Episode 18

How to Be Your Best CEO Self

With Dale Holewinski, Startup Founder & CEO Coach at Decode

By Ashu Garg


For the first episode of the new year and new decade, a startup-founder-turned-CEO coach offers some guidance on being your best CEO self.

I. The Recap

In this episode, I sit down with one of our portfolio alumni, Dane Holewinkski, a startup CEO coach and founder at Decode. Dane works with founders to advise them as they embark on the journey from the birth of a company to becoming a CEO.

Dane dives head first into the interview by answering the question, “What are the biggest mistakes you see founders make in the early stages?”

His answers:

  • Avoiding tough conversations — Feedback can be uncomfortable. As a leader, you owe it to yourself, your company, and your team to be straightforward about the challenges you face. It’s usually less awkward than you think.

  • Imposter syndrome — Many founders become worried that as the company scales, the board may be compelled to bring on a more experienced CEO. While this story is not uncommon, the lack of confidence is counterproductive to your success.

  • Not delegating — You can hire the most qualified team you can find, but if you don’t delegate, you aren’t getting the most out of your team. This is true for both the grunt work as well as the decision-making.

We hear more insights from Dane’s work with founders as he asks and answers the questions: Are you the best person to run this company?

Self-reflection is hard, especially when it means considering your own job performance. More specifically, ask yourself:

  • Do you still love your job? — Some CEOs enjoy the rush of starting a company, but lose this joy when scaling introduces more structural challenges.

  • Are you the best person to be leading this phase of growth?

Dane rounds out our interview by asserting that work-life balance is not optional. CEOs think that their investors will be angry with them for not working around the clock, but this is counterproductive. A company’s success relies largely on the ability of its leadership to think clearly – and without rest and balance, this is impossible.

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Published on 01.31.20
Written by Ashu Garg

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