6 Common One-on-One Questions Everyone Hates

As a manager, one-on-one meetings with employees are when you do some of your most important work as a leader. Your tools for doing that work are the questions you ask employees. 

Here’s something your employees won’t tell you: some of those questions aren’t working.

There’s a place for difficult and even unpleasant questions in one-on-ones, but some questions don’t serve your or your employees’ needs. 

At best, asking these kinds of counterproductive questions in a one-on-one will make your employee internally roll their eyes. At worst, they’ll damage the trust your team holds in you and compromise your position as a leader.

Let’s go over some questions that real-life employees have reported hearing from former managers, explore the good intentions behind them, and offer some alternatives that will get you the information you need without rubbing anyone the wrong way.

1. What’s your least favorite thing about me as a manager?

The good intention behind it: You want to invite constructive criticism so you can grow and tailor your management style to each team member.

Why people hate it:  You might think you’re saying “I’m coming to you with a humble request for feedback.” But what your employee hears is this:

 Over the course of a long, close relationship with an employee, you might develop the kind of trust where they would feel safe giving you honest feedback. But for the most part, your team member won’t want to risk offending the person to whom they report. 

In the event that a team member tries to give you feedback, they’ll self-censor, and will probably end up telling you something they can safely say is “bad,” but doesn’t overtly criticize you. You won’t learn anything useful, and you might walk away with an inaccurate picture of your own strengths and weaknesses.

What to ask instead: If posed in a more targeted way, requests for feedback can be totally healthy! But instead of inviting a critique of your whole management style, try narrowing your focus to specific behaviors, like “What could I start or stop doing that would help you work better?” or “How do you like to receive praise and criticism?” 

The answers to each of these questions will vary widely from one employee to the next, and that’s a good thing, since at the end of the day there’s no one-size-fits-all approach to management. By keeping it specific and personal, you’ll get more actionable feedback, preserve appropriate boundaries, and avoid coming off as insecure.

2. How do you think [X team member] is performing?

The good intention behind it: You want on-the-ground insight that you might not be able to see from your vantage point as a manager, or you might just be curious about whether two employees collaborate well.

Why people hate it: Employees hate to feel like they’re talking about colleagues behind their backs, or that they’re expected to be monitoring each other’s performances in an unofficial capacity. Furthermore, in asking this, you’re bound to make your employee wonder what you ask about them once they leave the room.

This question is bound to make your employee wonder what you ask about them once they leave the room.

What to ask instead: If you’re trying to figure out whether two team members work well together, you can simply ask “Do you think you and [X] are a good fit for this project?” By making the question about the dynamic instead of the individual, you can give your reports a chance to say “actually, our communication styles don’t really line up” without feeling like they’re trash-talking a colleague. 

But if what you’re really trying to figure out is if one of your team members is underperforming, that’s research you need to do on your own, by keeping an eye on their work. Aside from the fact that asking this question creates an atmosphere of suspicion, it’s unlikely to turn up impartial, accurate information. No employee has the complete picture of another’s performance, so their perception of each other’s work is likely to be incomplete and biased by their personal feelings.

3. Are you comfortable being one of the only [women/people of color/LGBTQ/other underrepresented group] who works here?

The good intention behind it: You want to foster a diverse and inclusive workplace, and you genuinely want to make sure that all your employees feel comfortable and respected at work. 

Why people hate it: There are a couple of problems with this question that make it problematic for minority employees (especially if the manager asking it is not themselves a member of a minority group). 

The first problem is that it tacitly places the burden of “feeling comfortable” on the individual employee. Intentional or not, this can increase the pressure your report feels to conform to the prevailing environment, even if the environment is the one that needs to change.

The second problem is that—unless this employee has already started a conversation with you about this topic—they almost certainly don’t want to be asked about it. By introducing this issue, you could very well make an employee who considered their identity a nonissue suddenly worry that they’re being singled out because of it.  

What to ask instead: When it comes to building an inclusive and equitable work environment, actions speak louder than words. For instance, if you’re worried a female employee feels isolated in a male-dominated workplace, the onus isn’t on her to feel more comfortable, it’s on you to hire more women. 

If you’re worried a female employee feels isolated in a male-dominated workplace, the onus isn’t on her to feel more comfortable, it’s on you to hire more women.

If you want to solicit feedback on this subject in a way that doesn’t make employees feel singled out, create an anonymous venue where your team can voice their concerns. Finally, no matter how evolved you are, implementing diversity and inclusivity training is a great way to update your toolkit and show that you are committed to making your entire team feel respected.

4. How do you think you’re doing at [X task]?

The good intention behind it: If an employee seems stressed despite doing good work, or seems confident even though they’re falling behind, you may want to hear a self-assessment and find the root of the disconnect.

Why people hate it: One employee succinctly described her reaction to being asked this question: “It feels like a trick.” 

Employees can’t hear this question without worrying what they’ve missed and what you’re expecting to hear. Their minds will be occupied with anxiety, and it will close them off from really hearing whatever criticism (or praise) you’re trying to deliver. While there’s room in one-on-ones for you to ask difficult questions about performance, you won’t get genuine answers unless employees feel psychologically safe. 

If you think they’re doing well but are self-doubting, say “I notice you seeming frustrated but your work is very good. Can you tell me what’s concerning you?”

What to ask instead: Offer some clues about your own opinions before asking people to self-report. If you think they’re doing well but are self-doubting, say “I notice you seeming frustrated but your work is very good. Can you tell me what’s concerning you?” If you think they’re doing poorly but don’t know it, start by saying “I want to go over what the expectations are for you right now, so we’re sure nothing is falling through the cracks.” 

5. I don’t have anything to discuss today. Would you like to talk about something?

The good intention behind it: You might want to give your employee the opportunity to guide the agenda and see what they come up with. Or you might just be overwhelmed and let planning for this meeting get away from you.

Why people hate it: Unless you’ve told an employee ahead of time that you expect them to lead the meeting, showing up without an agenda just makes you seem disorganized, and makes employees feel like you’re not taking their time seriously. 

What to ask instead:  There’s nothing wrong with letting a team member lead a one-on-one, but give them plenty of notice, so they feel empowered instead of blindsided. If you’re genuinely struggling to come up with one-on-one questions, refer to our templates for inspiration. When you don’t have any immediate, project-related concerns to go over, it’s the perfect time to introduce high-level topics about their career advancement. And if you truly don’t have the bandwidth for a meaningful interaction during a one-on-one, you’d be better off rescheduling than making an employee feel like an afterthought.

6. Do you see yourself doing this job in three months?

The good intention behind it: An employee seems disengaged, so you want to understand why, and to prepare yourself if you’re about to have to replace them.

Why people hate it:  This is a brusque and impersonal way to broach a very personal topic, and for employees, there is no right answer. If your employee is looking elsewhere for work, they’re not going to admit it, especially if you’ve given them no reason to. Even if they’re not seeking other employment, they might feel insulted, under-appreciated, or worried about their job security.

What to ask instead: If your report seems unhappy or unfocused, it’s crucial to probe the issue in a way that draws them out, rather than backing them into a corner. Talk to your team member about their long-term goals, ask what you can do to help them grow within their role, and discuss how they can stay engaged with their work. 

If your report seems unhappy or unfocused, it’s crucial to probe the issue in a way that draws them out, rather than backing them into a corner.

Their reaction will tell you a lot about how likely they are to stick around. You can even win back an employee who is on the fence by reassuring them that you are personally invested in their success.

Stay engaged and embrace change

If you’ve asked any of the questions on this list, don’t beat yourself up! Just use this as an opportunity to look at your old one-on-one habits with fresh eyes. Update your meetings with new questions, and allow them to continually evolve to reflect your individual relationships with team members. 

Uptick equips both managers and employees with the tools to communicate honestly and effectively in one-on-ones. It’s built around questions that push projects, careers, and relationships forward, so you and your employee come out stronger with every meeting.

Your employees deserve a plan.
Build it together with Uptick.

Scroll to Top