One-on-one questions you should avoid (and what to ask instead)

Asking vague or inappropriate questions can completely derail a one-on-one meeting and prevent your direct reports from opening up to you. In the worst cases, poor one-on-one questions could erode team morale and trust. 

Learn which one-on-one questions you should absolutely avoid and what you should be asking instead. Not a manager? Read Better one-on-one meetings: Employee’s guide for career growth.

What’s a one-on-one meeting and why do they matter?

A one-on-one meeting is a recurring time set aside for a manager and a direct report to connect. Essentially, one-on-one meetings are the foundation of the employee-manager relationship. They’re the #1 opportunity managers have to build rapport and form strong, trusting relationships with the individual members of their team. 

One-on-one meetings are also the ideal space to discuss key aspects of the job that shouldn’t be addressed in a public forum, such as performance evaluations, individual career coaching sessions, or venting sessions. If an employee is having an issue with the job or their coworkers, a one-on-one meeting is a safe space where these issues can be addressed. 

To realize the full benefit of one-on-one meetings, they must be scheduled regularly. Consistently scheduled one-on-one meetings: 

• Strengthen relationships
• Provide a safe space to deliver constructive feedback
• Enhance team engagement
• Allow managers to track projects and goals
• Keep employees and managers accountable to one another
  

Supporting your team is the primary responsibility of a manager, as a team can’t function if they don’t trust their leader. Regular one-on-one meetings keep your team engaged, motivated, and committed to continuous improvement. 

📚 Learn more about one-on-one meetings, including the importance and best practices of running one-on-one meetings.

One-on-one questions to avoid and what to ask instead

1. How's it going?/How are you doing?

While this is a very common, casual way to start any conversation, in the context of a one-on-one meeting, it’s too vague. “How’s it going,” is a greeting, not a real question. And the standard response, if you get one, is usually just “good” or “okay.” If you say “how’s it going” to a passerby on the street, they might even just say, “hi,” in return. 

“How’s it going” is tantamount to a polite nod of the head or a wave—it doesn’t provide the space to discuss specific, deeper issues. If you are really trying to ascertain how an employee is feeling, you need to be more specific. 

Instead of saying “how’s it going,” you could ask, “how is your day going,” “how is your week going,” or, “did you do anything interesting on the weekend?” These questions help to break the ice and provide the employee with more space to discuss what’s going on in their personal or professional life. 

2. What do you think of *blank* team member or *blank* team?

Asking an employee what they think about one of their coworkers is essentially inviting them to gossip about someone you both work with who isn’t there to defend themselves. Do not ask any question that could come across as gossip or lead to a rumor being spread. 

If an employee comes to you with a serious issue about one of their coworkers, then it’s important to hear them out and let them vent, but do not invite your employees to gossip about each other by asking a direct report about another team member. 

If you sense that your team is having difficulty working together, then it’s up to you to determine what the cause could be, but tread lightly when asking questions about specific members of your team, and do not share your own concerns. 

If an employee is venting about their coworker, listen attentively, but do not cast any aspersions of your own. People talk, and if the employee in question hears through the grapevine that you are concerned about their performance, their morale and engagement will disintegrate, along with their trust in you as a leader.

Gossip erodes trust—and a team can’t function without trust. 

3. What's the latest on *blank* project?

One-on-one meetings aren’t your chance to catch up on project status updates. Conversations about deliverables and project action items can and should happen asynchronously. A one-on-one meeting is your only opportunity to connect with the individuals that make up your team. Save project updates for Slack. 

Instead, ask “what’s been the most challenging aspect of *blank* project,” or, “what’s surprised you most about *blank* project,” or, “what have you enjoyed most about working on *blank* project?” These questions enable you to identify how the employee thinks through projects, and they allow you to determine any potential blockers or bottlenecks threatening the team’s morale or productivity. 

📚 Learn more about The Benefits of Asynchronous Communication. 

4. Do you need anything from me?

You may be asking this question with the best intentions, but it’s an ineffective way to check if an employee needs your help. Not only is it a vague question, but it also puts the employee on the spot. Keep in mind that you’re the manager, meaning you have authority over your direct report. You may be the best, friendliest manager around, but you’re still your employees’ boss, and it’s difficult for an employee to ask their boss for something or critique their performance. 

When you put your direct report on the spot, they’ll likely dodge the question for fear of inconveniencing or upsetting you. 

Instead, collaborate on a plan for your direct report’s career development and check in on the plan’s progress during each of your one-on-one meetings. If you sense that your direct report could use a little help on a project, suggest an action you could take and ask them what they think about your idea. 

Don’t ask your employee to come up with a plan for how you can help them. Suggesting an action you could take gives your direct report the space to share specific ways you could offer them support. 

One-on-one meetings are a space for coaching and checking in with each of your employees’ personal and professional development. The meeting belongs to both of you, so ask direct questions that leave room for your direct report to contribute. 

Plan effective one-on-ones with Charma

Charma is the best practice toolkit for managers to organize, motivate, and engage their teams, beloved by managers, HR, executives, and ICs alike.

Our platform helps both managers and employees execute one-on-one meetings with transparent scheduling, collaboration, and intentional goal-setting. Schedule and structure your one-on-one meetings with Charma, so every step is clear, and nothing is forgotten.

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