23 Workplace Coaching Questions for Managers and Leaders

Workplace coaching can involve set one-on-one sessions with employees, following a structured sequence such as the GROW Model, Kolb’s Experiential Learning Cycle, or any number of frameworks. For help on developing a personalized coaching program, specific to your organization, contact us here.

As leaders gain coaching experience, however, they also tend to find these questions a useful way of helping others develop – by working them into everyday conversations.

Clarifying Goals

Many coaching models take a results-focused approach by beginning with the goal in mind. Questions include (Harvard Business Review, 2014; HR Gazette, 2019; Lipovsky, 2019):

  1. What is one key thing you want to achieve at this moment?

  2. What are the three areas you wish to develop, enhance, or grow?

  3. What do you see as the real challenge right now?

  4. Imagine you’ve just ended the perfect week at work. What outcomes make you proudest?

  5. In what specific areas would you like to be at your professional best?

Open-ended ‘probing’ questions also come in handy when exploring the reasons behind a goal or challenge:

  1. Describe this goal or challenge a bit more…

  2. What are some ways this challenge is impacting you or others?

  3. Tell me about why you see this as an ideal professional outcome?

  4. Help me understand why this change is particularly meaningful to you?

  5. Could you tell me how this would help you and your team achieve its mission?

Generating Solutions

  1. What do you think would be a good first step?

  2. What has worked for you in the past when it comes to your professional growth?

  3. How might you draw on that same approach in this case?

  4. What do you feel you should do differently?

  5. Tell me about the resources that would be helpful? How or where might you acquire those?

If previous approaches have not been successful, leaders can help by encouraging their co-worker to think outside the box.

  1. What would you do if resources were not a concern?

  2. What else can you think of?

  3. How might you broaden your current line of thinking?

Encouraging Accountability, Commitment, and Motivating Action

  1. What are some concrete steps you could take to achieve this goal?

  2. How might you turn these steps into a plan?

  3. What will success look like? How will you know you’ve achieved your goal?

  4. How will you prepare for each step?

  5. How do you plan to motivate yourself when obstacles arise? What are some ways to motivate yourself to get started?

It’s critical to remember that these questions are intended to spark a guided discussion and that listening plays a crucial role in the coaching conversation that follows. There will always be points in a conversation where a leader needs to suggest alternatives, challenge an employee’s thinking, or offer resources to help them develop a viable plan.