Questions for 1-1s and teams – a primer for remote communication

This may seem counterintuitive, but asking questions and listening put you in control of the conversation. Because your questions require an answer, you are in a position of power. Good listeners are not only popular everywhere, but after a while, they learn a thing or two.

Power Questions by Andrew Sobel and Jerold Panas

Over the years, while leading a remote team and being exposed to various meetings and conversations in Automattic, I realized just how powerful questions can be. I’ve read several books on the subject to learn how to be a better leader, coach my team, and help them grow and overcome obstacles.

I’ve collected some of these questions into various themes to help me uncover what’s underneath the conversation to help increase the chances of having a positive impact.

It’s also important to distinguish between the various questions. Some are general; others are personal, some aim for growth or discovery, and plenty are just for fun.

What makes a question a good question?

Good leaders ask great questions that inspire others to dream more, think more, learn more, do more, and become more.

Good Leaders Ask Great Questions by John C. Maxwell

When leading a team, having a list of questions is one of the best ways to facilitate conversation and learn more about your team’s personal preferences. They can also be useful when you’re thrown into a new meeting or collaborating with a new group of people for the first time.

We’ve all answered some questions reluctantly in the past, and I found that for me, a good question should have at least 2-3 of the following:

Allows for self-expression: These questions are open-ended. It doesn’t have a right or wrong answer. It isn’t a yes/no answer.
Anyone can answer it: They are accessible to all. If your question is so niche that only a few people can answer it, only those few people will feel included at the expense of others.
They are fun: These questions are a time to come together with your team and bond, so the fun context helps with that.
They are personal: They help to learn more about the people in your team. They allow for self-expression within your own comfort level.
They encourage thinking differently: The most powerful and personal questions challenge our ways of thinking to help us grow.

For example, an icebreaker question during the first ever team call should be less personal, more fun, and completely inclusive.

An established team can dive into more challenging questions that allow self-expression and include everyone.

If you are coaching a team member, it’ll primarily challenge them to think differently, would be quite personal, and allow for self-expression.

Mix and match the above to get the best outcome from your questions.

How to incorporate questions into conversations?

Start creating a culture of decisiveness. Before you begin each meeting, ask, “What decisions do we need to make today?” After every meeting, ask: “What have we decided today?”

Power Questions by Andrew Sobel and Jerold Panas

Questions need to be part of the culture through setting expectations and leading by example. Prepare your teammates that there’ll be an icebreaker question in your next hangout. Try to drop the question earlier in the agenda to give people time to think about it.

If this is your first time doing this, keep the momentum by answering the question first and then guiding the next person. Start with less personal questions until you have some common ground already established. Keep it simple to start with.

After a few rounds of questions in 1-1s and hangouts (or even asynchronous discussions), people will learn to expect and know that it is safe for them to participate.

If you’re doing this in your 1-1s, acknowledge this might be personal information and consult your teammates before sharing info publicly.

With the current remote workforce growing, there are many ways of incorporating questions in 1-1s, smaller groups, division-wide, and company-wide. All of them can be used synchronously or asynchronously.

Remember, many questions can also be asked in multiple ways. One of my favorites has been to ask folks on my team about a time they’ve felt valued at work by a team lead, a colleague, or someone else. Conversely, I’ve asked about a time they’ve felt demotivated or not valued. In both cases, it offers opportunities to get to know them and the things that motivate or demotivate them.

I appreciate knowing more but also use these as opportunities to be a better lead and colleague. In team calls, a question like this can help us all see ways to cheer on a colleague or ways to support them.

Over time, you’ll be able to pinpoint which questions work best for you, and I recommend creating templates for any type of meeting you might have, whether it’s one-on-one or a team or division meeting.

Questions for one-on-ones and team meetings

Questions are places in your mind where answers fit. If you haven’t asked the question, the answer has nowhere to go. It hits your mind and bounces right off. You have to ask the question—you have to want to know—to open up the space for the answer to fit.

Clay Christensen, a professor at Harvard Business School | Better Decisions, Fewer Regrets by Andy Stanley

I’ve collected and compiled the questions into various buckets to help navigate between them. Many are great as icebreaker questions or simply to learn more about your team. Others help you dive deeper into specific areas or emotions to uncover the real motives to help your team. You should select the most personalized to your team’s personality and interests.

Personal preference questions

What’s your favorite app?
Best sandwich ever. What’s on it?
Are you an introvert or an extrovert?
What is your favorite television show right now (or when growing up)?
Are you a cat or dog person?
What’s the worst haircut you ever had?
If you didn’t have to work right now, what would you be doing instead?
Who’s your favorite poet/writer?
What’s your favorite way to get in some exercise?
What’s the most addicted to a game you’ve ever been?
What’s the most useless talent you have?
What are your get better from cold remedies?
You have to sing karaoke, what song would you pick?
What do you use to manage your projects and work?
How do you define an ideal project?
What causes you to feel stressed about your work? What gives you confidence?
What’s the highlight of your day? What motivates/energizes you in work?
Are there any roles in the company you’d like to learn more about? Who in the company would you like to learn from? What do you want to learn?
Any yummy dishes already planned for Xmas? (insert any public holiday)
What was your childhood nickname?
What would you do if you won the lottery?
What was the last photo you took?
Have you ever met a celebrity?
Do you miss working from office? What did you like about working from office?
There are now 25 hours in a day! How do you spend your extra hour?
What are you currently reading?
Do you play a musical instrument?
What’s one chore from everyday life that you wish you could eliminate (would happen automatically)?
Bring your fav mug and share why you love it/backstory
Have you been outside today? How often do you go outside for more than 15 minutes at a time
What brought you to this job/company?
Share your holiday item! (Around christmas/new year. This needs some prep)
What project did you have the most fun with this year?
Have you been pleasantly surprised by anything lately? A meal you’d reservations but turned out tasty, an amazing customer experience, anything that brought you joy?
What is your favorite holiday? How do you celebrate it?
Are you a morning person or a night owl?
What is your most used emoji?
A visitor has only one day in your city. What is one place they should eat at?
When you were a kid, what job did you want to do when you grew up?

Weather-related questions

What is your favorite season, and why?
What do you think is the “perfect” weather? What do you like to do outdoors on those days?
How do you like to spend a rainy day?
What’s your favorite summer activity?

Food & drink questions

What is your favorite type of desert?
Favorite movie theater food/drink?
Favorite midnight snack?
What is something you loved eating as a kid, but disgusts you now?
What is something you hated eating as a kid, but you enjoy now?
What is your favourite food (or comfort food)?
What’s your favorite guilty-pleasure food?
What’s your favorite candy?
What did you eat for breakfast as a child?
What’s your favorite local restaurant? What’s your favorite meal there?

Life moments questions

What is the most unexpected place you’ve ever made a friend?
What kind of posters did you have on your wall as a kid/teen?
If you could go back to your childhood and retrieve one object and bring it back to the present, what would it be?
What is your favorite personal/family tradition?
When you were a kid, what did you want to be when you grew up?
What was your first job?
What’s the worst time you’ve ever been sick?
What was the worst job you ever had?
What are you going to do when you retire?
How long was your journey to work before you worked remotely?

Personality questions

Who would play you in the movie of your life?
If you could swap places with anyone, celebrity, friend, or stranger, for a day, who would it be?
How would you describe yourself with just one word?
What made you smile this week?
What motivates you to do your best?
How do you relieve stress and anxiety?
What’s your personality type? (Myers-Briggs test)

Location questions

What was the best thing about the place where you grew up?
What’s something distinctive about the region where you live?
If someone had one day to spend in your region, what would you recommend they see, do, and eat?
What’s the highest altitude you’ve been to (excluding by aeroplane)?

Music questions

Is there an instrument you’d love to be able to learn and master?
What is the first concert you ever went to?
What is the best concert you’ve ever been to?
What is the worst concert you’ve ever been to?
What was the first music album you ever owned?
If there was a theme song played every time you entered a room, what would it be?
Who would you love to see in concert, but haven’t yet (or are unable to, for whatever reason)?
What’s your favorite song right now?

Travel questions

If you could travel anywhere for just one meal, where would you go and what would you eat?
What has been your favorite vacation and why?
Where is a place you’d love to visit, but haven’t yet?
Where is your favorite place to travel?
Where was your first vacation that you remember?
What is your fav kind of vacation? For example, Beach, safari, or forest vacation?
If you could time travel, when/where would you go?

Philosophical questions

Do you have a personal credo or mantra?
What’s some of the best advice you’ve ever received?
If you could go back to your younger self but only for 30 seconds, what would you tell yourself?

Fun questions

Do you play board/card games? If so, which is your favorite, or which do you have fond memories of playing as a kid?
You’re at a theme park for a day. How do you spend your time? Rides? Shows? Water park? Shopping? Food? Any particular favorites?
What’s your favorite book?
What’s your favorite movie?
What’s your favorite TV show?
What’s your favorite hobby?
What is your favorite smell?
Have you ever won a contest, drawing, or sweepstakes? What did you win?

Empowering questions for one-on-ones

After having gone through various leadership seminars and coaching sessions, one really helpful way to think about questions is through the lens of empowerment. Each question you ask should provide you with information that you can then use to empower your team, either by making them happier and more productive or generally learning something new about themselves so they can continue to grow.
Ironically, knowing the answer is not necessary to create an amazing impact on anyone you speak with if you know what questions to ask and when to ask them. Like with anything, the more you use the skill of asking questions, the better you’ll become, and that’ll help all areas of your life where you have conversations with people.

While this collection is a good starting point, remember, [[The True Power of Questions in Life]] goes beyond conversations with others but also applies to yourself and your inner-speak.

Discovering Importance

What do you want?
What’s important about that?
What are you excited about?
What is your intention?
What are you overlooking?
What would you like to accomplish?

Setting stretch goals

If you knew you’d succeed, what else would you do?
If you were to raise the bar, what would it look like?
How can you play a bigger game?
What’s the big picture?
What action would really excite you?

Expanding the mind

What is possible?
If you had a magic wand, what would you do?
What impact would you like to have?
What are your choices?
What would be possible if you did not censor yourself?

Breaking through barriers

What’s stopping you?
In an ideal world, how would you face this problem?
What would motivate you to change?
What would it cost you if things remained the way that they are?
Pretend you know the answer.

Reducing sense of overwhelm

What can you say “no” to?
What can you stop doing to make room for what’s important?
What can you stop tolerating?
What are you doing now that’s working?
If you only focused on one thing, what would that be?

Deeper Inquiry

Is your “why” aligned with the team’s “why”?
What values do you want to model? And for whom?
What part of yourself are you not bringing to work? And why?
What’s missing? And how are you keeping it out?
Aliveness-where are you most alive?
Depth-what is the deepest or wildest possibility?
Let go into-what is it to sink into yourself?
Alignment-with what are you most aligned within your life?
Being with-what is it to be with yourself?

Eliciting wisdom

What might you do differently next time?
What does your heart tell you about this?
When you’re at your best, what’s different?
What do you know in your gut?

Clarifying questions

What do you care about in this situation?
What value does this experience have for you?
What do you want? If you get that, then what do you want?
How does this plan honor your values?
What are you committed to?

Action Questions

How do you plan to achieve that?
How can you break that down into smaller steps?
What will you do, by when, how will I know?
Is there anything else you need to do?
On a scale of 1 to 10, how committed are you to this plan?

Celebration

When was the last time you celebrated something? What was it for?
How do you feel when others celebrate you?
Do you ever struggle to celebrate others? Why or why not?
Do you find that you tend to seek out things to celebrate or forget to celebrate things?
Tell us about attending your first Pride event. Share as much or as little as you want!
What’s your favorite official excuse to celebrate (holiday, wedding, birthday etc)?
Tell us about your most memorable birthday celebration. What made it so special for you? Who was there?
What do you do to celebrate things solo?
Tell us about a time you experienced a celebration in a culture other than your own. How did you feel? What did you take away?
Are there any foods that you particularly associate with celebrating something?
What’s something that’s celebrated in this world that you don’t understand?
What’s something you wish was celebrated more often?
What do you find others often celebrate about you?
If you were to create a brand new day to celebrate something, when would it be, and what would it be about?
What do you find difficult to celebrate about yourself?

Gratitude

What’s a little thing that you’re extremely grateful for?
Who is someone you’ve recently gotten close to that you feel thankful for? Have you told them? Why or why not?
What material item in your life that you’re particularly happy to have this year?
What’s a personality trait of yours that you’re thankful for and why? What about a personality trait in others?
Tell us about a book, article, or quote that shifted your thinking even a tiny bit about being thankful.
How do you show that you’re thankful for someone?
What did you learn about gratitude in your upbringing?
Tell us about a day this past year that you’re thankful for. Share as much or as little as you’d like!
What do you think others are often appreciative of you for? Does that align with what you want them to be appreciative of?
How do you practice gratitude in your day-to-day life?
How difficult or easy do you find it to be thankful and express that to others in your life that you’re thankful for?
Tell us about the last time that you paused to give thanks to someone else in your life. How did it go?
What’s something you should be thankful for, but you simply aren’t? Why do you feel pressure to be thankful? Why aren’t you?
What’s a challenging experience that you’re ultimately thankful happened?
On your worst days, what tends to come to mind to be grateful for? Why do you think that is?

Dealing with Fear

When was the last time you were scared?
When was the last time you avoided something that evoked fear?
What’s the first fear you can remember facing?
What are some fears that you’re facing right now?
What’s something that feels silly that you’re afraid of?
What role does fear play in your life (does it influence your decisions, give you something to face, etc)?
When was the last time you scared someone else?
What helps you face your fears?
What’s something you used to be very afraid of that you’ve outgrown or overcome?
How do you react when faced with something you fear?
A classic with a twist: What’s your greatest fear for yourself? For others? For humanity at large?
What’s something you’re not afraid of that many people are?
Do any childhood fears still come up in your adult life?
What fear-inducing things do you seek out? Which do you avoid? Why?
What has your fear taught you about yourself?
When do you listen to your fear? When do you ignore it?
What aspect of yourself scares you?

Encourage Learning

What are you learning right now?
What’s something you’ve always struggled to learn?
What’s something you’ve learned about yourself in the last year?
What’s something you want to learn, but haven’t taken time for it?
What’s your preferred way to learn something new? Read a book, podcast, classroom, etc.
How have you changed your approach to schooling/learning as you’ve gotten older?
How easy or hard do you find it to ask questions of others? Why?
What do you do to help motivate yourself to stay engaged in learning something new?
What bothers you most about “traditional” education systems (schools, college, “classroom learning”)?
What is something you’re embarrassed you haven’t learned more about?
If you were to give a lecture/teach a class on any topic, what would it be on and why?
Tell us about big teachers in your life (doesn’t need to be a teacher in the formal sense).
When was the last time you struggled to change your mind after learning something new that changed a long held belief you had?

Comfort

Describe your perfect room that would make you feel the MOST comfortable. Be as specific as you’d like!
What did comfort look like growing up?
What “scene” (bar, coffee shop, sporting event, etc) makes you the most uncomfortable and why?
Tell us about your favorite kinds of comfort food.
Where is home for you? Tell us about it.
When you’re upset, what helps calm you down?
How do you react when you’re uncomfortable (ex: sweaty hands, playing with rings, stammering, etc)?
What’s something new that you’ve learned brings you lots of peace as an adult?
What’s something that you’re comfortable discussing that others often aren’t? Why do you think that is?
What’s your relationship like to the idea of comfort? Do you resist it? Lean into it too much?
What can someone do to put you at ease immediately?
When was the last time you were incredibly uncomfortable? What were you doing? What led up to that point?
How do you know you’re comfortable being around someone?
What’s the fastest way to make you uncomfortable?
How do you try to create comfort for others?
How much do you seek out being uncomfortable?
Generally speaking, do you try to stay within your comfort zone or do you tend to try to venture out regularly?
When was the last time you made someone uncomfortable? What happened?

Decisions

Tell us about the people you turn to to make a decision.
Do you tend to be indecisive or decisive on the whole? Why?
If a friend was about to make what seemed like a really bad decision, would you confront them? Why or why not?
Do you have any mental frameworks or strategies to improve your decision making? For example, things like the Eisenhower matrix or thinking about the decision in the context of different timeframes.
Tell us about some of the little decisions you make every day.
What approach or role do you play when a group decision has to be made?
What feelings come up when you have to make a decision?
How do you know you’ve made the right decision?
Tell us about the last big decision you had to make.
What helps you make a decision?
How much sway do others have over decisions that only impact you?
While growing up, how much control or say did you have in decisions impacting your life?
Tell us about a time you didn’t like when someone decided for you. What about a time when that same action brought relief?
How do you feel when you’re put in a decision-making position for others?
What’s a decision you’re avoiding making right now?
Tell us about a really bad call you made in the past. What did you learn from it?
What’s something you’ve always struggled to be decisive on?

Family

Tell us about who you consider family. Share as much or as little as you’d like.
Tell us about any family members that you wish you were closer with.
What adjectives would you use to describe family?
What feelings come up when you think about family?
If your family were a high school friend group, what would your senior superlative be?
What role did you play in your family, and how has that informed other relationships in your life? What about your extended family?
Tell us a family story about you or someone else.
What was valued and praised in your family?
Describe your parents’ approach to parenting. Why do you think they took the approach based on their upbringing?
How has the family you were born into informed what family you seek to create?
How would you describe an ideal family?
What did you learn from your upbringing? What are you unlearning?
Tell us about the last big fight or drama with someone in your family (while being mindful of not sharing any private information).
Tell us about how your relationship with the family you grew up in has changed over time.
What’s a societal norm about family that you wish you could change and why?

Technology

What’s your favorite app on your phone, and why?
If you had to, would you rather show us your search history, notes, or photos on your phone? Which would you least like to share? Why?
What’s the last neat trick you learned to make using technology easier?
Tell us about a time when technology made your life easier. Share as much or as little as you’d like!
What was your first username online, and what did it represent? Tell us about other usernames and what they mean!
How do you feel about trading your privacy for convenience? When have you? When have you refused to?
What’s a type of technology you don’t understand but want to?
What technology in today’s world scares you? Why? What do you think should be done about it?
What technology do you wish was here already? How would you use it? How could it be used for evil?
How has the internet allowed you to explore a part of yourself you might not otherwise be able to?
How do you think your life would be impacted if you went without your phone for a month? What about the internet as a whole?
Tell us about your relationship with technology. How has it improved your life? How has it made things worse? Have you ever felt addicted?
Imagine you’re the CEO of a social media giant; what changes would you implement and why?
What’s the sketchiest thing that technology has enabled you to do?
Describe an experience of using technology that evokes a certain sensation/experience/feeling that we don’t currently have words to describe. Bonus points if you can come up with a word.

Do you think questions are powerful?

Asking questions is a powerful way of learning about people, helping them, managing a conversation productively, or even creating a precedent for a company or meeting culture. Questions can inspire people and bring about intrinsic change.

What questions will you experiment with? With who? How would that make your work and life better? And most importantly, what can you do to get consistently better at asking questions?