Builder or Sailor, CEO Coaching

Sailor or Boat Builder? Which one are you? Do you think you are both? After a few tough lessons, I realized that this belief was a limiting factor in growing the companies I was invested in, founding, and leading. While every company has a Founder (Sailor and Builder), not every Founder becomes the CEO (Sailor). Although Founders are the first CEOs of their companies, it takes two completely different skill sets to start a company (Builder) and run a business (Sailor). So, the question becomes, when do you, as a Founder, step away from being both and into one, the other, or neither? Start by asking yourself what really matters to you most. Do you want to remain the CEO or just think it is expected? Would you rather focus on vision and let someone else oversee the details? Consider the following when you conclude that it is time to “Hire the Sailor” (CEO):

  • Work in the boat, not on the boat: If you're an Owner or Founder who wants to focus on one facet of the business where you are an expert, it might be worth it to hire a CEO to manage all other critical areas, allowing you to focus on growing your business from inside the company (more boat building) by remaining an expert.

  • Navigating tricky waters: Perhaps there are regulatory issues, or your marketplace has significantly changed and become fraught with “rough waters.” Having someone at the helm who is an expert at navigating and growing your company through the rough patch is essential.

  • Navigating new waters (Blue Ocean): You may have started your company on a sea that you knew well. Now that your company has grown and is entering a new, blue ocean, you may want to hire someone who knows the new ocean and is expert at navigating it. Growing your company in new products, services, or areas that require innovation is necessary to continue growth and sustain what you founded, but not in your areas of expertise.

  • Experience in growth and financing: Founders are INCREDIBLY good at their company’s initial vision and problem-solving product/services set.

That said, once the company reaches a certain level of maturity, it is no longer a “start-up” and entering a growth phase. This requires experience in obtaining capital to sustain forward momentum as well as providing structure and handling details. If you find yourself NOT wanting to do this work, it is time to hire a CEO. 

I know from personal experience, both as a Founder and investor, how incredibly difficult this decision is to make. That said, it is better you make the decision yourself, rather than to be told by your team, investors, or board of directors that a change needs to be made. Please know that this decision is not a sign of weakness or failure, but the exact opposite; Asking for help is a sign of strength. Bringing in an outside CEO is necessary and good. It means you are emotionally intelligent and business savvy enough to understand what challenges lie ahead, anticipating when alone it all may be too much to manage.