Management algorithm: should I have a difficult conversation?

Spoiler alert: mostly, you should

Image taken from Wired

Disclaimer: I’m not going to pretend I know everything in here, this is just a note for me because I’m new to the management role. If your experience is different or you have something to add, hit me up on Twitter but I don’t guarantee a response :)

I’ve been feeling like a shitty manager lately, because I don’t always have the energy (or desire, to be honest) to have difficult conversations with people, or to bring up tough questions that might make someone (me first of all) uncomfortable.

I think it is fine to feel this way sometimes, but also it’s not the best feeling in the world. And I also have to remember that the difference between being an individual contributor, which I used to be until 6 months ago, and a leader is the influence of my decisions.

As an IC, in most (though not all) cases, if I don’t feel like bringing up a hard topic, I could just not do it. Or tell my manager and let them handle the situation. Basically you can rely on someone else to bring it up and just continue with your day, mostly.

As a manager, you don’t have that privilege of being silent and hoping for the best, which sometimes is a very tempting option. You have people you are responsible for, and what you’re being paid for is to remove obstacles on their way.

So if there is an obstacle that can be solved by talking about it, it’s not about how you’re feeling about the situation anymore, it’s about how not removing that obstacle is going to affect the team.

This is what I try to remind myself every time I need to have a conversation I would avoid if I were an IC. Obviously, there’s more things I need to think about such as delivering the message correctly, making sure the time for a conversation is right and so on. Those things are as important, but the hardest part for me with those discussions is to push myself through this “ugh, but I don’t want to” phase and to make a decision to have it.

Of course, not all conversations about obstacles are worth having. Sometimes a thing you’re stressing about can be small enough not to be addressed, if there’s no potential harm of going that route. But if you feel like a thing you need to discuss is important, (I don’t know how to say it properly so bear with my word choice here) makes people emotional, and not talking about it will make things worse, then do it.

So, if the consequences of not having a conversation weigh more than your discomfort about starting it, you have to do it.

Hope this helps.

Code version:

get shouldIHaveADifficultConversation() {
  return consequencesOfNotAddressingTheIssue > personalDiscomfort;