7 Sales Coaching Questions That Sales Managers Must Ask Their Sales Reps

Abhishikha Chatterjee
November 10, 2021
 mins read

Last modified on

Table of Content:

Sales managers own the key to a perfect sales coaching experience for the reps.

And, sales coaching is an indirect method to accelerate sales numbers

Essentially, managers must give their 100 percent in the sales coaching session to receive 100 percent results in the sales processes. 

So, a sales coaching process ✔️, a sales coach ✔️, a sales enablement software ✔️, and a sales playbook ✔️. There’s just one small missing piece which many managers overlook or don’t stress enough- the right questions to ask your rep during a sales coaching session. 

What you’ll find in this post?

1. Importance of asking questions to the sales reps
2. What are the 7 questions every sales coach must ask a sales rep?

  • Where do you face problems in the sales process?
  • How would you rate your sales performance? And Why?
  • What went well in the call, and what could have been done to improve?
  • Are you receiving help from your peers and the company? Is anything missing?
  • What sales strategies would you use for better sales results?
  • One thing that you’d like to change in your next sales call?
  • Where do you see yourself as a salesperson in the next 5 years?

Importance of asking questions in sales coaching

In our last post, we discussed asking the right questions to the prospect—the importance of framing good questions that achieve the intention of the sales meeting

Asking questions to reps also has a similar agenda. 

Unless you ask the reps questions and refine their skills, you can’t expect them to ask the right questions in the sales meetings. 

While asking questions to prospects helps in progressing the deal further, asking questions to the rep helps build the rep for complex sales meetings and motivates them for success. 

But as sales manager, didn’t you already know that? We’re sure you did. 

What we are worried about is asking questions. Are you asking questions to your rep? Or preaching the sales proven methodologies and best practices?

Here’s where the experts join in and recommend a little improvisation in the one-on-one coaching sessions. 

Try to follow a rule of thumb- As a manager, ask more questions to the rep. Help the representatives identify improvement areas and introspect their sales meetings.

Managers should invest 80% of the time in listening and only 20% talking. 

Coaching your reps begins with understanding the thumb rule. 

Now we can move ahead to framing the right questions and the sequential questions to get your sales rep in shape for the next big sales meeting.

What are the 7 questions every sales coach must ask a sales rep?

1. Where do you face problems in the sales process?

Instead of hiring and firing reps, try to understand the current challenges your incumbent reps face. 

The rep may be struggling with a weak spot within the company or an imperfect skill set they wish to improve urgently. 

So dig deeper and figure out where is that Achilles heel.

Sales managers can begin with the following questions:

  • Are you facing any challenges during your sales meetings?
  • What have you done to solve it?
  • What tools do you use?
  • How can the company and I help you?

Take these questions on a 1:1 basis with the reps and spend time learning how their day looks and where the performance gap is.

You may be shocked to know that a rep performing tremendously in pricing negotiation may get cold feet in the discovery round. Everyone approaches the sales process differently. 

So, find out what they are spending their time on and where the company and you can support them. 

2. How would you rate your sales performance? And Why?

The popular self-help book Atomic Habits by James Clear mentions a critical point that we all can agree on to-. 

“ Reflection and review ensure that you spend your time on the right things and make course corrections whenever necessary.”

Now here’s a clear difference between modern sales coaching and traditional methods.

Sales managers must help sales reps reflect on their mistakes and rate their performance. 

Ask reps-

  • How would you rate your call performance?
  • How do you think your prospect would rate you?
  • What would your prospect feel about your sales performance?
  • Did you add value to your prospect’s day?

Experts stress self-reflection and introspection because associates learn faster and implement the changes even faster. 

Frame questions to help the reps realize their flaws and areas of concern. 

3. What went well in the call, and what could have been done to improve?

Recently, a sales manager got on a call recording software to listen to their rep’s performance on the last call with a high-value prospect. 

The sales manager was shocked to hear that the call rose to his expectation but strangely, the technical details shared by the rep were completely flawed and taken positively by the audience. 

No doubt the next steps were clear, and a meeting was due in another week, but the manager needed to ensure the rep didn’t get into trouble. 

The next day the manager summoned a sales coaching session with the rep and asked a few simple questions that helped the rep-

  • I heard the call. I think you did a fantastic job. Yet, I’d like to know your thoughts on the call?
  • What do you think went well and stood out for you?
  • How could you have done it better?
  • How confident are you about the product features and functionalities?

The manager could have quickly spoken about the mistakes and tied the conversation to the product feature training. But he chose not to. 

Instead, gave the rep a chance to reflect and evaluate the call performance.

4. Are you receiving help from your peers and company? Is anything missing?

Sales coaching is incomplete without the knowledge of how the rep feels in the company. 

Do they feel isolated? Do they feel demotivated? Do they feel something missing?

While your rep may not open up immediately, you can expect them to get comfortable and speak their heart after a few coaching sessions.

But to make it easier, ask-

  • Can you tell me your sales experience in the last company you worked for? What did you like best about your previous organization?
  • Do you feel our company can learn and emulate something from your previous organization?

Once the rep opens up on these questions, you can switch to more direct and specific questions like;

  • Do you feel you’re receiving support on your sales activities? 
  • Is there anything you need?
  • Are you able to achieve your targets?
  • Do you feel satisfied with the incentives you receive?
  • Would you like to earn more? How do you think I can help you in achieving it?

That’s a win-win situation for the rep and company. 

You not only successfully reduce the churn rate but also motivate the rep to perform better.

5. What sales strategies would you use for better sales results?

Sales managers must not keep biases and stick to a single proven methodology. 

Your sales rep may surprise you by introducing an innovative method that otherwise would not have made it to the charts. 

Ask your reps periodically-

  • In order to improve your sales performance, what strategy are you going to use? 
  • Would you need my suggestion or help in implementing the strategy?

A few reps use very innovative methods of follow-ups. The strategies are never discussed and shared because of cutthroat competition. 

But the right questions can help you evaluate the outcome’s strategy and share good pointers with other staff members.

6. One thing that you’d like to change in your next sales call?

Sales coaching is anything but not training your rep.

The skillsets are known to the rep and the sales managers. 

But the skills need to be sharpened and used correctly on sales calls.

Ask your reps time and again-

  • What would you like to change from your last call?
  • Is there a particular skill set that you’d like to improve?

Once you realize your rep’s problem areas, you can help them better in improving the skillset. It could be as simple as asking the right questions to the prospects to as complex as mastering virtual selling tricks

7. Where do you see yourself as a salesperson in the next 5 years?

You already know a lot about your rep’s sales performance and their sales goals.

Have you ever tried to understand their personal and professional goals and envision themselves in the next 5-7 years?

Your reps may not want to stay as reps and want to step into a more strategic position. Some of your reps may see sales enablement as a lucrative option and something where they can add more value. Some may see entrepreneurship as a better option. Few reps even choose the path of a marketing professional or become a life coach changing lives across the world.

Based on the above discussion, it’s critical to identify their goals and choices timely. 

This solves two problems:

  1. You can coach them and help them in attaining the position they strive for.
  2. Second and very important, you can gauge who’ll continue with the organization and step down sooner or later.

Investigating the goals at the right time helps the organization in investing time and effort in the right employee and at the same time helps the rep in pursuing their choice of work. 

Asking questions is sales, and sales is about asking questions.

Now there we have our ducks in a row.

Your reps are all pepped up and ready for the next big customer engagement. 

Remember, sales coaching is not about training your sales reps. It’s about digging into the pain areas and discussing it and evaluating the rep’s performance gaps, and helping them improve.

And, don’t forget to use technology in the process to level up your reps and your sales coaching experience. Try it now

See Convin in action for FREE!
Results first, payment later.
Sign Up for Free
Say goodbye to unpredictable conversions
Download your copy

Featured Articles


How To Cold Call: 21 Cold Calling Tips for SDRs (From the Sales Masters)

Abhishikha Chatterjee
November 30, 2021

Mastering Virtual Selling: The Skills Your Team Needs for Success Today

Abhishikha Chatterjee
October 29, 2021

Importance of Sales Performance Management Software in the New Normal

Abhishikha Chatterjee
September 28, 2021

Subscribe to our Newsletter

1000+ sales leaders love how actionable our content is.
Try it out for yourself.
Oops! Something went wrong while submitting the form.
Bhive Workspace No.112,AKR
Techpark, A-Block, 7th Mile
Hosur Road, Krishna Reddy,
Industrial Area,
+91 7011464590, +91 8802881329
2093 Philadelphia Pike #5025
Claymont, Delaware 19703
(+1) 6282095776

Say goodbye to unpredictable conversions

Unlock the solid agent coaching framework for free!

Access the full report now

Please enter the correct email.
Please enter your workplace email.
Invalid Email
Thank you for downloading the report
Oops! Something went wrong while submitting the form.