72. Have that tough conversation

People say the success of your life can be measured by the number of tough conversations you’ve had. I won’t deny this. Because only from these cringe-inducing conversations that big decisions are made. Decisions that could make or break the future of a business or an individual.

I can attest to it through my fair share of tough conversations. I negotiated for my salary, fired a couple people, discussed equity split, initiated breakups. As a very people person, I naturally recoil from dealing with any of such situations. I care too much about what the other person thinks. I would spend days and weeks playing the scenarios in my head, googling and creating many versions of a script to go through the conversation.

But I’ve gotten better over time. I’ve started to build my tough-conversation muscle. I still refrain from having to go through those unpleasant moments. But when I have to, I will get down to it.

That’s because I’ve learned first-hand how the discomfort of having the talk is pale in comparison to the pain that ensues from not doing it. There were too many times I suffered from avoiding the conversation. I was too lazy, too cowardly. I assumed that things will get better over time. That somehow that person will turn into a psychic, read my mind and magically get on the same page with me.

No. It never works that way. The fear and reservations I had would most likely come true.

So clarify. Assert your position. Control your outcome. Address the elephant.