If leaders are expected to have all the answers, the same goes doubly for founders. You are often synonymous with the business, its guiding light. It makes it tremendously difficult to admit that you’re out of your depth, even drowning in your work.
This is ironic, because founders arguably face this challenge more than anyone else: as your business grows, the skills and temperament required to lead it change, often radically. The job warps beneath your feet.
Too often, founding CEOs ignore the new reality and keep going when they shouldn’t, instead of hiring someone who would do a better job.
I’ve seen born entrepreneurs who excel at business development flounder because they lack the ability to run operations at scale. Either they can’t bring themselves to hand the baton to someone else, or they don’t notice the signs that they should.
So how can you know whether you should step back and hire a new CEO, and if so when to do it?
Don’t be afraid to pause
The moment you start to question whether you’re the right person for the job, stop. It may be difficult in the frantic cut-and-thrust of entrepreneurial leadership, but carve yourself some time to reflect.
What skills does the business need for its next stage of growth? What are you best at? If there’s a mismatch, is it likely you will learn to do things differently? Do you actually want to? If you owned the company but didn’t run it, would you hire yourself now as CEO?
Don’t navel gaze but do probe. The idea is to tease out whether what you’re feeling is just natural self-doubt, which in small doses can be a healthy inoculation against hubris, or something deeper.
Talk to someone about it. I’ve had many conversations with founders that have helped them uncover some truths about themselves once they got over the initial embarrassment. Speaking to peers can help too – serial entrepreneurs in particular tend to acknowledge that they prefer starting to scaling, and their perspective can be invaluable.
Consider your options
If you do have legitimate doubts, it’s important to know that it doesn’t mean you have to walk away, or that the business is somehow better off without you.
Instead, think of it as an opportunity to pivot how you spend your time in order to add the most value.
That might be working on the product, which is what James Dyson did when he ‘demoted’ himself to chief engineer at his eponymous consumer electronics company, or Bill Gates when he switched CEO for chief software officer at Microsoft in 2000 (both remained chairman, with significant or total control).
If you’re more of a big picture leader, you may want to focus on strategy and vision, or to be the public face of the company while a more operationally-focused chief executive handles day-to-day issues. Reed Hastings did this by becoming executive chairman at Netflix in 2023, as did Whitney Wolfe Herd at Bumble.
It’s not uncommon for fashion bosses to focus on design, or Silicon Valley leaders to become chief visionary officer.
Whatever route you take, this moment of self-awareness can be the best thing not only for your business, but also for you. If you get it right, it allows you to do what you do best, with a full-time CEO to look after the rest.
If you’re interested in exploring what your business needs for future growth and how you can best contribute to it, give us a call.
