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The Leap Of Faith: From Startup Founder To CEO

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Karina Lyburn

In terms of the requisite skills, attributes and responsibilities, the roles of startup founder and company CEO are very different. It’s no surprise then that making the transition from one to the other is a challenge that many startup owners struggle with. Here, five entrepreneurs with the all important founder & CEO as their title, share how they did it.

Find your tribe

Mary Baird-Wilcock, founder and CEO of The Simplifiers, which she has transformed from fledgling startup to a multiple six figure company, says making a successful transition is about finding your tribe and your groove.

“Whether it’s through an accelerator programme, business incubator or simply an accountability group of likeminded entrepreneurs, find your tribe, soak up as much knowledge as you can and ask all the ‘dumb’ questions so you can grow as a leader in the early days,” she says.

Gone are the days of needing to hire people in your same city and office. A CEO in the making should be tapping into global talent pools and virtual assistants to build a superstar team comprising visionary people with skill sets that complement their own.

“Find your groove; sleep, morning routines, clean eating, journaling and tracking your progress - all super important to winning the long game,” adds Baird-Wilcock. "Above all, keep things simple. Set one primary goal per quarter and work your tail off to get there.”

Prepare for a sharp learning curve

Rajeeb Dey admits that he found transitioning from founder to CEO of Learnerbly very difficult, and feels it is a move that may not be right for everyone.

“Although it is a natural progression in a founder’s career from being a one-man band to a leader when you start scaling, it comes with its own challenges,” he says. “No one offers you a guidebook on how to make the changes.”

Dey overcame these early challenges by accepting that he wouldn’t have all the answers or the necessary skills, and embraced the need for continued developing and learning.

“Creativity and inspiration may come naturally to you, but developing other skills and leading a team might not,” he says.

Great self-awareness and drive are needed to develop those skills alongside the things that are more innate, and crucially, a founder making the transition to CEO will need support, whether from peers, or through informal mentoring, coaching or leadership programmes.

“Luckily, I find most founders are inherently curious and want to push themselves out of their comfort zone,” adds Dey. “That makes learning how to become a CEO a welcome challenge in itself.

Unite your teams

Launched in 2016, career advice website Uptowork grew its audience to 30 million users in 2017, catapulting co-founder Kuba Koziej to CEO inside a year. For him, the toughest moment came when the business went from 15 to 40 people.

“It's probably your make or break moment, in terms of staffing, HR, management, and making sure you're all rowing in the same direction,” he says.

Key to overcoming that milestone barrier is effective communication. The days when people knew everything, and if they didn't, they'd simply ask whoever was sitting next to them are over.

“Now you have teams, and each team starts operating as a separate entity,” says Koziej. “You need to define responsibilities and roles, because processes need owners, and to task the whole company with a shared mission.”

A CEO must also ensure that people are growing professionally as fast, if not faster, than the business itself. He adds: “Let people pick their strengths, help them maximise them, and make sure they're constantly broadening their competences as their careers progress.”

Develop strong empathy

Barnaby Lashbrooke, founder and CEO of virtual assistant platform Time Etc, started his first business at the age of 17. The challenge for him at that stage was his lack of emotional intelligence.

He says: “I didn't understand that my employees were not motivated by the growth of the business in the same way I was, and that they cared more about career progression, working hours, or increasing their salaries.”

It took him several years to work out that empathy is the key to strong, positive leadership.

“Without it you won't communicate your direction and vision in a way that resonates,” he says. “At a simpler level, people don’t like or respect leaders who cannot empathise.”

Learning to know, trust and like yourself to be a good leader comes with time and experience. “In the meantime,” adds Lashbrooke, “Make time for your people, listen closely to what they have to say, and think carefully about your response.”

Don’t lose sight of your founder roots

Chris Minas, founder and CEO of mobile agency Nimbletank, says that in order to make the leap from leading a startup to leading a larger organisation, entrepreneurs need to be able to learn from the past.

Startup founders need to be focused, often ruthlessly, on disrupting competitions quickly, taking risks, even if it means moving anything and anyone out of the way of launching the business, he explains. At CEO level the focus needs to slightly shift and encompass softer skills in order to be successful.

“The ability to learn from the past, strong communication skills, relationship building, positive leading and thinking are the essentials,” he says. “It's about adapting to necessary people and management styles with a smack of candour and compassion.”

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