When it comes to sales coaching, guiding a conversation with the artful and strategic use of well-crafted questions is a challenge for coaches of all levels. 

After coaching thousands of managers 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 because value was delivered, a new solution was co-created, a new possibility emerged.

That’s when this shift happens; the manager starts recognizing positive results from coaching and as such, their confidence increases and they begin 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 each conversation. But you still need to start with a baseline of best practices to provide a solid foundation. Only then can you make it your own and leverage your own style, strengths and personality into your coaching.

Baseline of Best Practices

I’ve listed ten coaching questions that I have found can work in practically every conversation you have. (Actually, I’ve provided you with more than ten questions but condensed a few questions together, as there are several ways to ask the same question, depending upon your own style of coaching and communicating.) These questions will expand your direct report’s thinking, while challenging them to bring out their best. This leads to greater accountability and ownership of the problem, as well as empowering your people with the responsibility to develop their own solution so that they are the ones who have created a new possibility, approach, outlook or way of thinking.

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, this is just one of many ways to facilitate an effective coaching conversation. And 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!)

10 Coaching Questions that Work in any Conversation

• What is the outcome you’re looking to achieve?
• Can you share the specifics of what’s going on?
• What have you tried so far?
• How have you handled something like this before? (What was the outcome?)
• Why do you think this is happening? (What’s another way to look at this/respond? What else can also be possible/true?  What assumptions could you be making here?)
• What’s your opinion on how to handle this? (If I wasn’t here, what would you do to achieve/resolve this? What options/ideas do you have? What’s another solution/approach that may work (which you haven’t tried yet?)
• What’s the first thing you need to do to resolve/achieve this? (What would that conversation sound like when you talk with...?)
• What resources do you need? (Who else do you think needs to be involved in this? How else can I support you around your efforts to complete this?)
• What are you willing to commit to doing/trying/changing (by when)?
• When should we reconnect to ensure you have achieved the result you want?

Two 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 question enables the person to see/articulate the measurable cost of not changing rather than being told the negative consequence. Remember, if they say it, then they own it. And if they own it, they act on it rather than being told the consequence, which often leads to resistance.