My Favorite 1:1 Questions

: Photo courtesy of wocintechchat.com

I’ve led software engineering teams since the 1990s having spent more than a decade at Accenture, followed by a stint at Deloitte, then I experienced the startup life at a few ventures, and now I’m a Staff Engineering Manager at GitHub. There are many practices I use as a manager, but one of my favorites is the 1:1 (also called a “1-on-1”, “one one one”, or “one to one”). This post includes my favorite 1:1 questions and techniques. But, first, let’s start with the basics.

Basics

What is a 1:1?

A 1:1 is a regular meeting between a direct report (“direct”) and their manager. As you may be able to tell from the name, it’s meant to be one person (the direct report) engaging with one other person (the manager) in a synchronous meeting. The purpose of a 1:1 is to provide time for both people to share their perspectives, concerns, goals, and expectations.

How Often Should I have a 1:1?

I’m a firm believer that 1:1s should be weekly. I think every other week, monthly, or longer periods between 1:1s dilutes the value of the context, clarity, correction, and other information the manager needs to provide. Also, weekly 1:1s let your directs know that they have dedicated time with you that is usually just a few days away at any given point during the week.

In addition to being a regularly scheduled weekly meeting, I also think that 1:1s should be at the same time each week. I usually try to have all of my 1:1s on the same day because that helps me deliver information to my directs at roughly the same time. I also find that the people I talk to earlier in the day often help me refine the message for those later in the day. I don’t think this refinement would happen if my 1:1s were spread across two or more days.

I never cancel 1:1s unless it conflicts with scheduled vacation time, one or both parties are ill, or there’s truly an emergency happening either at work or in someone’s personal life.

How Long Should a 1:1 Be?

I typically schedule my 1:1s for 30 minutes, but I’m always willing to have a follow up meeting if necessary. While I am not against hour long 1:1s, I’ve found that it’s difficult to schedule 1:1s of that length unless I have a small number of directs.

What 1:1 Tools Should I Use?

There are a few tools that have been purpose built for 1:1s, but I usually just create a document, share it with my direct, and then add new agenda items to the top. This document becomes a living artifact of my relationship with each person I manage which I think is pretty cool.

Now that we’ve covered the basics, here are my favorite 1:1 questions. Keep in mind that I often have to discuss topics like company events, share observations about the team or my direct, etc., during my 1:1s so I rarely get a chance to just ask these questions during the meeting. However, I usually try to insert at least one question into the agenda for each 1:1.

The first weeks of working with a new direct are comprised of “establishing 1:1s” where I’m setting context, cadence, and starting to build trust. I also have two special “types” of 1:1s that I do each month: performance 1:1s and relationship building 1:1s. As weeks and months pass while working with my direct, I’ll change the tone of the 1:1 questions from general in nature to specific queries I use to get to know the individual I’m managing. Ideally, I continually build trust with my directs as time goes on, and I can ask more intimate and impactful questions the longer we work together.

First 1:1

I like the first 1:1 to be very informal. I usually don’t have any agenda and check in on how their onboarding is going. The main outcome is to schedule our weekly 1:1.

Second 1:1

The second 1:1 is where I start to get more structured, and start the help my direct get to know me and, hopefully, encourage them to get to start opening up to me. I share the following information about me and then give them time to share the same.

Pronouns: he/him/his
Location: Houston, TX, USA
Hobbies: Travel, Reading, Writing

I also usually share Julia Evans’ excellent writeup on writing a brag document because I think it’s an excellent way to self-manage your career.

Performance 1:1s

I use the first 1:1 of a new month as a “performance 1:1”. We talk about the career expectations of the direct, and I usually pull up the career ladder and have the direct walk me through how they think they are doing. I do this whether the direct wants to get promoted at the next possible promotion period or if they don’t feel any urgency about getting promoted. I think it’s crucial to make performance management an ongoing conversation because, at the very least, the impact the direct is having will drive whatever rewards they receive from the company. Those rewards can include a promotion, but they will more frequently be base pay increases, if offered by the organization, a bonus or stock award.

If one of my directs is surprised by a promotion outcome or their rewards, then I’ve failed them as a manager. The monthly Performance 1:1s are ways for me to give the direct a data point about how I think they’re doing. It’s also an opportunity for me to discuss opportunities to discuss ways for them to improve their performance or find new areas to demonstrate impact.

Relationship Building 1:1s

Within the first three months of working with a direct, I start asking relationship building questions on the last 1:1 of a month. These are meant to help me better understand the person (not just the role) I’m managing. I usually answer the question first to give them a sense of how to formulate their answer (and also signal that it’s safe to share non-work interests).

I’ve sourced most of these questions (in this section and also this entire post) from Peoplebox’s Ultimate List of One on One Meeting Questions. I also selected some from a set of “getting to know you” cards from a restaurant in Houston called Daily Gather. Here are a list of my favorite relationship building questions (in the rough order I tend to ask them):

What books are you planning to read in the next 12 months?
What’s your proudest accomplishment?
What was your favorite subject in school?
What did you want to be when you were younger?
If you could live anywhere, where would it be?
What was your first job?
Who knows you best?
If you could credit someone for your success, who would it be?
What does your ideal work day look like?
Describe your perfect day.
How would you spend one million dollars in one hour?
Describe an experience with food or drinks that transformed the way you look at eating or drinking?
What’s the best decision you’ve made in your life?
You wake up tomorrow 10 years in the future. What’s changed?
What would you change about yourself if you could?
If you had to choose a topic to teach in college, what would you choose?
If you could only eat meal for the rest of your life, what would it be?
Who is the most famous person you’ve ever met?
If you could join any past or current music group, which would you want to join?
Who is the most intelligent person you know?
Would you like to be famous?
Who would play you in the movie of your life?
What personality traits do you share with your relatives?
Would you rather have the ability to fly or be invisible?
If you could be on a television show, what show would it be and why?
How has your perspective on the world changed over time?
What’s the coolest thing about your city?
What’s the best purchase you made for $100 or less?
What three items would you take with you on a deserted island?
If you could relive one moment in your life, what would it be?
If you could go back in time and give your younger self an advice, what would it be?
What is your favorite family holiday tradition?
Tell your best joke!
If you were to go back in the past and learn something you couldn’t, what would it be?
Describe one of your most memorable days.
If you could wake up one morning with a new quality, what would it be?
What signs should I look for to know that you’re in a bad mood?
What is one thing you will never do again?
How do you unwind after work or on weekends?
What self-care regime do you follow every week?
What do you do to cheer yourself up when you’re feeling low?
What do you wish you’d learned when you were younger?
Describe a time when you totally changed your mind about something.
What’s the craziest thing you’ve done in the name of love?
What is your biggest irrational fear?
Who has been the most influential person in your life?
What social causes are close to your heart?
Who are some leaders you admire and why?
Given a choice of anyone in the world, whom would you like to have as your dinner guest?
You find a suitcase with $100,000 in cash in it. What do you do?
What is one belief that has made you who you are today?
What’s something most people don’t know about you?
What have you gotten away with that you shouldn’t have?

After Three Months

At this point, my directs have formed their initial impressions of me. However, those impressions may have been formed based on incomplete information or perhaps not during my best moments. These questions help me reset and recalibrate their perceptions and, ideally, understand where I need to do a better job showing up for them.

What tools and resources would hurt the most if you suddenly couldn’t use or access them?
What were your big or small wins in the past month?
What is that one thing I can do to make you feel more recognized at work? Would you like that to be done publicly or privately?
What aspect of your work is extremely exhausting and demanding?
What kinds of flexibility would help you in balancing your work and home life?
On a scale of 1-5, how happy are you at work? How can I make it better for you?
What aspect of your role do you need more clarity on?
What type of work environment brings out the best in you?
Is the feedback I give you sufficient?
Is there anything your past managers did that frustrate you?
What changes can I bring in to our 1-on-1 meetings to make them better?
What makes you feel helpless at work or prevents you from reaching your full potential?
What is the one thing that’s holding the team back from performing at its best?
Which part of the day are you at your productive best?
What specific training & development opportunities will help you in your career growth?
What other skills do you have that you feel we are not fully utilizing?
Whom would you like to have as your mentor?
Who has done an incredible job on our team lately?
Whom did you help perform better and succeed at work recently? How?

After Six Months

At this point, my directs have a sense of my management style and probably also has confirmed what they like and don’t like about it. These questions provide opportunities for my directs to give me vital feedback that I can use to refine how we work together. I also use these questions to identify the hours where my directs will benefit from more direction and coaching from me.

If my directs don’t offer clear responses to these questions or respond with something like “everything is fine.”, then I know that I need to invest more in building trust with them.

Are there any changes you want to make to the duration or frequency of our 1:1s?
Is there anything you like in particular about my management style?
What would you want me to start doing as your manager?
What would you want me to stop doing as your manager?
What work routine helps you stay productive at work?
Are you able to share any kind of feedback with me openly?
What aspects of your work would you like me to direct you more in?
Is there anything I can do to improve the performance of our team?
Is there anything you would like me to clarify or re-explain to our team?
What are the biggest time wasters for you each week/month/quarter/year?
What’s the most important thing in your career right now?
Of the things you do on a daily basis, how much of it is aligned with your long-term goals?
Do you have clarity on our company’s strategy and how your role fits into it?
Do you feel like you’re growing in your role? What makes you say that?
What are some of the goals you would like to achieve in the next quarter?
Do you face difficulty in getting along with anyone in our team?
What do you think about our team’s relationship with other teams?
What is something about our company culture that impresses you the most at work every day?

After the First Year

Ideally, after the first year, we’ve built a strong sense of shared trust. We can start to get into challenging topics and, hopefully, find ways to navigate them together. These 1:1 questions are meant to solicit open and honest responses from the direct, but you’ll only get meaningful answers if you’ve built a solid relationship first.

Have any of your future career goals changed since the last time we spoke about them?
What can I do to build our team’s reputation in the company?
Can you think of an instance where I said or did something you didn’t like or agree with?
Do you have any worries related to your work, role or company? How can I help?
What’s stopping you from achieving your long term goals?
How can the training programs you’ve attended be made better?
How would you rate the level of loyalty our company shows to its employees?
How aligned are the members of the top leadership team with each other?
Do you have clarity about the company level goals set by top leadership?
What, according to you, is our company’s biggest problem?
What is one thing that we should definitely do to enhance our product?
How are your personal values aligned with the company’s mission and vision?
What changes would you bring in if you were given the reins of this company?

Your Directs Should See 1:1s as a Perk

When done well, directs will view 1:1s with their manager as important as other perks offered by the organization like retirement plans, vacation time, and health insurance. Two things I look for to see if I’ve elevated the value of my 1:1s to that level are engagement and frequency. If my directs independently add to the 1:1 agenda, that shows they are seeing the discussion as a valuable way to discuss important topics, share concerns, and solve problems. Similarly, if my directs keep the 1:1 on a weekly cadence, then that signals they see them as valuable. You wouldn’t ask your organization to pay you less frequently, would you? That’s because you see the value of your paycheck. It’s the same way with 1:1s.

If your directs aren’t contributing to the agenda for 1:1s or if they ask for them to be held less frequently, then I think these questions can be powerful ways to help them see the value of spending mutually interactive weekly time with you. You’ll have conversations that will help them see where you can guide them, and you’ll also get vital feedback that will make you a better manager.