4 Questions You’re Not Asking During Your Sales Coaching 1:1s (But Probably Should)

The single biggest sales coaching mistake you can make is simply choosing not to coach. So if you’ve got a coaching program in place, or you plan to start one soon, great job! You’re on the right path.

That being said, when it comes to sales coaching, you don’t get an A for effort. Your 1:1s shouldn’t feel like you’re just checking the box. In fact, if you can’t see a direct, measurable impact from your sales coaching program, then you’re doing it wrong — and you’re wasting everyone’s time (harsh, but true).

It’s no surprise that we get a lot of questions about the “right” way to sales coach. Specifically, we get questions about questions like, “Which topics do I cover?” “What’s the best way to frame them up?” “How do I guide the conversation while still listening well?”

Whether you’re a seasoned pro or you’re in a brand new managing position, if you’re asking yourself, “Am I asking the right questions?” — we’ve got you covered. Here are four smart coaching questions you should start using in your 1:1s that will lead to a productive and effective session, every time.

Question 1: What call, demo, or customer interaction did you absolutely crush last week?

It’s never a bad idea to kick off your session on a positive note. And it’s important to celebrate wins, no matter how small — that’s one of the fundamentals of a successful sales culture.

From a developmental perspective, this question encourages your team member to identify closing cues, prompting them to recognize why some things work and others don’t. Be prepared for your team member to not notice what’s working — it’s easier to focus on negatives than positives. You may have to point it out for them the first few times.

If you want to take it a step further, discuss how your rep can practice and replicate that skill or technique in the future. This puts responsibility and accountability onto your team member by asking them to isolate that intentional closing behavior and come up with a plan for perfecting it.

Question 2: Tell me the story of a call or demo that went wrong last week. What happened?

Failure is just part of the sales game. Asking this question in every 1:1 helps to normalize it — which is a good thing. Fear of failure is only going to hold your team back or slow them down (or both).

This question puts the ball in their court and, like the previous question, it allows them to begin the practice of self-awareness, identifying in their own mind any mistakes they may have made.

Placing blame on external sources is a red flag. Your team members should be able to identify something they can improve upon. If you agree with their answer, acknowledge that you agree. If you don’t, this is a good time to point out any suggestions of things you noticed.

Remember, it’s not black and white. Even if a call went downhill fast, see if you can pull out the positive — maybe they tried out a new technique or got creative. Maybe it didn’t save the situation, but digging into what went well will reinforce proper behaviors and keep confidence and motivation up.

Question 3: Tell me about one thing you want to try on your calls, but haven’t yet. A new channel, new approach, new script?

This question is a great segue from the previous question about areas in need of attention or improvement. And it’s a great lead-in to talking about the action plan for the week ahead.

By giving them the opportunity to brainstorm and self-learn, you’re allowing them to take ownership of their own success. Like any brainstorming session, it can be uncomfortable at first. Make sure they know it’s a no-judgment zone, so they should feel free to get creative and think outside the box without feeling silly or stupid. You may be pleasantly surprised with what they come up with (of course, don’t hesitate to give feedback and steer them in the right direction). Push them to open up about activities or changes they may be nervous about trying.

Question 4: What’s one thing you learned this week?

Never let your team members forget that learning is a success in and of itself. Even if your team members had an “off week,” if they took something valuable away that will make them better salespeople moving forward, then that’s worth acknowledging.

The key here is to make sure that the lesson really sticks and becomes part of their toolkit. One way to do that is to practice it — right then. Consider doing a quick role play to fine-tune whatever learning they mentioned.

Bonus: this is great for your relationship with your reps because it shows you truly care about their professional development. It also helps you identify the team members who care about their own professional development — the people who are really focused on learning and continued growth. More than likely, those are the team members who understand that acquiring new skills is important in an ever-changing sales landscape.

Other tips for successful coaching 1:1s include:

  • Sharing questions with team members in advance, so everyone is prepared for a productive conversation
  • Take notes and keep a log, so you know where to pick up next time with each team member

And remember, getting the right structure and questions in place is more than half the battle. But to really make those 1:1s worth everyone’s while, always end your sessions by creating action items and laying out tactical steps that will lead your team members closer to their goals — which, of course, should be 100% data-driven. The less that sales coaching feels like lip service — and the more that it produces dialogue-heavy, action-oriented meetings — the easier it will be to hit quota and build a culture of success.

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