140 Open-Ended 1:1 Questions to Build Trust and Create Better Working Relationships

1:1s are a time to build trust and form a deeper bond between managers and employees – for both people to show they value each other’s opinions, work, and feelings. These meetings are a priceless opportunity to have the undivided attention of the other. But sometimes these interactions can seem fluffy and sometimes even awkward, or worse–it becomes a conversation focused on work status updates. 

Asking open-ended questions can help. Not only do those open-ended questions help you avoid painful small talk (nobody wants to talk about the weather!), they also provide organic opportunities to create deeper relationships with your team. A manager who knows the right mix of questions to ask in their 1:1s has a better pulse on what frustrates, worries, motivates, and inspires their people. When managers are dialed in and employees feel heard and seen, everyone’s work gets better and employee engagement soars.

Closed vs. Open Questions 

Closed questions are a common mistake. They’re easily answered in a few words or less and very quickly get you nowhere: 

• Do you think we measure success well?

• Do you like this team? 

• Do you like my management style?

Open-ended questions allow the employee to pause, reflect and share a little deeper on “why” their answer is what it is.

• What would you change about the way we measure success?

• What do you enjoy about working with this team? (what would you change?)  

• How can I be a more helpful manager fo you?

If the responses are still abrupt, abbreviated answers, the person could just be trying to get used to your new format or feel unsure if you truly want them to open up in a way that they haven’t before. To combat this, tack on any of these on to their response: 

• Why do you think that?

• Tell me more about that. 

• What was the best part? 

Example Open-Ended Questions 

Here’s our list of questions to help guide the conversation in your 1:1 setting. 2-4 is plenty, and often the conversation goes where it needs to from there. 

Questions about growth and development

• What has been the highlight/lowlight from the past week at work?

• Who is someone in the company that you’d like to learn more from?

• What projects would you like to work on or be more involved in?

• What professional goals would you like to accomplish in the next 6 to 12 months, and how can you get there?

• What’s something you’re itching to try that you haven’t had the time or resources to do?

• What other roles at [your company] do you find interesting? What skills do those roles require that you would like to work on?

• What do you want to do next in your career? How can I help you get there?

Questions about the team

• What’s the best idea or suggestion you’ve heard from the team lately?

• What’s one thing we should stop doing?

• What would you change if you had my job? Why would you make that change?

• When was the last time you gave recognition to someone else at the company?

• Who is close or ready for promotion? For what roles?

• If you had to promote someone to [role x] who would you recommend and why?

• What’s one thing we can do to improve the performance of the team?

• What’s top of mind right now that our team hasn’t talked about yet?

• If you were managing the team, what would you do differently?

• Who is doing a great job on the team? What have they done?

• What would be helpful for me to re-explain to our team?

• What can I do to provide enough clarity to the team on our direction?

• What would make our team meetings more effective?

• What projects would you likemore insight on across the team?

• What’s an iinefficiency on our team I might not know about?

• What would improve cross-functional collaboration at accross the company?

Feedback on your management style 

• What can I do to make our time together more effective?

• What do you find challenging about my communication style?

• What would you change about the way we communicate?

• What do you like about my management style? What do you dislike?

• Where do you think I should be focusing more of my attention?

• What about my job do you feel you don’t know that you should?

• What is one thing I could experiment with doing differently this month? 

• What areas do you feel you need feedback on from me?

• If I could improve one skill between this meeting and the next, which would you choose?

• Which soft skills do you think I excel at most? What can I work on?

• Where has our communication faltered? How can I do better?

• How can I be a more effective manager for you?

• What do you wish I did less of? More of?

Questions to address recent change

• What do you and your team think of the recent changes?

• How do you feel [recent change] was communicated?

• What are your biggest concerns about [change y]?

• I’m thinking about making [change z], what concerns come to mind?

Questions to address roadblocks and concerns

• What inefficiencies exist in how we get the work done?

• What’s one thing I can do right now to make work better/easier for you?

• What questions do you have about what other team members are working on?

• If you were a hiring manager for our team, what role would you hire next? why?

• What’s something you’ve been putting off asking for / sharing?

• What’s your outlook on next week? 

• What are you least clear about, in terms of our company-wide strategy and goals?

• What's been stressing you out at work?

Questions about employee motivation

• If you were the CEO, what’s the first thing you’d change?

• What’s one thing we could change about work for you that would improve your personal life?

• What’s something you’re proud of that happened this week? This month?

• What are you feeling passionate about, personally or professionally?

• Who on our team deserves a shoutout for their work and why?

• What’s something past managers have done that’s inspired and motivated you?

• What’s something past managers have done that’s really frustrated you?

• What does an ideal, productive workday look like to you? Walk me through it.

• What makes you excited and motivated to work on a project?

• What would make you happier inyour role?

• What certifications or courses possibly interest you?

• What’s your least favorite part of your day-to-day at work?

• What’s one thing you would recommend to improve our workplace culture?

• What would make your home-office a better, more productive environemnt?

• What makes you proud of the work you do here?

• What would give you better work lif balance?

• What would make you more excited to begin the day?

Identifying Burnout 

• What do you do to rehcarge? Are you able to do it enough?

• What is the actual time put into the work each week and is it realistic what we have oin your plate?

• What do you look forward to about Mondays? What do you dread? 

• What's one thing you would change about how the work gets done?

• What inefficiencies exist on our team that frusterate you?

• What makes you proud of the work you're doing for the company?   

• What would make you happiest in this role?

If burnout is detected based on an answer from the previous section, here’s how to dig deeper into why the employee is burned out:

They don’t feel like their work matters

• What part of your role seems unimportant, or a waste of time?

• What has been unclear about where the company is headed?

• What is unclear about how your role makes a big impact at the company?

They have a skill gap 

• What certifications or training do you want to pursue?

• What moments of your day stress you out because you'reunsure how to do it?

• What doyou wish you were better at?

They feel overloaded 

• What about your workload is a little unfair?

• What tends to take up too much of your time?

• What would make deadines feel more achieveable?

Unclear on mission/vision/values/direction of organization

• What parts of our All Hands / Town Hall would you change?

• What parts of our All Hands / Town Hall are boring or uninteresting to listen to?

• Is it easy to recall our company mision/vision?

• Is it easy to recall our company values?

• What about our mission isn't exciting or compelling to you?

You’re Micro-managing them

• Where would you like me more or less involved in your day-to-day? 

• What could I do to make you feel even more supported in your role?

• How do you feel about our current level of communication?

• How do you feel about my involvement in your projects?

   

They feel no sense of community 

• Who do you connect most with at work?

• What people on other teams have you formed a friendship with / enjoy working with?

• When do you have themost fun at work?

They crave more ongoing development

• What training are you interested in to further your skillset? 

• What can I do to help you achieve your goals?

• What would help you feel you have a path to grow at our company?

• What do you think needs to happen for you to get to the next level at our organization? 

• What do you want to know about my job and responsibilities now?

Icebreakers

• What was your first job? 

• What’s a recent dream you had? 

• What’s your favorite movie? 

• What have you read or listened to lately? (book or podcast) 

• If you could explore the ocean or explore space, which would you pick? 

• What’s your spirit animal and why?

• What was your favorite vacation ever taken, why? 

• What’s one cuisine you couldn’t live without?

• What does your typical work from home uniform look like?

• How many cups of coffee, tea, or beverage of choice do you have each morning?

• Are you an early bird or night owl?

• Best book you’ve ever read?

• Best professional development book you’ve ever read?

• What’s your favorite way to get some exercise?

• If you could write a book, what genre would you write it in? Mystery? Thriller? Romance? Historical fiction? Non-fiction?

• What is your most-used emoji?

• What was the worst style choice you ever made?

• What was the worst haircut you ever had?

• Does your current car have a name? What is it?

• If you were famous, what would you be famous for?

• You have to sing karaoke, what song do you pick?

• What was your least favorite food as a child? Do you still hate it or do you love it now?

• If you had to eat one meal every day for the rest of your life what would it be?

• If aliens landed on earth tomorrow and offered to take you home with them, would you go?

• The 60s, 70s, 80s, 90s: Which decade do you love the most and why?

• What’s your favorite sandwich and why?

• What’s the best piece of advice you’ve ever been given?

• When you die, what do you want to be remembered for?

• What is your favorite item you’ve bought this year?

• What is your absolute dream job?

• If you had to delete all but 3 apps from your smartphone, which ones would you keep?

• If you could add anyone to Mount Rushmore who would it be; why?

• You’re going to sail around the world, what’s the name of your boat?

• What fictional family would you be a member of?

• What are you watching on Netflix? 

• What was your favorite game to play as a child?

• Are you a traveler or a homebody?

• What is your favorite musical instrument and why?

• What’s is one thing we don’t know about you?

• What was your favorite subject in school? 

• Are you a cat person or a dog person?

• If you could have someone follow you around all the time, like a personal assistant, what would you have them do?

• Would you rather live in the ocean or on the moon?

• Would you rather travel back in time to meet your ancestors or to the future to meet your descendants?

• Would you rather lose all of your money or all of your pictures?

• Would you rather have invisibility or flight?

• Would you rather live where it only snows or the temperature never falls below 100 degrees?

• If you were invisible for a day, what would you do?

• What is your favorite ice cream flavor and ice cream topping?