100questions

by Dan Brown

“The question is our most important tool.” – Erika Hall

Preface

One Hundred Questions is a project to capture my most favorite questions–the ones I ask time and again, if not on every project, then on most projects. They grew out of a quarter century of consulting, managing, directing, and researching–activities that that prioritize asking good questions.

For each question, I will provide context and flavor. I want to help UX professionals cultivate their own favorite questions, and do that by providing insight into why these questions are meaningful to me. Each question also includes variations, different ways to adjust to circumstance by shifting how I ask or frame the question.

What’s here

• There are over 100 questions.
• The Drafts list has questions for which I’ve written more detail. Each write-up follows the same structure.
• The Not Started list has the rest of the questions. I’ll move them up to Drafts when I’ve written something about them.
• My original list of questions and thought process is captured in a Google Sheet.
• A Proposal, targeted at prospective publishers.

What’s coming

• More detail. I will continue to write up individual questions and move them from Not Started to Drafts.
• Structure. For now, the questions are in no particular order. I just kinda dumped them here. I’d like to devise a meaningful way of organizing them.

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Introduction

Drafts

1. Are there any topics that are off limits?
2. Do you know what your priorities are?
3. How are things different one year from now?
4. How does this fit into the narrative of the project?
5. How does this observation impact the design?
6. How do we draw people into this process?
7. How is this different from what you expected? ⇐
8. How would you characterize the users of this product?
9. How would you describe this product in your own words?
10. How would you explain this concept in your own words?
11. If you could ask someone from the target user group one question, what would you ask?
12. If you were coaching someone else about this product, what advice would you give them?
13. Is there anything else you want to talk about?
14. Is there anything I can do to take this to the next level?
15. What about this activity makes me feel dread? ⇐
16. What aspect of the work do you find most energizing?
17. What aspects of this will your stakeholders be most interested in or concerned about? ⇐
18. What can my (team, manager, boss, organization) provide to help me make progress?
19. What do people need to know to participate fully? ⇐
20. What do you expect to see come out of the other end of this process?
21. What feedback would be most helpful right now? ⇐
22. What made this hard?
23. What problem are we trying to solve?
24. What’s the most important thing for us to get right?
25. When you’ve worked with other teams, what’s worked well?

Not Started

• How are we sacrificing the user’s time or money to support our own goals?
• How can we bring this effort to a good conclusion?
• How do you accommodate change?
• How do you see the problem differently?
• How do you stay up to date?
• How does this move the project forward?
• How does what I’m doing help me meet my goal or objective?
• How does your decision-making change over the course of a year?
• How might a bad actor take advantage of the system?
• How would you characterize the design problem?
• How would you characterize your working relationship with other members of the team?
• How would you do this differently?
• If I try something new, what do I expect to learn from it?
• If you could change one thing about this product, what would it be?
• If you were to meet them halfway, what would a compromise look like?
• If you’d had this product in hand last week, what would you have done with it?
• Is there anything else you think I should know about?
• Of your colleagues, who has the least understanding of what you do?
• What about this situation made me so upset?
• What are the kinds of decisions you make in a typical week?
• What are the risks with this approach?
• What are you most proud of?
• What are you working on this week?
• What aspect of the work do you find most draining?
• What aspects of the users describe the biggest differences between them?
• What considerations factor into your decision-making?
• What do you imagine is the hardest part of this effort?
• What do you need to make progress toward your goal?
• What do you want people to take away from this?
• What does a typical week look like for you?
• What does our product do to change the lives of our users?
• What gets in the way of you making a decision?
• What happens first?
• What happens next?
• What hypothesis does this work reflect or represent?
• What information would be most helpful to you in this process?
• What is expected of a designer’s performance?
• What is holding me back or getting in my way?
• What is my hypothesis?
• What is one thing I can do differently next time?
• What is one thing I can do right now to ease my stress or anxiety?
• What is one thing we didn’t talk about but should have?
• What is one thing your organization can be doing better for its users?
• What is standing in your way?
• What is the biggest decision you had to make recently?
• What is the biggest misconception about this domain?
• What is the one thing I can do to add value or make progress?
• What is your current level of motivation?
• What is your role in making decisions for the organization?
• What makes this problem unique?
• What makes this the most important thing for us to work on right now?
• What message are you trying to convey?
• What problem are you working on right now that this product might help you with?
• What purpose does this serve?
• What questions are we trying to answer?
• What questions will remain unanswered?
• What role do you want to play on this project?
• What role does your organization play in the lives of the users?
• What should we talk about first?
• What steps do I need to take to meet this goal?
• What story are you trying to tell?
• What surprised you?
• What tasks do we expect users to accomplish with this product/feature?
• What were you expecting to see but is missing?
• What’s the biggest challenge you faced last week?
• What’s your favorite part of the job?
• When you picture the final product, how big is it?
• Where do you expect us to spend the most time?
• Where is the leadership team least aligned?
• Which aspect of this work was the hardest?
• Who are the different people you work with?
• Who are your customers and stakeholders?
• Who else is important to this process?
• Who else should I speak to?
• Who is harmed by this?
• Why am I talking right now?
• With whom do you collaborate regularly?
• Where does this idea fit into the process: hypothesis? rough concept?
• How can I frame this to be most meaningful to the target audience?
• How can I help?
• How do you think the client would react to this?

This project is dedicated to my dad, Professor Richard Brown, who taught me that asking good questions isn’t just a method, it’s a craft.