Why we are obsessed with interviews

If I can summarize the biggest takeaway from my previous startups, is how important clearly understanding the problem is. Every advisor, investor, founder will drill this into you so the message isn't new in any way.

When I was running a 40+ person team at Revox, one of the biggest painpoint was having to juggle between the external and internal world; this includes project management, knowledge sharing, etc. Having a single source of truth for a client-facing consulting company seemed almost like a dream. Not only that, add on the ever changing docs with lack of changelogs, you not only have to worry about technical debt, you start experincing what I like to call "management debt".

We hired project managers and business admins to help bridge this gap, but I noticed teams moving slower not faster, even thought it seemed like we were more organized than before.

I recently came across this article by Ryan Hemlock, and I immediately had to share it with my team. Not only because it seems like he was also identifying a similar problem to what our team was focusing on, but also becuase of the really interesting parallels to our interview experience.

Thats when we decided to post our findings too. But, I wanted to share a bit of how we conducted the interviews and the reasons behind it.

Design thinking

I remember taking Prof. Loredana Padurean's innovation class when I was attending Northeastern, and she was obsessed with the story. She wasn't satisfied with just capturing her attention, you really had to keep it.

Thats when it clicked, finding the problem is easy; building a story around that problem is what's difficult. A story needs a character, a subject, someone you can empathize with and most founders overlook this.

Everyone talks about the importance of urgency, timing, size, etc. when it comes to the problem but rarely do you hear someone focus on the narrative. I had a reflection on this recently and to be honest, I think I might have been conducting my customer interviews the wrong way.

I already new the principles of design thinking, I mean, every single entrepreneurship curriculum covers it. I already knew the mom test, and hundreds of variations of it. So it was safe to say I knew how to pull things out of interviews in a way that "facillitates unbiased conversations"; but never was i ever thinking about how things tie back into a story. I was too focused on drilling into the problem that I was loosing sight of the fascinating stories interviews lead to.

So I tried something different for my recent interviews. I just went into the meeting with almost no prep other than researching about the person and company. I started with a simple question, "tell me about your day-to-day". I latched on to specific stories our interviewees were telling me and drilled on that instead of drilling on the problems they were facing.

This lead to crazy deep conversations, we were able to learn a lot more about their process rather than just their problems. I thought that this was quite eye-openeing. Problems were naturally uncovered during our conversations on their different stories.

What changed in our interviews

• We started with a real story, not a generic description.
• We laddered on consequences: “What happened next? Who was blocked? What was retyped?”
• We ended with constraints: “If you had a magic wand for one workflow, which one?”

This simple shift from “problem-first” to “story-first” made the hidden work visible. The bottlenecks weren’t theoretical—they lived inside specific messages, handoffs, and calendar slots.

Open questions we’re still thinking about

• Where does “good enough automation” end and “human judgment” begin for status and risk calls?
• What is the minimum viable narrative model that reduces management debt without forcing process theater?
• Who feels the problem of lacking "context" and who can beenfit most from a AI assisted tool in project management?

What's next?

We still haven't found the "silver bullet". Our interviews uncovered shared problems among project managers and stakeholders, but we have yet to identify a group of people that we believe would be the ideal early adopters for a new solution—those who feel the pain most acutely and are ready to champion change.