14 questions to ask an underperforming employee during a one-on-one meeting

When an employee is struggling, here’s what the best managers do.

Someone’s slipping. You see it. You feel it. You’re not on the same page. You desperately want to pull the person up, but you’re not sure exactly how. Do you encourage them? Switch them off the project? Change how you’re leading them?

You’re now facing one of the toughest tasks as a leader: How do you manage underperformance at work? And more specifically, how do you sit down and talk about their underperformance with them, during a one-on-one meeting with her or him?

It’s tempting to look outward first. To blame the person herself or extenuating circumstances. “They don’t pay attention to detail.” Or, “The client is being unreasonable with them.”

While those may very well be the case, you should also turn inward. As leaders, when an employee is underperforming, we must self-reflect. What are you doing that is stopping this person from doing their best work?

The hard part about managing an underperforming employee is choosing to look both inward and outward for the sources of underperformance at work: What are you doing to hold an underperforming employee back? And what is the underperforming employee doing to hold herself back?

Oftentimes, we think we know the answer to those questions. We have hunches about what’s causing the underperformance: “It’s their perfectionist tendency getting in the way, obviously…” or “It’s my lack of context I shared about the project, clearly…”

So, we just create a performance improvement plan based on those hunches and move forward.

That path is instinctual — but that path is flawed. Assuming what’s wrong doesn’t help you get any closer to finding out what actually is wrong. While your hunches may end up being spot-on, in my experience, I discover the truth of what’s really holding an employee back when I ask, not when I assume. Coaching a struggling employee to success begins with asking the right questions, not simply arriving with the supposed answers.

Given this, when you sit down in a one-on-one with an underperforming employee, what should you ask? What questions will help you look both inward and outward to get to the underlying source of underperformance?

Here are 14 questions to try. They are by no means the only questions you ask during a one-on-one (here are other ones to consider). But, they provide a good starting place to delve into how to better manage an underperforming employee.

Ask these questions to look inward.

You’re trying to figure out: “How have I been letting this person down? How have I been getting in the way?”

• Is it clear what needs to get done? How can I make the goals or expectations clearer?
• Is the level of quality that’s required for this work clear? What examples or details can I provide to clarify the level of quality that’s needed?
• Am I being respectful of the amount of time you have to accomplish something? Can I be doing a better job of protecting your time?
• Do you feel you’re being set up to fail in any way? Are my expectations realistic? What am I asking that we should adjust so it’s more reasonable?
• Do you have the tools and resources to do your job well?
• Have I given you enough context about why this work is important, who the work is for, or any other information that is crucial to do your job well?
• What’s irked you or rubbed you the wrong way about my management style? Does my tone come off the wrong way? Do I follow-up too frequently with you, not giving you space to breathe?

Ask these questions to look outward.

You’re trying to figure out: “What on the employee’s end is limiting them? What choices or capabilities of their own are keeping them from the results you want to see?”

• How have you been feeling about your own performance lately? Where do you see opportunities to improve, if any?
• What are you most enjoying about the work you’re doing? What part of the work is inspiring, motivating, and energizing, if any?
• What part of the work do you feel stuck? What have you been trying the “crack the nut” on, but it feels like you’re banging your head?
• What part of the work is “meh”? What tasks have you felt bored or ambivalent about?
• When’s the last time you got to talk to or connect with a customer who benefited from the work you did? Would you like more opportunities to do that, and should make that happen?
• Do you feel you’re playing to your strengths in your role? Where do you feel like there is a steep learning curve for you?
• Would you say you’re feeling optimistic, pessimistic or somewhere in the middle about the company’s future?

You’ll notice that none of these questions ask, “What do you think you’re doing wrong?” or “What do you think I’m doing wrong?” The point of these questions is not to end up in an accusatory place, either way. Your goal is to reach a place of better understanding.

By approaching the conversation with an underperforming employee with questions to ask, rather than answers or directives to insert, you create space for that employee to want to do something different. To actually change and improve.

That change, that improvement, is the goal, after all.

💫 To have this conversation about underperformance, you’ll want to hold a one-on-one meeting with your direct report. Use our One-on-Ones Tool in Know Your Team to get hundreds of one-on-one meeting question suggestions just like this, to help prepare you to have this conversation — and future one-on-one conversations — well. Give Know Your Team a shot today.

P.S.: If you did indeed enjoy this piece, please feel free to share + give it ❤️ so others can find it too. Thanks 😊 (And you can always say hi at @clairejlew.)