The existential loneliness of the founding CEO

If you want to know what it is really it’s like running a startup, there are a handful of people you need to talk to – and they’re not founders. They are the coaches of the founders.

They hear everything – skirmishes from co-founders, nightmarish investors, even founder’s fetishes – though they rarely name names.

And the reason why they know so much?

“Founders literally have no one to talk to,” says Julius Bachmann, a Berlin-based coach who works with dozens of startup founders at all times.

“The founders literally have no one to talk to.”

“They sit at the center of an organization that they themselves have built, and each stakeholder around them has a special interest. Their investors, employees and co-founders are all in the same tunnel and have their own issues. The founders’ life partners have their own lives and also want to be heard. And the founding families… they gave up trying to figure out what they were really doing 10 years ago.

“I think the founder’s job is exceptionally lonely,” says Ben Stephenson, founder of travel tech startup Impala. “And the job of founding CEO is an order of magnitude more lonely. You need to be quite a distance from the people you spend a lot of time with. You are unable to befriend your colleagues in a very close way, because you may have to fire them at some point… Your co-founder cannot help you, your investors cannot help you, your wife or your husband can not help you.

But coaches often can.

Gillian Davis, founding coach

The phenomenon of coaching

Coaching has been a thing in Silicon Valley for quite some time and is now “quite trendy” in Europe too, says Gillian Davis, a UK-based coach who has worked with startups like WeTransfer, MessageBird, Spotify and Typeform. “It’s the last sleeveless vest to have a coach.”

But that doesn’t mean it’s a frivolous hobby – maybe that’s what keeps some founders together during their toughest times.

“When a founder turns to a coach, it is almost always [the same story]Says Dave Bailey, a UK-based coach who has worked with hundreds of founders. “It’s basically: ‘My life is out of balance, I don’t sleep well, I don’t have any friends anymore, I don’t exercise, I worry about my health and I feel pretty blue’ . ”

“There have been times when I’ve been on the limit – and the person I would generally call under these circumstances is my coach.”

When Christina Richardson, founder and entrepreneur coach, asked hundreds of founders about their mental health in 2019, she said “Each person used the word lonely”. The study also found that 77% of founders felt that running a business affected their mental health. Not much has changed since.

“There have been times when I’ve been on the limit – and the person I would generally call under these circumstances is my coach,” said Stephenson. “Talking to someone who has a very deep understanding of your role helps remind you that it’s all about work. It helps contextualize the overwhelming crap of the decision you need to make or the thing that happened.

Julius Bachmann, founding trainer

On the coaches’ program

However, sheer shit storms and blackouts aren’t the only things on the agenda of a coaching session.

“The first mode calms the system,” explains Bachmann. “I have solo founders working with me every week, and 45 minutes of that hour is, ‘Everything flies to me and I don’t know what’s important.’

This mode is quite familiar to Jonathan Petrides, co-founder and CEO of vegan food startup Allplants, which announced a $ 52 million fundraiser this week. “A lot of times I’ve come to a coaching session with literally hundreds of priorities, I’m forced to create a synthesis by sharing what’s going on, asking myself thoughtful questions,” says Petrides.

“Asking open-ended questions and actively listening” are the signs of a good coach, Stephenson says, while “great coaches are also ready to challenge you and give you a sense of their own understanding.”

“You want someone to say, ‘Looks like you want to do this thing, but maybe you’re a little scared. Just do that thing, ”Stephenson adds.

Mode two, says Bachmann, “helps [founders] with a very specific transition ”- like moving from one stage of growth to another. “Especially in the phase of Series A where their role has to change drastically, each session is about trying to get them to let go more,” says Davis. “It’s all about prioritization.

Dave Bailey, founding coach

People problems

More than anything else, however, coaching sessions are about talking about “people issues”.

“Once you scale up, all issues come back to relationship and people issues,” says Bailey: Co-founder challenges, leadership issues, and management issues are extremely common.

“Once you evolve, all problems come back to relationship and human issues. ”

“Misalignment in terms of engagement is a big topic,” says Bachmann. “I’m seeing a lot of discussions with the teams right now, where they say, ‘It’s not about the extra two hours you put in. It is the fact that I don’t have the feeling that you are with me, as I can count on you.

Coaches can help founders get through difficult conversations that they might otherwise put off.

“There are times when you need to have difficult conversations with board members, investors or your team,” says Petrides. “It’s worth preparing well – play a role, talk about all the things I’m trying to unravel and figure out and figure out how to start this conversation in a way that will have the desired outcome. “

In these situations, the role of the coach is to bring the founder to a place where he really takes action. “It’s about putting the people I work with in a position where they’re able to do what’s courageous,” says Bailey – and follow up if they don’t.

Mikela Druckman, co-founder and CEO of Greyparrot

“At the end of the sessions [you make] commitments, ”says Mikela Druckman, co-founder and CEO of greentech start-up Greyparrot. “It’s a very important part. You agree to certain actions – and that’s the first thing you check in the next session. Things that slip through the cracks, like thinking about it, having that difficult conversation… typically the thing that is very important but that you put aside because of a million other things. [Your coach is] someone to hold you accountable.

Coaches can also help founders understand why a relationship has gone downhill. “We often tell each other stories, like ‘my co-founder is a psychopath’ and then you take it off, and it turns out they actually used the wrong word in a meeting or sent a Slack message to the wrong one. time of day, ”says Bailey.

“Very often their life equals the company. And the company lives up to their lives.

Gaining this sense of perspective is useful for founders who may be completely absorbed in the business. “Very often their life equals the company. And the company lives up to their lives, ”says Bachmann. “They are so annoyed with the smallest things that don’t work in the company, like a junior employee who doesn’t do a small task – [because] they consider it a personal offense.

“I try to determine with them the role that the company fulfillss, to show that their life is bigger than the business.

Ben Stephenson, CEO and Co-Founder of Impala

Personal development

Beyond meeting the daily challenges of startup life and unraveling an existential crisis, most founders working with coaches also want a dose of personal development.

“When people contact me, the most common thing they say is, ‘I want to be a better CEO or I want to be a better leader,” says Bailey, who thinks it’s odd that a lot more attention is not placed on the development of founders into leaders.

“When you play the role of CEO, no one gives you back. Nobody manages me – and not having that could be a real obstacle, ”says Petrides. Investors could try – “but part of the founder’s mindset will always reject that,” Bailey says.

“A coach is like that teacher at your school who taught you a few years ago but still watches you… It’s so different from the relationship you have with everyone on your board. They are part of the decision-making in the company – and their advice is geared towards that, ”adds Petrides.

Despite the benefits, many founders are unsure whether the cost of obtaining a coach is justified – or at least in the early days.

When Druckman first thought about taking a trainer, she said it seemed like “a luxury.” Her business was in the seed stage and she didn’t know what it would look like for investors.

“One of my concerns was whether this was going to be viewed as a frivolous expense by investors. Will it be good value for money? ”

Stephenson felt the same before working for the first time with a coach: “One of the concerns I had was whether this was going to be seen as a frivolous expense by investors. Will it be good value for money? ”

The two now think it’s totally worth it.

“All of your micro-interactions have such a big influence – being the best you can be has an impact on the whole team,” says Druckman. “Investing in myself is actually investing in the business, because the way I am has a huge influence. [on everyone else]. “

“The health and success of a startup can be unlocked or blocked by the health of their CEO and their entire team, and no matter how good you are at your job, everyone can be better with a coach.” , says Petrides.

Bailey agrees. “I never calculated the numbers, but if I were a venture capital fund and my clients were my portfolio, I would do extremely well. I don’t think it’s a question of causation – I think it’s highly correlated. CEOs who are relentless in doing whatever it takes to grow work with a coach because they really want help.

Amy Lewin is the associate editor of Sifted. She covers VC, foodtech and diversity in tech, and tweets from @amyrlewin.



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