Have you ever watched a brilliant leader shoot down a good idea, not because the idea was bad, but because challenging it was the only way they knew how to add value?
I worked with Jeff, the CFO of a life insurance company who was, by any measure, exceptional at his job. Nobody in the building understood the numbers better than he did. Give him a set of numbers and he could see three moves ahead of everyone else in the room. That skill had carried Jeff from analyst all the way up to finance leader, and along the way he’d built a habit that served him well at every level except the one he was in now: he went straight to solution. Someone raised a problem, and before they finished the sentence, Jeff already had the answer, plus the four things you hadn’t thought of yet.
Being Right Can Cost You Dearly
That habit came from somewhere real. Jeff had spent years being the smartest person on the numbers, and as he moved further from hands-on analysis and into an executive role, he was quietly fighting to feel like he still mattered. Underneath that, honestly, was something most of us carry around without ever naming it: the fear of not being enough. If his value had always come from having the sharpest answer in the room, then stepping back and letting someone else take the lead felt like becoming less relevant, maybe even less needed.
What Jeff hadn’t figured out yet is that a leader’s value doesn’t come from being the smartest person in the room anymore. It comes from bringing out the best in everyone else on the team. Instead of learning that, he kept doing the thing that had always worked for him: he found the flaw first.
That instinct came to a head when the revenue team pitched an idea to grow new business: give customers who opened a new policy a little extra coverage at no additional cost. Honestly, it wasn’t a bad idea. Bigger national carriers already did versions of this. But it needed some real work behind it, some numbers, some guardrails, a real sense of whether it would actually hold up for a company their size.
Instead of bringing that up in the room out of curiosity, Jeff went home and fired off an email with about twenty questions in it. Every single one started with some version of, “but have you thought of…?” Each question was fair on its own. Put together, though, the message the revenue team heard was: you didn’t do your homework, and I caught it.
The Wrong Way to Add Value
That’s when Jeff started coaching with me. We didn’t spend much time debating whether his critiques were right, most of them were. Instead we talked about what he actually wanted to have happen next, and whether a twenty question email was going to get him there. It wasn’t. All it was going to get him was a revenue team that either stopped bringing him ideas at all, or only brought him the safest ones they knew he couldn’t poke holes in.
We talked about the difference between being a critic and being a mentor, and what gets lost when every conversation turns into a test of whether someone thought of everything you would have thought of. Knowing the numbers better than anyone and actually being useful to your team, it turns out, aren’t the same thing.
The CFO knew the numbers cold. What he hadn’t shown the revenue leader yet was that he actually cared whether she too succeeded. There’s a line, often credited to Teddy Roosevelt, that captures this well: “No one cares how much you know until they know how much you care.” That’s the real value of human connection, and it’s why I tell clients all the time, relationship first, task second.
No One Cares How Much You Know…
So instead of sending another email, Jeff picked up the phone and asked for a face to face meeting. He opened the conversation simply: help me help you. Then he asked the revenue leader to walk him through her thinking, not so that he could correct her, just out of real curiosity. That one shift, choosing connection over another round of correction, changed everything. The revenue leader opened up about why she’d landed on the idea in the first place, and the two of them started working through the rough spots together. What came out of it was a stronger strategy than either of them would have built alone.
It also produced something that email never could have: a revenue team that felt like they’d built the strategy themselves, instead of being talked into it. That difference matters more than people think. An idea people are talked into tends to fall apart the moment things get hard. An idea people helped build gets defended and improved, because by then, it belongs to them too.
This pattern shows up constantly with technical experts who move into bigger leadership roles. The instinct that made them valuable, catching what’s wrong before anyone else does, doesn’t just disappear because their title changed. It has to be redirected. Their true value isn’t about having the sharpest answer in the room anymore. It’s about bringing out the best answer in everyone else, and helping the whole team succeed together.
So if your most capable leader keeps finding the holes in every idea before anyone gets a chance to develop it, ask yourself what they’re really afraid of losing if they mentor instead of correct. Chances are, it’s less about the numbers, and more about wanting to know that they matter.
