Why Your Best Coaching Questions Aren’t Changing Anything
Happy Wednesday. This one is for those of you who are trying to develop your people and can’t figure out why it’s not landing.
A VP told me last week that her one-on-ones feel like interrogations. She’s trying to develop her people. She’s read the books. She’s asking questions. But every conversation follows the same script in her head, and her direct reports can feel it.
I sat in on one. She asked a solid coaching question: “What do you think is getting in the way?” Her direct report started answering, and about ten seconds in, I watched her eyes shift. She was already preparing her next question. She missed the most important thing he said. He said, “I think part of it is that I don’t really know what success looks like here.” She heard it as a process problem and moved on to goal-setting. What he was actually saying was that he felt lost and didn’t trust her enough to say it directly.
If your development conversations feel productive but nothing changes afterward, the issue might not be what you’re asking. It might be that you’re so focused on asking the right question that you’re not actually hearing the answer. The best coaching conversations aren’t built on frameworks. They’re built on genuine curiosity, the kind where you stop planning your next move and let yourself be surprised.
What got me about that moment in her office was how close she was. She had the framework down. The question was textbook coaching. But the second she heard ten seconds of the answer, something in her brain said “okay, I got it, what’s next.” She wasn’t curious about what he was actually saying. She was curious about how to move him toward the answer she already had in mind.
After we debriefed that session, she asked me what the solution was. I told her the truth: there isn’t one. Not a tool, anyway. Curiosity’s not something you install. It’s a choice you make fifty times in a thirty-minute conversation to actually listen instead of plan. To sit with the confusion instead of jumping to the fix. To let yourself be surprised by what someone says when you’re not already three steps ahead.
I’ll tell you what confused me at first about this work. Leaders who struggle with genuine curiosity aren’t people who don’t care about their teams. They’re usually people who care too much, who’ve already figured out what their people need before the people figured it out themselves. They’re trying to be helpful. The problem is, that kind of helpfulness trains people to stop thinking. Why would you work through a problem when your boss already knows the answer? So the person stops bringing you their real thinking, and all you’re left with is the script they think you want to hear.
If you’re in the middle of something that one conversation can’t resolve, that’s the kind of work I do with leaders one-on-one. Not advice. Pattern recognition applied over time, so the pattern doesn’t just get named, it gets rewired. Reply to this email if you want to talk about what that could look like.
This week’s read is an article that I find useful: Humble Inquiry by Edgar Schein (Psych Safety). Schein talks about a thing called “humble inquiry,” which is basically asking questions because you genuinely don’t know the answer, not because you’re trying to guide someone toward your solution. It’s short and specific, and it’ll change how you listen in your next one-on-one.
Photo by Andrew Ridley on Unsplash
If you’re thinking about what to ask next, you’re not coaching. You’re performing. Your team knows the difference.