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This article was published on February 6, 2020

Here’s what tech founders had to say about their leadership mistakes

Here’s what tech founders had to say about their leadership mistakes
Yessi Bello Perez
Story by

Yessi Bello Perez

Former Senior Writer, Growth Quarters

Founding a tech startup is a risky business.

Entrepreneurs endure countless challenges. Delegating is not always as easy as it sounds, neither is resolving conflicts between employees. Hiring is never straight-forward, nor is it easy to appease all your co-workers and employees at the same time.

[Read: How to identify the gaps in your own leadership style]

With this in mind, Growth Quarters spoke to several tech entrepreneurs about their leadership mistakes and the powerful lessons they’ve learned along the way.

Here’s what they had to say.

Thinking you need to know everything

Serial tech entrepreneur Dan Murray-Serter, co-founded Heights, a smart supplement business, in November 2018.

One of his biggest leadership mistakes, he said, was thinking that he needed to have the answers to everything.

“I remember one instance when the team was asking my suggestions on where to double down in marketing spend, given a few channels were working for us, and at that time I didn’t have a good network I could ask. The team knew the answers much more than I did, but they kept trying to sense check it with me, asking what I thought,” he told Growth Quarters.

“I knew I didn’t have the time to really focus on finding out the answer properly but felt like they wanted it to come from me. So I made my best suggestion from what was really, a guess based on nowhere near as much insight as I would expect from a professional making a big decision like that,” he noted, adding “In the end, it was the wrong bet  […] I should have held firm that it was their decision, not mine.”

Being a mediator, not a leader

Rachel Carrell, the founder of Koru Kids, a tech platform that connects parents with trained and vetted nannies, told Growth Quarters she’d fallen into the trap of spending valuable time mediating between employees.

“In one specific instance, I decided to try and work with them separately and spent a lot of time with them individually, listening to their grievances against the other person and trying to give the other person’s perspective […] and it was a terrible idea.”

She was trying to do the right thing, but it completely backfired.

“Not only did I spend a lot of time doing this, but each of the two execs ended up thinking that I was completely on the other person’s side and that I didn’t really understand their perspective and they just became ever more entrenched. My strategy didn’t help to build bridges at all.”

Carrell is now resolved to never do this again. If conflict arises between team members, she makes a concerted effort to try and get them both in the same room so they can discuss the problem accordingly.

Not delegating and burning out

June Angelides, currently an investor at Samos Investments, previously founded Mums in Tech where she experienced issues with delegating.

“In the early days, I was running around constantly, trying to be at all the meetings and doing a lot of tasks that could have been done by someone else, who could do it much better and actually benefit from more responsibility. Finding the right talent is hard, and so sometimes we think it’s easier to keep doing it ourselves than going through the pain of hiring.”

“It took me almost burning out to realize that I needed to let go of certain roles in the business,” she continued.

When the business began to struggle financially, Angelides decided to keep the problems herself so as to avoid worrying her employees.

“This meant I carried that burden on my own and tried to find a solution. In the end, I had to break the news that the business could no longer operate and it came as a surprise to them,” she said.

Jumping to hasty conclusions — and not listening

Peter Reinhardt, CEO and co-founder of Segment, a customer data infrastructure company, spoke about the need to listen to customers and think carefully before making big decisions.

“It took a couple of failed concepts before my co-founders and I came up with the idea for Segment. At the time, I didn’t recognize its potential. Thinking it had no legs, I actually tried to kill off the idea by posting it to a developer forum. I reckoned that the community would vote it down, and it would soon sink to the bottom of the message boards,” Reinhardt told Growth Quarters.

“When I posted it to the forum, it really took off. Within 48 hours, we’d had hundreds of responses from businesses that recognized what I hadn’t — our product solved a genuine need that nobody else had answered for them,” he shared.

In hindsight, the founder said he would have made more of an effort to speak to his target customers and work out what their pain points were — and would have done so much earlier in the development process.

“Secondly, I wouldn’t have waited as long to make decisions. In general, I think founders spend too long pushing ideas that aren’t working. It’s important not to be afraid to keep experimenting and testing – if you find product-market fit, you’ll know it. The key is to listen carefully to real wants and needs, and not to impose your own grand visions on the world. Keep listening, and keep learning,” he noted.

Too focused on investment and hiring the wrong people

Christian Faes, co-founder of LendInvest, an online marketplace for property finance and investing, said he mis-hired a lot in the early days, and “learned the hard way.”

“Sometimes you’re better waiting to find the right person, rather than taking someone who can just ‘help right now’,” he told Growth Quarters.

Faes also said he would approach the whole process of security external equity investment in a completely different way. “We wasted so much time in the early days getting to know and building relationships with investors that were never going to be right for our business (and we were probably never going to be right for them either).”

“It’s good to have broad investor relationships in the market because you are getting feedback on your business through the process. However, if I was doing it again, I would probably have just have plugged away building the business and been less focussed on talking to investors,” concluded Faes.

Some mistakes are more easily rectified than others, but it’s important to acknowledge them and realize they are part of the tech business journey and an individual’s personal growth.

In the meantime, here are some important lessons to keep in mind:

  • Don’t feel forced to know everything — have faith in your team
  • Get people to resolve their conflicts together
  • Don’t wait until after you burn out to start delegating
  • Avoid jumping to hasty conclusions and listen to your potential customers
  • Focus on hiring the right people rather than spending all your energy on investors

Like what you’ve read? On Growth Quarters, we strive to go beyond generic ‘fortune cookie advice’ and learn directly from the people who have ‘walked the walk.’ And this summer, at TNW Conference 2020 in Amsterdam, we’ll take Growth Quarters offline again with a vibrant program dedicated exclusively to sustainable business growth. Listen to keynotes from leaders from the world’s most successful companies and get actionable guidance to help you grow professionally. Get early bird tickets now and learn more about the Growth Quarters track

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