Some sales leaders treat one-on-ones like mini forecast meetings. They spend time reviewing deals and numbers but forget to coach the person behind them. If you want your reps to grow (and not just give you another status update), try asking some better questions.

A blog post from The Center for Sales Strategy explains that the best one-on-ones don’t follow a complicated framework. Instead, they simply create space for reflection, ownership, accountability and growth. Whether you hold your one-on-ones weekly or biweekly, the post recommends asking 5 questions. We share more from The Center for Sales Strategy in this issue of PromoPro Daily.

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  1. What’s going well right now? According to the post, many managers instinctively begin with problems. Instead, start with success. This creates a positive tone and spotlights the behaviors worth repeating. When reps know what’s working, they feel more confident and become more intentional about repeating those good habits.

  2. Where are you stuck? Even top performers experience challenges. Maybe a client has gone quiet or a deal keeps getting pushed back. By asking this question, the post says that you’re creating space for honest conversation before small issues become larger performance problems. Don’t just assume everything is fine. Ask your team members if they’re stuck on anything.

  3. What’s your plan? This is another essential question for one-on-ones, according to the post, because it helps you coach the thinking part of the job, rather than just getting the answer. Try asking other variations like, “What options are you considering?” and “What do you think the next step should be?”

  4. What skills are you focused on improving? Performance follows development, the post says. Instead of trying to improve everything at once, help reps identify one specific skill to strengthen. For example, this could be improving their discovery conversations or objection handling. Focused development makes progress easier to measure and coaching more intentional.

  5. What support do you need from me? This last question moves the conversation from an inspection to a partnership. The Center for Sales Strategy post explains that sometimes people need coaching but other times they need encouragement or accountability. Whatever they need, asking this question reinforces an important message: We’re working on this together. 

It’s easy to fill your one-on-one meetings with updates or check-ins. But if you really want to bring out the best in your team, use that time to coach instead of just catch up. When you ask the questions above, you can uncover issues and help your reps continue to improve.

Compiled by Audrey Sellers
Source: A blog post from The Center for Sales Strategy.