247. Questions for your 1:1s 💡
51 questions to ask your team
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Hi there 👋
I was driving through town the other day and saw a sign for Unlimited Haircuts. Sounds like a typo, right? What does “Unlimited Haircuts” even mean? Well, this barbershop was advertising a subscription model: You pay $19.95 per month and can come in to get a haircut as often as you’d like. Ergo, Unlimited Haircuts! Brilliant? Mad? Personally I loved the idea. I’d be curious what you think.
Wishing you a great week,
Kevan
51 questions to ask in 1:1s
I have hour-long 1:1s with all of my direct reports every week, so it helps to have a bank of questions to turn to anytime I need some fresh ways to engage and find out how they’re feeling / what they’re thinking.
The following questions aren’t on every agenda. I sprinkle them in every now and then as needed. I’ll also add them to team surveys to get a broader snapshot of what the team is feeling and thinking.
What are your favorite questions to ask in 1:1s and team surveys?
I’d love to learn from you. Here are my favorite questions to ask in weekly 1:1s, team surveys, and self-reviews. Let me know if you get a chance to try any of these out.
My all-time favorite questions
1. When was the time you enjoyed working here the most?
2. Do you feel overworked, underworked, or just the right workload?
3. Who do you really admire? Why? (People often admire those they want to become.)
4. Have you seen something recently and thought to yourself "I wish we’d done that"?
5. Have you seen someone here do great work that’s gone unnoticed?
Questions to ask every week in a 1:1
6. What's on your mind?
7. Anything else?
(In the book The Coaching Habit, this question is framed as "And what else?" and is given the nickname AWE. In theory, you can keep asking this AWE question over and over in order to give your teammate a chance to share fully.)
8. What's the real challenge here for you?
9. What do you want? (Asked in a genuinely curious and expansive way, not in a sassy way. Obviously)
10. How can I help?
Questions to ask every once in a while
11. Are you afraid of anything at work?
12. Is there something at work you wish you knew more about?
13. Is there an aspect of your job where you would like more help or coaching?
14. Is there an area outside your current role where you feel you could be contributing?
15. Is there anyone at the company you wish you could apprentice under for a few weeks?
16. What part of your job do you wish you didn’t have to do?
17. What would make you leave this job for another?
18. What worries you?
19. What's the first thing you do when you start work in the morning? (This can tell you a lot about how a person is wired or what they're excited about.)
Questions about the company
20. Is there any part of the company you wish you were able to interact with more?
21. Is there something we should measure in the company that we currently don’t?
22. Are there things you don’t know about the company that you feel you should know?
23. What’s one thing we’d be regret not doing in the next quarter to improve our product?
24. Are there any benefits we don’t offer that you’d like to see us offer?
25. If you were CEO, what’s the first thing you’d change?
Questions about goals and performance
26. What’s one thing I could do today to help you with your long-term goals?
27. Could you see yourself making progress on more of your goals here? What would need to change to do so?
28. How many hours a day do you feel you’re productive? How could I help you be more productive?
29. What are the biggest time wasters for you each week?
Questions about me (the manager)
30. Would you like more or less direction from me on your work?
31. What would you like to know about me?
32. This manager feedback survey from Google is fantastic. It's a dozen statements with a Likert scale measuring if Googlers agree or disagree with the statements. Each statement is based on one of the ten behaviors of successful managers at Google.
I would recommend my manager to others.
My manager assigns stretch opportunities to help me develop in my career.
My manager communicates clear goals for our team.
My manager gives me actionable feedback on a regular basis.
My manager provides the autonomy I need to do my job (i.e., does not "micro-manage" by getting involved in details that should be handled at other levels).
My manager consistently shows consideration for me as a person.
My manager keeps the team focused on priorities, even when it’s difficult (e.g., declining or deprioritizing other projects).
My manager regularly shares relevant information from their manager and senior leadership.
My manager has had a meaningful discussion with me about my career development in the past six months.
My manager has the technical expertise (e.g., technical judgment in Tech, selling in Sales, accounting in Finance) required to effectively manage me.
The actions of my manager show they value the perspective I bring to the team, even if it is different from their own.
My manager makes tough decisions effectively (e.g., decisions involving multiple teams, competing priorities).
My manager effectively collaborates across boundaries (e.g., team, organizational).
What would you recommend your manager keep doing?
What would you have your manager change?
Questions about team dynamics
33. How could we change our team meetings to be more effective?
34. Who on the team do you have the most difficulty working with? Why?
35. On a scale from 0-10, how much do teammates volunteer to help each other when needed?
36. Do you help other members on the team? Do others help you when you need it?
Questions about life
37. How do you feel your work/life balance is right now?
38. What’s one thing we could change about work for you that would improve your personal life?
39. What did you do for fun in the past that you haven’t had as much time for lately?
Questions for self reviews
40. For annual reviews:
State an admirable feature about the teammate.
Ask what contributions they have made since the last review.
Ask what contributions they would like to make before the next review.
Ask how you & the company can help them.
41. For quarterly or monthly reviews: Lauds / Learnings / Looking forward
Lauds: What has gone really well this year that we might celebrate?
Learnings
What has been learned in the process?
What didn’t go as well or might have been done differently?
How do we “take stock” of where things are now compared to where we thought they might be?
Looking forward
What are you most excited about in this next year? What concerns you most?
What changes, if any, would you suggest in your functions?
What ongoing professional development will help you to grow in your current job and for your future?
How can I be of most help to you and your work?
When you think about your work in the year ahead, what specific goals will guide you?
Questions for difficult conversations
42. Follow this three-step process:
Step 1: Here is how I feel.
Step 2: Here is what I need.
Step 3: What do you need?
43. Giraffe language and non-violent communication:
Observation
Feeling
Need
Request
Questions for career conversations
44. Google's Goal / Reality / Options / Will (GROW) conversations
Goal: What do you want? Establish what the team member really wants to achieve with their career.
Reality: What’s happening now? Establish the team member’s understanding of their current role and skills.
Options: What could you do? Generate multiple options for closing the gap from goal to reality.
Will: What will you do? Identify achievable steps to move from reality to goal.
Questions to ask about how a new thing is going
45. The product-market fit question. A good result to aim for is that 40 percent or more would be very disappointed to see it go away.
How would you feel if we were to no longer have this thing: very disappointed, somewhat disappointed, or not disappointed?
Example: How would you feel if we were to no longer have Slack-free Fridays?
46. The NPS question
On a scale of 1-10, how likely are you to recommend this thing to someone?
Example: How likely are you to recommend our offsite experience to someone?
Questions to measure the strength of your workplace
47. The Gallup Q12 survey
Do you know what is expected of you at work?
Do you have the materials and equipment to do your work right?
At work, do you have the opportunity to do what you do best every day?
In the last seven days, have you received recognition or praise for doing good work?
Does your supervisor, or someone at work, seem to care about you as a person?
Is there someone at work who encourages your development?
At work, do your opinions seem to count?
Does the mission/purpose of your company make you feel your job is important?
Are your associates (fellow employees) committed to doing quality work?
Do you have a best friend at work?
In the last six months, has someone at work talked to you about your progress?
In the last year, have you had opportunities to learn and grow?
Questions about engagement
48. From CultureAmp's Engagement survey (my highlights)
To measure Team Dynamics
As a team we consistently deliver high quality work
I am proud of what we accomplish as a team
I believe I am on the best team for me right now
Being on this team enables me to do my best work
I feel I belong on this team
To measure My Experience
When I contribute ideas and thoughts, I believe my opinion is valued
My expertise is well utilized on this team
Working on this team provides me with opportunities that contribute to my development
When my teammates say they’ll do something, they follow through with it
To measure Team Climate
Team members volunteer to help each other when needed
Overall, team members are provided equal opportunities to speak during team discussions
We genuinely care about each team member's wellbeing
Team members encourage each other to share their unpolished thoughts and ideas
Team members give each other constructive feedback
If someone makes a mistake, they admit it to the team
To measure Our Alignment
I understand what our team is meant to accomplish
I know how my work contributes to the team's success
Where necessary, we have clearly defined roles and responsibilities for each team member
We have a shared strategy for how to achieve our team goals
I believe we can successfully accomplish our team goals
To measure Team Collaboration
Team members readily share their knowledge and lessons learned
Team members collaborate well with one another to get the job done
There is open and honest two-way communication within our team
We resolve most conflicts or disagreements effectively
To measure Our Processes
Workloads are divided fairly among team members
Our team meetings and discussions are effective
We regularly check in on how we are progressing towards our goals
We hold ourselves and our team members accountable for results
Generally, I support how decisions are made in our team
To measure Team Guidance
Our team goals are well aligned with the company goals
The company recognizes and celebrates our team's achievements
The work our team does makes a positive difference at the company
We share or rotate some leadership responsibilities in our team (e.g., running meetings, tracking goals, follow-up)
What is one thing that you would like our team to keep doing?
What is one thing you would like our team to do differently?
Stick to Questions Starting with “What”
49. Instead of “Why did you do that?” ask “What were you hoping for here?”
50. Instead of “Why did you think this was a good idea?” ask “What made you choose this course of action?”
51. Instead of “Why are you bothering with this?” ask “What’s important for you here?”
(via The Coaching Habit)
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Further reading (and my favorite resources for question-asking):
Lighthouse blog: 101 Questions to ask in 1-on-1s
Claire Lew: The 9 Questions That Uncover the Most Surprising Insights From Employees
First Round Review: These 13 Exercises Will Prepare You for Work's Toughest Situations
book: The Coaching Habit
Tools for question-asking:
CultureAmp (performance reviews)
OfficeVibe (weekly Slack check-in)
About this newsletter …
Each week, I share playbooks, case studies, stories, and links from inside the startup marketing world. If you enjoy what’s in this newsletter, you can share some love by hitting the heart button at the top or bottom. 💙
About Kevan
I’m a marketing exec who specializes in startup marketing and brand-building. I currently lead the marketing team at Oyster (we’re hiring!). I previously built brands at Buffer, Polly, and Vox.
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