From the infamous book by Kim Goodwin -- Designing for the Digital Age. You can find a deeper dive here
Things to watch out for
Presumed constraints—ask why they are constraints
Jumping to solutions—ask what problem the solution would solve
All stakeholders
What is your role in this project?
What did you do before this?
What is this product going to be?
Who is this product for?
When is the version we’re designing going to be released?
What worries you about this project? What’s the worst thing that could happen?
What should this project accomplish for the business?
How will you, personally, define success for this project?
Is there anyone you think we need to speak with who isn’t on our list? Who?
How would you like to be involved in the rest of the project, and what’s the best way to reach you?
Marketing stakeholders
Who are your customers and users today, and how do you want that to be different in five years?
How does this product fit into the overall product strategy?
Who are the biggest competitors and what worries you about them?
How do you expect to differentiate this product?
Using a few key words, how do you want people to see your brand (both the company brand and the product brand)?
What is the current state of the identity, and can we see a style guide (if there is one) and examples of it applied to materials?
Engineering stakeholders
What technology decisions have already been made, and how firm are they?
How large is the development team assigned to the project, and what are their skills?
Would you draw a diagram and tell me in lay terms how the system works? (existing products only)
Sales stakeholders
Who is typically involved in the purchase decision?
Why do customers buy a product like this one, and why this one over competitor’s?
When you lose sales, what are the most common reasons?
What things do customers complain about or ask for most often, and why?
Senior executives
Questions similar to those for marketing stake-holders, plus:
What do I need to know that you don’t think other members of your team have said?
If you had to choose between going to market on schedule with a flawed product, or going to market - late with a solid product, which would you choose? (If there seems to be some conflict on this point)
Subject matter experts
What are the typical demographics and skills of potential users, and how much variation in these is typical?
What distinctions in user roles and tasks would you expect us to see?
What sorts of workflows or practices do you think we’ll be seeing in the field?
Other product team members
QA: What problems do you currently see in development?
Support or customer service: What problems do you see most often?
Training or technical documentation: Where do users most often get confused today?
Sample Questions
From the infamous book by Kim Goodwin -- Designing for the Digital Age. You can find a deeper dive here
Things to watch out for
All stakeholders
Marketing stakeholders
Engineering stakeholders
Sales stakeholders
Senior executives
Subject matter experts
Other product team members