Powerful Coaching Questions Every Sales Manager Should Ask

Sales Management | Sales Coaching

On this episode, Kumarasen Govender asks: What questions should I ask during the coaching process? Our Chief Customer Officer Ray Makela shares a three-step approach to creating a sales coaching mindset; and three types of powerful coaching questions to help sales reps improve their skills.


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Video Script

Well, I love that question about sales coaching and specific types of questions you could ask. It gets to the heart of what we call the "coaching mindset, "and that's thinking about coaching in the right way.

When we approach sales coaching, we like to talk about the three A's. The first A is about asking great questions, which I'm going to get into more detail later.

The second A is about active listening; a critical skill whether it's for sales or sales management. That's the idea of leaning in, paying attention, and focusing on the speaker—not on what you're going to say next. And employing those active listening techniques to understand the intent, the context, and the meaning behind the words of the other speakers. Active listening is critical to coaching as well.

The third A is for assuming the best intentions. We should go into a coaching conversation assuming that the participant wants to get better, wants to do a good job and that we're there to help them get there. If we assume that they've screwed up, they're lazy, or didn't mean to do what we ask; it makes it more of a negative connotation, as opposed to, "Let's assume that they're trying to do well until they prove us otherwise."

So we're going to (1) Ask great questions, (2) Actively listen, and (3) Assume the best intentions, as a way of setting up and creating that coaching mindset for the conversation.

Next, specifically, to the types of questions that you want to ask in a coaching session, we think about them in three categories, and the first is observation-type questions.

Let's say we just came out of a sales call, as a sales manager I was observing one of my sales professionals in that call, and the first types of questions I might want to ask are just to get an understanding and have them participate in a conversation about how they think it went.

So, the observation might go, "Well, tell me about that sales call. How do you think it went?", "What do you think went well? What did you see? What did you hear? What was going on?" The purpose of this is to understand, Were they observing the same types of things that we were? What did they take away? And were they listening in and paying attention to the key concepts during that call with the customer? That's an observation type of question that we might want to ask.

The second area and the most important is around reflection. We might ask, "What did you like about that sales call? What went well for you? And what might you do differently?" So we're getting them to reflect on the call. We might even ask in a given situation, "Well, tell me what happened, what were you thinking when the customer got confused or when they brought up that objection?" We're getting them to reflect on what's going on, what they were observing, and take away and draw conclusions and thoughts about what they might do going forward.

The third type of question we want to ask is around the application; this gets them thinking—now that we've reflected on the sales call—about what went right, what we want to continue to do, and what we ought to do differently in the future. We want them to talk about and ask questions about how they're going to apply those concepts going forward.

For instance, we might ask questions like, "Well, what might you do to prepare differently in the future? What type of research might you want to do? Or how might you improve that skill before the next sales call? What could we do to practice that skill before we go in front of the client again?"

We want them to think about how are they going to apply and follow up on those critical skills so that they can continue to improve going forward and improve their conversations, and their performance in front of the client.

What we think about in all of these questions is getting them to reflect on the sales call after. So that even as a sales manager, if we're not there, reps can think about these questions themselves after the call and take five or 10 minutes to think through what happened, reflect on the sales call, their key takeaways, and how they might improve going forward. In other words, we want to get them to think about coaching themselves, and continuing to improve their skills—much like professional athletes reflect on their performance after a key game.

To recap, we want to ask great questions, actively listen, and assume the best intentions. Then we want to ask questions that get them thinking about the observation of the sales call, the reflection of what was going on, and ultimately, how are they going to apply those key takeaways and concepts going forward.

Looking for more insight on Sales Coaching? Try these articles.

SRG Insights is a Q&A video series where we answer your questions on the topics of sales, sales management, sales coaching, and sales training. Featuring sales experts with over 25 years of sales and sales management experience.  

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About Ray Makela

Ray Makela is CEO and Managing Director at Sales Readiness Group (SRG). He oversees all client engagements as well as serves as a senior facilitator on sales management, coaching, negotiation and sales training workshops. Ray has over 20 years of management, consulting, and sales experience and writes frequently on best practices for coaching and developing sales teams.