Product Teams

50 Questions for Your B2B SaaS Customers

Published Jan 26, 2016

I’m going to jump straight in …. I’ve got a lot of customer interviews coming up in the next week (I blame in-app scheduling) and figured that it was a good time to put some pen to paper. First, some context:

Interview Goals

  • Know customers and their “jobs to be done
  • Focus on problems vs. solutions

Remind customers that …

  • They can’t hurt your feelings
  • Your job isn’t to sell them, market to them, or take their feature requests
  • There are no right, wrong, or stupid answers
  • You’re happy to address support questions after the interview

Interview Tips:

  • Use words/phrases like “show me”, “tell me that story”, “what’s a real world example of that”, “why”, “who”, “how come”, “tell me more”, “how do you do that right now”, “sketch that” etc.
  • Be comfortable with awkward silences
  • Talk less as a rule. Let the customer do the talking.
  • Be aware of nonverbal cues, and “leading”. Take a deep breath and smile. Repeat words to yourself to stay in the zone like “curious”, “observant”, “patient”, “open”, “non-judgmental”, and “respectful”. Write these down as reminders
  • Use an audio recorder so as not to distract the customer. Or have a notetaker.
Notes from a recent meeting …


The Questions
Important: In these questions Acme is your product or brand. “You” is the customer.

  1. If you weren’t working as [customer title] what would you be doing?
  2. If you had one work-related superpower what would it be? How would it work? Every superhero has a weakness. What’s your weakness?
  3. If Acme was a brand of car, what would it be? Why?
  4. What is the least understood aspect of your job? Why?
  5. What is your unofficial job title?
  6. If you’re comfortable chatting about non-work things … what hats do you wear outside of work?
  7. Draw me the informal, real-world org chart of your department. How are things really connected? How does **it really get done?
  8. Describe your personal aspirations for your career. What are you looking for in terms of career development? What’s the next big hurdle? What strengths will you leverage?
  9. You have a magic ball. Money is no object. You can pick three metrics to put up on big monitors all over your team’s workspace. What are those numbers?
  10. Some things have a tangible value associated with them. Other things are intangible. What is an example of an extremely valuable — but completely intangible — aspect of your job I should understand?
  11. Describe a piece of software that gets out of the way and lets you get your work done. Now describe something that just manages to get IN your way all the time. What is the differentiator? Where does Acme fit in?
  12. You’ve had a tough day. You pick a song that characterizes how you feel. What song do you pick? After feeling sorry for yourself you crank up a song to move forward. What song do you pick?
  13. What “sixth-senses” do you have? How did you learn that intuition?
  14. When was the last time — outside of software vendors, but at work — that you experienced incredible customer service from a vendor? Why?
  15. A workaround is when you can’t initially get something done with the tools available, but you improvise and make things work. Describe a workaround from your work in the last month? How did you figure that out? Can you think of an Acme example?
  16. What is the most important lesson you’ve learned from working with YOUR customers? Any nuggets of wisdom there? How have you applied that to your day-to-day work?
  17. We all wear different hats during the day. You might be the “The Practical One” and then shift to “The Innovator” or “The Facilitator”. Imagine that you’re three different people, and that you juggle those three different personas each day. What would those hats be called? How do you act when you wear that hat? What is important to you?
  18. Most movies have that montage scene about 2/3rds of the way through when everything starts moving. It occurs immediately before the final obstacle materializes. Let’s say that movie is about your work and this organization. Tell me the story there. Walk me through the feel-good montage, and end with the big obstacle.
  19. Imagine a dream day here. Everything goes right and works smoothly. You’re in a state of flow and have a big smile on your face. Walk me through that. What is the biggest leap of faith in that description?
  20. Complete this sentence … “I hope Acme doesn’t screw up and ________________” . How could we become something that you hate? Where would we go wrong?
  21. How is your job performance measured formally and informally?
  22. No need to provide the details, but what are the last three big decisions you’ve had to make here? How did you go about making those decisions?
  23. What’s the last innocent — but damaging and disappointing — mistake that someone made while using Acme? Tell me the story there. What was the impact?
  24. Have you ever had a SFW work-related nightmare? What happened? Is it a recurring dream?
  25. Everyone has blindspots. In your opinion what is Acme’s blindspot when it comes to understanding you and the job you need to get done?
  26. Who do you interact with most frequently on a day-to-day basis? What are you collaborating on? What is the output?
  27. There is a major budget cut and software must go. You’re down to the bare essentials. You have to rank the importance of Acme between 1: Absolutely Essential and 10: Absolutely The First To Go … where are we at? Why? Who is ahead us and behind us?
  28. Describe a conversation where Acme came up “at the watercooler” … one positive, and one negative. What was the story?
  29. It’s Sunday and you have that sinking fear about work that’s keeping you from relaxing. What are you worrying about?
  30. What is the meat and potatoes (or veggies and seitan) of your business?
  31. You have a new employee at the company. You’re giving them the lay of the land, describing the tools they’ll use, and how they’ll use them. You have to describe Acme. How do you describe us to the newcomer?
  32. How would you rank the following in terms of your personality and work style. Do you prioritize: 1) Efficiency, 2) Creativity, 3) Accountability, 4) Flexibility, 5) Resilience , or 6) Influence? Why?
  33. For most jobs there is the “theoretical” way something gets done … it is nice and neat and tidy. And then the “real world” way it gets done. Can you draw me a flowchart of both? How does the real world differ?
  34. If you could automate one part of your job (and keep your job) what part would that be? What would you do with the extra time?
  35. It is twenty years ago. Replace Acme with a person who got this work done. What would that person’s title be? What is their job description?
  36. I’ve got ten cards here describing different things you can do with our product. Without saying anything — it’s best if we don’t talk, and remember you can’t hurt my feelings — I’d like you to draw a frowny face, smiley face, or a deadpan face on each card describing how you feel when you use that feature. And then I’d like you to sort them in terms of how important they are to your day-to-day job.
  37. Think about the other software tools you use. Fill in the blanks. Compared to ________ Acme is doing a great job, but compared to __________ Acme has a lot to learn.
  38. Acme is a restaurant. What is it like eating there? What do we do well? Where do we fall flat? What is your best/worst dish?
  39. I’d like you to take a quick stab at writing the new Acme marketing tagline. It is short and snappy. It cuts to the chase. What is it?
  40. Times are tight and we are all busy. If you had more budget for your department, and more time to focus, what would you spend that money and time on?
  41. Imagine you’re at a meeting discussing our product. People are relaxed and speaking candidly. We’ve done a good job and have met your needs. Complete this sentence … “Acme has paid for itself many times over by _______________ .”
  42. Have you ever used a piece of software that left you feeling that the developers didn’t actually try the feature? What’s that area of Acme? Where are we clueless? What’s a train wreck?
  43. Trust is earned. How can we earn your trust? How can we lose your trust?
  44. It’s one year from now. You’re responsible for creating a report card to decide whether to renew your contract with us. What’s on that report card? And where do we sit right now? Let’s draw it out …
  45. When was the last time you celebrated as a team because of something work related? Why?
  46. For most jobs you can let a lot of stuff slide in the short term. But there is something that simply MUST happen. If you don’t deliver in that regard you’re screwed. What is that “one thing?”
  47. This is your moment to shine. You are presenting to the whole company. You’re about to show the magic slide … the slide that rocks everyone’s world, secures your raise, and turns you into a rockstar. Can you draw it for me? What would it say? What are the three bullets?
  48. We’ve all witnessed purchasing fails over the years … that one software tool that got everyone super excited but then failed to deliver. Without naming names, could you briefly describe the “promise” (what you hoped the purchase would achieve), and then the reality when the rubber hit the road?
  49. How would you disrupt your own business if you could? You get to start over and tear it all apart. Where are things going?
  50. Describe an intractable problem from your work world … something that no amount of work, research, meetings, and discussion — formal and otherwise — can seem to fix. What is the sticking point?

This post was originally published on Medium by our very own product development nut and work/life hacker John Cutler, Senior Product Manager. Get great tips like these, and stories from the product management trenches every week, delivered right to your inbox when you subscribe to the Pendo blog.