11 Questions to Ask Your Employees (& Your Manager) in One on One Meetings

Guest Post by Kelly Riggs

A few years ago, I wrote the book 1-on-1 Management: What Every Great Manager Knows That You Don’t. Admittedly, the title sounds pretentious. After all, who am I to suggest you don’t know something?

However, most people do know the difference between an effective and an ineffective manager. What separates the two?

In my experience, one thing great managers understand that their ineffective counterparts do not is the value of one-on-one meetings. In fact, you might be surprised to know that the vast majority of managers do not meet individually with employees on a regular basis.

Learn how to run more effective sales meetings using this playbook. 

But there is some distinction between an effective one-on-one meeting and two people who happen to have a meeting of some kind. Simply passing in the hallway and talking together doesn’t qualify as a one-on-one. A meeting to discuss a current project might involve just two people, but that doesn’t qualify either.

One-on-One Meeting Template

The one-on-one meeting has a very distinct purpose and structure, and it is designed specifically to benefit the employee, not the manager. Yes, the manager does benefit as well, but the intent of the meeting is to help the salesperson reach his or her potential through coaching and accountability. That’s the critical difference.

So, how do you structure your meeting to best support your salespeople? Use this step-by-step guide to help you create an agenda for each meeting.

1. Select a time to meet.

Schedule your one-on-one meetings weekly, bi-weekly, or monthly for the same time and day. If you run into a scheduling conflict, reschedule the one-on-one. Depending on salesperson’s experience level and how much coaching they need, the meeting time can vary from 30, 45, or 60 minutes in length.

2. Set expectations with your employees.

Communicate to the salesperson that they should come prepared to each meeting with topics to discuss and questions. For added accountability, have them send you an agenda or document ahead of time, that outlines what they’d like to cover in the one-on-one. Not only does this help the salesperson, but it also allows you to prepare before the meeting.

3. Review the salesperson’s metrics.

Before each meeting, review your employee’s metrics. This helps you see if they’re meeting their targets and identify areas where they might be struggling (even if they haven’t communicated those struggles to you yet.)

4. Prepare questions.

Based on your review of the sales rep’s performance, come up with some questions to ask during the meeting. Cater your questions so they’re specific to each rep, their experience level in the role, and the goals they’re working towards.

One-on-One Meeting Agenda

With all these steps in mind, here’s a one-on-one meeting template you can use to outline an agenda.

  • 5-10 minutes: Catch-up
    • Ask about the previous week
    • Actively listen to the salesperson
  • 30-40 minutes: Discussion
    • Review the salesperson’s weekly performance
    • Ask your questions for discussion
    • Listen to the salesperson’s insights, questions, and concerns
  • 5-10 minutes: Prepare for the upcoming week
    • Collaborate with the salesperson to set up goals
    • Write down the action items and steps to achieve the goals
    • Share the action items with the salesperson

And here are the magic questions I’ve structured my one-on-ones around for years that keep the focus squarely on the rep.

1. “Tell me about last week.”

The primary objective of one-on-one meetings will vary depending on the salesperson’s specific situation and level of experience, but the mechanics of the meeting are fairly consistent. In fact, my one-on-one meetings for 30 years have started with one very simple phrase:

“Tell me about last week.”

I know it sounds ridiculously simplistic on the surface, but trust me, there is a lot behind the curtain. You see, the real objective of a one-on-one meeting is to encourage dialogue.

Like any effective sales call, a sales manager should ask good questions and listen carefully. Unfortunately, in my opinion, too many one-on-one meetings become one-on-one beatings, where a manager focuses solely on numbers, constantly corrects behavior, dictates activity, and solves every problem.

But being a sales manager isn’t just about sales forecasts and KPIs. In fact, the critical aspect of sales management is actually the coaching and leadership involved. The one-on-one meeting provides a prime opportunity to instill confidence, demonstrate support, provide encouragement, and tune in to motivation. Done well, the dialogue created in consistent one-on-one meetings allows the effective manager to transform potential into top performance.

And it is this one simple question that gets the ball rolling. By letting the rep start the meeting with their view of the past week, the manager avoids the temptation to criticize and dictate. Just sit back and listen. Very carefully.

In my experience, when the salesperson does most of the talking, the manager will develop tremendous insight into that rep and their attitudes. You will understand why her performance is the way it is. You will know what is creating challenges for her. You will see how she reacts to adversity and failure.

During the meeting, I listen for specific areas that may need to be addressed. For example:

  • Does she create an effective plan each week; one that is consistent with her overall sales plan?
  • Is she executing her plan?
  • Does she have a strong understanding of our sales process?
  • Is her sales pipeline full of qualified opportunities?

However, I resist the need to correct and criticize every problem I see. Don’t jump into major correction during the first two or three one-on-one meetings because you’ll want the pattern to surface and become apparent through observation.

2. “What do you think the problem is?”

When it is necessary to address a particular issue, I take a very specific approach. I first tell the salesperson what I am seeing and then ask her for potential solutions:

“Jane, the past couple of weeks, I have noticed you’re struggling to follow through on some of your key priorities. What do you think the problem is?”

It’s way more work, and is probably less satisfying than jumping in and solving the problem personally, but salespeople approached in this matter begin to understand that they are expected to think, plan, and solve problems. Also, there is an enormous amount of information to be gathered from how the salesperson answers this simple question. Do they make excuses and blame others? Or do they openly talk about issues and ask for help? Then together you can identify root causes and create plans for behavioral change.

When things are going poorly, I may observe poor planning, poor execution, a failure to meet expectations, attitude problems, and so forth. And the one-on-one meeting provides the perfect opportunity to address these issues. I certainly don’t want to wait for the end of the quarter or, worse, the annual review!

In those situations when I most definitely want to offer specific advice, I actually ask permission: “I have a couple of ideas that I think might help. Would you like me to share them with you?” You will be surprised at the difference it makes to ask rather than simply dictate next steps.

3. “What about this week? What are your plans and priorities?”

The review of last week’s activity is the perfect set-up for the second phase of the meeting. In each one-on-one, after the rep and I have reviewed the past week’s performance, I then ask the following question:

“What about this week? What are your plans and priorities?”

As they tell me about their plan, I jot down a few notes, which I can then refer to in next week’s one-on-one meeting. This means that the following week, when they describe their activity, I can compare it to their stated goals and answer some important questions. Did they accomplish what they set out to do? Did they follow through on key objectives? Did they actually work their plan, or did they just tell me what they thought I wanted to hear? Most importantly, I get to evaluate their ability to plan and prioritize, which are critical skills for any salesperson and especially important if they aspire to sales management.

4. “What’s one thing that worked and one thing that didn’t, last week?”

It’s important to get specific about their wins as well as their challenges. This question gets to the heart of both. Alternatively, you can ask your employees to list one thing they’d like to start doing, one thing they’d like to stop doing, and one thing they’d like to keep doing.

For sales, this might look like:

  • One thing to start doing: “I’d like to start being more proactive about entering prospect data into our CRM. I’m going to do this by blocking off 10 minutes after every meeting to enter data immediately.”
  • One thing I’d like to stop doing: “I’ve been emailing prospects when I really should be calling them. This week, I’m going to call each of my prospects at least one time before sending a follow-up email.”
  • One thing I’d like to keep doing: “My meeting prep has been paying dividends lately. I’d like to keep my prep work rolling so I’m ready for the different needs each prospect brings to the table.”

This keeps your meetings actionable, your reps honest, and their path forward positive.

5. “Do you have any feedback for me?”

It’s just as important to ask them for feedback on your performance during your time together. I recommend using the SBI model of feedback. It looks a little something like this:

  • Situation
  • Behavior
  • Impact

In a feedback setting, your rep might use the SBI model this way:

  • Situation: “Last week, we had a meeting with Marketing to discuss the state of our pipeline.”
  • Behavior: “Mark kept interrupting me, and you stepped in and made sure I was able to finish my thought.”
  • Impact: “I felt heard and valued, and it was great to know you had my back.”

This ensures, whether the feedback is constructive or positive, it’s always specific, which gives you actionable steps to repeat or work on.

The one-on-one meeting has a singular purpose — to develop the salesperson’s potential through the improvement of critical skills. By prompting the rep to lead the conversation, you keep the focus on them. And if you’re executing the meetings well, one-on-ones will help you develop your relationship with the salesperson.

As an employee, how do you ensure you get the most out of your one-on-one meetings?

Come prepared with talking points and questions Here are some questions to ask your manager to ensure you have an effective meeting.

1. “What should I know about your communication and management style?”

This is a question you can use if you recently started a new job or received a promotion. Management styles vary from person to person, and it’s nice to know your manager’s style. They might even provide additional resources like a “how to work with me” document that provides some more details on how they prefer to communicate and work.

2. “What are your goals and priorities?”

For additional perspective, ask your manager what their priorities are. You’ll get a better understanding of the higher-level metrics your manager and your team are held to.

3. “What skills should I develop to excel in my job?”

If you’ve been through coaching and shadowing sessions with your manager, they likely have some recommendations about areas for improvement. This gives you an idea of what to focus on in the upcoming week or month.

4. “What do you think I can do to improve [skill/competency]?”

Asking for feedback will help you identify skills to work on, and goals to set. Your manager can likely provide additional resources and recommendations on how to develop these skills.

These questions and template will help you run an effective one-on-one meeting. If you have questions on how to improve your sales one-on-one meetings, check out my website:  BizLockerRoom.com . And to learn more, check out the ultimate guide to sales coaching next.

Kelly Riggs


Kelly Riggs is an author, speaker, and business performance coach for executives and companies throughout the United States and Canada, who is widely recognized as a dynamic thought leader, powerful speaker, and successful performance coach in the areas of sales, management leadership, and strategic planning. Kelly is a former sales executive and two-time national Salesperson-of-the-Year with well over two decades of executive management and training experience. His background as a coach, and an owner or partner in four different business ventures has helped him to create a wildly successful track record of helping individuals and business owners dramatically improve their business performance.

He has written three books: “1-on-1 Management: What Every Great Manager Knows That You Don’t” and “Quit Whining and Start SELLING!  His third book, co-authored by his son, Robby Riggs, is entitled, “Counter Mentor Leadership: How to Unlock the Potential of the 4-Generation Workplace”


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