How to Ask Open-Ended Questions (& The 150 Best to Ask)

Did you know? When you ask someone questions about themselves, it makes you more likable^{1 https://dash.harvard.edu/handle/1/35647952} !

But research shows, the way you ask a question^{2 https://hbr.org/2018/05/the-surprising-power-of-questions} makes a big difference, too. 

Watch our video below to learn how to start a conversation with anyone using these killer conversation starters:

Some of the best conversations start with open-ended questions that lead people to open up and form deeper connections.

In this article, we’ll look at open-ended questions, their benefits, and various scenarios where you can use them to boost your conversation skills (and likeability!).

What are Open-Ended Questions?

Open-ended questions are questions that are designed to encourage people to share more than a one-word response and typically start with words like “what,” “how,” or “why.” Open-ended questions help people expound on an idea or issue and carry the conversation forward without getting stunted in potentially awkward silence or little to no information for someone else to bounce off of.

Some of the best places to use open-ended questions include:

• Social gatherings
• Dates
• Networking events
• Job interviews
• Feedback meetings
• Sales calls
• Brainstorming sessions
• Qualitative survey data research
• Counseling and therapy sessions
• Conversations with kids (or anyone!)
• Medical appointments

“Ask questions the other person will enjoy answering.” —Dale Carnegie

To avoid stunting your conversations, you may want to stay away from closed-ended questions. But what’s the difference? Let’s look at how to avoid those awkward silences.

What’s the Difference Between Closed-Ended and Open-Ended Questions? 

Closed-ended questions lead people to give a one-word response like “yes” or “no,” whereas open-ended questions are great conversation starters or boosters that help bring energy to an interaction.

How you ask or write open-ended vs. closed-ended questions comes down to a few simple adjustments to the words you choose to ask your question. 

To write a more open-ended question, think about where you want to lead the conversation and consider adjusting your opening words.

Open-ended questions often begin with words like this:

• What…
• How…
• Why…
• Tell me about…
• Describe…

Closed-ended questions tend to start with words like this:

• When…
• Are…
• Did/do…
• Can…
• Will…
• Have…

Closed-ended questions may not always lead to “yes” or “no” responses. Sometimes they can lead to short answers as well. For example:

Closed-ended: What’s your favorite color?

The answer to this question will likely be something short, like “blue.”

One simple way to turn this question into an open-ended question is not necessarily to dismiss the closed-ended question altogether, but to follow it up with an open-ended question as well. For example:

Open-ended: What’s your favorite color and why?

It should be noted that there is a time and place for closed-ended questions. They are not inherently “bad,” but they generally don’t work as well to keep conversations going. 

Example Open vs. Closed-Ended Questions

Context	Closed-Ended Question	Open-Ended Question
Social Gathering	Did you have fun at the party?	What did you enjoy most about the party?
Date	Do you like your job?	What do you like most about your job?
Networking Event	Are you enjoying the event?	How has this event been beneficial for you?
Job Interview (Interviewer)	Are you an organized person?	How do you stay organized in your daily tasks?
Job Interview (Interviewee)	Do you like working here?	What do you enjoy about working at this company?
Feedback Meeting	Did the project go well?	What aspects of the project went well?
Brainstorming Session	Can we solve this problem?	What are some possible solutions to this problem?
Sales Conversation	Do you need this product?	How do you see this product benefiting you?
Survey & Research	Would you recommend our service?	Why would you recommend our service?
Counseling Session	Are you feeling okay?	How are you feeling today?
Medical Appointment	Do you have any symptoms?	What symptoms have you been experiencing?
Conversation with Kids	Did you have a good day at school?	What was the best part of your day at school?

What are the Benefits of Open-Ended Questions?

Why are open-ended questions important? Some of the best conversations are generated from open-ended questions that lead people to open up and form deeper connections.

Here are some of the other benefits of open-ended questions:

• Bring energy to a conversation. By increasing likeability and simultaneously making others feel more confident, there’s a natural energy induced into the conversation!
• Reduce awkward silences. A close-ended question might cut a conversation short, but an open-ended question might keep it moving along. 
• Boost self-esteem. As people feel your interest in them with open-ended questions, they may get a confidence boost. Your interest makes them feel more interesting!
• Provide better feedback. Instead of a one-sided view, open-ended questions provide a clearer picture from various perspectives about a situation, ultimately allowing people to solve problems better and address issues.
• Encourage people to open up. Open-ended questions feel like permission to share feelings and ideas with others who are interested in hearing them.

Now that we understand what open-ended questions are and their benefits let’s dive into the best scenarios where we can use them with examples for each category.

110 Open-Ended Question Examples 

Open-Ended Questions for Any Social Gathering

Open-ended questions are great for any social situation, and we have lots of great question ideas to spark conversation with anyone. Here are a few to get you started!

1. What are you looking forward to this week?
2. Have any big vacations coming up?
3. What do you love most about what you do?
4. What cheers you up on a bad day?
5. If you could have any five people at a dinner party, who would be there and why?
6. Tell me about your family.
7. What’s something people are usually surprised to learn about you?
8. Tell me about the last TV show or movie you loved (or hated).
9. What do you love most about where you live?
10. Who’s been the most inspirational person in your life and why?

Open-Ended Questions for a Guy or Girl You’re Dating

If you want to get to know someone on a deeper level, using thoughtful, open-ended questions is a great way to get there. They’re also a great way to boost someone’s self-esteem by making you appear more engaged and interested in what they have to share. Here are a few open-ended questions to ask on a date!

11. If money were no object, and you knew you could not fail, what would you do?
12. What was the last thing that made you laugh to tears?
13. What was your favorite thing to do growing up?
14. When you were a child, where did you imagine you might be today?
15. What activities make time feel like it’s flying by?
16. How would you describe your perfect day?
17. What are you most grateful for in this season of your life?
18. What’s something you’re proud of doing in your life?
19. What is your most treasured memory?
20. If you could be famous for something, what would you want to be famous for doing?

For more dating icebreakers, try one of these 131 non-awkward ideas!

Open-Ended Questions for Networking Events

Networking events are classic places for open-ended questions and icebreakers with people you’re meeting for the first time. Want to avoid awkward silence? Use an open-ended question!

21. What kind of people are you hoping to meet here today?
22. What’s your background, and how did you get to where you are now?
23. What’s the most exciting thing you’ve been working on lately?
24. What’s this work season like for you?
25. What kind of problems are you trying to solve these days?
26. What kind of projects would you love to get into if you had more capacity?
27. What are your goals for the next season?
28. What’s something that inspires you when you’re having a rough day?
29. What’s something you wish people knew about you?
30. What’s been the biggest twist or surprise in your (career or personal) journey?

Open-Ended Questions for Job Interviews

Job interviews are a great place for both the interviewer and the interviewee to ask open-ended questions to help understand what each other is bringing to the table to inform better decision-making. 

Questions for interviewers:

31. What’s your greatest professional achievement?
32. How would your boss or coworkers describe you?
33. What motivates you?
34. How do you like to be managed?
35. What’s something I should know about you that might not be on your resume?

Questions for interviewees:

36. What do you enjoy about working at the company?
37. What are your goals going into the next year?
38. How do you see this role best helping you achieve your goals?
39. What are your biggest opportunities going into next year?
40. What are the top three qualities you’re looking for in this role?

Open-Ended Questions for Team Building Activities

Fostering strong team dynamics is essential for achieving success in any collaborative environment. These open-ended questions are designed to break the ice, deepen connections, and unlock the full potential of your team during team-building activities.

1. What was the most memorable team activity you participated in and why?
2. How do you like to contribute to a team project?
3. What skills do you bring to the team that you’re most proud of?
4. What’s the biggest challenge you’ve faced as part of a team?
5. How do you think we can improve our team’s collaboration?
6. Describe a time when your team overcame a significant obstacle.
7. What motivates you to work well with others?
8. How do you handle conflicts within the team?
9. What are your favorite ways to celebrate team successes?
10. How can we better support each other’s growth and development in the team?

Open-Ended Questions for Feedback Meetings

Open-ended questions, when you give and receive feedback, are a great way to open up a conversation and understand where the other side is coming from more clearly. Here are some questions you can ask after a project is complete:

41. What are the things that went right on our latest project?
42. What was confusing about the last project?
43. How did we fall short on the last project?
44. What are our opportunities for growth?
45. What is our biggest learning from this experience?
46. How would we do this differently next time?
47. Where were we working on our strengths? Our weaknesses?
48. If we need to, how could we reorganize for a better outcome?
49. What kind of support or resources do we need to improve next time?
50. What are you looking forward to next time?

Pro Tip: Receiving feedback can be tough—and how you respond to it can make all the difference. Check out this goodie to learn more:

Open-Ended Questions for Brainstorming Sessions

Open-ended questions used in brainstorming sessions are a great way to get people’s juices and ideas flowing as they begin to open up their imaginations. Here are a few questions to get you started in your next brainstorming session.

51. What’s the best thing that can happen?
52. If money were no object, and we knew we could not fail, what might we try to do?
53. What’s the big problem we’re trying to solve?
54. When you imagine success for this project, what do you see?
55. What makes us unique in solving this problem?
56. What can we learn from past mistakes and successes?
57. What obstacles do we have to overcome?
58. What opportunities or low-hanging fruit do we need to pay attention to?
59. What are others doing to solve this problem? How are we different?
60. In one year, what will matter most about what happens with this project?

Open-Ended Questions for Sales Conversations

Open-ended questions during a sales conversation help salespeople understand the needs of their customers and make them feel heard and understood. Here are some open-ended sales questions to put your potential customers at ease:

61. Tell me about yourself and what you’re trying to accomplish.
62. What is one of your biggest challenges?
63. What are your goals?
64. What are your opportunities for growth?
65. What kind of resources/services are you using now?
66. What do you wish the resources/services you had did better?
67. What kind of resources/services do you wish you had?
68. What kinds of things are you looking for in a product/service?
69. What are your biggest priorities this season?
70. What are your criteria to determine whether or not you will move forward with a product/service?

Open-Ended Questions for Leadership Development

Great leaders inspire, motivate, and guide their teams to achieve remarkable goals. These open-ended questions will help you uncover insights, identify strengths, and foster growth in your leadership journey.

71. What do you think are the key qualities of a great leader?
72. How do you handle conflict within your team?
73. What has been your greatest leadership challenge and how did you overcome it?
74. How do you motivate your team during tough times?
75. What leadership skills are you working on improving?
76. Can you describe a time when you had to make a difficult decision as a leader?
77. How do you build trust within your team?
78. What strategies do you use to inspire and engage your team members?
79. How do you balance leading and listening within your team?
80. What is your vision for the future of your team, and how do you plan to achieve it?

Open-Ended Questions for Surveys & Research

Open-ended questions are a great way for researchers in any industry to explore and expound upon their data, including some of the close-ended, quantitative responses. 

For example, a survey might say, “Would you recommend our services to a friend?” They might then ask an open-ended question like, “Tell us why you would recommend our services to a friend.” to explore the qualitative data behind the close-ended response.

Note that most of the questions below are written in the context of a product or service. However, survey questions vary by industry and purpose (e.g., scientists!). The most important thing to remember is to keep open-ended questions specific to your intention of providing qualitative data you can learn from.

81. What do you like about this product/service?
82. What would improve your experience?
83. How would you describe the company/product/service to a friend?
84. If you could change one thing about X, what would it be?
85. What made you choose X over another product/service?
86. What can we do to serve you better?
87. What is the best feature of our product/service?
88. If X wasn’t available, what would you do/use instead?
89. Why did you decide to work with us vs. someone else?
90. How do you use our product/service?

Open-Ended Questions for Counseling & Therapy Sessions

Open-ended questions are common for counselors or therapists to ask clients because they help them process their feelings and thoughts more clearly. Here are a few open-ended questions you might hear during therapy:

91. What brings you here today?
92. How does that make you feel?
93. What have you done in the past to deal with this issue?
94. How does it feel in your body?
95. Tell me about a time you felt X as a child. What happened?
96. What is your relationship like with your parents?
97. What emotions do you feel as you talk about that?
98. How did you feel when X happened?
99. Tell me more about that…
100. What do you want to do?

Open-Ended Questions for Medical Appointments

Open-ended medical questions^{3 https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8758184/} are helpful for those in healthcare^{4 https://samples.jbpub.com/9781449652722/9781449645106_ch01_001_036.pdf} to get a deeper understanding of the issues their patients might be experiencing. Here are some examples of open-ended questions from a doctor or nurse you might hear as a patient:

101. What brings you here today?
102. What are your concerns?
103. What questions do you have?
104. How are you taking your medications?
105. What symptoms are you experiencing?
106. Describe what it feels like…
107. What else is bothering you?
108. What happened?
109. What would you like me to address first?
110. What are you afraid of?

Open-Ended Questions for Mentorship and Coaching

Mentorship and coaching are crucial if you want to have career success. Think of the most successful people you know, and chances are they’ve had a mentor (or two, or three…). Here are the best questions to ask any mentor.

111. What are your long-term career goals and how are you planning to achieve them?
112. What has been the most rewarding experience in your career so far?
113. What obstacles are you currently facing and how can I help you overcome them?
114. How do you define success for yourself?
115. What new skills are you interested in learning?
116. Can you describe a challenge you recently faced and how you dealt with it?
117. What do you think are your greatest strengths and how can you leverage them more effectively?
118. How do you stay motivated and focused on your goals?
119. What feedback have you received that had the most impact on your personal or professional growth?
120. How can I best support you in your development journey?

Open-Ended Questions for Conflict Resolution

If you’ve gotten into an argument recently, chances are you could’ve asked better questions. The next time you’re fired up, try shifting your tone and ask one of these questions:

121. What are your main concerns regarding this issue?
122. How do you feel about the current situation?
123. What do you think is the root cause of this conflict?
124. How can we work together to find a solution?
125. What outcomes are you hoping for from this discussion?
126. Describe a time when you successfully resolved a similar conflict.
127. What do you think each party could do to improve the situation?
128. How has this conflict affected your work or personal life?
129. What steps do you think we should take to prevent similar conflicts in the future?
130. How can we ensure that everyone’s needs are addressed moving forward?

Open-Ended Questions for Customer Feedback

Gathering detailed customer feedback is crucial for improving products and services. These open-ended questions will help you gain valuable insights into your customers’ experiences, needs, and expectations.

131. What do you like most about our product/service?
132. How can we improve your experience with our company?
133. What other features or services would you like to see us offer?
134. What problems are you hoping our product/service will solve?
135. How do you feel about our customer service?
136. What has been your most memorable experience with our product/service?
137. How can we better meet your needs and expectations?
138. What made you choose our product/service over others?
139. Can you describe any challenges you’ve faced while using our product/service?
140. What suggestions do you have for enhancing our product/service?

Open-Ended Questions for Conversations with Kids

Asking kids how their day is will often receive a short response. (Any parents out there relate?!) But if you can frame your questions to inspire them to share, you might be surprised by their openness (this goes for preschoolers all the way up to high schoolers!).

141. What was the best part of your day?
142. What are three things you’re grateful for today?
143. If you could choose to have any superpower, what would it be and why?
144. If you could time travel, where would you go and why?
145. What do you love most about your friends?
146. Tell me about your favorite teacher and why they’re special.
147. What are you excited about doing this weekend?
148. What’s something you wish you could do if you had the skills/strength/know-how?
149. What do you think technology will be like in 100 years?
150. If you could change something about how the world works, what would you change?

Open-Ended Questions FAQs

Open-Ended Questions Key Takeaways

In summary, remember these benefits of open-ended questions.

• Bring energy to a conversation. By increasing likeability and simultaneously making others feel more confident, there’s a natural energy induced into the conversation!
• Reduce awkward silences. A close-ended question might cut a conversation short, but an open-ended question keeps it moving along. 
• Boost self-esteem. As people feel your interest in them with open-ended questions, they may get a confidence boost. Your interest makes them feel more interested!
• Provide better feedback. Instead of a one-sided view, open-ended questions provide a clearer picture from various perspectives, ultimately allowing people to solve and address problems better.
• Encourage people to open up. Open-ended questions feel like permission to share feelings and ideas with others interested in hearing them.

For more conversation-starter ideas, check out our article for 57 killer conversation-starters to start a conversation with anyone.