Cofounder Question Framework

The Hardest Hire You'll Make

Core Insight: Bad cofounder < Solo < Good cofounder. Choose wisely.

Solo vs. Cofounder: Decision Framework

✅ Solo Works If You:

[ ] Comfortable with sales: Can close deals yourself
[ ] Handle weight alone: Resilient under pressure
[ ] No critical gaps: Full-stack or can hire fast
[ ] Clear on role: Know exactly what you need to do
[ ] Strong network: Can get advice when stuck

✅ Cofounder Works If You Have:

[ ] Complementary skills: Tech + business, design + eng, etc.
[ ] Worked under pressure together: Startup, big project, crisis
[ ] Compatible work styles: Communication, pace, decision-making
[ ] Shared vision: Aligned on what success looks like
[ ] Mutual respect: Trust their judgment in their domain

⚠️ Bad Cofounder Signs:

First person who said "yes"
Met at networking event last month
"We'll figure it out as we go"
Unequal commitment (one full-time, one part-time)
No prior working relationship

Rule: 3-month trial before committing. Test the relationship under real pressure.

The 5 Essential Conversations

Have these BEFORE you commit to working together.

Conversation #1: How We Handle Disagreements

Questions to Ask

1. "Tell me about a time you had a major disagreement at work. What happened?"

Listen for: How they resolved it, their role, the outcome

2. "What if we disagree on a critical decision and can't reach consensus?"

Listen for: Process vs. ego, willingness to be wrong

3. "Who has the final say if we're deadlocked?"

Listen for: Clarity on decision authority

Framework: Decision-Making Authority

Option A: Domain-Based

text

Product decisions → CEO/Product cofounder
Technical decisions → CTO
Design decisions → Head of Design
Financial decisions → CEO (after consulting CTO)

Option B: Majority Vote

text

Major decisions → Must agree (raise capital, sell company)
Minor decisions → Owner's call (their domain)
Deadlock → External tiebreaker (advisor, investor)

Document this. Write it down. Sign it.

Conversation #2: Equity Split (Day One)

Questions to Ask

1. "What equity split do you think is fair? Why?"

Listen for: Their reasoning, how they value contributions

2. "What happens if one of us wants to leave in 6 months?"

Listen for: Understanding of vesting

3. "Should we split 50/50 or weighted by role/risk?"

Listen for: Ego vs. pragmatism

Framework: How to Split

Equal (50/50):

Both full-time from day 1
Similar risk (both quit jobs)
Complementary skills
Equal commitment

Weighted:

One person came up with idea + built v0.1
One person full-time, one part-time
Different financial risk (one has savings, one has mortgage)

Standard Structure:

text

Founder A: ___%
Founder B: ___%
Employee pool: 10-20%
Total: 100%

Vesting: 4 years, 1-year cliff

Red Flags

"Let's do 50/50 but I'm only part-time" → Unfair
"I should get more because I had the idea" → Ideas worth $0
"We'll decide later" → Recipe for disaster

Document this. Write it down. Sign it. File vesting paperwork.

Conversation #3: What Does Success Look Like in 5 Years?

Questions to Ask

1. "Where do you want to be personally in 5 years?"

Listen for: Alignment with startup timeline

2. "What does a successful exit look like to you?"

Listen for: $10M vs. $100M vs. IPO expectations

3. "Would you sell the company for $50M in year 3?"

Listen for: Build vs. sell mentality

Framework: Alignment Check

Misalignment Example:

text

Founder A: "I want to build a $1B company and IPO"
Founder B: "I want to sell for $20M in 3 years and retire"

This will destroy your partnership.

Alignment Example:

text

Both: "We want to build a lasting company. If we get a great
offer (>$100M) early, we'll consider it. Otherwise, we're in
this for 10+ years."

Alignment matters more than the specific number.

Conversation #4: Work Style & Commitment

Questions to Ask

1. "What energizes you? What drains you?"

Listen for: Compatibility of work preferences

2. "How many hours per week are you willing to commit?"

Listen for: Equal commitment

3. "What's your communication style? (Async vs. sync, meetings vs. docs)"

Listen for: Can you work together?

4. "What are your non-negotiables? (Family time, vacation, hobbies)"

Listen for: Realistic expectations

Framework: Work Style Matrix

Red flags:

One full-time, one part-time
Radically different risk tolerance
Incompatible communication styles
Mismatched urgency

Green flags:

Both full-time or both part-time
Similar urgency and pace
Overlapping work hours
Compatible communication preferences

Conversation #5: Reference Checks (Work Under Pressure)

Questions to Ask

1. "Who have you worked with that I can talk to?"

Listen for: Transparency, willingness to share references

2. "Tell me about a time you were under extreme pressure. How did you handle it?"

Listen for: Resilience, problem-solving, honesty about failures

3. "What will your references say about working with you?"

Listen for: Self-awareness

Framework: Reference Questions

What to ask references:

1. "How does [name] handle conflict?"

2. "Tell me about a time they failed. What happened?"

3. "Would you work with them again? Why or why not?"

4. "What's their superpower? What's their kryptonite?"

5. "If I'm about to start a company with them, what should I know?"

Red flags from references:

"Difficult to work with"
"Blames others for failures"
"Doesn't take feedback well"
Reference hesitates or is lukewarm

Green flags:

"I'd work with them again in a heartbeat"
"Best [role] I've worked with"
"Handles pressure better than anyone"
Specific examples of their impact

The 3-Month Trial

Structure

Month 1: Part-Time Collaboration

[ ] Work on one project together (side project, prototype)
[ ] Meet 2-3 times per week
[ ] Observe: Communication, follow-through, conflicts

Month 2: More Serious

[ ] Customer discovery together (50 calls)
[ ] Split responsibilities
[ ] Observe: Work ethic, complementary skills, shared vision

Month 3: Decision Point

[ ] Build MVP together
[ ] Have "the hard conversations" (above 5)
[ ] Decide: Commit or part ways gracefully

Decision Criteria

✅ Commit if:

[ ] Enjoy working together
[ ] Complementary skills proven
[ ] Resolved conflicts well
[ ] Equal commitment demonstrated
[ ] Aligned on vision

❌ Part ways if:

[ ] Constant friction
[ ] Unequal effort
[ ] Values misalignment
[ ] Can't resolve disagreements
[ ] Gut says "this isn't right"

Trust your gut. If it feels off, it is off.

Cofounder Agreement Template

markdown

# [Company Name] Founders' Agreement
Date: ___________

## Founders
- Founder A: [Name], [Role]
- Founder B: [Name], [Role]

## Equity Split
- Founder A: ___%
- Founder B: ___%
- Employee pool: 10-20%

## Vesting
- 4-year vesting schedule
- 1-year cliff (nothing vests until month 12)
- Monthly vesting thereafter

## Roles & Responsibilities
- **Founder A:** [Specific responsibilities]
- **Founder B:** [Specific responsibilities]

## Decision-Making
### Major Decisions (Unanimous Required):
- Raising capital
- Selling company
- Hiring executives (C-level)
- Pivoting business model

### Domain Decisions:
- Product roadmap → [Name]
- Technical architecture → [Name]
- Go-to-market strategy → [Name]

### Deadlock Resolution:
- [Advisor name] serves as tiebreaker
- OR: CEO has final say (specify domains)

## Commitment
- Both founders commit [X] hours/week minimum
- Both founders commit for at least [1-2 years]

## Exit Scenarios
### Voluntary Departure:
- [60-day] notice required
- Unvested shares return to company
- Company right to repurchase vested shares at FMV

### Involuntary Departure (Termination for Cause):
- Define "cause": fraud, criminal activity, breach of duty
- All unvested shares return to company
- Company right to repurchase vested shares at [discount]

## Non-Compete
- [6-12 months] non-compete in same market
- [Geography if applicable]

## IP Assignment
- All IP created for company belongs to company
- Pre-existing IP listed in Exhibit A

## Signatures
- Founder A: _________________ Date: _______
- Founder B: _________________ Date: _______

Have a lawyer review this. Worth $1K-$2K.

When to Walk Away

Red Flags That Mean "Don't Do This"

[ ] Met recently: Haven't worked together before
[ ] Different commitment levels: One full-time, one "weekends only"
[ ] Ego issues: "I should be CEO because..."
[ ] Vague on equity: "We'll figure it out later"
[ ] Bad references: People warn you about them
[ ] Values misalignment: Disagree on fundamental priorities
[ ] Gut feeling: Something feels off

It's easier to not start than to break up later.

Success Stories: What Good Cofounders Look Like

Example 1: Complementary Skills

Founder A: Technical (built v0.1)
Founder B: Business (sold first 10 customers)
Result: Neither could do it alone, together they're unstoppable

Example 2: Prior Working Relationship

Worked together at Google for 3 years
Shipped major project together under pressure
Know each other's strengths and weaknesses
Result: Trust and velocity from day 1

Example 3: Clear Roles

CEO: Fundraising, vision, sales
CTO: Product, engineering, hiring
No overlap, no confusion, mutual respect
Result: Each focuses on their superpower

Solo Founder Success

Can you succeed solo? Yes.

Examples:

Spanx: Sara Blakely (solo until $100M+ revenue)
Plenty of Fish: Markus Frind (solo to $575M exit)
Craigslist: Craig Newmark (solo for years)

Solo advantages:

No cofounder conflict
100% ownership
Full control of vision
Move at your own pace

Solo disadvantages:

Loneliness
No one to share burden
Critical skill gaps
Slower execution (one person)

If solo: Build advisory board, hire strategically, join founder community.

Resources

50 Questions to explore with a Co-Founder by First Round
Founders’ Agreement By Penn Law
The Founder's Dilemmas by Noam Wasserman: Cofounder splits and equity
Y Combinator: Cofounder matching (ycombinator.com/cofounder-matching)
On Deck: Founder communities and cofounder search

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*