I've written previously about what it is to have an effective 1:1, and this article won't repeat that. This article aims to provide inspiration for 1:1 questions to improve the quality and conversation you have with your team. If you find:

  • That you are rarely getting topics brought by your team member
  • That 1:1s are regressing into status updates
  • That 1:1s are either skipped, or cut short because there isn’t value seen in them

Then the below questions can help you bring an element more to them.

If any of the above are true, typically the best way to start with some of the below is to have a deliberate conversation in a 1:1:

“I really want these 1:1s to be more useful to you - I love when you bring topics to talk about that are important to you, but I’ll also start to bring topics along that perhaps will encourage us to have richer conversations”

Start there, and it’ll be less problematic as you introduce the below into your 1:1 agendas.

Most of these are focused on the manager asking the question, though many of them can be turned around to be asked by the team member. I've also included some questions that are more 'team' focused, as these can be useful to bring to the 1:1 to discuss.

Relationships

  • What would you have liked to have done differently in a recent interaction?

    • What’s a recent situation you wish you handled differently? What would you change?

  • Who do you admire at [Company]? What things about them do you admire?

    • Is there anyone you struggle with?
  • How is everything going with the people you work with/on your team?
  • Have you seen someone else doing something you felt worked really well? What was it?
  • What’s the most important thing you need from your team right now?
  • How are you building relationships and developing “seconds” to make sure you can be away sometimes (without worrying)?

Elicit feedback about how I’m doing as a Manager

  • What’s one thing you need from me that will enable you to be successful?

  • What do you wish we talked more about?

    • What do you not find so useful in our chats?
  • What could I do differently that would make your life easier?
  • What’s one gift, skill or talent you have that I’ve perhaps overlooked, under-valued, or under- utilised?
  • What could I do to help you enjoy your work more?
  • What’s the thing you see me doing that’s helping me best contribute to the team?
  • What’s the thing I do that may be detracting from our success?
  • What’s one thing I need to know about you that will improve our relationship?
  • What’s one thing you need from me that will help you be more successful?
  • What motivates you and how can we bring more of that to your work?
  • What’s one thing you wish I did more of/less of/differently?

The “Awkward Questions”

From The Art of the Awkward 1:1 and the follow up post. It’s never a bad thing to bring the harder questions to 1:1s, those things that are often not talked about, but may be important.

  • We never seem to talk about X. Why is that?
  • What worries you most in our team? At [Company]?
  • What is impacting trust between us at the moment?
  • How good is our relationship? What could we do to improve it?
  • What’s going on for you at the moment that makes you feel less engaged?
  • Where do you feel I'm letting you or the team down?

To Understand Team Psychological Safety

These questions are linked to Amy Edmondson’s Psychological Safety Survey (the questions are highlighted below too) to measure psychological safety, though you can turn the questions around for 1:1s. Recommend not asking them all in a single 1:1, though they can be useful to introduce if there have been events in the team that would warrant them.

  • What would happen if you made a mistake on this team?

    • Original measure: If you make a mistake on your team, is it held against you?

  • When did you last disagree or want to push back on something in the team?

    • Original measure: Are you able to bring up problems and tough issues?

  • How do you feel about others on the team? Who do you struggle to be your best self with?

    • Original measure: Do people on the team sometimes reject others for being different?

  • What would happen if you took a risk on this team?

    • Original measure: Is it safe to take a risk?

  • What does supporting each other look like in the team? What would better look like?

    • Original measure: Is it difficult to ask other team members for help?

  • How would you rate your trust on the team with the person you trust the most out of 10? How would you rate it with the person you trust least?

    • Original measure: Do people on the team deliberately act to undermine your efforts?

  • Which of your talents are we not leveraging effectively at the moment?

    • Original measure: Are your unique skills and talents valued and utilized?

Goals and Challenges

  • Last time we spoke you said X was a challenge for you, how is that going?
  • What do you need clarity on right now?
  • What’s holding you back from doing the best work you can do right now?
  • What has challenged you [over a period of time]?
  • What have you found difficult over the past few weeks/at the moment?
  • What’s one thing (or a few) you learned this week?
  • Since we last met, what are you most proud of and why?
  • What has energized you in your role [over a period of time]?

Career and growth

  • Do you feel that your current responsibilities and job align with your future goals?
  • What accomplishment in your career are you looking forward to this year?
  • What do you want to be doing in 3 months that you can't do now?
  • What do you love to do?

Questions for Employees to Ask their Manager

  • What are one or two things you see me doing. that you feel are adding least value?
  • Where do you feel my strengths are? How should I focus in on this?
  • What's one thing we can do to improve the performance of the team?
  • What one thing could I improve to make me more effective?
  • Where do you feel I should focus next in my career growth?
  • Where could I take ownership of something? What would good look like if I did that?
  • What are your priorities and how are you measured? How do you see me contributing to their success?
  • I’ve found X difficult, can we explore that?
  • Where do you see gaps in our team? How can I help?
  • I’d like to understand more about {our strategy/hiring plans/growth plans/strategic areas} - can we talk about that?
  • What advice do you have for me at my current career stage to get the most out of my growth?
  • What do you feel I’m doing well at the moment?
  • We talked about {Growth Area} previously - how am I doing with that? What observations can you share with me?
  • You gave me a shout out/nectar for {thing I got praise for} - what in particular did you like from that so I can make sure I do more of it?
  • Where do you think I’m perhaps holding myself back from being my most effective? How would you suggest I change that?
  • How are you measuring me at the moment? What are the most important factors?
  • I’ve recently found {challenging thing} difficult, what advice would you give me on better handling situations like this?
  • What do you feel most unclear with about my work?
  • What feedback do you have about {recent event} that could help me improve?

First 1:1 Template

Stolen shamelessly from many sources, though the basis is lara hogan.

One-to-ones are our opportunity to connect, to build an effective relationship so that I can support you, coach, and help you grow. It is your meeting, so any agenda items that you have will always be more important than mine. The below is a template I’ve used in the past for first one-to-ones, but please feel free to edit it, change the order, and add anything you feel would be useful.

  • Introductions and background

    • Who are we? What do we care about? What do our lives look like away from work? (share as much or as little as you like here, I will share too)

  • 1:1s

    • It’s your meeting, your agenda
    • Cadence - I prefer weekly - 45mins, but will be steered by you
    • What makes 1:1s the most valuable for you?

  • Feedback

    • Approach: Continuous, Trust, Radical Candor
    • Please give me regular, candid feedback - I will always appreciate it
    • How are you with receiving feedback? What should I avoid?
    • How do you feel about giving peers or managers feedback?
    • How do you prefer to receive recognition? (public / private)

  • What makes you grumpy?

    • How will I know if you’re grumpy?
    • What can I do to help when you are grumpy?

  • Company + Process

    • For longer term employees:
    • How are you feeling at [Company]?
    • What would you like to see change at [Company]]?
    • How are your relationships?
    • What slows you down and prevents you from being your best self?
    • For new employees:
    • What were you most nervous about in joining [Company]]?
    • What are your top three hopes for the culture and ways of working at [Company]?

  • Growth

    • What do you feel your gaps are at the moment?
    • Are you getting enough time for growth?
    • How do you like to learn?

  • Progression

    • Existing Employees: Do you feel rewarded for what you do?
    • What are your goals? Do you have a career plan?

  • Management

    • Who is the best manager you've ever had? What made them great?
    • If you felt fully supported by me, what would our interactions look like? What sort of things would be in place? How would I be supporting you?
    • How can I help you be successful?
    • What would you like to know about me that I haven’t shared?

Alternative Questions for a First 1:1

To be used in the employee’s first 1:1, in order to set the scene for the future. Important: take notes of the answers.

  • Preferred frequency and duration of 1:1s
  • How do you prefer to receive feedback?
  • How do you prefer to receive praise - publicly or privately?
  • Who has been your best manager?
  • What are your management pet peeves I should know about?
  • What makes 1:1s the most valuable for you?
  • What makes you pissed off? How will I know you’re pissed off? How can I best help you when you’re pissed off?
  • What does a good day look like for you?
  • Any surprises since you’ve joined, good or bad, that I should know about?
  • How do you like to learn?
  • If you felt fully supported by me, what would our interactions look like? What sort of things would be in place? How would I be supporting you?
  • What would you like to know about me?

What about you?

What advice would you give? What pointers? What resources?