Problem Interviews Template for Technical Founders (Copy This)

Copy this. Adapt the brackets. Run your first technical-founder problem interview this week. Templates exist so you stop overthinking and start moving.

1. Outreach Message

Three sentences. Sent over LinkedIn, email, or a relevant community DM. Nothing else.

Subject (if email): Quick research question on [topic]

Body:

Hi [Name], I noticed [specific reason - their post, their stack, their company size]. I am researching how engineering teams handle [specific behavior or problem area] and I am not selling anything. Would you have 30 minutes in the next two weeks for a short call? Happy to share what I find.

Thanks,
[Your name]

2. Calendar Invite

Title: [Your name] x [Their name] - 30 min research chat

Description: Casual conversation. I am researching [topic] in engineering teams. No pitch, no sales. Looking forward to it.

3. The Opening (First Two Minutes)

Read this almost word-for-word the first few times.

"Thanks for the time. Quick context: I am researching how teams handle [problem area] right now. I am not selling anything today, I just want to learn from people who have actually lived through it. So I am going to ask mostly about your own experience and try to listen more than I talk. Cool if I record so I can focus on the conversation? Happy to delete it after."

4. The Three Questions

The spine of the call. Ask each, then follow up with "tell me more about that" until you have an actual story.

Q1 (Story prompt): "Walk me through the last time [specific incident type] happened. What were you trying to do, and what went sideways?"

Q2 (Workaround): "What did you try to make it less painful? Did anything stick?"

Q3 (Internal tool / spend): "Have you ever paid for something or built something internal to handle this? What does it do?"

5. The Deflect (When They Ask About Your Idea)

"Honestly, still figuring it out, that is why I am asking these questions. Can I keep poking at the problem first and we can come back to my direction at the end if there is time?"

They will say yes. If you have time at the end, two sentences max. Not the point of the call.

6. Notes Template

One doc per call.

Date: [date]
Name and role: [name, title, team size]
Audience filter match: [yes / partial / no]
Stack mentioned: [tools, only if relevant]

Story (Q1): [specific incident, with one direct quote]

Workaround (Q2): [what they tried, what stuck, what failed]

Internal tool / spend (Q3): [tools paid for, scripts built, time invested]

Surprises: [what I did not expect]

Vocabulary: [exact engineering phrases worth keeping]

Private hypotheses (DO NOT SHARE): [design ideas the call triggered]

7. Follow-Up Message (Within 24 Hours)

Hi [Name], thanks again for the time today, that was genuinely helpful. One favor: would you be open to a 15-minute follow-up if I have something concrete to show in the next month or two? No pressure either way.

Thanks,
[Your name]

8. Synthesis Block (Every 5 Calls)

New doc. Answer using only quotes and behaviors from the last five calls.

If those answers point in a clear direction after fifteen calls, you have warranted confidence. Build the smallest version and put it in front of the same fifteen people.