Due Diligence Checklist

Customer Validation Framework

Purpose: Validate your idea with real customers before building. Platform engineers already do this when evaluating tools—now apply it to your startup.

The Mom Test: Core Principles

❌ Bad Questions (Hypothetical)

"Would you use a tool that reduces deploy time?"
"Do you think this is a good idea?"
"Would you pay for this?"

Why they fail: Hypothetical, polite "yes," no commitment

✅ Good Questions (Past Behavior)

"Walk me through your last deploy. What broke? What did you try?"
"Tell me about the last time this problem cost you money."
"What solutions have you tried? Why didn't they work?"

Why they work: Past specifics, real pain, leads to commitment

Pre-Interview Preparation

Target Customer Profile

[ ] Role: Title/function (e.g., Staff Engineer, VP Engineering)
[ ] Company size: 50-500 employees (adjust for your ICP)
[ ] Budget authority: Can they buy? Who approves?
[ ] Pain frequency: Daily/weekly/monthly problem?

Your Hypothesis to Test

1. Problem hypothesis: "Teams spend 4+ hours debugging production issues"

2. Solution hypothesis: "Distributed tracing reduces MTTR by 75%"

3. Willingness to pay: "They'll pay $500/mo per engineer"

Interview Question Framework

Opening (Build Rapport)

"Thanks for your time. I'm researching [problem area]."
"I'm talking to [role] at [company type] to understand [workflow]."
"This isn't a sales call—I'm genuinely trying to learn."

Problem Discovery (15 min)

Goal: Understand their current pain

1. "Walk me through your [workflow] last week."

2. "What broke? What was the impact?"

3. "How long did it take to fix? Who was involved?"

4. "How often does this happen?"

5. "What's the worst incident you've had?"

Listen for: Time wasted, money lost, stress/frustration, frequency

Current Solutions (10 min)

Goal: Understand what they've tried

1. "What tools/processes do you use today?"

2. "Why did you choose those?"

3. "What's working? What's not?"

4. "What would you change if you could?"

Listen for: Gaps in current solutions, workarounds, manual processes

Budget & Authority (5 min)

Goal: Qualify if they can buy

1. "How do you typically evaluate new tools?"

2. "Who's involved in that decision?"

3. "What's your approval process?"

4. "When's your next budget cycle?"

Listen for: Decision-making authority, budget availability, urgency

Validation Signals

✅ Strong Signals (Keep Going)

Specific pain: "Last Tuesday, our database went down for 4 hours"
Quantified impact: "Cost us $50K in lost revenue"
Frequency: "Happens 2-3 times per week"
Current workarounds: "We have 3 people manually checking logs"
Budget confirmed: "We spend $10K/mo on observability already"
Commitment ask: "When can we pilot this?"

⚠️ Weak Signals (Dig Deeper)

Vague pain: "It's kind of annoying sometimes"
No metrics: "I don't know how much time we spend"
Rare occurrence: "Hasn't happened in months"
Happy with current: "Our current solution works fine"
No budget: "We'd need to find budget"

❌ Red Flags (Pivot or Abandon)

Polite interest: "This sounds great!" (but no specifics)
No pain: "We don't really have that problem"
Can't quantify: "I'm not sure this costs us anything"
No authority: "I'd need to ask my boss"
Ghosting: No response to follow-up

Commitment Ladder

Move prospects up this ladder during conversations:

Level 1: Learning

[ ] They agree to talk (30-minute call)

Level 2: Interest

[ ] They share specific pain points
[ ] They introduce you to colleagues

Level 3: Action

[ ] They agree to a follow-up call
[ ] They share documents/data
[ ] They invite you to meet their team

Level 4: Commitment

[ ] They sign an LOI (Letter of Intent)
[ ] They commit to a pilot (with timeline)
[ ] They give you a deposit/pre-order

Level 5: Payment

[ ] They become a paying customer

Key Insight: Move fast or move on. If they're not climbing the ladder, they're not your customer.

4-Week Validation Sprint

Week 1: Initial Outreach

Goal: 50 conversations scheduled
Target: 20 completed calls
Deliverable: Pattern recognition (common pain points)

Week 2: Deep Dives

Goal: 20 more conversations
Target: 5-10 strong signals
Deliverable: Refined problem statement

Week 3: Commitment Asks

Goal: Extract commitments
Target: 5 LOIs or pilot agreements
Deliverable: Proof people will act, not just talk

Week 4: Refine & Repeat

Goal: Prove repeatability
Target: 3 more LOIs
Deliverable: Validated ICP and go-to-market motion

Interview Notes Template

text

INTERVIEW DATE: __________
NAME: __________
TITLE: __________
COMPANY: __________

PROBLEM DISCOVERY:
- Current workflow:
- Last incident:
- Impact ($, time, people):
- Frequency:

CURRENT SOLUTIONS:
- Tools used:
- What works:
- What doesn't:
- Workarounds:

BUDGET & AUTHORITY:
- Decision maker: Y/N
- Budget available: Y/N
- Approval process:
- Timeline:

VALIDATION SIGNAL:
- Strong / Weak / Red Flag
- Commitment level (1-5):

NEXT STEPS:
- [ ] Follow-up scheduled
- [ ] Intro to colleague
- [ ] Send LOI
- [ ] Pilot agreement
- [ ] No action (dead lead)

NOTES:

Common Mistakes

1. Talking Too Much

Mistake: Pitching your solution
Fix: Listen 80%, talk 20%

2. Leading Questions

Mistake: "Don't you think X is a problem?"
Fix: "Tell me about your workflow."

3. Ignoring Weak Signals

Mistake: Hearing what you want to hear
Fix: If they're not excited, move on

4. Not Asking for Commitment

Mistake: Ending with "This was helpful, thanks!"
Fix: "Can I send you an LOI for a pilot?"

5. Talking to the Wrong People

Mistake: People who can't buy
Fix: Ask "Who makes the decision?" early

After 50 Conversations

Patterns to Look For

[ ] Common pain points: What do 80% of people complain about?
[ ] Willingness to pay: Did 10+ people commit to LOI/pilot?
[ ] Market size: Are there enough people with this pain?
[ ] Your moat: Can competitors easily solve this?

Decision Framework

STRONG SIGNAL (Proceed): 10+ LOIs, clear pain, budget exists
WEAK SIGNAL (Pivot): Some interest, vague pain, uncertain budget
NO SIGNAL (Abandon): No LOIs, no pain, no budget

Resources

The Mom Test by Rob Fitzpatrick: The definitive guide
Lean Customer Development by Cindy Alvarez: Practical tactics
Jobs to Be Done framework: Understand customer motivation

Download all 12 templates: sanscourier.ai/qconsf-2025

*From the QCon SF 2025 talk: "From Staff Platform Engineer to a16z Founder: What I Wish I'd Known" by Gonzalo (Glo) Maldonado*