The Ultimate Startup Executive Playbook: How to Pick Your Next Boss

At Primary, we don’t just evaluate markets and products—we assess founders and their ability to grow into world-class CEOs. As our People leader, I also help operators considering roles at portfolio companies assess how they could fit into various teams and grow alongside these founders.

Your career is a bet on leadership. So be intentional. When evaluating the CEO before you join, ask yourself: Am I betting on the right leader? Am I becoming the kind of leader others would bet on? The best careers—the ones that change the game—are built on leadership worth following.

With this article, I’ll share a framework based on patterns we’ve observed and insights from the investors and coaches we work alongside, all with the goal of helping startup operators find the fit that will fuel professional growth.

Why does this matter? CEOs shape everything
A company’s culture, leadership style, and long-term success all start at the top. A great CEO sets the tone, creating an environment where people thrive. But here’s the reality—your CEO can make or break your career. The right leader accelerates your growth, opening doors and creating opportunities. The wrong one can limit your impact, slow your progress, and push top talent away.

The good news? Great CEOs aren’t guesswork. Clear, objective indicators separate an average leader from an excellent one.

The DNA of outlier founders
Many investors seek out outlier founders—the ones who challenge norms, see opportunities others miss, and build movements. They think differently, execute relentlessly, and inspire people to follow them.

Outlier founders have the rare ability to start companies from nothing—but that doesn’t always mean they’ll excel as CEOs as the business scales. Their greatest strengths—bold vision, high-risk tolerance, relentless drive—are what spark innovation and disruption. But as a company grows, leadership demands shift. Running a large, complex organization requires structured decision-making, operational discipline, and the ability to lead through others. For example, the same obsession and paranoia that fuel innovation can also lead to micromanagement, poor delegation, or resistance to feedback.

A CEO must delegate effectively and build a strong executive team—not just hustle and grind like they did in the early days. The real question isn’t just whether someone is a great founder—but whether they can adapt and grow into a great CEO. It's worth asking yourself: Do they still think like a founder, or have they evolved into a CEO?

The Primary Framework: How to assess founders & CEOs before you join
Great CEOs come in many forms. According to this framework, the best ones excel in six key areas: market edge, adaptability, leadership, discipline, personal grounding, and storytelling. We delve into each area in the following sections to help you identify the green and red flags when considering a startup opportunity.

1. Market Edge: Do they have a clear right to win?
The best CEOs don't just stumble into an industry. They bring unique insights, a clear understanding of industry pain points, a strong network of industry contacts, and real credibility that gives them an unfair advantage. Think about the founders who just get it—they see shifts before the rest of the market and have the insider expertise to execute with conviction.

Red flags for founders who lack market edge:

• Struggles to define the problem they’re solving
• Lacks recognition or respect in the industry
• Relies on charisma instead of expertise

Key question to ask: What’s a belief you hold about the future of this industry that most seasoned insiders would disagree with?

The right answer reveals true insight—and that’s the foundation of real Market Edge.

2. Adaptability: Can they evolve and make hard calls?
If there’s one constant in startups, it’s change. Markets shift, competitors emerge, and the best-laid plans fall apart. The best CEOs aren’t just smart—they’re adaptable. When assessing a CEO, adaptability comes down to looking for three indicators:

• Constantly iterates and improves themselves and their business
• Stays open-minded, welcoming disagreement, challenging their thinking, and listening to feedback
• Has high EQ, being able to read the room, adjusting their leadership style as needed, and influencing effectively

Red flags for CEOs aren't truly adaptable:

• Refuses to recognize or acknowledge past mistakes, and what they learned from them
• Lacks self-awareness and doesn't see how their words and actions impact those around them
• Struggles to balance conviction with flexibility — they get suck either clinging to bad ideas or pivoting without a strategy
• Doesn't seek continuous improvement for themselves or their company

Key question to ask: Tell me about a time you had to change your strategy due to unexpected challenges.

Their answer will tell you everything about how they think, how they lead, and whether they can evolve when it matters most.

3. Leadership: Can they build, inspire, and retain a world-class team?
A CEO’s vision is only as strong as the team that executes it. The best CEOs aren’t just brilliant strategists—they are great leaders. What does that mean in practice?

• Drives collaboration and alignment across teams. Gets buy-in from key stakeholders
• Knows how to identify, attract, and empower top talent. Ensures the right people are in the right job
• Shapes a strong, positive culture, where people want to stay and do their best work

Red flags for poor leadership:

• Struggles to attract and retain great people
• Tolerates low performers for too long, frustrating top talent
• Constantly shifts vision, leaving teams feeling lost
• Allows favoritism and internal politics to shape decision-making instead of merit

Key question to ask: Can you share an example of someone who has grown significantly under your leadership? What did you do to support their development, and how do you think about empowering leaders?

The way they answer tells you whether they’re building a high-performance team—or just a group of people working under them.

4. Discipline: Do they have a relentless focus on execution?
Startups are chaotic by nature. There’s always a million things you could be doing, but the best CEOs are ruthlessly disciplined about what actually matters. This comes down to four key traits:

• Focuses on a singular problem—knows how to balance ambition with resource utilization and realistic execution
• Communicates priorities clearly—consistent about plans and goals for a company, so their team knows exactly what to focus on
• Brings structure and organization—has clear, organized ways of ensuring goals, processes, and stakeholders are aligned
• Is intellectually honest and confronts reality head-on, even when it's uncomfortable—looks at every perspective with curiosity and respect

Red flags:

• Frequently shifts priorities without rationale, leaving teams confused
• Lacks awareness of resource constraints, burning resources recklessly or stretching teams too thin
• Dismisses or downplays risks and challenges, refusing to engage with difficult truths
• Avoids hard decisions, letting problems fester and causing bottlenecks

Key question to ask: Can you share an example of when you had to realign your team around a critical change or challenge?

Great CEOs don’t just have a vision—they have the discipline to execute it. And that’s what separates busy leaders from effective ones.

5. Personal Grounding: Do they stay resilient under pressure?
Startups are pressure cookers. The best CEOs don’t just survive the chaos—they stay grounded through it. Personal grounding is what allows leaders to make smart decisions under stress, handle setbacks, and inspire confidence in their teams. This comes down to four key traits.

• Self-awareness—knowing their strengths and weaknesses and acting accordingly
• Composure—staying resilient and calm under pressure
• Being measured—avoiding knee-jerk reactions and impulsive decisions
• Confidence without arrogance—projecting credibility without coming off as naive
  

Red flags for leaders lacking grounding:

• Struggles to delegate because they think they can do everything better
• Makes panic-driven decisions instead of strategic ones
• Relies on charisma over execution
• Prevents teams from bringing up issues because of fear of unpredictable reactions

Key question to ask: Tell me about a major setback. How did you handle it, and what did you learn about yourself as a leader?

At the end of the day, brilliant ideas won’t save a company—strong leadership under pressure will.

6. Storytelling: Can They Inspire People to Believe?
The best CEOs don’t just have a great product—they know how to tell a credible and compelling story that pulls people in. Storytelling is one of the most underrated yet powerful skills a leader can have. Look for these traits:

• They establish credibility quickly—people trust them instantly
• They have a strong, unique view of the world—they see the future before others do
• They are highly convincing—they make investors, employees, and customers want to be part of their journey
• Their thinking and communication are crystal clear—no fluff, no jargon, just a compelling vision.

Red flags:

• Gets lost in technical jargon, making the story inaccessible for non-experts
• Struggles to connect their company’s mission to a broader, inspiring narrative
• Struggles to get investors, employees, or customers excited about the company's vision
• Only sounds compelling when reading from a script—true storytelling means being able to inspire off the cuff

Key question to ask: Tell me about a feature rolled out that your customers love.

At the end of the day, if a CEO can’t sell their vision—they’ll never build a company that lasts.

When to walk away
Remember, the CEO makes or breaks the company. Some founders have the raw ingredients to lead, scale, and win—others don’t. Not every founder is worth betting on. Major red flags to look out for include: high executive turnover, lack of self-awareness, unclear vision, toxic leadership style, poor decision-making under pressure, weak network and market insights. If these red flags appear without signs of self-awareness or change, trust your instincts—and walk away.

Betting on potential vs. reality: Can coaching help?
Everyone loves the idea of coaching. We all want to believe that with enough support, founders can develop the skills they’re missing. And to some extent, that’s true—decision-making, communication, and leadership can all be improved.

But here’s the reality: coaching takes time. And in startups, time is a luxury founders don’t have. The real question isn’t just “Can this founder improve?” It’s “Can they improve fast enough to meet the demands of a high-growth startup?” Because in the world of startups, potential is great—but execution is everything.

Choosing the right leader is one of the most important decisions you’ll make for your startup career. Choose wisely.