Startup Founders vs. Enterprise Leaders: What Sets You Apart—and What You Can Learn from Each Other

Whether you’re a startup founder or a leader in an enterprise, the desire to succeed is similar. I work with and coach both, and over the years I've come to see how they navigate through their professional journey in a similar way, yet quite often they do not run in the same circles to leverage the value from each other.

Here’s how you compare—and what you can learn from each other:

The Similarities:

• Vision and Strategy: Both startup founders and enterprise leaders are driven by clear visions for the future and create strategies that guide their teams toward that vision.

• Building Teams: Whether you’re hiring your first few people or leading a global workforce, the ability to build, inspire, and manage high-performance teams is crucial.

• Navigating Through Change: Startup founders and enterprise leaders both face complex challenges and change where problem-solving, critical thinking, and agility are assets.

The Differences:

• Resources: Enterprise leaders tend to have access to established resources, including large teams, processes, and budgets. They also have people, or many people, who have held their positions before them. Founders, on the other hand, often operate with limited resources, have little history to work from, wearing many hats and making decisions in a scrappy, agile environment.

• Risk Tolerance: Founders are known for taking big risks. They have to, as they build something from the ground up with fewer safety nets. Enterprise leaders tend to be more risk-averse, working within established frameworks and structures.

• Decision-Making Speed: Startups move fast. Founders often make quick, gut-driven decisions because the survival of their business depends on it. In contrast, enterprise leaders typically navigate more bureaucratic layers, leading to slower, more calculated decisions.

What You Can Learn from Each Other:

• What Founders Can Learn from Enterprise Leaders: Processes, scale, and structure. Founders can benefit from adopting the operational efficiency and systems that enterprises excel at, helping them scale without losing control of their business.

• What Enterprise Leaders Can Learn from Startup Founders: Agility, innovation, growth mindset and risk-taking. Founders excel at adapting quickly, innovating on the fly, and taking bold risks. Enterprise leaders can bring fresh energy to their organizations by thinking more like founders—creating innovation, empowering teams to understand each other and move faster, and having a useful relationship with mistakes and failure.

What you can both learn from each other is that you share the same leadership insecurities and challenges with your mindset. Most startup founders and over 80% of enterprise leaders have experienced feeling like an imposter where they did not trust themselves or feel worthy enough to speak up or step up in certain scenarios.

As a founder or leader, it is invaluable to have a community or collective or peers and people who can support with addressing these issues. If you have a mentor, advisor, or 1:1's with senior leaders in your company - ask them about their experience with doubt, trust, confidence, and insecurities. You will be amazed with what they share. It's quite refreshing, and for some, a relief to know that you are not the only founder or leader who feels doubt, overwhelm, or insecure, because again the fact is the vast majority, and I would place a high bet that all of founders and leaders feel like way from time-to-time. The value is in addressing it, hearing from your peers, and learning from and supporting each other.

Both startup founders and enterprise leaders are navigating different challenges, but there’s so much potential in learning from each other’s strengths and experiences. At the end of the day, great leadership—whether in a scrappy startup or a global enterprise—is about vision, trust, and the ability to learn from mistakes and failure, and inspire your team to innovate and grow.

?? In the comments, share your thoughts: What’s one thing you’ve learned from either startup founders or enterprise leaders that has added value to your leadership?

Want to know more about your own personal leadership impact? Take our mini leadership development assessment to discover what leadership strategy is best for you to transform your team into a high-performance unit. You can also connect with me at: [email protected]