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Finding your people and being open and honest will help you become a better CEO and person, says YPO Global Chairman and entrepreneur Raymond Watt.

The pressure to appear all-knowledgeable and enigmatic in order to fulfill the ‘strong leader’ stereotype can create situations that only make being an effective leader difficult.

Raymond Watt, Global Chairman of YPO, a worldwide leadership community of chief executives formed in 1950, says that in his experience, being open about your shortcomings and willing to listen to the experiences of others is essential – but it requires the power of community and being surrounded by people who can inspire and uplift you on your journey.

“It’s becoming more acceptable to say, ‘I just don’t know everything and I need support.’”

While Watt feels there has been a shift away from the concept that a leader should be someone ‘finished’ and with all the answers, he believes there is still work to be done to appreciate the importance of lifelong learning.

“It’s becoming more acceptable to say, ‘I just don’t know everything and I need support,’” he says.

“You can still do it in a way which honors your successes. As a business leader you don’t want to seem like you don’t know what you’re doing because it’s unfair – both to shareholders and your customers. It’s finding that balance and I do think that’s why the notion of a community that is secure and confident helps you overcome those things.”

The Accidental Leader

For Watt, that community has come from his membership of YPO, which aims to facilitate better leaders through lifelong learning and idea exchange. After joining just nine years ago, following a move from South Africa to the United States, he was nominated Global Chairman in 2023 by his peers after he had just taken a position on the board.

Speaking to him, it’s obvious that his enthusiasm is boundless and infectious. Rising through posts in the organization quickly was less intentional and more what he calls being an ‘accidental leader’ because he is open to opportunities and is curious and interested in seeing where saying ‘yes’ takes him.

“I just thought I would apply and was as surprised as anyone else when a few months later they announced me as the incoming Chair,” he explains.

“But it also showed me the beauty of YPO because one of the premises is that the moment you join, everyone is equal. No matter what size your business is, we show up without those trappings. So for me, my accidental champion journey is another example of just how YPO actually works.”

“I just thought I would apply and was as surprised as anyone else when a few months later they announced me as the incoming Chair.”

There is no doubt YPO and the members within it have been transformative across all areas of Watt’s life. A well-established figure in the United States tech space, he is Chairman of big data analytics company Rimar.ai, and Co-Founder and CEO of Omnislash, a data-aggregation platform in the gaming space.

He now finds himself bringing his YPO way of interacting into the boardroom and passing on important insights from events he has attended. After learning more about how other leaders manage their work–life balance, his YPO experience has even influenced how he parents.

“I shared with a member my own struggle of work–life balance, which is the struggle of every human,” he explains.

“He told me how he manages this by traveling alone with each of his children for one week a year. I felt that could work for me, too, and now I’m doing it as well. It has strengthened my relationship with my kids and the depth of our bond, which is great, but it has also removed a lot of my own insecurities about being a dad.”

Opening Up to New Approaches

Watt insists the YPO mindset and outlook can be accessed by any of us, wherever we live and at whatever stage we are at in our career path. But it means allowing an attribute, which is often seen as negative in leadership positions – vulnerability.

“I was just not used to that level of openness and low-key vulnerability until I met YPO members,” explains Watt of his personal experience.

“I used to go to an event but I just showed up. As I surrounded myself with people who showed up in that state of vulnerability and trust, it made me behave this way. It’s a very human behavior to mimic those people around us. My father used to say, ‘You become the people you surround yourself with,’ and I understand that now.”

He says as well as becoming better at listening to alternative ways of doing things and how they could have a positive impact in his life, the flipside is that he’s also become better at giving advice by now accepting it might not be right for the person you’re trying to help.

“We rarely respond to people telling us what to do,” he adds. “But we are inspired by people showing up in an inspiring way. It makes us want to try new ways and that doesn’t just count for business.”

From left: Orlan Boston, Senior Partner, EY; Fleur Heyns, CEO & Co-Founder, Proof; Florian Kemmerich, Managing Partner, Bamboo Capital Partners; and Raymond Watt, YPO Global Chairman at the 2024 YPO Global Impact Summit in Rwanda

Which is also why having a community and therefore more places to seek guidance and be inspired is key. “Anything becomes overwhelming when you’re in isolation,” he explains.

“You could be the strongest person but if you find yourself isolated, with nobody understanding what you’re going through – that is hard. Humanity has shown us communities are necessary and I think community around business leaders is important.

“The fact you know you’re not alone, that there are people that have your back, I have seen that to be the transformative agent. There are so many beautiful communities out there for leaders, CEOs and entrepreneurs, just find the best community for you.”

“Humanity has shown us communities are necessary and I think community around business leaders is important.”

As well as the personal benefits this shift in mindset can bring, it can also influence the culture of your business and organization. “I believe leadership really permeates culture,” he says.

“When someone tells me, ‘My company doesn’t have a good culture,’ I’m willing to share my ideas, but say, ‘I know that when I bumped into those issues in my business, it’s typically me.’ If I have anxiety about something and I’m not sure if it’s going to be successful, every single time I show up in a way that permeates culture.

“If you shine your own light you also give permission for other people to shine their light,” he says.

In this way, positive cultural shifts will be passed on and continue the constructive and uplifting mindset – surely a win all-round.

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