10 Coaching Questions Managers Use That Work In Any Conversation

By Keith Rosen

Whether you’re a seasoned manager or just starting your career in management, one thing is for certain. When it comes to coaching, and more specifically, guiding a conversation with the artful and strategic use of well crafted questions, managers, regardless of age, location or experience, struggle with the right questions to ask when coaching.

After coaching thousands of managers and thousands of salespeople across the globe, I’m overly sensitive to the fact that great coaches coach from their heart, not from their head. However, just like learning anything new, such as how to swing a golf club, you’re initially focused on the mechanics of your swing, each movement, step by step. It is only after consistent repetition of the same movement, does it become your own. You stop thinking about the mechanics, and habitually just do it.

This also holds true when it comes to the questions managers ask when coaching. I certainly know there’s a multitude of different questions you can use in any coaching conversation. However, when the best ones are used and used consistently, the conversation becomes magical and both the coach and coachee walk away from that experience feeling great.

That’s when this shift happens; the coach starts recognizing positive results from coaching and as such, begins to trust their intuition, their gut, their coaching abilities and their instincts more and more. The byproduct? The right questions just show up naturally and organically within the conversation. But you still need to start with a baseline of best practices as a solid foundation to build from before you can make it your own and leverage your own style, strengths and personality into your coaching.

That’s why I’ve listed ten coaching questions here which I’ve used over the years that I have found can work in practically every conversation you have. These questions will guide the person to greater accountability and ownership of the problem so that they can in turn, develop their own solution or create a new possibility.

Of course, depending upon the conversation, you may not need to leverage every single question. However, as you use them throughout your coaching efforts, you’ll start recognizing how many of these questions you need and which ones are the most appropriate. Keep in mind, if you don’t have a great manager or a coach in your corner, you can also leverage some of these questions for self-coaching! (Just don’t argue with yourself over the responses you hear! ;- )

1: Can you share the specifics of what’s going on?

2. What is the outcome you’re looking to achieve here?

3. What have you tried so far?

4. How have you handled something like this before? (What was the outcome?) Why do you feel this is happening?

5. What’s another way to look at this/respond? What else can also be possible/true? (And…..?)

6. What’s another solution/approach that may work (which you haven’t tried yet)?

7. What’s the first thing you need to do to (resolve/achieve this)?

8. What resources do you need? (Who else do you think needs to be involved in this? How else can I support you?)

9. What are you willing to commit to doing/trying/changing (by when)?

10. When should we reconnect on this to ensure you achieved the result you want?

BONUS QUESTIONS: If you sense any resistance to change or a lack of ownership around the issue, goal or problem, you can weave in one of these questions here:

*What would it mean to you if you could (achieve this, resolve this, etc….)? (This question helps the person visualize what’s in it for them – and it’s the thing that they want rather than the manager trying to tell or ‘sell’ them on what the benefit is.)

*How would this impact/affect you (your team, career, etc.) if this (continues, doesn’t change, doesn’t get resolved)? (This second question enables the person to see/articulate the measurable cost of not changing vs. being told the negative consequence. Remember, if they say it, then they own it.)