A few years ago I started working with a VP of Sales who was convinced his team loved him.
Great energy. Always available. Open door, literally and figuratively. He told me in our first session that 1-on-1s were one of his strengths.
So I asked his team.
The feedback was almost identical across all seven of them.
"He talks the whole time.""I leave with a to-do list — but it's all his ideas, not mine.""I never really know if he actually heard me."
He wasn't a bad leader. He was a genuinely caring person who wanted to help. But somewhere along the way, 1-on-1s had become a place where he performed leadership instead of practiced it.
That's more common than most leaders want to admit.
The problem usually isn't bad intentions. It's no structure. When you have no framework walking in, you fill the space — with updates, advice, your own stories, your own solutions. And the person sitting across from you leaves feeling managed instead of developed.
Over the years I've landed on six questions that fix this completely. I've used them with founders, VPs, and first-time managers. The framework is almost embarrassingly simple. But simple is what actually gets used.
YOU—"How are you?"
Don't skip this. Before you touch targets, projects, or problems — check in with the actual person in front of you.
Leadership isn't just about delivering results. It's about developing people. When you ask this genuinely and actually listen, you often uncover the conversations that matter most. Struggles at home. Something weighing on them. Something that's been sitting unsaid for weeks.
Most leaders rush straight to the agenda. Always start with the person.
CELEBRATE—"What's gone well since we last spoke?"
Progress deserves attention.
Too many leaders only talk about what's broken. The problem with that is people stop believing their best work gets noticed. When you ask this question, you give someone permission to talk about what's going well. You get to catch them doing something right. You reinforce what you want to see more of.
Never underestimate the power of a leader who actually celebrates.
CHALLENGES—"What's your biggest challenge right now?"
Before a problem can be solved, it has to be named.
Too many people feel pressure to project that everything is fine. Your job is to create a space where they don't have to. Where honesty isn't a risk.
This question isn't about finding problems. It's about teaching people to face reality — and to do it without shame.
DOING—"What are you doing about it?"
Resist the urge to fix it for them.
I learned this the hard way with my own kids doing homework. I kept giving answers. They kept coming back. I wasn't helping them learn — I was making myself the solution to every problem. Leadership works exactly the same way.
Your job isn't to have all the answers. It's to develop people who can find their own. When you ask "what are you doing about it?" something shifts. Ownership increases. Confidence grows. The dependency stops.
HELP—"How can I help?"
By the time you reach this question, they've often already figured out what they need. Which means you've already done your job.
But when they do need something — listen carefully. Sometimes it's a resource. Sometimes it's an introduction. Sometimes it's simply hearing you say you trust their judgment.
The goal isn't to rescue. It's to enable. There's a big difference between the two.
NEXT—"What's the next step, and when will you take it?"
Every good conversation should end with clarity.
Not a vague intention. A commitment. A date. A specific action.
Without it, even the best 1-on-1 just becomes another meeting that felt good in the room and disappeared by Thursday.
Six words:YOU. CELEBRATE. CHALLENGES. DOING. HELP. NEXT.
Simple enough to remember. Powerful enough to change how someone experiences being led.
Because the best 1-on-1s aren't about the leader having all the answers. They're about helping someone think more clearly — and leaving the conversation with more confidence than they walked in with.
That's what leadership development actually looks like up close.
