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.

About the author

Henry May

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 3.5 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.

  • cahu5401

    When the article starts out, it gives a very personal feel to it with how the author speaks of his experience with a startup. I think he did this to give the reader a different view of the article, a more personal one rather than a different one. Talking to people is such an important aspect of business but of course even more so in the startup of a brand new one. What all do these startup conversations consist of, and with whom? With all of the work and effort put into a startup, the length at which the company really gets going is different for everyone. Is there really a difference though, in how companies start up? Or are they all the same, it’s just the people that make the difference? I really like the statistic comparing failed marriages to failed businesses due to co-founder conflict. With that rate being so high though, then it must be the people that make the difference in the speed of a startup to strong, self-standing company. Conversation is key in almost every aspect of life, and conversation in business is very important, especially between co-founders, so it is a little odd to me that these two co-founders in 10 months never sat down and conversed about their business. It sounds like this author had a hard time with conversations in his start up, but eventually learned and the hard way. This article just points out to me even further that I need to be more comfortable with uncomfortable conversations and that talking with people is one of the most important parts of business.

  • Carlie Bugos

    I really enjoyed reading this article because a.) it gives a lot of personal insight and b.) it can be applicable to every day life, whether or not you’re the CEO of your own start up company. Communication is an important aspect in the business world, and the author makes it very clear that having difficult conversations in the end makes everything better. Having difficult conversations is an opportunity to build trust and respect with your coworkers. When we learn to build trust through communication, we also learn that we can challenge each other without fear which means our relationships with other people and other organizations improve greatly. I think especially as the CEO of a company, difficult conversations are uncomfortable, but the intentions are always good and CEOs should be willing to be uncomfortable for the benefit of the individual, relationship, and the company. The purpose of having these conversations is to be constructive, not about teaching them a lesson, and I think the author struggled with that differentiation when he first tried to start up his company. But, when you label a conversation as “difficult”, how do you not feel nervous beforehand? Wouldn’t it be better to frame it in a positive way? Instead of having a conversation about “negative performance feedback”, wouldn’t it be better to phrase it like “constructive conversation about development”? I feel as though a “difficult” conversation goes better when you treat it like a normal conversation.

  • Ryan Tagawa

    I found this article very interesting because it shows our tendencies to avoid difficult, “awkward” situations. The avoidance of these topics do not only occur in the workplace but in personal encounters as well. The relationship between the founder and co-founder dynamic is almost like any other type of relationship, and when an issue arises you need to address it fully because issues do not just go away. The article states that 65% of startups fail due to this “co-founder conflict,” but I believe this conflict is not only a co-founder and founder problem, but it is a business wide communication problem. If the founder and co-founder of the company fails to communicate with each other it is extremely unlikely that these two are adequately communicating to the rest of the team. By putting emotional boundaries aside you enable yourself to make your business come first, but does that have to come at the expense of your friends and colleagues? Also, the split between personal connections and work connections is displayed in this article, but do family businesses have to operate the same way, or is it the families ability to communicate from the start, which measures their likelihood of being a successful company? An entrepreneur has to take the first uncomfortable leap of starting a business and putting their product and their team out there, but it is clear that if they fail to continue making uncomfortable steps, such as having the uncomfortable conversations highlighted in this article, the company will eventually break apart from the inside and fail.

  • Ian Pastorius

    This article goes deeper than the surface of a lot of business knowledge. In school we are constantly taught about the economics and the finances and accounting and everything logistical that we have to do for a business or a business start up, but it is often overlooked that maintaining interpersonal relationships is equally, if not sometimes even more, important. The author addresses a fear that many of us have, difficult conversations. Whether it be with a complete stranger or someone who you are close with, it is often within human nature to avoid confrontation and instead brush it off rather than dealing with an issue directly. Like the author touched on, the avoidance of these discussions often directly leads to issues within the business itself. Being able to deal with difficult conversations if often a skill that is overlooked or that we do not prepare ourselves for. But in order for the business as a whole to run smoothly, there must be minor bumps and issues along the way that need to be confronted. Especially in this article, both the author and his co-founder struggled to communicate and ultimately lead to the co-founder leaving the business for something that he thought was better. While it is inherently easy to ignore conflict, if it is never worked out it can build up and then lead to much bigger problems down the road. In all relationships this level of communication is important, but especially so in business relationships. Not being able to deal with problems as they arise can sink your business or have massive implications in the future. This article forewarns readers not to fall into that same trap, and for that reason, I found it extremely useful.