26 Questions to ask your team in their next 1:1

We’ve all been there — that awkward half hour — no one really knows what to say, there’s work to get done, how’s this one-to-one going to help?

You’ve most likely been on the receiving end of a stilted 1:1, and if you’re reading this, you’re perhaps struggling to get much out of the conversation as a manager too.

But one-to-one conversations get a bad rap. With the right questions, and a clear definition of what a 1:1 is and isn’t, employees and managers can start to see real value.

This list is primarily for managers wanting to supercharge their 1:1 conversations with their team members. But if you’re an employee uninspired by the format of your one-to-ones, why not share this blog with your manager.

Benefits of 1:1 conversations

One-to-ones are an important part of the manager/team member relationship. For managers, it’s a chance to really get to know your team, and have an authentic, unfiltered conversation. And for team members, it’s a chance to air your concerns, ask questions and talk to your boss on a more human level.

1:1s are great for:

Building relationships between managers and team members
Providing support
Building trust
Increasing productivity
Enabling open and honest conversations
Tackling issues before they get too big
Collecting honest feedback.

With the right approach, one-to-one’s are a great way to really get to know each other. And with better relationships comes a happier team, who’re more likely to stick with you. It’s a win win.

How to get the most out of your 1:1

Stop! Step away from the calendar. Before you send that invite, it’s really important to define exactly what a one-to-one is first.

Here at Progression we approach 1:1s like this:

A 1:1 should be focused on human things: feedback, growth and "how's it going" not craft things: code, status updates, backlog refinement.

1:1s are for team members. Managers will come along with discussion points, but ultimately, it’s up to the team member to decide what they want from the conversation.

The most important thing is not to overthink it!

During the 1:1 itself, try not to focus too much on scribbling everything down — you need to connect on a human level, which requires eye contact. Just make sure you note down any key points or actions so you’ve got something to refer back to.

Use our free 1:1 meeting template to document your conversations in a consistent way.

What to ask in a one-to-one

Now we’re not suggesting you use all 26 of these questions in your next 1:1 (remember, they’re chats not assessments), but try testing out a few in each meeting. You’ll soon work out what resonates best with your team, but keep mixing it up so things don’t get stale.

It’s really important you share the list of questions you might ask ahead of the 1:1, so there’s no nasty surprises and your team member has an idea of what they can expect. Here at Progression, we create a 1:1 document in Notion for every member of the team when they start — it includes the list of questions as well as all the notes we make when we meet.

Get personal

1. How are you feeling today?

If the answer’s vague, they may have something on their mind

2. Outside of work, what’s been your biggest accomplishment since we last met?

Try to connect on a more personal level

3. Do you feel like you’re getting enough downtime?

If the answer’s no, follow-up by asking how you can help change that

Ask for feedback

4. How has the last week been?

A ‘warm-up’ question if you like, and a chance to reflect — the answer to this question may well inform the others you choose to ask

5. What's been most enjoyable this week or since we last talked?

This shouldn’t be about a completed task — it might be a team retro that ended with some really interesting discussion, or even a team lunch that brightened an otherwise stressful day. Whatever the team member’s enjoying, try to facilitate more of it!

6. What’s inspiring, motivating, and energising you right now?

In a similar vein to question 5 — whatever the answer, make sure you enable more of it

7. What part of your job are you enjoying the least?

This can be a tricky one to dig into, and you might not get a real answer the first couple of times you ask it. But persevere — as the trust between you grows, your team member will feel more comfortable talking honestly with you

8. What is frustrating or boring you right now?

A reframing of question 7. Sometimes there’ll be an action off the back of it, either for you or the team member. If not, try offering another perspective — instead of ‘yes, auditing is boring’ try ‘yes, this auditing task is monotonous right now, but once it’s done, you’ll have a much clearer idea of the direction you need to go in’

9. What is the one task you would love to stop doing if it was possible?

Whatever the answer, really try to dig into this one. Perhaps your team member doesn’t see the point of a task — explain the background and provide your reasoning. Perhaps your team member feels less confident in this area — block out some time to give them the training they need

10. What has been challenging?

An alternative to questions 8 and 9

11. What are you anxious about?

This is a great example of a question that can help address an issue before it gets too big — we’d recommend asking this one often to ensure you’re giving your team member all the support they need

12. What's one thing you think could be better about working at the organisation for you?

Sometimes, the best answers come from the most difficult questions

13. Do you have any feedback for me?

If the answer’s vague, try digging deeper with question 14 or 15

14. What's one thing I could do better to help you?

Don’t be shy asking what more you can do

15. What do you think I should be doing that I'm not?

An alternative to question 14

16. How can we improve this time?

This might be an improvement the team member identifies they can make, or it might be a suggestion for you

17. If you were to apply for a new job outside of the organisation right now, what would you be looking for that we don’t offer?

A particularly good question for employees who’ve been with the organisation for a while

18. What are you looking forward to?

A nice one to end on, especially if parts of the conversation have been more negative

Think longer term

19. How are you feeling about your growth at the moment?

This question isn’t about a team member’s immediate actions, or even their projects over the next quarter — this is about their skills and career more generally

20. Is there any progress at your end?

If your employee has a career plan in place, now’s a great time to dig it out. If not, and the employee doesn’t feel like they’re making much progress, consider setting aside some time to make one

21. Are your growth goals still relevant?

If your team member’s not making much progress with their growth goals, it might be time to revisit them altogether

22. Are your goals still the right ones?

A reframing of question 22

23. Is there anything I can help to unblock?

If the answer’s not forthcoming, it’s fine to make a few suggestions

24. How can I help with your growth goals?

An alternative to question 23

25. What would you like to know about the company?

Try to encourage questions that the team member might be too afraid to ask in an open forum. If you don’t know the answer, that’s fine — just make a note to find it out

26. What do you think the founder/CEO should be paying more attention to?

Whatever the answer, make sure it’s captured and shared with your leadership team

Supercharge your next 1:1 with Progression

1:1s are difficult — goals are hard to set and progress hard to follow and measure. When you’re not clear on the outcomes, and you’re tight on time, that weekly half hour can fall by the wayside.

But it doesn’t have to be this way. Progression can help you have better career conversations with your team.

Get on the same page 📖

Create a progression framework to quickly show your team what’s expected of them in their role, and where the opportunities are for them to grow within your organisation.