How do you coach an employee to take more initiative?

Stop giving the answer. When they bring you a problem, hand it back with a question: "What’s one decision you can make right now without me?" or "If this were yours alone, how would you handle it?" Do this consistently and they learn that you expect them to move — which is how initiative is built, not instructed.

The leadership hack · a 1-on-1 cheat sheet

Leadership coaching questions

Q: What are good leadership coaching questions?

The best coaching questions push a person to think and act rather than wait for an answer. Organize them around three traits that predict leadership: Initiative ("If you weren’t waiting on me, what would you do first?"), Applied Grit ("What’s the next hard part you’re willing to stick with?"), and Learnability ("What did you learn that you’ll do differently next time?"). Each takes under a minute and changes how your people show up.

Q: What questions should I ask in a one-on-one?

Skip the status update — they can send that in writing. Use the one-on-one to coach: ask what their next step is, what decision they can make without you, what hard part they’re willing to stick with, and what they learned from something that didn’t work. Questions that hand the problem back build leaders; questions that gather status build followers.

15 copy-ready prompts that coach the three traits that actually predict leadership. Tap any question to copy it into your next one-on-one.

By James Carter · Updated July 2026

The short answer

Most leaders coach skills and ignore the behaviors that make or break a person under pressure. Coach these three instead: Initiative (do they act, or wait to be told?), Applied Grit (do they push through, or stall?), and Learnability (do they grow, or repeat mistakes?). Below are 15 ready-to-use questions — five per trait. Each takes under a minute in a 1-on-1, check-in, or hallway conversation, and it changes how your people show up.

How to use it: pick the trait you want to build in someone, ask one question, then stay quiet. The power isn’t in the question — it’s in resisting the urge to answer it for them. Hand the problem back and let them carry it.

Free · no email required · print it and keep it where you have your 1-on-1s.

Trait 1 of 3

Initiative

Push them to act without permission. Do they see the work that needs doing — or wait to be told?

Trait 2 of 3

Applied Grit

Build resilience and follow-through. Do they push through when it gets tough — or stall out?

Trait 3 of 3

Learnability

Turn every step into growth. Do they grow from each challenge — or just repeat mistakes?

Coaching your people starts with coaching yourself.

Take the free Leadership Scorecard — it shows whether your leadership is building your team or bottlenecking it, in about four minutes.

Take the Leadership Scorecard →

Want these three traits scored across your whole team?

These prompts help you spot Initiative, Grit, and Learnability one conversation at a time. Prove measures them across everyone — a color-coded view of who’s ready to lead, before you have to guess.

See what Prove measures →

Turn better questions into better leaders.

A Calibration Call is 15 minutes. Bring the one person you’re trying to develop and we’ll show you exactly how to coach the trait that’s holding them back — whether or not we work together.

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Straight answers

What are good leadership coaching questions?

The best ones push a person to think and act instead of waiting for the answer. Organize them around three traits that predict leadership: Initiative (“If you weren’t waiting on me, what would you do first?”), Applied Grit (“What’s the next hard part you’re willing to stick with?”), and Learnability (“What did you learn that you’ll do differently next time?”). Each takes under a minute.

What questions should I ask in a one-on-one?

Skip the status update — that can be written down. Use the time to coach: ask what their next step is, what decision they can make without you, what hard part they’re willing to stick with, and what they learned from something that didn’t work. Questions that hand the problem back build leaders; questions that gather status build followers.

How do you coach someone to take more initiative?

Stop giving the answer. When they bring you a problem, hand it back: “What’s one decision you can make right now without me?” Do it consistently and they learn you expect them to move — which is how initiative is built, not instructed.

Keep reading

The Leadership Scorecard Are you building your team, or bottlenecking it? Find out in 4 minutes. The Mindset Gym Short workouts that build the mindset behind the coaching.

About the author

James Carter

Founder of Be Legendary and creator of the Flag Model™. Twenty-five years inside executive teams; co-author alongside Stephen Covey, Ken Blanchard, Deepak Chopra & Brian Tracy, and featured on CNN and in Business Insider. More about James →

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