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

1 minute • Jun 11, 2021Employee Engagement

1:1s are a time to build trust in relationships 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: 

  • Are you happy with your role here? 

  • Do you like this team? 

  • When do you like to start your workday?

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

  • How should we be measuring the success of our campaigns? 

  • Why do you think there hasn’t been much participation at our All Hands? 

  • Where do you want to take your career and how can I help?

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? 

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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’s 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 your 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?

  • Do you have 1:1s with others? Why or why not? 

  • When was the last time you praised one of the people on our team?

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

  • Who are the best people on our team? What are they doing well?

  • 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?

  • Is there anything that would be helpful for me to re-explain to our team?

  • Am I providing enough clarity to the team on our direction?

  • What needs to change around our team meetings?

  • Are there any roles on the team that you feel unclear about?

  • What’s a problem we have on our team that I might not know about?

  • How could we improve cross-functional collaboration at [your company]?

Feedback on your management style 

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

  • Do you find it easy to communicate with me? What makes you feel that way?

  • Are you happy with our level of communication? How would you change it?

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

  • On a scale of 1-10, how has my level of support/presence been over the past month?

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

  • Is there anything about my job that you feel you don’t know that you should?

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

  • Am I giving you enough feedback on your work?

  • What is everyone around me neglecting to share with me?

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

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

  • Where has our communication faltered? Can you give me an example?

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

Questions to address recent change

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

  • What tweaks would you make to [change x] to help you and your team?

  • What are you and your team’s biggest concerns about [change y]?

  • I’m thinking about making [change z], how long would it take to privately solicit feedback from your team on it?

Questions to address roadblocks and concerns

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

  • Do you have any questions about what other team members are working on?

  • What do you need? What could make your day-to-day easier?

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

  • What’s something you’d like to share but is a little stressful to bring up in person?

  • What’s your outlook on next week? 

  • Do you have any questions that, if answered, would help you in your day-to-day? 

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

  • Do I have anything outstanding for you that I haven’t done yet?

  • What, if anything, is stressing you out?

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 do you wish I did less of? More of?

  • 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?

  • Are you happy in your role? What could make it better for you?

  • On a scale of 1-10, how happy are you at work?

  • 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?

  • Do you find your physical work environment productive? Is there anything preventing you from being productive?

  • Are you proud of the work you do here?

  • How do you feel about the balance between your individual work vs. managing?

  • How do you feel your work/life balance is? What would you want to change, if anything?

  • Are there any goals we have on a company, team, or individual level that you feel are entirely unattainable? If so, why?

  • What’s the best thing about working here?

Identifying Burnout 

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

  • If you had to choose again, would you choose to work here? Why or why not?

  • Are you proud of the work you’re doing for this organization?  

  • Do you see yourself working here a year from now? 

  • Are you happy in this role? What could make it better for you?

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

  • Do you feel like the work you do has meaning and purpose? Why or why not? 

  • Do you feel your job in this organization is secure? Why or why not? 

  • Do you enjoy the work that you do in this organization? Why or why not? 

They have a skill gap 

  • Do you understand everything expected of you in your role? What can I help you with?

  • Do you ever consider taking training or getting a certification?

They feel overloaded 

  • Do you feel the workload on our team is distributed evenly? Why or why not?

  • Is your workload manageable lately? What has been taking up too much of your time? 

  • Do you feel comfortable with the deadlines you’re given with projects? Why or why not?

Unclear on mission/vision/values/direction of organization

  • Do you feel our Leadership is committed to setting a clear vision and mission that guide our organization? What could they do better? 

  • Do you feel our organization’s strategy and goals are communicated transparently? What could help everyone understand them better? 

  • Do you think our colleagues live authentically by our organization’s values? Why or why not?

  • What could make our mission, vision, and values easier to remember?  

  • What could management change to more clearly communicate business goals and objectives to all of us? 

You’re Micro-managing them

  • Do you feel I give you enough authority to make the decisions you need to make? What’s a recent example where I could have done better? 

  • What could I do to give you more space to get your work done? 

  • What could I change about the way that I’m managing you?


They feel no sense of community 

  • Do you feel like you have one good friend at the organization? If so, who? If not, who would you like to forge a better working relationship with? 

  • What could we change to make teams feel like they could be more friendly with one another? 

They crave more ongoing development

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

  • Do you feel like your career goals are achievable? What can I or the leadership team do to help you? 

  • 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?

Open-Ended Questions Just for Fun 

  • 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?

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