6 Sales Coaching Questions That'll Help Your Reps Hit Quota

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Michael Pici
Michael Pici



When you become a sales manager, your “customers” become your salespeople. Your top priority should be helping them succeed. After all, if every individual reaches their potential, you’ll definitely hit -- if not exceed -- your team quota.

Just like asking your prospects the right questions is crucial, asking your reps the right questions is crucial, too.

These questions, which are ideal for one-on-ones, will help you identify your reps’ strengths, weaknesses, and motivations.

Sales Coaching Questions to Ask Your Reps

1) “What would you like to accomplish in the next six months? Year? Two years?”

The best sales managers know what their reps are striving toward. Some salespeople want to save up for a big purchase, while others are working hard to get a promotion.

This question should delve into both personal and professional goals. If their first answer is professional, follow up with, “Great. What are you hoping to achieve on a personal level?”, or vice versa.

Once you know what each rep wants, you can tie your coaching to those drivers. For instance, if you want to motivate a BDR looking to buy an apartment, you might offer them a cash incentive for increasing their call-to-meetings rate by 10%.

Meanwhile, someone who wants a promotion to account executive (AE) will be encouraged by career milestones, such as, “After your percentage of leads accepted is X percent or higher four months in a row, you’ll become an AE.”

2) “Which part of the sales process do you find most challenging, and why?”

Every rep has an Achilles’ heel, and it’s your responsibility to find those weaknesses and correct or mitigate them. You should be able to discover many through simple observation -- but it’s always a good idea to get your reps’ feedback as well.

Design a coaching program around these areas. For instance, if a salesperson says she has a hard time surfacing objections, you might work with her to develop questions or roleplay scenarios with hidden objections.

Most worrisome? When the rep says they don’t struggle with anything. They’re either overconfident or reluctant to be honest with you, neither of which bode well.

3) “What would your prospects say about working with you?”

This question forces salespeople to consider their prospects’ point of view. Even the best-intentioned reps can become consumed by meeting their quota, which causes them to prioritize their needs over the buyer’s.

You’ll discover bad behaviors while there’s still time to fix them. For example, your rep might answer, “The prospect would probably say I’m pushy -- I’ve been pressing them to connect me with the signing authority.”

Or perhaps they reply, “I think she appreciates the suggestions I’ve given her for evaluation criteria but would like more transparency around pricing.”

Once you’ve helped your rep see themselves through the buyer’s eyes, you can work together to improve their relationship with the buyer.

4) “What went well during your [initial connect, discovery call, demo, sales presentation, meeting with X stakeholders, negotiation]? Where do you see opportunities for improvement?”

This prompt is a classic for a reason. If your salespeople never reflect on their performance, they’ll never grow.

Sure, you could tell them exactly what they did successfully and where they fell short, but you won’t observe 90% of their conversations. It’s far more effective to put them in the habit of analyzing themselves -- so even when you’re not listening to the call or shadowing their meeting, they can improve.

5) “Which strategies you use and/or steps will you take to work on X?”

Honing in on a weakness isn’t productive unless the rep also comes up with a concrete fix. Again, while it’s easier for you to give them an action plan (like, “Develop a roadmap for the call in advance so you can keep the conversation on track”), they’ll be more bought-in if they’ve had a part in crafting it.

If their initial response isn’t specific enough, go deeper. Here’s some sample dialogue to illustrate:

Manager: “Which strategies will you use and/or steps will you take to reduce discounting?”

Rep: “I’ll establish the product’s value earlier in the sales conversation.”

Manager: “How will you do that?”

Rep: “I’ll create a custom one-page site with three or four testimonials from customers similar to my prospect and a third-party review from a well-known publication in their industry.”

Manager: “Sounds great. And what will you say if they request a discount anyway?”

Rep: “I’ll turn the question around by asking, ‘Why?’”

6) “How have your team members helped you this [week, month]? How have you helped them?”

The most successful sales teams work together. Not only can every rep learn from their peers’ product knowledge, sales experience, and insights, but they can also benefit from each other’s support and friendship.

To encourage a spirit of collaboration, ask this question during every one-on-one. You’re looking for answers like:

  • “Jamie gave me some tips on writing better outreach emails.”
  • “I roleplayed a few negotiation scenarios with Oleana to help her practice pausing.”
  • “Max, Ankit, and I made a case study library for the whole team to pull from.”
  • “Sarah ran my demo because I didn’t feel well.”

Consider sharing the best examples during team-wide meetings. Doing so gives your reps a model for great teamwork, rewards the people who went above and beyond, and lessens the air of over-competitiveness that plagues many sales teams.

These sales coaching questions will make your salespeople more productive, successful, and engaged. Your bottom line will reap the rewards.

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