We need to talk about CEO succession

Lack of public discussion of this sensitive topic doesn't help the tech ecosystem.

They say that being a CEO is a lonely job. Choosing whether to step down as a CEO is a particularly lonely moment. In the foreword for my book Startup CEO Succession, Jerry Colonna, author of Reboot, wrote:

Of all the many, many heart-wrenching and mind-numbing challenges of leadership, nothing compares to the challenge of letting go of the embodiment of your wishes and dreams.

At first, I was surprised. Nothing compares? Is it not an overstatement, given all the other challenges of leadership? But on reflection, I saw Jerry’s point. It really is a dramatic shift affecting every area of the founder’s life. And, at that moment, the founder often feels particularly alone.

One reason for this is that so few people have direct experience with this transition and so few people can empathise. But another, much bigger reason, I believe, is that we don’t talk about it as a tech community — at conferences, networking events or social media — unless it’s a private, off-the-record conversation between two people who trust each other.

I know VCs who don’t know how to tell a portfolio CEO that they should step down. I know founders who don’t know how to tell their boards they’re preparing to leave. I know founders in the process of leaving who feel like they can’t be fully open with their boards.

I’m also confident the topic rarely comes up in fundraising conversations, with both founders and investors silently pretending the CEO will stay in their job forever.

DALL-E’s idea of a room full of founders and investors who aren’t talking to each other about some difficult topic :)

This is understandable. VCs don’t want to lose the deal by giving the impression that they might ask the CEO to step down one day. Founders don’t want to lose the deal by giving the impression they might leave one day.

There are two unfortunate consequences. One is that founders and boards tend not to talk about it until they have to, which is often a bit too late. The earlier this conversation starts, the more room for manoeuvre they have.

The other consequence is we don’t learn from the experience of others. Knowing how other founders and investors have navigated this territory can help us do better at our companies and make it feel much less lonely.

Such a public conversation would, I believe, also benefit the tech ecosystem in the UK. We will all collectively do better if there’s an exchange of experience and ideas, leading to a better flow of talent.

Ideally, every startup needs to be led at all times by a CEO who’s absolutely committed to the growth of the business and has relevant skills. Often, it’s the founder, but that’s not always the case. And if it’s not, everyone would probably be better off discussing the possibility of bringing in a new leader before they have to.

Here’s what I imagine it will look like one day:

• Founders and investors talking about the possibility of CEO succession during fundraising without feeling threatened

• Founders saying to their boards they’re considering leaving without fear of being pushed out

• Investors clearly outlining under what conditions the CEO will be asked to step down without coming across as unhelpful

• Founders reaching out to get the support they need during CEO succession

• Founders choosing to be more open about reasons they chose (or were asked) to step down when they share their stories later

It is a complex topic, but we, as a tech community and as a society, are gradually learning to talk about topics that might have been taboo in the past: mental health, sexual preferences, gender identity, pay transparency, diversity in the boardroom, political preferences etc. Yes, it is a complex topic that needs to be handled with care, but that’s not a reason not to try.

So my hope for us, as a tech community, is that we start talking about CEO succession more openly in the public. We will all — founders, investors and the tech ecosystem overall — benefit from not treating this topic as if it were taboo.

And that, I’m sure, will make the challenge of stepping down as a CEO a bit less heart-wrenching and mind-numbing, which it often is today.