Have the Tough Chats (even if you don’t want to)

Carlos E. Espinal
3 min readApr 25, 2022


Photo by Priscilla Du Preez on Unsplash

Over the past 6 months, I’ve witnessed several founder relationships and several inter-company relationships fall apart for one reason: delaying a possibly adversarial conversation that needed to happen. Had these conversations happened in a structured and well thought out way, I’m convinced that the universe of options available would have been much broader than those that came to be when things were too late and too inflamed.

I hate interpersonal conflict as much as I suspect most of you do. The idea that talking through a problem can quickly escalate into a full-blown conflict always daunts me, and in some cases even has paralysed me in the past.

Most well-adjusted people in a startup just want to get along with their colleagues (many of which feel like family), but I’ve experienced the hard way that failing to address an issue early on can have disastrous consequences later. That’s why I learned to have tough chats to address unresolved/underlying tensions that would otherwise result in a much larger conflict down the road.

Tensions exist in any group, whether you like it or not, and particularly in high-growth environments like startups, tensions are a natural part of evolving quickly. Speed of execution & hiring vs. cost management, seniority of external hire vs. promotion from within — are part of these daily trade-offs. If balanced well, these tensions drive growth. But too many unaddressed tensions over time can lead to a company’s downfall. Founders fighting about the business trajectory and unable to resolve underlying tensions is a classic example of how companies are torn apart from within.

So tensions are, in essence, both good and bad. But why do they often end up in a ‘cataclysmic event’? They get out of hand when you repeatedly avoid having the tough chats.

I define ‘tough chats’ as well-prepared/structured conversations with a constructive end in mind, with an openness to hear the other person out and find ways of reconciling differences to move past obstacles. Tough chats are NOT impulsive; they are NOT knee-jerk chats letting someone know how you feel in ‘that instant.’ They include emotions but are not ruled by them.

The ‘toughest’ part in tough chats, I believe, is in that they require effort on your part for them to go well. They are extra tough because you can’t expect the other person to do any of the work in advance (even though you hope they do). There is no way around it. You have to put in effort and preparation for them to be constructive. (update: if you struggle on how to structure the chat, feel free to get some advice from someone that isn’t partisan to the issue so you can better calibrate how you structure your chat).They require time, energy, and empathy to understand your colleague’s perspective before you approach them and reflect on how you’d like to react to their opposition.

Additionally, you need to decouple your ego from the outcome, see the bigger picture outside of your ‘victory,’ and visualise a positive/constructive result, even if you don’t get your way. Lastly, take the time to outline the essential topics you want to cover to find a resolution to your problems. You can’t get rid of tensions, but you can move aim to move past individual ones and to find a common ground / solutions to the issues.

The more you get into the habit of having tough chats at the individual or organisational level, the more likely you are to transform conflict avoidance into constructive problem solving and personal/business growth… and… the more you will likely avoid the very thing we all fear the most: a tougher chat down the road.