How to Have a Difficult Conversation: 3 Practices

difficult conversations

“Whenever two or three are gathered, there will be all kinds of problems…”
– Something Jesus did NOT say (but is true nonetheless)


My frustration with a particular staff member had been increasing over several months and was now at a steady simmer. When I hired him, I saw him as a young, smart and driven millennial with tons of leadership potential. Things started out great, but the honeymoon was coming to an abrupt end.

Once an optimistic go-getter, he now seemed like a negative naysayer. Every time I submitted an idea for his consideration, I was met with pushback and complaint. Once humble and teachable, he now seemed prideful and arrogant. Whenever we were gathered as a team, he consistently defaulted to the role of teacher, informing others (including me) of the right answers.

He was becoming a problem. And not only was I feeling it, but so were others around me. I was feeling pressure from staff, both vertically and horizontally, to set him straight.

Something clearly needed to be done. But what? And how? How to have this difficult conversation?

Name and blame

A few years ago, my plan would have been simple and straightforward: name and blame.

I would have leveraged my positional power as his boss to apply pressure toward the desired outcome. I would have sat him down, named the problem, provided evidence for the problem, demanded that the problem be rectified, and attached a deadline to ensure a timely fix.

Here’s the problem. Here’s why this is a problem. You need to fix this problem. This is how much time you have to do it. Oh, and is there anything I can to do help you fix this in time?

The conversation would have taken no more than 15 minutes, I would get my point across, and the onus would be on him to improve things…or else!

But what I’ve been learning is that this approach doesn’t do good work for anyone involved.

For the leader, putting others in their place by demanding change requires zero vulnerability or humility, let alone empathy or compassion. And for the one being led, they typically walk away feeling called out and shamed, not understood and empowered.

Additionally, the underlying frustrations are rarely resolved. Not really. It tends to produce mounting frustration that pops up somewhere else, usually resulting in a resignation, either forced or voluntary.

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Mac McCarthy
Mac McCarthy has been in Christian ministry for over 15 years. He has experience in a variety of ministry roles and contexts, but his greatest passion is to coach larger church teams transition from a Sunday-centric consumer-based culture to a culture that multiplies disciples to join God’s mission in the world.

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