Customer discovery conversations are most valuable when you capture them consistently. This guide gives you a simple framework for preparing each conversation, staying on track during it, and recording what matters afterward. Use it before your campaign — ideally across five to ten conversations with people who match your target customer profile. The patterns that emerge across multiple conversations become the foundation of your investor narrative.
Part 1: Before the Conversation
Who are you talking to?
Name or identifier (no need to be formal — “Retailer contact via LinkedIn” works fine):
_______________________________________________
Why this person?
In one sentence, why do they represent your target customer?
_______________________________________________
_______________________________________________
Your hypothesis going in:
Before the conversation, write down the problem you believe this person has. Be specific. You’re not trying to confirm this — you’re checking whether reality matches your assumption.
_______________________________________________
_______________________________________________
_______________________________________________
What would surprise you?
What’s one thing they could say that would genuinely change your thinking?
_______________________________________________
_______________________________________________
Part 2: During the Conversation
These are not a script. They are starting points. Let the conversation go where it needs to go — your job is to listen, not steer.
Opening
- “Thanks for making time. I’m working on something in [your space] and I want to make sure I actually understand how this works for people before I build anything. I’m not pitching you — I just want to learn.”
Core questions
- “Walk me through the last time you dealt with [the problem area]. What actually happened?”
- “What have you tried in the past to solve it? What didn’t work about those approaches?”
- “On a typical week, how much does this come up for you — or does it?”
- “What would it mean for your business if this problem just went away?”
- “Who else on your team or in your world deals with this?”
Follow-up probes (use when you want to go deeper)
- “Can you say more about that?”
- “What did you do when that happened?”
- “How does that affect [the downstream thing they mentioned]?”
- “That’s interesting — what made you try that approach?”
Closing
- “Is there anything about this that I haven’t asked that you think would be useful for me to understand?”
- “Would you be open to me following up in a few months once I have something more concrete to show you?”
Part 3: After the Conversation
Complete this within 30 minutes of the conversation while your memory is fresh. Don’t over-edit — write fast and capture what actually happened.
Date: _______________ Duration: _______________
The problem they described in their own words:
(Use their language, not yours. Exact phrases in quotes if you can remember them.)
_______________________________________________
_______________________________________________
_______________________________________________
_______________________________________________
How often does this problem come up for them?
☐ Daily ☐ Weekly ☐ Monthly ☐ Rarely ☐ Unclear
What does it cost them? (check all that apply and add notes)
☐ Time: _______________________________________________
☐ Money: _______________________________________________
☐ Customers / relationships: _______________________________________________
☐ Frustration / morale: _______________________________________________
☐ Other: _______________________________________________
What workaround(s) are they currently using?
_______________________________________________
_______________________________________________
Moment of highest emotion:
When did they get animated, frustrated, or light up? What were they talking about?
_______________________________________________
_______________________________________________
What surprised you most?
_______________________________________________
_______________________________________________
Did this conversation confirm, challenge, or complicate your hypothesis?
☐ Confirmed ☐ Challenged ☐ Complicated ☐ Irrelevant — wrong person
Notes:
_______________________________________________
_______________________________________________
_______________________________________________
Part 4: Cross-Conversation Pattern Tracker
After three or more conversations, use this section to start identifying what’s consistent — and what isn’t. Patterns across multiple people are what turn anecdote into evidence.
Problem language that came up more than once:
_______________________________________________
_______________________________________________
Costs or consequences mentioned by multiple people:
_______________________________________________
_______________________________________________
Workarounds that kept appearing:
_______________________________________________
_______________________________________________
Assumptions from your hypothesis that were wrong or incomplete:
_______________________________________________
_______________________________________________
One sentence that captures what you now know that you didn’t before:
_______________________________________________
_______________________________________________