Title: How to Conduct Customer Interviews, with Freckle’s Nathan Merzvinskis
Session context
- Format: Talk + live Q&A + doc walkthrough (pre-mortem, interview guide, pricing survey, design partner program)
- Host: Michael Batko (Startmate); Speaker: Nathan Merzvinskis (Freckle; ex-Everproof → acquired by Go1; ex-Schedulo)
- https://www.linkedin.com/in/nathan-merzvinskis/
- Focus: End-to-end customer discovery system from idea → MVP → pricing → ongoing feedback loops
Why customer interviews (beyond “talk to users”)
- Reduce time-to-wrong: validate need, ICP, and monetization before building
- Build champions: discovery participants become design partners, then first paying customers
- Fundraising edge: evidence-rich discovery (transcripts, tagged insights, quotes) answers investor risks upfront
Core workflow overview
| Stage | Purpose | Output |
|---|
| Pre-mortem | Identify top risks/assumptions | Clustered assumptions/failure reasons; prioritized risk quadrant |
| Interview guide | Non-leading, specific questions | 30–45 min script centered on real tasks, events, and pains |
| Synthesis | Turn qual into decisions | Tagged insights; persona fit/no-fit; next tests |
| Design partner program | Repeatable feedback mechanism | 5–10 partners; biweekly sessions; clear give/get; path to paid |
| Pricing discovery | Test value metric + willingness to pay | Van Westendorp range + pricing hypotheses |
| Ongoing loops | Post-MVP prioritization and feature tradeoffs | Slack channels, rapid sprints, continual interviews |
Pre-mortem (start here)
| Step | How | Why it matters |
|---|
| Solo brainstorm (20 min) | Green: “I assume that …”; Pink: “This failed because …” | Surfaces implicit beliefs and failure modes |
| Cluster + label | Combine into themes (pricing, ICP, regulation, competition, unit economics, etc.) | Reveals blind spots across co-founders |
| Prioritize on 2×2 | Likelihood (low→high) vs Impact (low→high) | Focus interviews on top-right risks first |
Common top-right risks:
- Real need/pain priority for target user
- Willingness to pay / viable value metric
- ICP clarity (who buys, who uses)
- Regulatory or switching constraints (market dependent)
Interview fundamentals
| Principle | Practice |
|---|
| Avoid bias | No pitching up front; disclose only the problem space; ask non-leading, specific, time-bound questions |
| Specific over general | “Walk me through yesterday” vs “usually”; “last time you …” vs “would you …” |
| Persona consistency | Run 6–7 interviews per persona; switch personas if you see weak pull |
| Record and tag | Get consent; use Fathom/Granola for transcripts; tag in Dovetail (or equivalent) |
| Build rapport, then dig | Reflect back terms; ask “Can you tell me more?”; chase throwaway comments |
Favorite question patterns:
- Context: “Was yesterday a typical workday? Walk me through it from start to finish.”
- Pain: “Top 3 biggest challenges last week? Which cost you time/money/stress?”
- Trigger: “Tell me about the last time you tried to solve this. What did you do first?”
- Substitutes: “What tools/spreadsheets/processes are you using now? What’s broken?”
- Constraints: “What would stop you switching? Who else needs to approve?”
- Value: “If this were solved, what improves? Time saved, revenue, risk, compliance?”
- Price framing (later): “At what point would this feel too cheap/too expensive?”
What not to do:
- Don’t pitch at the start
- Don’t ask hypotheticals (“Would you use/pay?”) without anchoring to past behavior
- Don’t skip qualitative before surveys or AI-simulated “users”
Designing and running the guide
| Section | Examples |
|---|
| Primer | Explain discovery vs pitch; request permission to defer solution until end; ask to record |
| Kickoff | Role, responsibilities, tools, org structure |
| Day-in-the-life | Timeboxed walk-through; locate pain moments |
| Problem deep dive | Last incident, frequency, workaround, cost-of-pain |
| Alternatives | Current stack (incl. spreadsheets/do-nothing); switching frictions |
| Buying dynamics | Who decides; budget; procurement constraints |
| Wrap | Offer design partner slot; ask for 1–2 intros to similar peers |
Timebox: 30–45 minutes. Be explicit that you’ll read from a guide to stay on track.
Synthesis and decision-making
| Tooling | Use |
|---|
| Dovetail (or Notion tags) | Upload transcripts; tag by theme (pricing, ICP, workflow, compliance, etc.) |
| Persona boards | SPICE framework: Situation, Pain, Impact, Critical event; include representative quotes |
| Risk tracker | Map new evidence back to pre-mortem clusters; mark validated/invalidated/unknown |
Stopping rule:
- After 6–7 consistent interviews per persona, you can usually predict answers → move to next risk or next persona.
Design partner program (turn interviews into revenue)
| Element | Details |
|---|
| Who | 5–10 ideal users with strong pain and engagement |
| Cadence | Biweekly 30–45 min sessions; Slack 1:1 channel for fast feedback |
| Give/get | Early access; 50% Y1 discount; input to roadmap; you get structured feedback and case study |
| Exit | Clear expectation to become paying customers post-beta if value delivered |
Pricing discovery (when to run and how)
- Run after need and scope are clear; before heavy build
- Define value metric(s): seats, credits, usage unit most aligned with delivered value
- Use Van Westendorp (4 Qs) to get price bands; add willingness-to-pay probes in interviews
- Validate packaging and buyer economics in follow-ups; keep evidence for investors
Reference: Nathan’s Medium guide on pricing discovery (Van Westendorp) and value metrics.
Post-MVP: keep interviewing
- Use interviews to prioritize features with equal build cost/time
- Set up 1:1 Slack channels with top customers (e.g., 25 key accounts)
- Continue short sprints: question set → calls → decision → ship
Benchmarks and pacing
| Area | Practical bar |
|---|
| Interview volume | 10–20 across 1–3 personas; 6–7 per persona before switching |
| Guide discipline | Non-leading, time-bound, past-behavior anchored |
| Evidence quality | Recorded, transcribed, tagged; quotes curated into persona boards and investor-ready notes |
| Conversion | 20–50% of strong-need interviewees join design partner program |
Selected Q&A highlights
| Topic | Takeaway |
|---|
| B2B vs B2C counts | Similar “6–7 per persona” rule; ensure persona consistency |
| Warm vs cold contacts | Warm enables lighter disclosure; still avoid pitching upfront |
| Competition | Not inherently bad; beware winner-takes-all markets; include substitutes and “do nothing” |
| Quant surveys/AI “fake users” | Use only after qualitative rounds; AI simulators miss serendipitous insights |
| Recording tools | Fathom (fast summaries), Granola (invisible presence), Dovetail for tagging |
| Fundraising without product | Possible with high-quality discovery evidence, mockups, and design partners |
| Post-launch interviews | Yes—use to choose between features with similar effort; maintain slack channels for continuous input |
| Feature whiplash | Keep 80/20: founder vision 80%, feedback 20%; avoid reactive, incoherent product |
8-week execution template (fill this in)
| Track | Baseline (now) | 2-week goal | Weekly target | Success criteria |
|---|
| Pre-mortem | Assumptions not captured | Run session; cluster and prioritize risks | — | Top-right risks defined for discovery focus |
| Interviews | 0–5 recent convos | 10 interviews across 1–2 personas | 5–10/wk; recorded + tagged | 6–7 consistent per persona; clear need signal |
| Synthesis | Unstructured notes | Dovetail/Notion board; SPICE personas with quotes | Update after each batch | Decisions logged; next hypotheses queued |
| Partners | None or ad hoc | 5+ design partners confirmed | Biweekly sessions; Slack channels | Ongoing feedback; 50%+ convert to paid later |
| Pricing | Unclear value metric/WTP | Define metric(s); run VWSM survey with partners | 5–10 responses | Price band + packaging hypothesis validated |
Practical metrics you can choose
- Need strength: # interviews where pain ranks top 3; cost-of-pain evidence
- Signal quality: % of interviews producing referrals; willingness to be a design partner
- Pricing: VWSM acceptable range; early trial → paid conversion
- Evidence readiness: transcripts tagged; investor-ready quote board (“wall of love”)
Workshop logistics and follow-ups
| Item | Details |
|---|
| Tools | Fathom/Granola (record), Dovetail/Notion (tag), Miro (pre-mortem), Calendly (booking) |
| Artifacts | Pre-mortem board; interview guide; SPICE persona boards; pricing survey; partner one-pager |
| Investor pack | Curated quotes, tagged insights, persona summaries, pricing results |
Your 5 next actions
- Schedule a 90-minute pre-mortem with your co-founder; prioritize top-right risks
- Draft a 30–45 min non-leading interview guide; book 10 calls across 1–2 personas
- Record, transcribe, and tag; create SPICE persona boards with verbatim quotes
- Invite 5–10 strong-fit participants to a structured design partner program
- Define value metric(s); run a Van Westendorp pricing survey with partners and synthesize results