Learn from the best: 6 pieces of advice from leading tech CEOs

Imagine sitting down to chat with more than 30 of the top thinkers in today’s tech startup landscape. One by one, hearing their stories of mistakes, victories, and learning the pearls of wisdom that pushed them to the top of their field.

Over the past few years, we’ve been fortunate enough to collect hours of exactly these kinds of conversations with the interviewees for the Unicorn CEO series on Tyto’s Without Borders podcast.

Now, we have decided to compile the best nuggets of advice from these interviews into ‘The Tech CEO Communications Playbook’ – a series of four free-to-download guides that focus on how these successful tech leaders have developed and honed their communications skills – both internally and externally.

To give you a taste of knowledge contained in the guides, here are the highlights from a handful of CEOs and executives quoted throughout the series.

Making remote work, work

Remote work has had a transformational effect on business across the globe, offering benefits including a better work-life balance, cutting operational costs and the ability to hire talent anywhere in the world. However, building and managing remote teams does not come without challenges.

As Zeb Evans, CEO and founder of productivity and collaboration company ClickUp, cites: “The hardest thing to scale remotely is culture and connection.”

We spoke to several CEOs about how to solve this issue using effective internal communication. One idea expressed by many business leaders was the importance of being open, honest and transparent.

“I see my main job as communicating and making sure people understand what our mission is, what our purpose is, what the problems are. A lot of companies don’t want to talk about their problems. It’s uncomfortable, but I very much see my job as to do almost exclusively that,” says Joshua Motta, CEO and co-founder of Coalition.

By being more open, you can bring everyone along the company’s journey and help them engage with your organisation’s mission and purpose.

Learning from your mistakes

“The biggest mistake that you can make is not following up, not fixing things,” says Job van der Voort, CEO and co-founder of Remote.

Every successful startup has failed at something along the line – avoiding failure is impossible. The CEOs we spoke to recognised the importance of learning from mistakes and the importance of embracing errors: how you respond and react to failures can be crucial.

One common area for making mistakes concerns diversity, equity and inclusion (DE&I). Many companies today recognise the benefits of building diverse teams, but often stumble when it comes to communicating how they are achieving diversity. DE&I initiatives can backfire if poorly constructed and promoted, which is why communication around them is so important.

“Diversity is a big challenge in communication. Most companies don’t really know where to start and they don’t know how to approach DE&I in a way that is kind of meaningful and isn’t a performative thing,” adds Mariano Gomide De Faria, co-CEO and founder of VTEX.

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Overcommunicate, overcommunicate, overcommunicate

Across the series, we asked executives what advice they’d give their younger selves and to others to help avoid common pitfalls. A common refrain was the need to repeat communications regularly to ensure everyone – team members, partners and clients – is on the same page and understands the company’s mission.

“When you communicate, you need to overcommunicate. When you’ve said it three times, you probably need to say it three times more than that. A huge part of communication is understanding that the receiver is from another world, looking at it from another viewpoint. For them, it’s hard to understand what you are saying and remember it. Overcommunicating is probably my biggest advice,” says Michael Gronager, CEO and co-founder of Chainalysis.

Another piece of advice is to use stories and analogies to bring technical concepts to life and make it easier for your audience to grasp the magnitude of what your company or product can do.

“Often what we’re communicating is something that’s very deeply technical, and we might be communicating to a non-technical audience. Translating what we’re doing in a way that can be understood and consumed has been key to clear communication. The way that we’ve achieved that is through analogies. We’re very strong at using biological analogies in what we do,” adds Poppy Gustafsson, CEO and co-founder of cybersecurity company Darktrace.