26 Questions that reveal user problems.
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What's the most frustrating part about your job? Your day?
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What do you hear your colleagues complain about the most?
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What's one part of your job you wish you didn't have to do?
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Are there any daily tasks you would like to outsource?
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How have you tried to simplify or reduce your workload?
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What's one problem you've been trying to solve over time?
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(Seriously), what keeps you up at night?
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Is there anything you'd like to fix that your boss won't go for?
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If you had unlimited resources, how would you simplify your job?
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What is the least favorite part about your career?
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What advice (that you didn't get) would you give about your job?
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What took the longest to learn on your own? Why?
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If you had a magic wand for work, what would you wave it on?
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How would you scare me out of "wanting" your career?
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What's one thought about your job you wouldn't tell your boss?
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Tell me about the most painful customer experience you've had.
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If you were given $5,000 to spend on your job, where would you use it?
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When do you find yourself hesitating the most?
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What's your biggest professional fear?
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What do you think your boss's or customer's biggest fear is?
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Have you ever thought about spinning off? What would you do?
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Oh, Really? Why's That? (Don't forget to ALWAYS dig deeper).
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When is the last time you missed a deadline, why?
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What would you hire a consultant to help you with?
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What makes you the most nervous about your job?
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Who do you think your biggest competition is? Why?
Most people don't even realize that the painful part of their day is something worth mentioning. Its just reality, so instead they mention more minor issues like their annoying desk neighbor.
I like this one. Much more specific.
Great list !
I also ask question about motivation for exemple : What do you like most in your job ? What are you proud of ?
Update, I made a bigger list:
https://www.indiehackers.com/post/149-insanely-good-questions-to-get-to-know-someone-good-for-user-interviews-dates-or-deep-conversations-with-friends-d00bda6501
Great list!! You should make another one less focus on the person's job and look at other audience types (students, retired, hobbyists, etc)
Great questions. I spent some time asking these to myself :)
I really like no. 7! That’s actually a question I kept from the book 1-Page Marketing plan. It reveals true problems of people not just „I-would-like-but-also-never-googled-a-solution“ problems. Thanks for the list!