Transition from Manager to Leader

with Sara Canaday

Coaching Questions for Leaders

Define the Challenge
These questions can be used to help others identify specific problems that need attention, uncover career
aspirations, and overcome hurdles to advancement. At the same time, the answers provided will give you
the background information and context needed to coach them more effectively.
• What do you make of _________?

• How do you feel about _________?

• What concerns you the most about ________?

• What seems to be your main obstacle?

• What do you mean by __________?

• What else can you tell me about _________?

• What is holding you back from __________?

• What would make an ideal work situation for you?

• What special interests do you have?

• What activities inspire you the most?

• Do you believe you are being perceived the way you intend?

• Have you done anything to identify your blind spots?

Analyze the Progress

These questions can be used to lead others through an analysis of efforts made so far to resolve the
problems identified. By looking at this progress in a strategic way, individuals can focus more clearly on
future actions with the greatest chance of generating positive results.

• What solutions have you tried?

• What has worked for you already?

• How could you do more of that?

• What hasn’t worked so far?

• What did you learn from trying_________?

• What do you think is stopping you from trying ________?

• What could you change about the solution to get a better result?

• What will you have to do to get the job done?

Transition from Manager to Leader with Sara Canaday

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Inspire Targeted Action
These questions can prompt others to find greater clarity about the outcomes they desire and then
develop targeted plans to achieve them. Helping them link action items to results will strengthen their
decision-making skills and improve their confidence.
• What solution do you propose?

• What is your ideal outcome?

• How will the results be measured?

• How do you want ____________ to turn out?

• What benefits would you like to get out of__________?

• What obstacles could get in the way of success?

• How can you overcome those obstacles?

• If you do this, how will it affect ________?

• What is the cost of NOT doing this?

• What else do you need to consider?

• What do you need from me and/or others to help you achieve this?

• What is your overall plan to implement this solution?

• What are your next steps?

• How will we know when you have succeeded?

Transition from Manager to Leader with Sara Canaday

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