Hard conversations
You can’t always be comfortable and get what you want
I’m not sure what we think of Tim Ferris nowadays, but one thing he says that’s stuck with me is “A person's success in life can usually be measured by the number of uncomfortable conversations he or she is willing to have.”
Hard convos in relationships, with friends, shit even standing up for yourself at the doctor’s office — hard conversations are hard because the stakes are high, and that’s also what makes them important.
At work there are so many opportunities to have hard conversations:
You have to challenge your boss
You have to challenge your boss and it’s in front of other people
You need to accept responsibility for a mistake
One of your teammates is struggling and you empathize with what they’re going through
A report is struggling and you need to tell them to step it up
One of your peers is struggling, and you have the opportunity to help them even though it might be “none of your business”
On any given day, it’s easier to have easy conversations. Oh a quick project came in that doesn’t really make sense but won’t take long? Whatever, just easier to do it. One of your reports submitted subpar work, and fixing it will be faster than giving detailed feedback and having them fix it? Well the thing is due today, so easier to just fix it. Your boss comes in hot about something they care about but you couldn’t give a shit about? Give them what they want until they go away.
There’s a give and take here — you don’t want to have hard conversations every day, and neither does anyone else — but there are some types of hard conversation that won’t happen unless you force them to happen.
“Your performance isn’t up to scratch” to a report. Or “the core assumption of your strategy is wrong” to a boss. You have to gear up and make those conversations happen, and you’ll be frustrated for as long as they’re not happening.
(Note: but don’t frame either of those conversations like that).
If you get good at having hard conversations, you can have conversations that people feel good about afterwards. Everyone feels respected, everyone said their piece, and even if not everybody gets what they want, everyone feels better for having talked about it.
How to have hard conversations at work
You are on the same team. You are on the same team. You are on the same team. You are on the same team. I am going to say it a few more times. You are on the same team. You are on the same team. You are on the same team.
To have a productive hard conversation at work, you need to be able to point to a place and say “we agree that we are trying to get there. So how can we get there?”
Hard conversations fall apart when they are accusatory (towards the other person or someone not in the room). They also fall apart when one person doesn’t really listen to what the other person is saying — not just the words, but their emotional undercurrent.
Both problems go away when you put yourself on the same team. Here’s what that looks like in a few situations:
In a disagreement, focus on where you agree. Find the common goal first. Then genuinely listen to the other person’s perspective — not just their recommendation, but a full walkthrough of how they arrived at their conclusions. When people explain their thought process they feel heard and it’s more likely that you’ll find common ground.
When someone is struggling, don’t minimize. If you have a peer, boss, teammate (or really, anyone) that’s going through a rough patch, don’t minimize their problem. It’s easy to slip in phrases like “it’s not a big deal” (it feels like a big deal) or give answers (the problem isn’t not knowing what to do), when what the other person really needs is for someone to appreciate what they’re facing. Ask them to tell you.
When you make a mistake, own the mistake. You’ve been in a conversation where someone didn’t own their mistakes, right? How did you feel about that person? When a mistake is made, you own the mistake — but you also say “this was the cause of the mistake, this is what I should have done instead, and this is how I’m making sure that it happens right the next time.” Showing your thought process addresses the other person’s fear that a mistake could happen again.
When people are mad at you, be curious at them. When you get defensive, the other person gets motivated to break through your defenses. It only makes them madder. If you come in with curiosity (“what’s going on” “tell me about that”) anger is less useful for the other person — the gates are open and there are no walls to tear down, and anger is better at bulldozing than it is at answering questions. (Note that if someone is angry because of a mistake you made, this will make them angrier, and you should refer to the previous bullet).
Wait...did you have the conversation or didn’t you?
The most important parts of a hard conversation are:
That it happens
That everyone agrees it happened
You can go a long way by confronting hard things head on, but I’ve seen a lot of conversations that only one person thought happened.
On the manager’s side, managers ask their reports how they are doing, how the work is going, what’s being done to address a miss. But if the manager is too “nice” about the conversation, the report never actually realizes that a problem is being addressed. There’s a kind way to raise performance issues so that everyone feels respected — half-mentioning them for fear of being mean isn’t it.
On the report’s side, I’ve seen people ask questions like “what’s the objective here” or “what do you think about overcoming [problem with an idea],” which to them is pushing back against the boss. But most of what managers hear day-to-day is some type of complaint or problem-solving — so this doesn’t register as pushback, the report feels ignored, and the manager doesn’t realize anything happened at all.
You are on the same team. If everyone has that mindset, you can have open conversations even when those conversations are hard.