The beauty of hindsight: The CEO guide to what advice successful leaders would give to their younger selves

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Building a successful business requires blood, sweat, and tears. Building a unicorn company worth over $1 billion requires an even greater level of effort and heartache. But the years of hard work mean that the CEOs and founders of these companies possess a wealth of experience. If they could turn back time, what pearls of wisdom would they offer to their younger selves?

That’s the question we posed to over 30 tech entrepreneurs as part of our Unicorn CEO interview series for our Without Borders podcast. We’ve collected the key pieces of advice these tech leaders would give to themselves and other entrepreneurs in our new Tech CEO Communications Playbook: Winning strategies for success, a free resource for any CEO, tech marketer, or entrepreneur to access. Here are some of the highlights from the guide in this series entitled The beauty of hindsight.

Overcommunicate, overcommunicate, overcommunicate

Many founders struggle to spread their vision to others. They need to learn a crucial lesson that not everyone can necessarily see that vision or understand the goals, motivations and decisions going on in the founder’s head.

This was the experience of Zeb Evans, CEO and Founder of our client ClickUp. He says: “I think people always assume that everyone knows what’s inside of their head when they don’t.” His solution was to repeat communications regularly to everyone, including the team, partners and clients.

“If you repeat it, there’s no downside to doing that,” he adds. “You’re going to be able to get your vision across much more. If you have creative vision or marketing vision, you should continue reiterating that and repeating it as much as possible to drill it in.” 

The importance of transparency 

Is it better to try and be a perfect leader, or to show weakness and admit mistakes? Larry Gadea, CEO and Founder of the workplace platform Envoy, revealed that he tried to be a guarded leader, focused on showing that everything was going in the right direction, but over time he has learnt the power of being transparent and honest.

“I would say to myself, in the beginning, that you can tell the people that are with you more about your concerns, your fears,” he says.

Larry adds that, if he could do it all over again, he would invest heavily in building a culture of transparency and honesty right from the beginning, starting with himself and extending throughout the team. “Engage with the people on that honest front. That will be my advice to myself.”  

Make the hard decisions, quickly

The journey from start-up to success is rarely smooth sailing, and founders will face tough choices along the way. How you handle those moments can have a big impact. 

Mark Lee, co-founder of DeviceVM which later became the software provider Splashtop, shared the painful memory of having to downsize his company from 300 staff to 60 over the course of a year and half when the company experienced a tough period.

“In retrospect, it would have been better if we cut harder and faster versus extending that drive,” recalls Lee. “It was tough on our founders, too, because a lot of them considered their team almost as family members. So for them, continually letting go of new, different groups of people that we trusted and have worked with for years over an 18-month period was really rough.”   

In conclusion, the key pieces of advice leaders would want to give to their younger selves are: 

  • Communicate often and regularly. Remember that the audience may have a different viewpoint or understanding to you. 
  • Be transparent and honest, especially with your team. It’s okay to lower your guard. 
  • Make tough decisions more quickly. It will reduce the pain in the long run and show leadership in challenging times. 

For more insights and advice on other crucial business objectives, check out the Tech CEO Communications Playbook homepage and download your guide today. Other topics include managing internal communications in a remote setting, how to communicate your failures and encourage a healthy error-culture, and the role of mentors in the start-up world and lessons to pass on.  

And if you are interested in listening to interviews with these and other unicorn startup leaders such as Poppy Gustafsson, CEO and Co-Founder of Darktrace, Vijay Tella of Workato, Job van der Voort of Remote, or Greg Jackson of Octopus Energy, you can do so on our Without Borders podcast.