Guess the biggest reason why managers do not have a regular 1:1 session with their direct reports? 

They do not like uncomfortable conversations. 

Everything else is an excuse. Disguised as something else. But pointing to the same reason above eventually. 

Here is a trick that has helped me navigate through this

Before such conversations, ask yourself this question and respond honestly

“Do I want this person to win? Or lose?”

If you genuinely want the person to win, you will have a very different conversation. Right from its content to its tone to its impact. 

And if you want the person to lose, don’t fuck around. Any conversation you have will force to always find faults. They can try as hard as they might. 

“Why do I have to tell him to be there when there is a release. He should know it for himself. He should care”

Do you want him to win or lose? 

“I need this in the next 2 hours and I don’t care how you do it”

Do you want him to win or lose? 

“You are not hitting your numbers. And if this continues I will have to fire you” 

Do you want him to win or lose? 

“How could you not think of this? It’s so obvious”

Do you want him to win or lose? 

Good managers are always looking for ways to make their team members win.