Powerful Sales Coaching Questions Every Sales Manager Should Ask

To have the most productive coaching sessions, start with these two elements - the right mindset and powerful questions. Whether you're a seasoned sales coach or just starting, focusing on your mindset and asking the right questions can transform your coaching sessions.  

Change Behavior with a Coaching Mindset

A coaching mindset is essential for your team's growth and long-term development. Shifting your mindset creates a more collaborative and supportive environment that's not just focused on short-term results.

When sales reps are part of the coaching process and empowered to find a solution, they will take ownership and are more likely to change their behavior. Shifting away from coaching that tells reps what to do to a collaborative approach helps identify and address the root causes of performance issues rather than just treating the symptoms. 

To create a collaborative sales coaching mindset, think of the 3 A’s:

#1 Ask Before Advocating

Advocating your position is more effective when you begin with questions. Questions will draw in the rep and help create a collaborative approach. Use your questions to promote self-discovery even if you already know what the salesperson has done wrong on the sales call. This is the most persuasive motivator of behavior change. Salespeople are more likely to change if they discover the behavior gap themselves. 

#2 Actively Listen 

The second A is active listening, a critical skill whether it's for sales, sales management, or coaching. The key to listening is leaning in, paying attention, and focusing on the speaker—not on what you will say next. Use active listening techniques to understand the intent, context, and meaning behind the other speaker's words. 

#3 Assume the Best Intentions 

Enter into every coaching conversation, assuming that the sales rep wants to do a good job and get better and that we're here to help them. If we assume that they've screwed up, were lazy, or didn't mean to do what we asked; it's a much more negative connotation. Disregard any past negative scenarios and accept that the rep is trying to do well until they prove otherwise.

Gain Clarity with Powerful Questions 

Once you're in the coaching mindset, craft the specific questions to ask the sales rep. Again, the goal is to gain insights about what happened and use these insights to shape future behavior.

There are three main question categories:

#1 Observation Questions

Let's say we just came out of a sales call. As the sales manager,  you were observing one of your sales professionals. Even though you were on the call, ask specific questions to get the rep's understanding of what happened. These observation-type questions will also engage the rep to discuss how they think it went with questions like: 

• "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?"
• "What were the key concepts during the call?"

The answers prove that you and the rep observed the same things, including the takeaway. It also shows if the rep listened and paid attention to the customer during that call. 

#2 Reflection Questions

The second and most important questions are about reflection. For these insights, it's helpful to  ask:

• "What did you like about that sales call?
• "What went well for you? And what might you do differently?"

The goal is to get the rep to reflect on the call and what they were observing. We might even ask in a given situation, "Well, tell me what happened. What did you think when the customer got confused or when they brought up that objection?" These questions help the reps draw conclusions on what happened and form thoughts about what they might do going forward.

#3 Application Questions

Now that the rep has reflected on the sales call pivot to ask questions about future applications:

• "What might you do to prepare differently in the future?"
• "What type of research might you want to do?"
• "How might you improve that skill before the next sales call?"
• "What could we do to practice that skill before meeting with the client again?"

These questions identify what went right to reinforce that the rep should continue to do these actions in the future. It's also about determining what to do differently next time. Ideally, we want the rep to talk about and ask questions about how they will apply those concepts in the future. We want them to think about exactly how they will use those critical skills in the future to continue improving their client conversations and performance. 

The goal of using these powerful questions is to get the rep to analyze what happened and determine the next step. Then, in the future, even if we are not there, reps can take five or 10 minutes to think through what happened, reflect on the sales call, determine their key takeaways, and use that to decide how to improve going forward.

In Summary

Successful coaching starts with an ideal mindset that asks great questions, actively listens, and assumes the best intentions. Using the three powerful types of questions gets the rep to think about sales call observations, reflect on what happened, and determine how to apply those key takeaways and concepts next time.

Ultimately, a coaching mindset fosters a culture of continuous learning and improvement, which leads to more engaged and motivated sales teams and better overall results. Over time, reps will discover the answers for themselves and continue to improve their skills—much like professional athletes reflect on their performance after a key game.

💬 Join the Conversation

Do you have any favorite coaching questions that you use with your team? Share your tips and experiences here.

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

• 5 Deal Coaching Questions Every Sales Manager Should Ask
• How to Deal with Sales Reps Who Don't Want To Be Coached
• Three Mindset Traits Top Sales Coaches Have in Common
• Six Sales Coaching Activities That Will Set You Apart As a Coach
• When Sales Coaching is Most Effective

Do you want to give your sales managers powerful coaching tools to increase team performance and close more deals? Then, check out High-Impact Sales Coaching™. This training program helps sales managers leverage a proven coaching process, prioritize what skills to coach, and allocate coaching time by ROI. Click here to learn more about this training and how it can transform you and your team.