Knowing which sales coaching questions to ask when is both an art and a science. Asking sales coaching questions is an art since you adapt your questions to what your salespeople say during your sales coaching sessions.

As you know, what works in one conversation may not necessarily work in the next. Each team member thinks differently. Each team member processes information differently. And therefore each team member sells differently. It is these differences that cause your questions at each sales coaching session to be different. 

Despite these differences, there are also commonalities to your sales coaching questions. These similarities make up the science of your questions. There are aspects to your sales coaching questions that consistently give you and your team members the results you all want. When you ask your sales coaching questions effectively, your salespeople remember more clearly what to do to improve, and, as a result, they perform better. 

To improve your sales coaching questions, utilize these guidelines:

1. Coach to your team’s reality

Most salespeople know what they should do but they don’t always do it. It’s like asking people what they should eat to be healthy. They know the best things to eat. Yet, if you ask them specifically what they ate (say last Saturday for dinner), you discover they didn’t follow their own advice. Instead of eating a salad with chicken breast, they ate fried chicken with french fries as their entree and a double chocolate brownie banana split as their dessert. 

If you choose to coach your salespeople on what they could have done, your sales coaching conversations will stay at the abstract theoretical level and result in very little, if any, improvement in their sales behaviors. If instead you coach your salespeople on the specifics of what happened during their sales interactions, your sales coaching conversations will be focused on how they can do better next time, resulting in improved sales behaviors.

When you ask your team members about their specific sales interactions, you get them talking about what really happens in their sales world. This way, your sales coaching conversations become more real and more helpful. Coach to your team’s reality, not theory. Coaching reality is where your team can gain some serious sales improvement. 

2. Build your sales coaching questions from general to specific 

Your sales coaching conversations will build naturally if you develop your questions from general to specific. If you get too specific too soon in your sales coaching conversations, you’ll experience awkward moments that interrupt the flow of your discussions and slow down the coaching process.

For example, a question like, “How did the client respond when you transitioned to cross selling?” may seem innocent enough on your part. But from your team member’s perspective, it may be perceived as jumping the gun, particularly if he didn’t cross sell during his sales conversation. 

The question is a decent question. It may just be a little too specific too soon. Instead, you can ask, “Did you get a chance to cross sell during the call?” If your team member says he did cross sell, then it’s an ideal time to get more specific and ask your earlier question, “How did the client respond when you transitioned to cross selling?”  But if your team member says he didn’t cross sell, your earlier question would be irrelevant. 

3. Solicit commitment at the end every sales coaching conversation

Every effective sales coaching conversation includes your team members committing to using a new sales approach. These commitments from your team members are the foundation for their ongoing incremental sales improvement. Without them, your sales coaching conversations become nothing more than just hopeful talk. 

Your commitment questions can be as simple as, “Of all the ideas we discussed, which one are you going to use next time you are in a similar situation?” These new approaches your team members commit to doing are not meant to be long-term commitments. Instead, they are short-term trials. They are test runs whose success and value are measured later by their impact on the individual’s sales improvement. 

Follow these three sales coaching question guidelines to help you improve your sales coaching sessions with your salespeople. You and your team members will begin to see even greater improvement in their numbers. 

About the author

Peri Shawn is a sales coaching thought leader who transforms the complexity of getting salespeople to perform better into the fewest number of action steps to help them sell more. Shawn’s company, the Coaching and Sales Institute (CSI), has been in the sales coaching business for 25 years and is the sales training and coaching behind the launch of such products as the debit card and Blackberry in Canada. Shawn has authored Sell More with Sales Coaching (Wiley, September 2013) as well as the three corporate guidebooks.

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