What I learned about interviewing from 15 customer development interviews

I recently interviewed 15+ people to learn about how they do high-level project management (I wrote about the actual learnings on the Building Burndown blog).

I’ve done a lot of customer development interviews in the past, but never frequently enough to feel like I’m good at the interviews. Every round results in new learnings and improvements.

Here's what I learned about interviewing this time around:

Have a template; update it after each interview

I made a list of assumptions, and then used The Ultimate List of Customer Development Questions to create a list of questions that would hopefully validate or invalidate my assumptions.

My big takeaway was religiously updating the template after every interview. Previously, I liked to keep the interviews sort of the same because it made comparisons easier. Nope. Doing it after every single interview maximizes the learnings and assumptions validated/invalidated.

For example, I added a series of questions to my Burndown interview template on how and why project managers do estimation. I also started asking about how quickly they know a project is behind schedule (the answer is typically "really soon, because all our projects are behind" or "right before it's due").

Sometimes I take the edits back out if the new line of questioning isn’t useful, but most of the time I’m iterating my way towards deeper learnings.

Don't ask for advice

Everyone loves giving advice, right? Why not just ask for it? Asking for advice in an email resulted in instant offers for paid consulting and scolding me for wasting their time.

Instead, I’m more upfront about the nature of the conversation. I call it an interview. If it’s on a topic they’re interested in or pain point they’re feeling, they’ll agree to spending time with me.

Ask what they like and don’t like

I learned this trick from my wife (who learned it from the management transition book, The First 90 Days). Don’t ask people what’s important to them. The question is too open-ended and loaded. Instead, just ask what they like or dislike about XYZ. That will naturally tell you what is important to them.

Ask if they’re the decision-maker

While a fairly obvious question within a sales cycle, it’s a new question to my customer development repertoire. Especially within large organizations and B2B tools, it’s common for the purchasing decision-maker to be different from the end-user. For example, in our other product, the DocRaptor HTML-to-PDF API, developers care about our documentation quality and having libraries in their programming languages. But the CTOs making the decisions care about our SOC2 and HIPAA compliance.

Frequently share internally

I used to do a round of interviews, look for commonalities, and then share with the rest of the team. Now, I share the raw interview notes more frequently, especially in the early stages where I’m less confident in my takeaways. It’s noisier, but people have different perspectives and see things I missed. Additionally, our CTO shared that he really enjoys the interview updates and they make him feel more engaged in the customer research process.

At a minimum, share each interview with at least two other people. If you’re a solo founder, find a buddy (I’m happy to help, hit me up).

Those are my notes from this round. Let me know what you think or if you have other customer research interview tricks!