Why founder growth and company growth are two sides of the same coin

A growing company is one of those “great problems” to have. Great, because it’s clearly better than the alternative; a problem, because with every win, hire and investment round comes a bucket of new – and complex – challenges. These start as early as the first day of investment, when a founder is almost always asked to take on the job of CEO, or step into another leadership role.

This leadership position changes a little more with every new milestone in a company’s journey. In fact, there are few other contexts in which individuals must adapt to meet so many different challenges at such pace – but there’s a reason founders, and the CEOs they become, are a unique breed. Still, even for the boldest pioneers, such rapid-fire adaptability is demanding. A leader’s personal growth journey is never over, which got us curious about the ways founder growth impacts a company.

We wanted some insight, so we turned to an expert. Jake Bornstein is an exec coach to start-up leaders. As avowed cheerleaders for executive coaching, Jake is someone we recommend to the founders and CEOs we back when they’re wrestling with a dilemma. He was generous enough to share his thoughts on the interplay between founder and company growth.

Meet Jake

Jake has been coaching for a decade, and co-founded his latest coaching business, Studio Metis, three years ago. On a mission to coach tech industry leaders through their scale-up journeys, Jake’s approach starts with the work itself: what are you trying to build, and what’s unique about your vision? Everything else follows from there. ‘I don’t think you need to be some Zen monk superhero to be a great founder,’ Jake says. ‘What great leaders are really good at is being clear on what they care about and doubling down on those strengths.’

The Growth Curve Startups Demand

As a rule of thumb, Jake suggests you can identify an organisation’s biggest challenges by looking at a leader’s weak spots – or at least points of major aversion. ‘Whatever a founder least wants to deal with becomes the biggest problem in their company.’

Jake’s party trick is to talk to business leaders, learn about them, and then tell them everything that’s (probably) going wrong at their company: it’s a trick borne from experience. ‘The things founders don’t want to face in themselves,’ Jake says, ‘get reflected in the company’s dysfunctions’. Jake has seen almost every one of the challenges he helps resolve before – and, he argues, they can be identified simply by understanding the people at the helm.

When a start-up is going well, challenges compound exponentially. Team size doubles, product complexity multiplies and board dynamics intensify. At a headcount of 30-50, patterns that worked before start getting more dysfunctional. By 150 people, they break the company entirely.

And, often, they’re oriented around weak spots. So, the founder who says they hate politics, for example, almost always finds themselves at the head of an extraordinarily political organisation. Their discomfort with interpersonal dynamics and reticence in a clear distribution of power sparks power plays, as different teams battle for resources.  By the same token, the founder who avoids international expansion because their spouse doesn’t want to move will construct elaborate, strategic rationales for staying local.

Through these examples an uncomfortable truth emerges: the founder’s ceiling is the company’s ceiling.

Growth happens through three, key areas

Jake views the rewarding challenge of founder growth through the lens of work, and breaks it down into three distinct areas:

Clear intent in the face of complexity. As more stakeholders arrive – your board wants this, employees are attached to that old feature, financing pressures mount – can you still say ‘This is what matters?’ Founders must hold onto a clear sense of truth without self-deception. Jake suggests this is mostly inner work: cultivating the self-awareness to know when you’re saying something because people want an answer versus when it’s a real intuition.

Shaping work and allocating power. Early on, it’s you and a small team. That works until it doesn’t. Growth means visualising how work actually works: who needs what capabilities, how decisions get made and who should have power. The subsequent emotional challenge lies in actually allocating that power, knowing it will upset people. Most founders, like most people, are conflict averse. Companies fail when everything is designed around keeping people happy – not what the work actually needs.

Making good decisions under complex circumstances. This is a three-part challenge: partly intellectual (holding a bigger game board), partly emotional (most bad decisions come from fear), and partly physical (sleep, regulate your nervous system, connect with your partner). Engaging with each piece will lead to better outcomes, but there’s also velocity: founders have to make decisions fast, because people will run in circles if you don’t.

‘Anything you neglect or wall off becomes a blind spot,’ Jake says. The three areas hold another lesson: that where the average individual contributor can improve in their role mostly through improving work-related soft and hard skills, the leader’s key position in the company means they must do work on themselves, if their start-up is to thrive. Yet more proof that the role is not for the faint of heart.

Where Growth Gets Blocked: Hiring and Delegation

Hiring and delegation are hard, and almost no one is naturally good at either. It’s a skill that can be learned, but it requires, yes, some founder growth, too.

Senior hires fail 65% of the time, through two regular modes, both of which, generally speaking, come back to leadership. Either, founders or CEOs can grip tightly onto every decision, because it’s scary to let go, or they can sidestep them entirely. ‘I trust you – go do your thing.’ It’s all well and good for longstanding colleagues, but both of these create paths to failure for even highly experienced hires. They are, after all, still finding their way in a new context.

Jake’s solution? The concept of a ‘mandate’. This isn’t just a role, but an expectation (or set of expectations) about what someone actually needs to deliver. When hiring a head of marketing, for example, founders should ask what, exactly, they need to move the needle on. It might be unlocking a new market, or learning about new customer segments (or both!). This is their mandate; the next question a founder needs to ask is, ‘What do they need to accomplish to do this?’

‘None of this is super complex,’ says Jakes. ‘It’s just taking the time to interact at that level. It’s remarkable how rarely it actually happens.’

Where a coach can help

There are a few key indicators that Jake looks out for as confirmation that his clients are growing:

More introspection. Coaches teach founders to notice their own thought and behaviour patterns in real time. ‘Oh, my co-founder is going to be unhappy about that, and I was shying away from it. But I should just go and talk to her.’

Increased personal responsibility. Early on, coaching sessions are full of complaints. The head of marketing doesn’t get it, sales people are bad and everyone is at fault. Then it shifts: ‘Engineering is behind schedule. I wonder if they’re clear on priorities? Maybe I’m throwing too much at them.’

Greater comfort with challenging feelings. Being willing to sit with fear, uncertainty or a feeling of being overwhelmed, and admitting it, is critical. When you recognise it you engage with it, stop being reactive and start thinking clearly.

More effective. Improvements in a founder’s mood and feelings trickle down to team, but this doesn’t necessarily guarantee great business outcomes. People can be chilled and happy, even when the wheels are falling off. Success in growth means everything starts to work: everyone knows what’s expected of them and shares ambitions for the future – and the present. Customer happiness, closed sales and excitement for new products and markets.

Sustaining growth

While flushes of growth are readily achievable, if a solution is going to attract investors, land in the hands of everyone who needs it and truly change the world, growth needs to be steady, sustainable and constant. Easily said – harder to do, but Jake suggests there’s a straightforward approach to achieving it: connection to clear intent.

In other words, if you really care about what you’re building, you’ll constantly meet the challenge of growth. As Jake says, this isn’t so much a mission statement as an articulation of a feeling: there’s something unique about bringing something you care about into the world.

Jake also recommends slightly less glamourous personal strategies to building the stamina needed to keep on growing: basic self-care. Eat well, drink less, sleep more and work out. ‘I’ve come to appreciate just how much of a physical endurance test this is,’ Jake says. Better to build those habits early.

Throughout it all, highs and lows alike, leaders would do well to hold onto one key belief: however things are going, growth happens when founders believe they can be better tomorrow than they are today.

Starting the Work

If you’re considering working with a coach, Jake’s advice is not to over-index on method or credentials. ‘Nine times out of ten, you don’t actually know what you need.’ What’s more helpful is recognising trust and a sense of being challenged. Could you be fully open with this person? Do they – or could they – challenge you? An ideal coaching relationship is one of deep trust – and discomfort.

‘I have so much admiration for my clients,’ says Jake. ‘I’m blown away by what they do every day.’ In the face of unrelenting criticism, founders assume responsibility not just for a workforce – but for one of the most intense and demanding personal growth journeys that can be undertaken.

It’s a crucible, one that reflects back to you everything you’d prefer not to think about, with added stress and extra consequences. But it’s not about the pursuit of perfection. It’s about keeping connected to what you care about, maintaining clarity on the work required – and being willing to step up, experience discomfort and grow when you have to, to shape yourself for the role being demanded of you.’

A company can only grow with its leader – but founders and CEOs aren’t alone. At Octopus Ventures we support the leadership of all the businesses  we back, whether it’s through operational support, introductions with coaches or linking them to those who’ve been there and done it before.

Learn more about how we work with founders here on our website, and if you like what you read and have a world-changing solution you think we should know about – get in touch.