Leadership Coaching Questions: 24 Questions for Leaders on Vision, Influence and Themselves
Leadership coaching works at two levels: what the leader is trying to achieve in the organisation, and who the leader is being while they do it. The strongest questions move between the two — from the strategy to the pattern underneath it and back.
- Vision and strategy — 6 questions
- Influence and stakeholders — 6 questions
- The leader's own patterns — 6 questions
- Commitment — 6 questions
Vision and strategy
Clarify what the leader is really trying to build.
- “What are you trying to make true here that isn't true yet?”
- “If your team described your priorities, would they match yours?”
- “What are you saying yes to by default that you'd rather decide about?”
- “What would you stop doing if you were braver?”
- “What does 'winning' look like in two years — and who else needs to believe that?”
- “Which decision are you postponing, and what is the cost of the delay?”
Influence and stakeholders
See the system around the leader.
- “Who needs to be with you for this to work, and where are they now?”
- “How do your peers experience you in the leadership team?”
- “Whose support are you assuming?”
- “What does your boss need from you that you are not giving?”
- “Where are you spending influence you don't have to spare?”
- “If you were the CFO, what would you say about this plan?”
The leader's own patterns
Surface the habits that shape everything else.
- “What do people have to do to get your attention?”
- “When do you take work back from your team, and what triggers it?”
- “What feedback have you received more than once?”
- “What are you protecting by not delegating that?”
- “What did you learn about leading from the worst boss you had?”
- “What would your team say you are afraid of?”
Commitment
Turn insight into a visible change.
- “What is one thing you will do differently in the next leadership meeting?”
- “Who will notice, and what will they see?”
- “What might pull you back into the old pattern?”
- “How will you hold yourself to it?”
- “What support do you want from me between sessions?”
- “What did you take from today?”
How to use these questions
- •Executives are used to advising and being advised. Name the contract early: 'I'll ask more than I tell.'
- •Bring the system into the room: 'What would your board say?' often opens more than 'What do you think?'
- •Patterns beat incidents. When the same story appears in three sessions, coach the pattern.
Leadership Coaching coaching questions FAQ
What questions should a leadership coach ask in the first session?+
What do you want to be different in six months? Who else has a stake in that? What has worked and not worked with coaching or feedback before? How hard do you want to be challenged? And: what would make this engagement a waste of time?
How is leadership coaching different from executive coaching?+
The terms overlap. Executive coaching usually refers to coaching senior leaders on business and organisational challenges; leadership coaching can apply to any level and focuses on how the person leads. Both work on results and on the leader's patterns.
Should a leadership coach give advice?+
Rarely, and with permission. Leaders are surrounded by advisors; what they lack is someone who helps them think. Share an observation when it serves the client, then return to their thinking.
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