20 Psychological Questions That Reveal Whether Someone Will Be a Good Cofounder
Finding a cofounder isn't like hiring an employee—you're choosing someone who will share decision-making power, equity, and the emotional rollercoaster of building a company. Yet most founders approach cofounder selection with less rigor than they'd use to hire their first engineer.
Research shows that 65% of startups fail due to cofounder conflicts. The difference between success and failure often comes down to psychological compatibility rather than technical skills or domain expertise.
After coaching hundreds of founding teams, I've identified the core psychological factors that determine cofounder compatibility: values alignment, self-awareness, conflict navigation style, and unconscious motivations. The questions below are designed to surface these deeper dynamics before they become partnership-threatening issues.
The Psychology Behind Cofounder Selection
Before diving into specific questions, understand what you're really evaluating:
Values vs. Preferences: Values are fundamental beliefs about how business should be conducted. Preferences are surface-level choices that can be negotiated. Value conflicts create recurring tensions; preference differences can actually strengthen teams.
Self-Awareness: The ability to recognize personal patterns, limitations, and triggers. Self-aware founders can communicate needs clearly and take responsibility for their contributions to conflicts.
Stress Response Patterns: How someone handles adversity, uncertainty, and pressure will determine how they show up during the inevitable difficult periods of building a company.
Unconscious Agreements: Often there's an inexplicable "click" between potential cofounders. While this intuitive connection matters, it's crucial to surface the unconscious expectations and needs driving that attraction.
Using These Questions Effectively
These questions work best as a structured conversation, not an interrogation. Take turns answering each prompt and discuss areas of alignment and difference. Remember:
Listen to the process, not just the content: How they think through answers reveals more than the specific response
Red flags are gifts: Disagreements or concerning answers now save you from larger problems later
There are no universally "right" answers: You're looking for compatibility and self-awareness, not perfection
If you can't work through tensions productively during these conversations, that's crucial information about how you'll handle conflict as cofounders.
20 Revealing Questions
1. Which frustrates you more: product problems or people problems, and why?
What you're evaluating: Natural inclinations and problem-solving preferences.
Look for: Their reasoning process and self-awareness about their strengths and limitations. Both orientations can be valuable, but understanding their natural tendencies helps predict how they'll allocate time and energy.
2. What are your most significant challenges when working in high-pressure situations?
What you're evaluating: Self-awareness and vulnerability.
Red flag: Anyone who presents as having no significant challenges lacks either self-awareness or honesty. Both are problematic in a cofounder.
Look for: Specific examples, evidence of learning from experience, and strategies they've developed to manage their challenges.
3. When you're overwhelmed with competing priorities, how do you decide what gets your attention first?
What you're evaluating: Decision-making frameworks and time management under stress.
Look for: A systematic approach rather than purely reactive responses. Their strategy should complement rather than duplicate your own approach.
4. What support systems help you maintain resilience during difficult periods?
What you're evaluating: Emotional regulation and independence.
Entrepreneurship creates unique isolation. Founders who depend entirely on their cofounder for emotional support create unhealthy dependency. Look for diverse support networks including friends, family, mentors, or professional resources.
5. What interests and activities outside work help you recharge and maintain perspective?
What you're evaluating: Ability to prevent burnout and maintain identity beyond work.
Red flag: Someone whose entire identity revolves around work is more likely to experience burnout and may have difficulty maintaining perspective during challenging periods.
Look for: Genuine passions that provide energy rather than drain it.
6. If you could have pursued any other career path, what would it be and why?
What you're evaluating: Core values, interests, and alternative ways of thinking.
This reveals what motivates them beyond entrepreneurship and can indicate whether they're choosing startups for the right reasons or as escape from other challenges.
7. What's the most impactful insight you've discovered about yourself or how you work?
What you're evaluating: Capacity for self-reflection and growth.
Look for: Evidence of genuine learning from experience rather than surface-level productivity tips or borrowed insights from others.
8. How do you typically respond to uncertainty and situations outside your control?
What you're evaluating: Stress response patterns and emotional regulation.
Remember this is partly aspirational—how they wish they responded—and partly actual patterns. Look for honest acknowledgment of their challenges rather than exclusively positive responses.
9. Tell me about a time you felt rejected or excluded. How did you process that experience?
What you're evaluating: Vulnerability, resilience, and learning from difficult experiences.
Entrepreneurship involves constant rejection from customers, investors, and employees. Understanding how they handle these experiences predicts how they'll navigate startup challenges.
10. What drives your need to achieve and succeed?
What you're evaluating: Core motivations and unconscious drivers.
Look for: Self-awareness about deeper motivations beyond surface-level answers like "making an impact." Understanding whether they're driven by proving something, creating something, or compensating for something affects how they'll handle success and failure.
11. When things go wrong, do you tend to look for external causes or examine your own contribution first?
What you're evaluating: Accountability and growth mindset.
Look for: Nuanced responses that acknowledge context matters while demonstrating personal accountability. Exclusively external or internal attribution both create problems in partnerships.
12. After conflicts or disagreements, do you typically move on quickly or need time to process?
What you're evaluating: Conflict recovery style and emotional processing needs.
Different styles aren't inherently good or bad, but mismatched styles can create secondary conflicts. One founder wanting to resolve things immediately while the other needs processing time can create tension if not understood and accommodated.
13. What's an important conversation you wish you could have had with your parents or family members?
What you're evaluating: Family dynamics, unresolved issues, and relationship patterns.
This reveals potential unconscious patterns they might bring to business relationships and what kinds of connections they may be seeking through cofounding partnerships.
14. Do you recharge through solitude or social interaction?
What you're evaluating: Energy patterns and communication needs.
Understanding introversion vs. extraversion helps predict their communication style, decision-making process, and what they need during stressful periods.
15. How do you experience family or social pressure about your career choices?
What you're evaluating: External influences and motivations.
Pressure from family can be a source of strength or unconscious motivation. Understanding how it affects them helps predict how they'll handle the social aspects of entrepreneurship.
16. Where do you fall on the risk-safety spectrum, and how does that show up in your decision-making?
What you're evaluating: Risk tolerance and decision-making frameworks.
This affects everything from product decisions to fundraising strategy. Significant mismatches in risk tolerance create ongoing tension in strategic decisions.
17. Do you prefer collaborating across different areas or focusing deeply in your domain?
What you're evaluating: Working style and boundary preferences.
Critical importance: This must be aligned before you start working together. Mismatched expectations about collaboration vs. autonomy create immediate and recurring conflicts.
18. Are you someone who thinks out loud or processes internally before sharing conclusions?
What you're evaluating: Communication and decision-making style.
Both styles are valuable, but significant mismatches require explicit strategies. One founder who needs to talk through problems while another prefers to present solutions can create mutual frustration without proper management.
19. Rank these five values from most to least important: [Insert Your Top Values + Others]
What you're evaluating: Value alignment and priorities.
Customize this question: Include 2-3 of your most important values along with some that matter less to you. For example: "Innovation, work-life balance, rapid growth, social impact, financial security."
Look for: Overlap on your top values and respectful discussion of differences. Value conflicts create the deepest and most persistent tensions in cofounder relationships.
20. Tell me about a time you received difficult feedback. How did you process and respond to it?
What you're evaluating: Receptivity to feedback and personal growth capacity.
Cofounder relationships require ongoing feedback and adjustment. Someone who becomes defensive, dismissive, or unable to act on feedback will create ongoing partnership challenges.
Beyond the Questions: What to Look For
Self-Awareness: Do they understand their patterns, triggers, and limitations? Can they articulate how their background shapes their approach to work?
Growth Orientation: Do they learn from experience and adapt their behavior? Or do they repeat the same patterns regardless of outcomes?
Emotional Regulation: Can they stay present and responsive during difficult conversations? Do they have strategies for managing their stress and reactions?
Value Alignment: Where do your core beliefs about how business should be conducted align and differ? Can you respect differences and work through conflicts about values?
Complementary Strengths: Do their natural tendencies and developed skills complement rather than duplicate yours?
Red Flags to Watch For
Lack of self-awareness: Can't identify personal challenges or areas for growth
Blame orientation: Consistently attributes problems to external factors
Inflexibility: Unwilling to consider different perspectives or approaches
Emotional volatility: Unable to regulate reactions during difficult conversations
Value rigidity: Cannot respect different approaches to business or relationships
Isolation: No support systems outside the potential cofounder relationship
Green Flags That Indicate Strong Potential
Thoughtful self-reflection: Can articulate their patterns and growth areas
Emotional maturity: Stays present during difficult conversations
Learning orientation: Demonstrates growth from past experiences
Respectful disagreement: Can discuss differences without trying to convince you they're right
Complementary perspective: Brings different but compatible approaches to shared challenges
Sustainable motivation: Driven by intrinsic rather than purely compensatory factors
Moving Forward
These questions are just the beginning of cofounder selection. If you have positive responses to this conversation:
Dig deeper: Spend time working together on a project before making commitments
Test conflict resolution: Intentionally navigate a disagreement to see how you work through differences
Meet their network: Understand how they interact with others and what people say about working with them
Check references: Talk to people who've worked with them in high-pressure situations
Remember: you're not looking for perfection, you're looking for self-awareness, growth orientation, and psychological compatibility. The best cofounder relationships are between people who can navigate differences constructively rather than those who never disagree.
Your cofounder choice will shape every aspect of your company. Invest the time to understand the psychological dynamics that will determine whether you build something extraordinary together or become another cautionary tale about partnerships gone wrong.