54 Most Relevant 1:1 Meeting Questions Every Manager Should Know

Akshit Dangi

Almost every successful manager agrees that having 1:1s is a surefire way of facilitating dialogue around coaching and feedback with their team members. Despite that, 1:1s are nothing more than simply exchanging status updates.

Why is that?

One key reason why this happens is that less experienced or first-time managers usually struggle with what they should ask their team members. This results in them sticking to simply collecting updates from each team member and calling it a day.

If you find yourself in a similar situation, fret not, for this is just as common as Spider-Man facing his enemies (which is a lot!). 

That said, let’s go through some of the top 1:1 meeting questions to fuel your upcoming 1:1 check-ins.

How to structure your 1:1 meetings

So, there are four specific dimensions that every 1:1 meeting must focus on:

  • The current KRs, goals, and productivity
  • Exchanging feedback
  • Coaching for career paths
  • You and your team member’s mood

Structuring your 1:1 around these topics can help you understand what motivates your team members and how you can align their ongoing career trajectory with your organization's overall goals.

However, we need to move a level deeper here. By further breaking down these four dimensions into 1:1 action- items that your meetings can revolve around, we can then look at the exact questions that will assist you in making these 1:1s a success. Let’s do just that, shall we?

1:1 meeting questions to ask new joiners

Many managers tend to underestimate their 1:1 check-ins with their new team members. They think of it as nothing more than a practice of asking the joinee how well they are settling in. In doing so, managers then tend to miss out on a goldmine of forming the best first impression and laying the groundwork for future 1:1s. 

To better utilize these check-ins, managers can ask the following questions:

  1. Are there any specific skills you’d like to develop while working alongside us?
  2. Is there anything you’d like to share or teach others from your past professional development experience?
  3. Do you prefer scheduled 1:1s or have impromptu meetings?
  4. Is there anyone in the organization that you’d like as a mentor?
  5. Do you have a career path planned out? Any ambitions that you’d like to see fulfilled, and how can I help?

1:1 meeting questions for checking in

Your main objective as a manager, with these questions, is to develop and nurture your manager-direct reports relationships further, understand how an individual is doing, and celebrate big and small wins while identifying the problems that may have occurred:

  1. How are you feeling and how did your past week/month go?
  2. What topic is on top of your mind right now? Are there any immediate concerns that you’d like to discuss?
  3. Last time we spoke, you mentioned certain roadblocks you came across. Were you able to overcome them?
  4. What’s the biggest challenge that you’re currently facing?
  5. What went well with the team recently? Is there anything in particular that you’re proud of?

1:1 meeting questions for setting goals and tracking progress

The idea here is simple, as a manager, you must ensure that all key results and goals are progressing as planned. If that isn’t the case, then your job is to work with your team member and identify all past and upcoming challenges:

  1. How has our progress been on the OKRs?
  2. Are there any concerns regarding your current set of projects?
  3. Were there any circumstances that prevented you from progressing as planned?
  4. Is there anything I can do to improve your day-to-day tasks?
  5. Is there anything on your plate that is not aligned with your short-term goals?
  6. What opportunities within the current KRs align with your long-term goals?
  7. How are you currently tracking your progress against the goal?
  8. As things stand, do you think you’ll be able to achieve your goals?

1:1 questions for career development

Coaching and career development is arguably the most significant part of any 1:1. As such, it is imperative that you be your team’s guiding light and help them tread on a career path most suitable for them:

  1. Are there any advancement opportunities that attract you in particular?
  2. What projects would you like to work on after the current one?
  3. Are there other areas within this company that you’d like to explore?
  4. What kind of feedback, recognition, and reward matters to you?
  5. What knowledge and skills do you need to advance on your career path?
  6. How would you like to make a bigger difference at the workplace?
  7. What comes to mind when you think of yourself in a year or two’s time?
  8. Are there any ways I can better facilitate your career advancement?
  9. What can you start/stop/keep doing to help you reach your development goals?
  10. Are there any L&D programs that you wish to enroll for to upskill yourself for your dream role?

1:1 meeting questions on exchanging feedback

Giving feedback has been a part of every leader’s responsibilities since time immemorial. However, it is important to understand that feedback is a two-way street. It’s meant to be exchanged and not simply given. That said, the main objective of these questions is to give constructive feedback on an individual’s work and receive upward and honest feedback on your performance as a manager:

  1. How can I make work easier for you?
  2. What do you like and/or dislike about my management style?
  3. Are there any resources that I can help you with?
  4. What are the things that you’d like me to do differently?
  5. What is the one area that I should improve on?
  6. What is the one area in which you think you consistently excel?
  7. In which aspects of your daily work do you see me becoming a bottleneck?
  8. Are there things I’ve been unable to help you with?
  9. One thing we discussed in our last meeting was your work on <project name>, how has the progress on that been?

1:1 questions on personal lives and relationships

It isn’t mandatory for a 1:1 meeting to strictly revolve around the workplace. It also serves as a conversation to understand your team member personally and ask how they’re doing outside of work, provided that you respect their boundaries at all times:

  1. How’s life outside of work? Any trouble balancing work and personal life?
  2. Do you still spend time <hobby>? How’s that going?
  3. How was your weekend?
  4. What are your favorite books, podcasts, and films? Can you recommend some for me to get started?
  5. How is your progress on <personal goal>?
  6. You spoke about pursuing further studies earlier. How’s that going?

1:1 questions on productivity

  1. How much of your time is spent on meetings and assigned tasks?
  2. When do you get your best work done? Morning, afternoon, evening, or night?
  3. How do you determine whether you’ve had a productive day or not?
  4. When are you most available and least available for meetings and huddles?
  5. Is there anything at work that feels like a duplication of efforts to you?
  6. How can I help you be more productive? (in case they’re struggling in this area)

1:1 questions to wrap up the conversation

  1. Can we quickly summarize everything that we’ve discussed today?
  2. Can we walk through all our commitments and assignments between now and the next 1:1 meeting?
  3. How fruitful was this 1:1 catch-up for you? Was I able to help you with your challenges?
  4. Are you happy with the current structure and cadence of our 1:1 check-ins?
  5. Any last thoughts that you’d like to share?

That’s about it for the questions. As long as you stick to these specific aspects of 1:1 and focus on asking pointed and thoughtful questions, it will be a walk in the park. If you do it well, you can even potentially replace your engagement surveys as the objectively best way of retaining and keeping your team engaged.

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