Transformation as you scale your business

Early exit from our own business is a tough moment for sure. Whether things go well and there's money in the bank, or they don’t, and the exit is unexpected or unsuccessful, there’s usually a good deal of grief to explore. I wrote about that here.

The more surprising thing I’ve found over the twenty odd years working alongside Founders and early CEOs, is the depth and quality of gnarly grief that can accompany scale and success.

The move from Creator to Custodian is rarely smooth and the change in identity creeps up slowly on many, not always in a way that’s welcome.

It can be very confusing for Founders who are managing to reach the very thing they’ve dreamed of every night for years. Revenue is up; the team’s growing; the investors are thrilled to bits. But here come the time sheets and the processes that just won’t work smoothly. The meetings move from a bunch of good friends having a lovely time in a coffee shop, to governance and graft.

We’ve been working recently with a small organisation to help the CEO move from working from a stance of “I want” to “what the business now needs” and it’s been challenging and resistant work for them, where the senior leaders are struggling to elevate their role. They're more comfortable feeling playful and free. There can be a large gap between who you’ve been and what the business now requires. 

I recall when I started working with a scaling Martech company. For the previous two years, the CEO had called out each person’s birthday in the weekly meetings, with cake and some love. It was part of the normal ritual of belonging there. How do you suddenly stop that kind of loving gesture, when it starts to take longer than the meeting itself?

The existential crisis of trying to turn your ‘family’ (as your own company can feel) into a system that can work without you, is huge. It can bring up all sorts of feelings of loss, rejection, exclusion, betrayal even. How can this family think it can work without you? The very personality of a Founder is likely to find the early hustle and creativity to be compelling. The serotonin buzz of the game, the gang of cool people and the unreliability are all part of the dream.

Avoiding ‘an office job’ by creating a funky start-up is all well and good until you realise you’ve accidentally created your own office job.

The diary fills up with regular meetings and you need internal comms to tell people all the news. A quick beer after work won’t spread the information like it used to, and this brings a real sting of "normalness". Adulting really is a bore for many. Decisions slow down and as CEO, you’re no longer even needed in most of them. 

This is a crunchy moment of growth for anyone, and certainly a time when executive coaching can be most powerful. One of my recent clients had a struggle regulating his emotions in a way that a larger team needed him to do. He wasn’t long on patience or tolerance for process, and this was causing friction with the very people he’d brought in to help him grow. Becoming more strategic and outward facing was now his role, and drowning in Slack messages nearly made him throw in the towel. This moment of growth and the associated change in emotions can trigger a real crisis for a Founder, especially as it’s so rarely discussed openly. 

You stated your dream and slogged after it for several years until it became real. How do you now confess out loud that you’re hating it most of the time? There can be a risk of stepping back or even deciding to blow things up, which may not be necessary at all.

It absolutely IS possible to change your relationship with this. If you’re a Founder reading this and feeling that it resonates, all is not lost. Getting help to explore your sense of it; grieve what was, and deciding how and whether to evolve to your next chapter, will make a huge difference, because the early days are over now forever in this business. There is no going back.

Just because your business doesn’t need you in the same way, doesn’t mean it doesn’t need you at all. Working out your role in this 'family' now, is critical..or perhaps you secretly want to leave home. The relationships I see between CEO and scaling company remind me so much of raising teenagers. The business starts to rebel and push back. Having been a cute and cuddly youngster that used to ask to snooze in your lap, it now has a view beyond our own and finds us surplus to requirements. It won’t do what it’s told and gets heavily affected by its moods (and the mood of others, like markets, investors and the board). You know you love it (because you’ve loved it more than anything for so long now.) But it’s actually becoming a pain in the arse and you’re sad because it used to be such fun. 

The good news is that teenagers can become great adults if we’re able to grow OURSELVES well enough to stick with them. It’s brave, interesting, life-affirming and griefy work growing a family and growing a business. And such an incredible ride if you surround yourself with allies and champions to help you think differently. 

If you’re curious about your own Founder’s journey, I’d love to speak to you about it. Help yourself here to a convenient time to get the conversation started. Or find me on Linkedin.

I'm Aly King-Smith. Director of Clearworks Coaching. I work online across the UK & Europe; Face to face across the South and South West of the UK and, favourite of all, in my home county of Devon. Come and work on the South West Coast Path here with me and work this stuff out.