Top one-on-one questions to ask your team

One-on-ones getting stale? Worried your conversations are turning into status updates? The SoapBox one-on-one question suggester bot is here to help!

This is one of our users’ favourite features of SoapBox: once you create your one-on-one agenda, the question suggester will recommend agenda items to add to make the conversation as meaningful as possible!

We first shared some of these suggested questions in a blog post a year ago. But since we got such a great reaction, we thought we’d do a little end-of-year update!

Use our handy little one-on-one question guide below to get into the good stuff with your direct reports. Just choose your topic, and see what kind of goodies the question suggester bot has to offer!

Or better yet, get our free meeting agenda app to see the Question Suggester in action! Click here to get started.

To talk about…company mission, vision and goals

It comes up in virtually any management book imaginable: every member of your team should be able to succinctly dictate your company mission, vision and goals at any time. If they can’t you have a communication problem on your hands.

These one-on-one questions will help you to keep company direction top of mind at all times:

• If you were CEO, what’s the first thing you’d change?
• What are you LEAST clear about, in terms of our strategy and goals?
• Are there any aspects of our culture you wish you could change?

To talk about…teamwork and collaboration

The iceberg of ignorance is very real: the higher up you are in a company, the less you know about what’s going on below you. That’s why it’s so important to talk to your team about what’s going on among their ranks. This helps to identify red flags before the become bigger issues.

These one-on-one questions will help you to learn what’s going on in your team:

• What’s the biggest blocker affecting the team from performing to their fullest potential?
• What’s a problem we have on our team that I might not know about?
• Is there anything that would be productive for me to re-explain to our team?

To talk about…increasing productivity

This is classic one-on-one stuff. You want to help your team do the best work possible. But first, you need to learn what’s standing in their way. The beauty of this conversation is that there are probably roadblocks or time wasters that you had no idea existed – and might even exist for other team members, too.

These one-on-one questions will help you remove roadblocks:

• What does an ideal, productive work day look like to you? Walk me through it.
• What are the biggest time wasters for you each week?
• What projects would you like to work on or be more involved in?

To talk about…growth and personal development

Another go-to one-on-one topic. Some managers like to save one one-on-one meeting every month or quarter to dive solely into this topic, because sometimes it can take some time. Or, you can ask a question each meeting to make it a continual conversation.

These one-on-one questions will foster career conversations with your team:

• What areas of the company would you like to learn more about?
• What skills would you like to develop right now?
• What professional goals would you like to accomplish in the next 6 to 12 months, and what makes you say that?

To talk about…accountability

Holding your team accountable isn’t always easy because it involves fostering long-term habits. Asking questions around ownership and team accountability every time you meet will help to build a culture of accountability – not to mention encourage your team to honour each other when needed.

These one-on-one questions will help foster a culture of accountability:

• What can I hold you accountable for next time we talk?
• Who on our team deserves a shout out/recognition for their work and why?
• Who from other teams deserves a shoutout for their help and why?

To talk about…feedback for you

Good managers deliver feedback to their team on a regular basis. Great managers foster a trusting relationship where their team feels comfortable returning the favour. Giving feedback to your manager isn’t the easiest thing in the world, so you need to encourage it over time.

These one-on-one questions will encourage your employees to manage up:

• Am I acting like the best manager you could wish for? What could I be doing better?
• What do you like about my management style? What do you dislike?
• When’s the best time to give feedback on your work?

To talk about…how they really feel

Ooof – this is a tricky section. These are the questions you’re afraid to ask. The questions that some managers avoid at all costs – but then pay for it when their team members quit unexpectedly. You need to have a pulse on your employees at all times, even if it’s uncomfortable to get into it.

These one-on-one questions will prompt the more “icky” conversations you should be having:

• What’s something you’d like to share but is a little stressful to bring up in person?
• On a scale of 1-10, how happy are you at work?
• Which one best describes you during the past month? 😀 | 🙂 | 😐 | 🤔 | 😒 | 😳 | 😰 | 😤

To talk about…personal stuff

Another area that’s sometimes tricky to dive into – especially if you’re normally keeping one-on-ones focused on project updates. But work/life balance is super important to your team, and part of your role as manager is to do what you can to make that happen.

These one-on-one questions will open up a conversation about work/life balance:

• What’s one thing we could change about work for you that would improve your personal life?
• How do you feel your work/life balance is? What would you want to change, if anything?
• Is your job what you expected when you accepted it?  If not, where has it differed?

These one-on-one questions should get you started with your next agenda! But if you want to see more, sign up for the free SoapBox app to see the question suggester in action!

Have amazing one-on-ones with SoapBox