Prompts, your guide to starting a conversation

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A prompt will kick start a great conversation, a great insight, and a great relationship. Here are lots of prompts. For fun, pick a prompt at random and ask it to someone else, or answer it yourself. However, it takes a lot of trust and vulnerability to answer these questions, so make sure the person feels very empowered to not answer a question.

Work Prompts

From the awkward 1:1 and Holloway’s remote management guide

Give extra honest feedback

  • Are they acting like the best manager / report / partner you could wish for? Are you? Why or why not? Discuss.
  • What have you already told someone else about this person (or heard others say)? Share with them. Discuss.
  • What is everyone around neglecting to tell this person?
  • What’s the work equivalent of this person having food stuck in their teeth? Be a good friend / coworker and tell them.

Receive extra honest feedback

Remember skip the fluffy answer and ask again until you get something real.

  • Tell them a growth area you’re working on currently. Tell them why you picked it (even if it was one of those “not-really-optional” ones!).
  • Ask for advice.
  • Check for your own role in a weird situation.
  • Pick a thing you’ve recently complained about. Ask them — “What could I’ve done differently in that situation?” Ask for feedback on how to be better.
  • Admit a fault or a mistake. Ask for support and advice. Ask them if they noticed you making it or not.

Career Growth

  • When did you recently get an opportunity to learn and grow? How can we create more of those?
  • Have you seen someone else doing something you felt worked really well? What was it?
  • What should I know about you that would help me support you better?
  • What are you doing here that you feel is most in line with your long-term goals?
  • If you could be proud of one accomplishment between now and next year, what would it be?
  • Is anything holding you back from doing the best work you can do right now?
  • Is there a project or area outside your current role where you feel you could be contributing?
  • Which areas make you feel like your hands are tied or you are unable to reach your full potential?
  • If you were to create your ideal position, how would it differ from what you are currently doing?
  • At what point in the past week were you most frustrated with or discouraged by your work? What can I do to help you manage that?

Seeking feedback

To get some deep feedback, use the prompts in getting extra honest feedback.

Or ask the more boring questions

  • Would you like more or less direction from me?
  • Would you like more or less feedback on your work? If more, what additional feedback would you like?
  • If you were coaching me to have a greater positive impact, what would you tell me?
  • What can I tell you about myself that might make it easier to understand me and work with me?
  • Have you seen a product or initiative at another company recently and thought to yourself, ‘I wish we’d done that’?
  • What vibrations (news, rumors, dynamics) are you picking up that you think I should know about?
  • What’s our biggest oversight, and how do we resolve it?
  • What do you feel is our biggest risk right now?
  • What was the most useful part of our conversation today?
  • What are you worried about right now?

Building relationships

  • How’s life?
  • What’s going on for you these days outside of work?
  • What is something you’ve done that you’re proud of?
  • What was something you were scared of as a child? Have you overcome it?
  • What fictional character do you most identify with?
  • Would you rather be known or unknown? Why?
  • What hot topic usually turns into an argument for you?
  • Do you have a motto or personal mantra?
  • What’s on your bucket list?

Transition and change questions

  • Imagine it’s two years from now, and things have gone well: What has been your role in that? What does your role look like?
  • What are you worried might happen if you made this transition?
  • What will happen if you don’t take this step?
  • What would need to change for you to get to a point of “let’s do this” or “I don’t want this”? What information do you need?

Team dynamics

  • How would you say we’re doing at working together as a team? What makes you say that?
  • What do you think the rest of the team is most concerned about? (People may also share what they are personally concerned about; this framing makes it easier to share.)
  • Who on the team is doing really well right now? (Also listen for names that don’t come up.)

Well-being

  • Are there any decisions you’re hung up on?
  • I’ve noticed you’re a little quieter than usual. Is there anything you’d like to talk about?
  • Do you feel stretched thin? (This wording is useful to measure subjective stress, not objective workload.)
  • What, if anything, did you used to do that you find you don’t have time for right now?
  • What is your takeaway from this discussion? (This is especially helpful to get to action steps from a thorny issue.)
  • In our last one-on-one you mentioned you were frustrated by X and wanted to try Y as a solution. How has that been going?
  • During this meeting you’ve mentioned that you’d like to pursue X. What steps can you take toward that before our next one-on-one?
  • What could we change about work that would improve the rest of your life?

Conflict resolution

  • What does your ideal outcome look like? (Could be about a specific conflict that’s come up, or approached hypothetically.)
  • What’s hard for you in getting to that outcome?
  • What do you really care about?
  • What’s the worst-case scenario you’re worried about?

Getting deeper

  • Are you afraid of anything at work?
  • I’ve noticed that our last several one-on-ones have stayed pretty surface. What are your honest impressions of this meeting? What could we be doing differently or better?
  • What’s something you used to strongly believe in that you no longer do today?
  • Before making a telephone call, do you ever rehearse what you are going to say? Why?
  • What are three things you and I appear to have in common?
  • What do you feel most grateful for in your life?
  • Take four minutes and tell me your life story in as much detail as possible.
  • If you could wake up tomorrow having gained any one quality or ability, what would it be?
  • Is there something that you’ve dreamed of doing for a long time? Why haven’t you done it?
  • What do you value most in a friendship?
  • What, if anything, is too serious to be joked about?

Meta & Feelings

Talk about emotions. Label one you’re feeling, or what you sense from other person. Boom, instant awkward and great discussion.

  • Any meta-conversation about your conversations.
  • We never talk about Topic A, we just always talk Topic B. Why is that?
  • When I tell you about Topic A, you always react like this, and that’s why I don’t tell you that stuff. When I bring up Topic B, how do you feel? Why is that?
  • Ask for their fears. What are they afraid of (for their career, the project, an upcoming tough meeting)? Why? Share your own.
  • Trust check. How easy is it for both of you to share intimate things with each other? Why? What would make it easier? Discuss.

Friendship Prompts (Not For Work)

From berkley’s building closeness

Find a time when you and your partner have at least 45 minutes free and are able to meet in person. For each set of questions, each person should answer each question, but in an alternating order, so that a different person goes first each time.

Spend 15 minutes on Safe, then Deep, and then on Vulnerable prompts

Safe

  • Given the choice of anyone in the world, whom would you want as a dinner guest?
  • Would you like to be famous? In what way?
  • Before making a telephone call, do you ever rehearse what you are going to say? Why?
  • What would constitute a “perfect” day for you?
  • When did you last sing to yourself? To someone else?
  • If you were able to live to the age of 90 and retain either the mind or body of a 30-year-old for the last 60 years of your life, which would you want?
  • Do you have a secret hunch about how you will die?
  • Name three things you and your partner appear to have in common.
  • For what in your life do you feel most grateful?
  • If you could change anything about the way you were raised, what would it be?
  • Take four minutes and tell your partner your life story in as much detail as possible.
  • If you could wake up tomorrow having gained any one quality or ability, what would it be?

Deep

  • If a crystal ball could tell you the truth about yourself, your life, the future, or anything else, what would you want to know?
  • Is there something that you’ve dreamed of doing for a long time? Why haven’t you done it?
  • What is the greatest accomplishment of your life?
  • What do you value most in a friendship?
  • What is your most treasured memory?
  • What is your most terrible memory?
  • If you knew that in one year you would die suddenly, would you change anything about the way you are now living? Why?
  • What does friendship mean to you?
  • What roles do love and affection play in your life?
  • Alternate sharing something you consider a positive characteristic of your partner. Share a total of five items.
  • How close and warm is your family? Do you feel your childhood was happier than most other people’s?
  • How do you feel about your relationship with your mother?

Vulnerable

  • Make three true “we” statements each. For instance, “We are both in this room feeling…”
  • Complete this sentence: “I wish I had someone with whom I could share…”
  • If you were going to become a close friend with your partner, please share what would be important for him or her to know.
  • Tell your partner what you like about them; be very honest this time, saying things that you might not say to someone you’ve just met.
  • Share with your partner an embarrassing moment in your life.
  • When did you last cry in front of another person? By yourself?
  • Tell your partner something that you like about them [already].
  • What, if anything, is too serious to be joked about?
  • If you were to die this evening with no opportunity to communicate with anyone, what would you most regret not having told someone? Why haven’t you told them yet?
  • Your house, containing everything you own, catches fire. After saving your loved ones and pets, you have time to safely make a final dash to save any one item. What would it be? Why?
  • Of all the people in your family, whose death would you find most disturbing? Why?
  • Share a personal problem and ask your partner’s advice on how he or she might handle it. Also, ask your partner to reflect back to you how you seem to be feeling about the problem you have chosen.

Kids

Fun

You can probably ask these to grown ups as well, but I suspect kids will be more opening to discussing.

  • What is something that made you laugh today
  • If you wrote a book, what would you name the main character and where would he go?
  • What is your favorite thing to do?
  • If you could design a t-shirt, what would you draw or write on it?
  • What was your favorite part of your day/school/activity…?
  • What is your favorite memory about being ___ years old?
  • If the story of YOU became a movie, how would the movie end?
  • Do you have any jokes to tell me?
  • What’s the funniest thing you saw today/this week?
  • How would you describe a perfect day for you?
  • If we had an airplane to take us on vacation right now, where would you want to go?
  • If we could go to (insert name of favorite place) but couldn’t use a car to get there, how do you think we could get there?
  • If you could have any animal in the world as a pet, where would you go to get it and what would it be?
  • If you could do something just like your friend (use name of friend) what would you do?
  • If you could do something like your Dad/Mom do, what would you want to be able to do?
  • If you could change anything about school what would it be?
  • If you could change anything about our family what would it be?
  • If you could change anything in the world, what would you change and how?
  • Who is your favorite tv/book/story character and what do you like about him/her?
  • If you could eat lunch with (insert favorite character’s name) where would you go and what would you eat together?
  • If you could wake up tomorrow with a superpower, what superpower would you want to have?
  • If you could have any 3 wishes granted, what would they be?
  • If all your clothes could only be one color, what color would you choose?
  • If you could change the lunch menu at (school/home) what would you change?
  • What is your biggest dream?
  • What is your biggest worry?
  • If you could change your name, would you want to and what name would you choose instead?
  • What are you proudest of in your life?
  • Where is your favorite place to be?
  • What is something you never thought you could tell me but maybe want to tell me now?
  • Is there anything you have always wanted to ask me but didn’t? Do you want to ask me now?

Coaching Prompts

See the extensive prompts in the Coaching post.