How to Help Founders Get Out of the Day-to-Day

It’s easier than you might think

One of the hardest parts of the journey from founder to CEO is to let go of the details. It’s as painful as slowly pulling hot wax off their legs (or so I assume — I haven’t waxed my legs recently).

However, there is a simple way for CEOs to speed up the process, and metaphorically rip themselves from daily operations with minimal pain.

Take a two-week vacation.

‘Absolutely impossible,’ I hear them say. ‘The company will fall apart!’ And, of course, what happens next is quite predictable.

The CEOs begin to burn out and eventually have to accept that a year — or three — perhaps is too long to go without a break. After a little encouragement and ‘permission’ (as if they need permission), they book a trip to some beach.

It might just be for a week, but I always push for two, since the second week is when they can get some real distance.

A couple of weeks later, they return to work energised and optimistic.

‘Dave, the team really stepped up,’ they beam.‘ I’m so proud of them.’ Then, there’s a pause and they say cautiously, ‘What am I supposed to do now?’

I look them in the eyes. ‘Now,’ I say, ‘you become the CEO your company needs.’

About me

Hi, I’m Dave Bailey and I coach tech CEOs from Series A to pre-IPO. Find out more about my coaching programs and podcast.


How to Help Founders Get Out of the Day-to-Day was originally published in The Founder Coach on Medium, where people are continuing the conversation by highlighting and responding to this story.

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