Make Hard Conversations Less Hard

As a manager, you might find that undertaking difficult conversations is one of your biggest weaknesses. While it’s easy to see how someone’s weaknesses get in the way of their own or the team’s success, it’s comparatively difficult to find the words to articulate those weaknesses back to someone in a way that doesn’t risk damaging your relationship, demoralizing your employee, or undermining your team’s willingness to take calculated risks.

One reason that conversations focused on delivering critical feedback are hard is that we tend to overlook a key element: these are conversations that include both the person we’re communicating a message to and also ourselves. We are parties to the dialogue. We bring all kinds of baggage (much more on that later). We also bring our own egos into the conversation whether or not we choose to acknowledge them. 

To help make a hard conversation easier, take some time to come to terms with what you’re bringing to the discussion. Have you long harbored frustration that is just now surfacing? Are you generally happy with performance but trying to level up? Do you believe your broader team lacks confidence in you? How could those things show up in your conversation? How will you prepare for and manage them? And what will you do if your nerves get in the way of your being clear and direct?

I’ll unpack a few other elements of what makes hard conversations hard in future posts, but I often find that this one reframing step is a powerful lever in shifting managers’ confidence and effectiveness during hard conversations. Give it a try.