31 Good Coaching Questions For Leaders To Ask

Guest Post by

Whether it’s in a small company or a multinational, the ability to coach others helps leaders grow their organizations in many ways. Asking the right coaching questions of your teammates can be a strategic way to ensure you’ve always got developing talent while sharpening your firm’s competitive edge and nurturing future leaders.

So what coaching questions should you ask, and why?

Why Ask Coaching Questions?

By asking powerful coaching questions, leaders help their co-workers chart a direction forward, without handing over all the answers. First and foremost, good questions encourage self-reflection and motivate the coachee to find their direction and means of getting there.

The most powerful questions that a coaching leader can ask will trigger a sense of ownership in their co-workers, pushing them to explore their perspectives and possibilities in new ways as they seek to grow.

We’ve asked our TTGG coach Marc Vanschoenwinkel for his favorite questions that – in some form another – should be part of every coaching process.

How To Ask Powerful Coaching Questions

Good coaching questions serve at least four key functions.

1. Establishing a direction

When asked at the right point in time, good questions reveal what your coachee needs and wants to achieve. For example, “What specifically are you hoping to achieve during our time together?” “Tell me what your ultimate outcome would be from our talks?” “What is the most important thing driving you in your career right now?”.

Clear expectations on both sides allow you as a leader to build trust and provide relevant support as your work together progresses; for this reason, it can be invaluable to dig a bit further into your coachee’s underpinning values. For example:

• What is especially important to you about developing this capability? Furthering this skill? Taking this career step?
• What is it that you would like to see happen, and what does it mean to you professionally?
• Tell me a bit more about this ideal accomplishment?

2. Analyzing and Clarifying – Perspectives and Reality

They allow you to delve deeper into their development needs and come out with a clearer picture of their motivation, real and perceived obstacles, and points of view. For instance, “Why do you feel this is necessary?” “What do you hope to achieve from acquiring these skills?” “What do you think has stopped you in the past?”

It can be helpful to take a brainstorming approach during this stage, summarizing to show understanding and suggesting to open up new alternative pathways. When it comes to identifying perceived barriers, it can help to get a bit more specific:

• In your opinion, what has prevented you from taking the first step? What resources could you draw on to help you? What might you need or ask for?
• What happened the last time you tried asking for those resources? Do you know anyone else who has tried this? What happened to them?
• On a scale of 1 to 10, how close do you feel you are to reaching this goal?

3. Developing Options

Good coaching questions help you and your co-worker collaborate on possible next steps, laying the foundation for a way forward at later stages. “What will help bring you closer to your goal?” “What are the advantages and shortfalls of this option?” “What would you choose to do if you had unlimited resources?”

Leaders are often able to take a slightly more active role than independent coaches in coming up with options. Being familiar with your company allows you to offer relevant tips on resources, potential connections, and even make introductions where you feel it is appropriate.

• Who do you feel you could ask to help you? How could they help?
• Which option do you feel capable, willing, and equipped to pursue?
• What do you believe would occur if you pursued that pathway?

4. Implementing a Way Forward

Taking the next steps forward, it is time to move in one direction and start getting even more specific. Helpful questions will elicit concrete actions, creating accountability, and building motivation. “What’s the very first thing you need to do?” “How will you know you’ve succeeded at that stage?” “How do you intend to deal with any challenges along the way?”

It’s important to remember that your coachee is responsible for their progress, so introducing a goal-setting framework such as SMART criteria can be useful.

• How much time will you give yourself to take these steps?
• When will you make the first move, where, and with whom?
• How can you enhance your commitment to this path, and how will you keep up your motivation?

What’s Required of Me as a Coach?

Powerful questions are essential in any coach’s toolkit, but the best coaching leaders are also careful active listeners. They are not afraid to probe further into responses to clarify, focus their co-workers’ attention, and extract fresh ideas where required to keep the conversation flowing productively.

For example:

• What means the most to you personally about this?
• Could you tell me more about why, how, or where…?
• Could you describe a similar example of when you’ve encountered this obstacle?
• Is there someone else who’s managed to achieve/overcome this? How?
• If I understand you correctly…
• Can you suggest some alternatives? What do you see? and
• Why do you think you see things that way?

With the right questions and a genuine desire to help your co-workers develop, a leader can adapt his or her communication style to fit the context and achieve their coaching goals. They can build true, effective connections with their co-workers while encouraging them to overcome mental barriers and reach their professional goals.

Have you got any questions that you use when coaching your co-workers? Share them with us on our Time To Grow Global LinkedIn!

Govert van Sandwijk


Govert van Sandwijk is Time To Grow Global’s Managing Partner, specializing in Strategy Facilitation, Leadership development and Organizational performance. Reach him on our Time To Grow Global LinkedIn.


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