper, but a genuine fit for the role, for the team, for the culture we were building. And it worked the way Georgia said it would work. Here's what I took from that experience. I'd been assessing that first candidate almost entirely on credentials, track record, methodology, what he'd done before. And all that was real. He probably was a brilliant salesperson. But credentials tell you what someone else has done. They don't tell you who they are. They don't tell you who they'll land, how they'll land. They don't tell you what will happen when they walk into a room with your senior team And the pressure is on. Georgia knew that instinctively. She'd been trained to look past the surface, to read the person, not the resume. I hadn't been, and I almost made a decision that could have cost us significantly as a result. I think about that moment often, particularly now, because here I am, 58, in the middle of a psychology degree. People ask me why. And part of the honest answer is Georgia. That conversation showed me that understanding people, genuinely understanding people, not just reading their performance data, is a skill, a learnable, developable skill. And it's one of the most important skills a leader can have. The higher you go, the more the job becomes about people, about reading the room, about knowing which person in front of you is telling you What you want to hear versus what you need to hear. About understanding who will perform under pressure and who will fold. And if you haven't developed that skill, if you're still leading primarily from the data and the credentials and the track record, you will make expensive mistakes. I was lucky. Georgia stopped me from making one of them. But she won't always be in the room, of course. The question is, when she's not there, what are you relying on to read the person in front of you? The best CEOs I've known— and I've known a lot of them through 30 years in the room and 14 as a Vistage Chair— are not just exceptional operators. They are exceptional readers of people. They know how to look past the performance and see the person. They know when something's off. is off before it shows up in the numbers. They know how their own presence lands, and they've done the work to make sure it lands the way they intend. That's not talent, that's development, that's interior work. And it's the work that almost never appears in leadership programs because it's harder to teach and harder to measure than strategy or governance. But it's the work that determines whether you become a great CEO or or just a capable one? I'm Greg Stevenson. That's what I work on privately with senior executives preparing for the top job. And if this conversation is live for you, the link is below. 30 minutes, no pitch, just an honest conversation with you. Thank you.