What is your relationship like with [topic ... e.g. money, fitness, etc.]
How do you currently go about [problem / task]?
How much time do you typically spend on [problem / task]?
Tell me about the last time you tried to [problem / task]?
What do you like about how you currently [problem / task]?
What is the biggest pain point related to [problem / task]?
Why do you keep doing [problem / task] ... why is it important to you?
What type of work-around have you created to help you with this?
What is the hardest part about [problem / task]?
What are you currently doing to make this [problem / task] easier?
How does this [problem / task] impact other areas of your life / work?
What other products or tools have you tried out?
Have you paid for any of these other products or tools?
How did you hear about these other products or tools?
What do you like or dislike about these other products or tools?
Are you looking for a solution or alternative for [problem / task]?