Take a moment and imagine a great founder; describe them in your mind. Now, picture a great CEO.
How do these two images compare? Are they the same, or are they different?
If your vision of a great founder differs from that of a great CEO, you’re not alone.
Every investor Jonathan Lowenhar has interviewed conjures up an image of a courageous and tenacious founder, but when they describe a great CEO, they paint a different picture.
To these investors, a great CEO isn’t necessarily ambitious and courageous, but rather someone who exhibits a certain set of skills. Someone who can build a system, based on clear, strong communication, and effective team management.
Jonathan was obsessed with answering the question, “How does a founder become a great CEO” and came to a conclusion: there is no single, universally agreed-upon path going from founder to CEO. However, we do expect founders to make the transition with ease. Building a successful startup is a two-part challenge: first, building a product people want to buy, and second, building a company that can scale around that product.
Jonathan and his team at Enjoy the Work lead with the understanding that most founders need training to transition from founder to CEO. He came to Startupfest to share valuable insights on the dos and don’ts that will guide a founder to the second part of their startup journey.
Here’s what I took away, you might want to jot some of these down.
The DON’Ts: Pitfalls to Avoid
Jonathan and his team at Enjoy the Work have identified some common "failure archetypes"—the kinds of CEOs you want to avoid being. If any of these archetypes sound familiar, it’s not too late to make changes.
- DON’T Be The Robot CEO:
This is the CEO who believes emotions have no place in the workplace. They see work as purely transactional and ignore the emotional well-being of their team. Emotions are an inevitable part of life, and ignoring them will only create a toxic work environment, not make your company more efficient. - DON’T Be The Pleaser CEO:
The Pleaser CEO says what they think everyone wants to hear and avoids difficult conversations, leading to a lack of direction and decision paralysis. As uncomfortable as it may be, engaging in tough conversations and providing constructive feedback is necessary while scaling a business. - DON’T Be The Perfectionist CEO: Perfectionism in startups is a recipe for failure, you can only be good and fast enough. Seeking perfection will just add weight to your back while you climb an already steep mountain.
- DON’T Be The Angry CEO:
This is someone no one wants to work with…or even be around. While holding your team to high standards is important, leading with anger will only alienate people and drive talent away. Leadership requires emotional intelligence, not just authority. - DON’T Be The Laissez-faire CEO:
This CEO believes they are an individual team member, and not the one responsible for steering the ship. Hiring a strong team is crucial, but your role as CEO is to lead and manage the team, not sit back and hope for the best. Stay involved and provide the support your team needs to succeed.
The DOs: Key Skills for Success
Great CEOs do many things but excel in the following areas:
- DO: Learn to run the business, don’t just build a great product.
A great CEO needs to understand what it takes to run a company, and how to build systems that will scale alongside you. From communication systems to financial planning, you must manage the business operations side of things just as much as the product side to succeed. - DO: Understand the key roles that report to you.
You don’t need to be an expert, but having enough knowledge to have a meaningful conversation about every aspect of your business is essential. Whether it’s sales, tech operations, or marketing, you can provide guidance by having enough understanding to make informed decisions. - DO: Cultivate a strong and positive work environment.
A great CEO creates an environment where employees feel heard, valued and motivated. Be someone who holds themselves accountable, encourages high performance and resolves conflicts without blame. - DO: Care about being great at the job.
If you don’t know how you are doing, ask! Be proactive in identifying areas for improvement and consistently strive to become a better leader. - DO: Check out Jonathan’s full talk now and learn more about Enjoy the Work!
Jonathan and his team are doing fantastic work supporting founders worldwide. They offer resources and insights that will help your journey from founder to CEO.
Stay tuned for more expert insights from Startupfest and don’t forget to subscribe to our content!