really enjoying the process of leading an education startup in Colombia. It’s been over three years now, and thankfully, we are still alive and moving forward. It isn’t easy, but I love what I do. The journey has been intoxicating: I have swung regularly from euphoria to despair, just like most entrepreneurs do. I have cried. I have felt higher and prouder than I thought was possible. I have wanted to give up. Welcome to the family of broken, open-hearted warriors.


Across the entrepreneurship ecosystem, we have our priorities all wrong. Along the way, during my time with CoSchool, I have had the chance to work with some wonderful mentors and advisors. I’ve read many books about the journey. I’ve taken part in accelerator programs in Colombia and the U.S. And yet, nobody told me the single most important thing you need to learn how to do as an entrepreneur: having difficult and honest conversations. This should be Day 1, Hour 1, Lesson 1 of any curriculum for entrepreneurs. The rest can wait.

In the high-octane, fast-paced, first months and years of a startup, there’s a whirlwind of canvasses, Post-its, late nights, endless “quick chats over coffee” (with people that will probably have nothing to do with your business), projections, decisions, and action. In the middle of it all, I believe something fundamental to both the existence and success of your startup gets forgotten. And that’s bad news for all of us.

As the wise Khalid Halim wrote in his 2014 article on co-founder conflict: “In 2012, Harvard Business School professor Noam Wasserman studied 10,000 founders for his book “The Founder’s Dilemma.” His research found that 65 percent of startups fail as a result of co-founder conflict. That’s higher than the divorce rate.”

I split up with my co-founder Carlos after 10 months together. We’re still good friends, and he’s actually working with us again, but we made a rookie mistake (in our defense, we were rookies and nobody told us) when we started out. Not once in 10 months did we sit down and have a difficult conversation. We never shared feedback. I moaned about him to the voice in my head and to my friends, whilst no doubt he did the same with his circles; CoSchool sprang into life, and we got busy being busy.

Too busy to notice, perhaps, that our relationship wasn’t going to withstand the first head-turning offer from another organization? As it turned out, those rocky last few weeks together (Carlos and I were both head-hunted by another startup; he decided to leave, I stayed) forced us into our first difficult conversations. But it was too late by then.

No two startups are the same. There is no playbook, no script to follow. You are out in the wild, on your own, the first of your kind. Inevitably, you will face totally new challenges with new people and need to find new solutions practically all of the time.

Most importantly, you will need to have difficult conversations. All of the time. Hiring people. More clients. Suppliers. Mentors. Press. Firing people. The list is endless. As the months go by, your world grows rapidly. Before long, if you grow even moderately, you are juggling potentially hundreds of relationships while walking a tight-rope, tense with stress.

What are difficult conversations, then? A few examples, from my experience:

  • Speaking to disgruntled clients
  • Addressing performance issues
  • Letting people go
  • Breaking bad news (Dear team, We have no money…)
  • Solving internal disputes because the buck, ultimately, stops with you
  • Addressing the press when shit goes wrong
  • Talking about money and salaries (regularly)
  • Shares and vesting and all that jazz
  • And, of course…having difficult conversations with yourself! (radical self-inquiry)

My education in an English boarding school from ages 8–18 left me mildly crippled in terms of my capacity to have difficult and truthful conversations. I learned (and was taught) that one should never create awkward situations. So I didn’t. I kept things locked down and bottled up. Conversations about emotions or feelings were strictly off limits. Vulnerability was forbidden, so all of this has been pretty new to me.

This “very British problem” isn’t unique to Britain — the muscle of having difficult conversations is something that many of us do not exercise, but being CEO of a startup has given me no place to hide. I have had to figure out how to have difficult conversations.

Last year, I was too ambitious. I pushed the team hard to triple our revenue and achieve an unreachable investment target. I got everyone fired up with a dreamy vision. But on both counts, we failed, and it was down to me. We were plunging into the red by September.

My experience at a Reboot boot-camp in October seemed to come at the appropriate moment. I got five days of no-BS vulnerability from fellow CEOs, who demanded the same of me. It was the training I needed to handle what came next: In November, CoSchool decided that we had to let five people go from our team of 15. Laying off 33 percent of your team isn’t easy.

I am proud of how I dealt with the situation, and so proud of my team, but that was a gritty, shitty few weeks. It was a terrible challenge to break the news to the team, share my shame at my failures, and handle the one-on-one process of telling people that their time was up. You learn how to have those conversations, or you’re in the wrong job – but I wish somebody had told me.

So, to any new entrepreneur out there: look for these conversations, notice the need for them, practice having them, have them often, do not put them off, and prepare yourself — for this is, I believe, your most important job as CEO of a startup.


Henry May

Author Henry May

Henry is the CEO of CoSchool, a startup that challenges the status quo of education in Colombia by providing a range of programs (lasting for one day, one week, four months) that build character and leadership skills in students. He has lived in Colombia for the last 5 years, and has also been involved with the NGO, The Huracan Foundation, which he set up in 2011 following a story involving the power of football (soccer) to connect people and transform lives.

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