Five Questions Every Sales Manager Should Ask During One-on-Ones

Most sales managers know regular one-on-ones are important. But too often, those conversations turn into status updates, pipeline inspections, or rushed check-ins, leaving little room for meaningful development.

In this episode, Matt Sunshine breaks down five simple questions that can transform one-on-ones into stronger coaching conversations.

You’ll learn how to:

• Reinforce what is already working
• Uncover where salespeople are getting stuck
• Encourage reps to take ownership of their next steps
• Make skill development more focused and measurable
• Identify the support each salesperson needs to succeed

The best one-on-ones do more than review performance. They create reflection, accountability, trust, and long-term growth.

Because when managers ask better questions, salespeople give better answers, and better answers lead to better performance.

Matt Sunshine

The Center for Sales Strategy

Transcript

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Welcome And What To Expect

Matt Sunshine 0:05

Welcome to Improving Sales Performance, a podcast highlighting tips and insights aimed at helping sales organizations realize and maybe even exceed their goals. Here, we chat with thought leaders, experts, and gurus who have years of sales experience from a wide range of industries. I'm your host, Matt Sunshine, CEO at the Center for Sales Strategy, a sales performance consulting company. Most sales managers know they should be having regular one-on-ones with their team. But here's the problem. A lot of one-on-ones become status updates or pipeline inspections or rushed conversations, squeeze between meetings. And when that happens, the biggest opportunity gets missed. Development. The best one-on-ones create accountability and growth. They help salespeople think more clearly, solve problems faster, and improve performance over time. The good news, you don't need a complicated coaching system to make that happen.

Why One On Ones Go Wrong

Matt Sunshine 1:09

Today, we're breaking down five simple questions every sales manager should consistently ask during one-on-ones to create better conversations, stronger accountability, and more effective coaching.

Question One Start With Wins

Matt Sunshine 1:22

Number one, what's going well right now? Many managers jump straight to problems, but starting with wins does two important things. It builds confidence and it reveals repeatable success patterns. You're looking for momentum and confidence, positive behaviors worth reinforcing. This question helps salespeople recognize what's actually working instead of only focusing on the pressures or the challenges. And often the things going well reveal strengths that can be leveraged elsewhere.

Question Two Find The Stuck Point

Matt Sunshine 1:58

Number two, where are you stuck? This is where coaching really begins. Top performing salespeople still get stuck. Deals stall, prospecting slows down, confidence dips, priorities just get messy. Great managers create space for the honesty. Because if reps feel like they always need to have everything figured out, they stop bringing problems forward. This question uncovers obstacles, skill gaps, decision-making issues, and avoidance patterns. And really important, it helps managers coach before small issues become big performance problems. Overwhelm usually comes from trying to learn everything at once.

Question Three Put Ownership On Reps

Matt Sunshine 2:45

Question three, what's your plan? This question shifts ownership back to the salesperson. One mistake managers make is to solve every problem themselves. But development happens when reps learn how to think through challenges independently. So instead of immediately giving answers, ask, what do you think the next step should be? Or how would you approach this? Or what options are you considering? By doing this, it builds critical thinking, confidence, accountability, and better decision making over time. Managers should coach the thinking, not just create dependency.

Question Four Choose One Skill

Matt Sunshine 3:29

Question four What skills are you focused on improving? Too many one-on-ones only focus on the numbers, but sustainable performance comes from skill development. Maybe the focus is on the discovery meeting or handling objections or prospecting consistency, closing conversations, or even business acumen. The key is to stay specific. When reps actively focus on one skill at a time, improvement becomes measurable, coaching becomes clearer, progress becomes easier to see. Development shouldn't feel random. It should feel intentional.

Question Five Ask How To Help

Matt Sunshine 4:08

Number five, what support do you need from me? This question changes the dynamic completely because great managers don't just inspect performance, they remove obstacles. Sometimes reps need coaching or clarity, they need availability to resources, prioritization helps, encouragement. Sometimes they need accountability. They simply need to feel supported. This question reinforces the partnership, the trust, and the accessibility. And it reminds the salesperson hey, we're working on this together.

Wrap Up Better Questions Better Results

Matt Sunshine 4:47

So as I wrap this up, the best one-on-ones aren't all that complicated. They're consistent. And the goal isn't to review performance, it's to develop people. So the next time you sit down for a one-on-one, make sure you're asking questions that create time for reflection, ownership, accountability, and of course, growth. Because when managers ask better questions, salespeople give better answers, and better answers lead to better performance. This has been Improving Sales Performance. Thanks

Subscribe And Find More Resources

Matt Sunshine 5:24

for listening. If you like what you heard, join us every week by clicking the subscribe button. For more on the topics covered in the show, visit our website, the Centerfor Sales Strategy.com. There you can find helpful resources and content aimed at improving your sales performance.