Most leaders end conversations with action items.

But the best ones end with insight.

After one coaching conversation, Rachel had come full circle.

From overwhelm to awareness. From guilt to clarity. From overcommitting to redefining what it means to contribute meaningfully.

She named what was really on her mind.

She explored the deeper patterns.

She saw what her yeses were costing her.

She reclaimed what she truly wanted.

And she asked for the kind of support she actually needed.

We’d covered a lot. And before we closed, I asked one final question:

“What was most useful for you today?”

She paused—thoughtfully this time.

Then said,

“It wasn’t just one thing. It was being asked questions that made me think differently. I came in feeling stuck, and I’m leaving feeling seen. I know what I need to do—but more than that, I know why. And I don’t feel like I’m carrying it all alone anymore.”

That moment reminded me why this matters.

Not just for the person being coached—but for the person doing the coaching.

Because real leadership isn’t about being the smartest person in the room.

It’s about asking the questions that help others find their own clarity.

Why this question matters

This is the Learning Question, and it’s one of the most powerful coaching tools you can use.

Michael Bungay Stanier reminds us: People don’t learn when you tell them something. They learn when they reflect on what just happened.

Asking “What was most useful for you?” does three things:

• Reinforces the value of the conversation

• Anchors learning in their own words

• Makes insight more memorable—and actionable

 It’s not about fishing for praise.

It’s about giving someone the gift of self-recognition.

When and how to use it

Use “What was most useful for you?”:

• At the end of a 1:1, coaching session, or feedback conversation

• When you sense the person has discovered something

• When you want the learning to stick

Even if the answer is small—“just being listened to”—it matters.

It turns a moment into a takeaway.

With Rachel, it wasn’t a checklist or solution that shifted her.

It was feeling seen, supported, and given the space to think for herself.

Why it matters:

Growth doesn’t come from advice.

It comes from awareness.

Asking this question builds a habit of reflection.

It teaches people to value insight, not just instruction.

And it reinforces the kind of leader you’re becoming—curious, present, and committed to drawing out the best in others.

Your Turn:

Before your next conversation ends, try this:

“What was most useful for you?”

Then listen.

The answer might surprise you.

And the impact might outlast anything you planned to say.

Next week on Wisdom Wednesday:

We’ll wrap up this 7-part series with a full reflection on Rachel’s journey—and explore how these deceptively simple questions can reshape the way you coach, connect, and lead with intention.

#LeadershipDevelopment #TheCoachingHabit #CoachingMindset #GrowThroughLeadership #LeadToLearn #WisdomWednesday