The Coaching Effect Blog

6 Surprising 1-on-1 Questions Sales Managers Don't Think to Ask

Posted by Stacia Jorgensen

October 9, 2018

Sales Coaching 1 on 1 taking place between a sales manager and sales personAccording to EcSell Institute research, one-on-one meetings with salespeople may be one of the most critical factors in helping them perform. In our Through the Eyes of the Rep survey, we see strong relationships between sales people that rate their one-to-one meetings with their managers as effective and sales people that rate their managers as excellent leaders, coaches and effective at motivating them to greater sales importance. 

These relationships indicate that one-to-one meetings are one of the most critical activities you can do with your sales people. (Tweet thisRead more about the effectiveness of these meetings in this best practice document

Best Practice_ One-To-One Meetings

As a survey researcher, I’ve asked people a lot of questions in my career. In a moment of thinking about the number of questions I may have asked, it led me to ponder not just what questions have I asked, but which ones (were I a manager) should I ask.

With my experience in not only research, but qualitative sales research, here’s my list of the six most beneficial questions sales managers should be asking their sales people when they meet with them one-on-one:  

1) How are YOU?

No, really. See the emphasis on the word, “you”? This question has been used so that the intent behind it is often lost. But as a manager, you should be asking each member of your team how they are doing on an individual level and in a way that shows you really want to know.

Ask it in a meaningful way. Don’t let them give a simple answer of “good” or “fine”. Ask follow-up questions. Pause and let them really share with you in a meaningful way. Listen, remember, and care.

2) What’s something you’ve learned since we last met?

One of the best ways we move forward in our personal and professional lives is to continually learn and explore. This question serves two purposes.

First, if you ask this question regularly of your team members, you are setting the expectation that it will be asked again. And when the question is expected, your team members will be more purposeful about learning, exploring, and remembering new things that they might not otherwise.

Second, this practice is a great way for you to pick up some new information that you may not otherwise have gained on your own.

3) What’s something that’s worrying you or making you proud?

If you really want to get to know your team members, learn about their proud moments and their worry triggers. Asking about both gives your reps the opportunity to choose which is most fresh in their mind. If it was something positive, make sure to give praise and celebrate the achievement.

If there is a worry, use this as an opportunity to give them support, commiserate, and problem solve if possible.

4) What’s the most important thing to get done this week/month/quarter?

I love this question. Sales is a crazy, hectic, and complex career. With so much bustle and noise, this question creates a focal point. Feel free to adjust the time period so that it best suits your team’s dynamics. By asking this question, you give the sales person an item where they can work towards a “win” and give you an action item for accountability.

*A bonus here is that if you think his or her most important item is not what it should be, there’s an opportunity for course correction.

5) What’s something that I could do that would really be helpful to you?

This one might make a few managers shudder. After all, if you ask that means you need to deliver on the answer (or at least do your best). If you’re reading this, however, you’re likely the kind of manager who will really work to do something with the answer. And even if their response are things beyond your locus of control, acknowledging their response and talking through the issue can be helpful even if a clear solution isn’t possible.

6) What else should I know?

I love a good final question to help uncover any lingering problems, thoughts, or feelings. When asked sincerely, this question gives your team member a chance to tell you anything that might still be on his or her mind and impacting their performance.

Whether it be something big or little, this vague question, when asked sincerely, allows your team members that extra opportunity to share what is still on their mind and could be essential for you to know.

Have you noticed the one thing these questions all have in common? Not one of these inquiries are specific to the work or role as a sales person. These questions don’t ask about how their pipeline is looking or how that sales pitch went last week. Instead, they are all intended to engage your sales reps in conversations that are specific to them as individuals. Here, the focus should be on them as a person, not a sales producer.

Use these items as a guide to help avoid leading your team through task-specific updates but instead create dialogue that generates information and understanding that is distinct, meaningful and personal to each of your team members.


And if you want to make your one-on-one's even more effective we encourage managers to use a consistent format. Here's the template we share with our clients. Make sure to include the six questions above  to ensure that your one-on-ones create a positive impact in the lives of your salespeople.

And remember, one-on-ones are only ONE of the FIVE high payoff sales coaching activities. If you want to learn about the the other four activities download the white paper below. 

The 5 High Payoff Sales Coaching Activities White Paper 

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Topics: one on one meetings, sales coaching, sales coaching activities

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