9 Questions to Ask When You Start to Notice Underperformance

Troubleshooting performance early, when you’re not entirely sure what the issue is...

Jun 05, 2025

👋 Howdy! Claire here, Founder & CEO of Canopy. I've spent the last decade training 50,000+ managers and studying 50+ years worth of leadership and team dynamics research, so you don’t have to 😅 I distill all my learnings in this weekly newsletter.

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Underperformance doesn’t hit like a tidal wave. It creeps up slowly, like the gentle rise of water along the shoreline. Often, you only notice once the water level has shifted.

You notice a team member who isn’t quite their normal self. It’s the small things: They are typically early to meetings and they’ve been late to the last few. Usually the first person volunteering ideas, now they stay quiet. They are close-to-flawless when knocking out to-dos and all of a sudden you start to see errors on even basic tasks.

It’s not necessarily a disastrous slip in performance — but that’s what almost makes it more precarious. You’re not sure if you’re seeing just a temporarily blip on the screen, or the first indicators of a larger nose dive to come. You’re concerned that tolerating the so-so performance might devolve into perpetual underperformance… and the project you’re working on right now can’t afford that right now (or, ever, really).

It would almost be easier to address if they had completely blown a project or missed a critical deadline. But these smaller, subtler issues feel trickier to bring up, especially with someone who has historically done well.

You’re concerned about appearing nit-picky or “hovering.” Worse yet, you’re worried about seeming insensitive, especially if you later discover a deeply personal issue affecting them. (No one wants to be the leader who criticizes an employee’s performance just after they’ve learned their dad’s cancer is back.)

If you find yourself nodding along here, I get it. There’s a part of you that should applaud that instinct: It’s beautiful that you care deeply about your employee’s experience. Your first impulse is understandably to avoid rocking the boat unless absolutely necessary.

However, if we truly care about our team members, it’s essential to speak up compassionately when we notice changes. We’re not rocking the boat — we’re ensuring it’s still headed in the right direction. The sooner you discuss these concerns, the better. Addressing performance early gives them a genuine chance to correct course, which may be the most compassionate act of all.

You’ll want to ask questions that open up dialogue without projecting assumptions about the cause. This isn’t an interrogation or a probe into their personal life. Instead, create space for them to share openly about what’s affecting their performance, allowing you both to collaborate proactively.

Here’s a starting point with the 9 best questions to troubleshoot performance:

1. “How’s your energy level these days?”

This is a deceptively simple question that reveals what factors might be affecting their work, without pressuring them or assuming it’s one thing or another. We all show up to work each day with different energy levels, whether that’s an external factor (e.g., kids have been super sick lately, dog sadly passed away) or something related to the work itself (e.g., unclear on priorities overloaded with projects, need some support and training). But rather than butting in and brusquely asking, “Are you sick, or what’s bugging you lately?” this question helps them space to share what they feel like is responsible to share, on their own terms.

2. “How’s your workload and bandwidth lately?”

As leaders, we often check-in on the work itself, the timeline, the deliverables — but we forget to check-in on the capacity that our team members have. Do they have space to hold all stuff in the first place, or has too much been piled on? This is particularly a great question to ask the person when you have sort of a silent soldier who usually says “all is fine” and they tend to take a lot on.

Then, I suggest kindly sharing a few observations of where you’ve noticed drops in the quality of their performance…

3. “I’ve noticed some things falling through the cracks lately, like [INSERT SPECIFIC EXAMPLES]. How might we work together to address this moving forward?”

It’s important to not pretend that things aren’t just hunky dory — that you’re observing some things different in their performance, specifically. Notice though I don’t say vaguely “some things have been missed”. You’ll want to be as specific as possible, so the other person isn’t confused by what you mean that you feel performance has dropped.

You’ll also notice that I didn’t sugarcoat and say “and it’s all okay,” nor did I linger on “you used to do things like this…” You’re focusing on the future, and you’re focusing on what can you BOTH together do differently. Because of course, as their leader, there are always things that you can and want to do better to support them.

Which leads me to my next suggested question…

4. “I’d love to be as helpful as I can here. Can I clarify priorities, take something off your plate, or provide more context on anything?”

You are offering something specific as a way to help — not just, “Anything I can do?” When you offer specifics, then the other person is more likely to take you up on your offer. You can always offer something specific: More prioritization, more context, taking something off a plate, connecting the dots on something, streamlining an initiative, communicating something to upper leadership, getting clarity on something.

If the employee is uncertain about why their performance is slipping, consider asking these questions that prompt deeper reflection…

5. “What feels harder lately than it should?”

I love this question because it is really about the delta — the difference between what is expected vs. reality. You can identify performance blockers and friction points more easily this way.

6. “What feels clear or unclear to you?”

Oftentimes, the source of slipping performance has to do with something not being clear: The expectations aren't clear, the context isn’t clear, the stakeholders aren’t clear, the level of detail isn’t clear, etc. And so you’ll want to ask upfront, what does or doesn't feel clear?

Additional helpful questions you may want to ask, to get to the root cause of the underperformance…

7. “What part of the project feels draining for you right now?”

Identifying where the greatest burden in the project can often lead you to where the greatest opportunity for support is.

8. “What part of the project feels energizing for you?”

Understanding what motivates them can help realign tasks to connect to what they find energizing, and help to turn performance around.

9. “Do you have any pointers for how I’ve been communicating?”

Crossed wires and communication breakdowns often are obstacles to performance that we’re not always cognizant are present. As a result, you’ll want to invite their perspective on how communication between the two of you can be improved.

Your conversation, of course, is with a real human — not a block of text. And so when you ask these questions, listen actively, thoughtfully, and kindly to understand what’s genuinely happening and how you can help.

You don’t want to assume reasons for underperformance, but you do need clear and upfront expectations. Respecting the person and respecting the work go hand-in-hand. You care about how this person is feeling and you care about the work getting done. These two things are not mutually exclusive. And your effort to get this conversation right is proof of it.

I look forward to hearing how the conversation goes.

-Claire

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📣 Invite me to deliver team keynotes and workshops, remotely or in person on this very topic: “What To Do When Someone is Underperforming.”
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🌿 Use Canopy, our lightweight leadership learning app, in your day-to-day.
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