🏃 Healthy Avoidance | Career Development

How To Avoid Hard Conversations

Palms sweating? ✅. Heart racing? ✅. I’m preparing for what I anticipate will be a hard conversation at work. The difference between work and personal hard conversations is that at home I can just avoid them. (Totally healthy, right?). Whenever I find myself in one of these situations, I can usually mentally trace backwards to the fork in the road from where this moment began.

The “original sin” usually occurs with little fanfare or obvious consequence. It may be a design decision that won’t prove sustainable, or a staffing decision that isn’t just quite right. It may be a developer who’s implementing your customer’s vision or it could be a customer who’s testing your software. If the consequences were obvious immediately we would do something about it immediately or avoid doing it all together. It’s easiest to course correct (or even preempt) if the consequences are readily apparent. It’s the situations where the consequences are abstracted into the future and far away from the original sin that lead to difficult conversations. Usually when I realize a situation is growing towards a difficult conversation that means I have not been taking steps to course-correct on regular intervals.

Course-correcting on regular intervals makes these conversations so much easier because it practically eliminates them. Part of what makes conversations hard is the stakes. Course-correcting regularly allows you to reset your direction before a big mistake has occurred (or shortly after a small mistake has occurred). Weekly check-ins don’t eliminate the possibility of a budget overrun, but they practically eliminate the risk of a 5x or 10x budget overrun because 1 person doesn’t have the time in this reality to go 5x over on a task’s budget within the span of a week (when that budget is tied to time worked).

The other thing that makes hard conversations difficult is because you and this other person have different realities. Presuming you’re the bearer of bad news, it is your task to deliver this news that will result in a swing in the other persons expectations, plucking them from their reality and settling them into yours. And when people’s expectations swing (such as from highly positive to negative), their emotions aren’t far behind. While we can never predict with certainty how someone will react to news (unless you’re a determinist), we can guess. It’s the same as when people react with joy when they’re promoted…only in the opposite direction. This is another good reason for regular check ups. They prevent the problem from escalating. The longer the delay, the bigger the reset in expectations and the likelier the severity of the emotions. And emotions can make these conversations harder than they need to be. You can think of it like good forest management, clearing away the brush so that when the forest has its renewal fire it can be controlled.

TL;DR — If you’re a manager make sure you hit on the unpleasant topics in your 1:1s with your team and with your customers before they become fear-inducing, nauseating topics. If you are not a manager, it may be intimidating to deliver unpleasant news upwards, but it doesn’t hurt to start practicing early in your career.

Thanks for reading.

Angry bird. Photo by David Knox on Unsplash