Four Things That Make Difficult Conversations Difficult

What are difficult conversations for you in the AE workplace? What do they look like?

By Morrissey Goodale May 8, 2023

What do you do when someone in your company is complaining to you because you did something wrong? Or maybe someone did something to you, and now you’re the one complaining. Are these easy conversations to have? Usually not.

What makes them difficult is that we have relationships with people in our companies. Sometimes we’ve known our co-workers for decades and spend more time with them than our own families. It’s a much different scenario when a cashier short-changes us. We typically don’t mind immediately pointing out the problem, often with gusto. It’s the same when an airline bumps us from our flight. When that happens, we don’t say, “Thank you! May I have another?” It’s more like, “Are you (insert your favorite word here) kidding me? I have to get home! My (insert your real or made-up crisis here) if I don’t get home tonight!” In situations like these, we have no problem complaining and voicing our dissatisfaction. But with our coworker who has performance issues—well, that’s a different matter. You are with that person all the time—coffee, lunch, any number of social situations, etc. It’s not so easy to tell the guy you’ve been working with for 25 years that he’s slacking and needs to pick it up. So, what is it that we fear in these difficult conversations? A number of things. They might resent you, take it personally, or not perform the best they can for you. All those things could happen, or at least we imagine they could.

But think for a moment. If the roles were reversed, would you risk the position you hold in your firm to punish that person? Make no mistake—there are people who will do that. They’ll give you an attitude, give you the cold shoulder, or try to marginalize you in some way. It’s all part of punishment.

But one of the things that makes difficult conversations difficult is that our imaginations get the better of us. While it’s true some people don’t forgive and forget, or forgive but don’t forget, most people have good intentions and want to stay in good relationships. Sure, there are jerks. We have all met them. They do what they do and justify their actions, and we should rid our organizations of them. Oftentimes, for whatever reason, we put up with them, and we all have to suffer—but that’s another article.

In the end, thankfully there are not that many full-fledged jerks. Now make no mistake—none of us are perfect. Even the best of us exhibit jerk behavior from time to time. What is jerk behavior? Doing something we shouldn’t be doing even though we know we shouldn’t be doing it—changing lanes without signaling (that’s pretty much everyone in Boston), leaving the cap off the toothpaste, or leaving the shopping cart in the middle of the parking lot. We know better, but in the moment, we are distracted by what usually turns out to be our own interests (e.g., the person who moved from lane to lane is late for a flight, which got in the way of him doing what he knows he should do—use his signal).

Put the jerks aside. Let’s talk about the majority of people—people like us who, while not perfect, are well-intended. What makes difficult conversations difficult for our group?

  1. In some way or another, we can forget we are talking with human beings. They may be irrational or emotional human beings, but human beings, nonetheless. All too often, we forget we can treat each other like people as opposed to micro-managing jerks, short-fused hot heads, or sneaky phonies. In the end, we’re just people. To move from what is difficult to something not so difficult, just remember we’re having a conversation with a person who, like us, carries with them things that are great and not so great.
  2. No practice. The thing we don’t do very often looks hard. If we only make a pie at Thanksgiving, it’s difficult. If we make pies all the time, it’s easy—because we’re well-practiced. The same goes for difficult conversations. It’s much easier, some of us think, to just avoid them. But the more practiced we are, the easier they become.
  3. We make inferences about the circumstances of the other person. We can see or hear what happened, but we don’t know what the person’s intentions were. Maybe we infer that our partner is trying to undermine us. She was? Really? How do we know that? All she did was say the staff meeting we just ran wasn’t one of our best, but since she said it in front of the other board members, now we’re filling in the blank. With only partial information, we make inferences, and they are often negative. Why? It’s what we do (Congress does it all the time). It’s just the way our brains work. But if we’re conscious of it, we can check ourselves.
  4. We take things personally. Taking things personally is a result of letting assessments (opinions) live like the truth (like assertions) in our minds. (“It’s a negative opinion and it’s about me, so it has to be true!”) Breaking that cycle will inevitably break the reaction of taking things personally. When we believe we’re each interested in the other doing well, productive conversations will replace angst and hard feelings.

Bring curiosity and the spirit of openness and good intentions to difficult conversations, and you’ll find they aren’t so difficult after all.

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