Making technology more human-friendly, one word at a time.

Three questions to ask your customers

Photo by Daria Nepriakhina on Unsplash

Photo by Daria Nepriakhina on Unsplash

My role as a product marketer has led me to uncover more questions, rather than answers, about our product and our users. For example, why do some companies find our tool fantastic while others don’t, even when both businesses seem to look exactly the same on paper?

Over the summer, I led a series of interviews to better understand our key customer segment. We started by defining them as belonging to specific verticals and generating a magical amount of revenue annually. It was my first ever large-scale project where I got to enlist the help of my entire team and was allocated a budget to execute the project. I knew that the results of this project could be very useful / could change the direction of our marketing strategy so every step was questioned and debated in my head until I was satisfied with the answer.

After deciding who we wanted to interview, we had to determine what to ask so that we could answer the nagging questions we had. Since I typically take a reverse planning approach to new projects, I had to first decide how to structure my output: Buyer personas or Jobs-to-be-done?

Deciding between Jobs-to-be-done vs Buyer Personas

Since starting my career, I’ve come to rely on Intercom and HubSpot a great deal as they were good starting points to learn about content and product marketing. HubSpot uses buyer personas a lot while Intercom seems to prefer the “jobs-to-be-done” model for understanding prospects and customers.

From my understanding, the buyer persona framework places a stronger focus on the ideal customers’ characteristics to help companies “relate to our customers as real humans”. More than a year ago, we did our research and came up with personas based on our user base, ran internal workshops to make sure everyone was on the same page and now, we rarely use them. Furthermore, our product and development team couldn’t connect the dots between Manager Margie to the features they were building.

As for jobs-to-be-done, it seems to focus on what your customer hires your product to do. Let me rephrase that: What does this customer segment expect your product to do for them? While both methods rely on insights from existing users, the first focuses on the company’s needs and the decision process they took to finally purchase your service. The latter instead focuses on the company’s need and how they currently use your tool to solve that need. Get the difference?

I prefer the latter since it helps us get actual information into how companies use our product and why. Given the seemingly random pattern amongst our happy and frustrated customers (a cohort of customers driven by personas), I decided to test out the second approach.

The final set of interview questions

My first draft had over 30 questions.

My final draft had 29 questions and a preliminary questionnaire.

The preliminary form contained basic information about the people we were speaking to, for example their names, position in company, and prior experience with similar systems. Interviewers also needed to compile background information about the company that we could easily pull from our database. These were mostly numbers and subscription plan data.

As for the actual interview, I structured it into four parts:

  1. Personal information

  2. Company information - What is your company about? [Buyer persona questions]

  3. Company needs - What is your company trying to get done? [Jobs-to-be-done questions]

  4. Company’s future - How can we assist your plans for growth?

When briefing the interviewers, I made sure to emphasise the need for follow-up questions, asking why if an answer wasn’t clear or if it just needed more detail.

Afterwards, interviewers had to fill out a post-interview questionnaire to summarise key findings and add comment if we were serving this client to the best of our ability.

In case you’re wondering, each interview took an hour and interviewers took an extra 30 minutes to fill out the pre- and post-interview questions. I am forever grateful for their time. My team is the best. Like, better than yours.

The most Valuable answers emerged from these three questions

As I was writing up the interview questions, I found this great article written by Chuck Liu on questions to ask users to help us get to the real reason for why customers purchase and continue to use our products. (Spoiler alert: Always ask why.)

I decided to add his questions to the interview, as well as a few more from discussions with my team and other materials I read.

  1. How do you use our product from start to finish?

    If possible, ask them to share their screen and show you how they get things done. When necessary, ask WHY.

    I found that most of our customers were not using the product as it was designed. They were either using workarounds, had developed habits from previous tools that they didn’t break when transitioning to our tool, or some other reason that I wouldn’t have uncovered if I didn’t ask this question.

  2. What other systems do you use alongside ours?

    Firstly, it blew my mind when I realised that our product does not exist in a vacuum. It’s used alongside other systems and tools. I mean, duh! Secondly, asking them “Why” here was really helpful.

    Again, I uncovered unexpected user behaviour. For example, why did some customers use our calendar sync and others didn’t? Why did some customers insist on exporting and manipulating data on a spreadsheet while others were happy with what our system offered?

  3. If our product disappeared today, what would you miss most about it?

    Follow-up question: Why? Seriously, don’t stop asking why until you’re satisfied with the answer.

    This helped us uncover the value we continue to deliver to our customers and why they continue to hang around. It’s also very useful to know what your product is good at and why its loved by customers.


These insights were tremendously helpful in understanding our users and their behaviours. After running my findings past our Customer Success Team to determine if these behaviours were anomalies (or not), I found that a product fit between our solution and our customer’s end product was essential to their long-term satisfaction, not just getting them through the door. More importantly, the interviews uncovered specific characteristics that can determine the success of our users from the get-go. I was also able to deliver useful insights to our Sales team to help them with qualifying prospects and gained valuable feedback with real use cases to pass on to our Product team.

I like this blended approach to understanding our customers and drawing out valuable insights based on their actual behaviour rather than on how we think they use our product. Probing customers with whys also led to a lot of conversation around the product that was productive for both of parties.

So… what’s next?

Well, I’m now left wondering what to do with our existing customers who are unhappy with our system. Do we keep them on and try to make it work? Do we adapt the product to solve some of their problems just so they’ll stay? What about other customers who have the potential to really grow with us? How do we identify them and what can do to speed up their progress?

For our Sales and Marketing, do we adapt our overall message to attract more of these customers? If yes, how? What should we say instead of what’s currently being said on our website, emails, social media, pitch decks, blog, ebooks, webinars in FOUR different languages? How can we be certain that this change will bring in results? Hang on a second, do these customers even exist? Is there enough of them to ensure our profitability?

Finally, how can I convince my managers to let me run more experiments to find answers to these questions? Is there a missing piece to this picture?

Before I completely lose my train of thought, what I’m trying to say is that I thoroughly enjoy the freedom I have to find and solve problems across teams and departments. With each new problem holds a brand new challenge and I’m lucky to have the right people to tackle these problems with me.