Having Uncomfortable Conversations on a Team

Uncomfortable conversations are super important on a team, because teams benefit from diverse perspectives. On healthy teams, the conflict is a debate about ideas, not the value or worth of the individuals that share them.

In this episode, Richard and Peter answer the question: “We want to get better at having uncomfortable conversations on our team. We either avoid them or don’t handle them well. How can we improve at this?”

Episode Transcript

Peter Green

Welcome to the Humanizing Work Show podcast, where we dig into topics large and small related to our mission, which is to help make work more fit for humans and all of us humans more capable of doing great work. You can learn more about humanizing work at Home – Humanizing Work.

Richard Lawrence

Welcome to the Humanizing Work mailbag where we answer questions from the humanizing work community.


If you have a question you’ve been pondering, email us at mailbag@humanizingwork.com, and we’ll see how we might answer it.


Today’s question came up in a recent workshop with a team. They said something like, “We want to get better at having uncomfortable conversations on our team. We either avoid them or don’t handle them as well as we’d like. So how can we improve at this?”


This is a topic we hear about quite a bit, and so we want to hit on a few different aspects of this. The first one is, why is this even important on a team? And if we think about why teams are more effective than individuals, one of the key components of that is that on a team we have more than our own perspective.

We have lots of different lenses on how we see the world; different perspectives. So a good team should benefit from the diversity of perspectives and opinions. But they can only benefit if we’re willing to share those opinions and have some debate and conflict about them. So it’s super important on a team that we’re able to have these uncomfortable conversations so that those perspectives come out.

The second thing around this is how do we create conditions where it’s more likely for us to have good yet uncomfortable conversations? And some of the conditions that we talked about with that team and that I think are true across multiple teams, is that these are more likely to happen when there’s more psychological safety or trust on the team.

So we might think about how we can create more safety or trust. Another idea that came up is that the more frequently we have these conversations, the more likely we’re willing to enter into them– because if you only have uncomfortable conversations when things are really bad, it feels like, “Oh, no, something just blew up. And now we’re going to have a hard conversation,” and there’s a lot of angst around it.

But if we regularly have these types of conversations where there’s a conflict, then it gets more common, and we get better at having them. The third thing that we can do to make these more likely is to learn some skills around how to have an uncomfortable conversation. We’ve studied this and read lots of books, and we practice several of these things. We’ve noticed that books like Nonviolent Communication, or Crucial Conversations, or the Art of Focused Conversation, all share patterns for steps that we should take in a conversation to get a good outcome, especially when there’s conflict.

And we’ve noticed that there is an underlying theme in almost all of those patterns. They all start with stating the objective facts–what actually happened; not how we feel about it or the story we’re making up about why it happened. But this thing actually happened, and saying that out loud and getting aligned on that is an important first step because we often jump right over it.

The next step is to name and own your emotional response to that thing happening. Naming how we feel can be really hard, but when that thing happened, “I felt angry” or “I felt frustrated” are examples of actually naming the thing and owning that I feel it. It’s not, “You made me angry when you did this thing.” They didn’t make you do anything.

A thing happened. Owning your emotional response to it is the second part of almost all of these patterns.

The third one is some kind of interpretation around that. In the Nonviolent Communication model, it’s interpreting what needs aren’t being met. “You know, when this thing happened, I felt upset because my need for fairness wasn’t met.”

In the Crucial Conversations model, there’s a focus on “The story I’m telling myself right now is that you don’t care about my needs because you didn’t do this thing.” Those are interpretations for why we’re feeling that way, and it’s helpful to share those out loud.

Finally, the last step is always some kind of action, and that can be deciding what to do about it collectively. It can be, “I’m going to make a request,” again, in the Nonviolent Communication model, the last step is always, “Would you be willing to,” and then propose something. That happens on a team as well.  “Let’s propose a change that we might make based on this discussion.”

I taught this pattern to my kids very early on, specifically Nonviolent Communication, and I remember that my son Aaron abbreviated those four steps so that he could remember them as Fact, Emotion, Need, Request, and he called that a FENR. So we started saying, “Hey, could you give me a FENR about that?” When somebody is upset and struggling to communicate effectively about it, “Would you give me a FENR?” And then I started to see our kids mentioning that to others. If two of our kids were arguing, then another one might come up and say, “Hey, it sounds like you guys need to do a FENR.”

That shorthand was really helpful in our family to help make a difference, to remind us that there is a good pattern to use here.

And then once we have this basic idea of how to have the conversation well, now we can focus on the frequency of going through this in the step-by-step way to build trust over time. That can increase the level of safety. Of course, it’s not always going to be night and day better next week, but it can be by next quarter. If you start practicing it on your team or in an individual relationship, it does get better over time.


Now, by the way, if you are a leader on a team, whether by title or by reputation, you’ve got a special role to play for a few reasons. Probably the most important is that you influence other people and they’re watching what you do. So it’s more important what you do than what you say because you set the tone.

If you are willing to go into these conversations and go into them with vulnerability and humility, you’re modeling what that looks like for the team. Something to be aware of as a leader is that you may have a lower level of discomfort than others because you have more safety; because you have more power. So recognize that things may feel better to you but not actually feel better to other people and be aware of that from others.

Finally, for leaders, your personal connection with individuals on the team can increase safety. If that’s missing, it’s really hard to build that safety on a team. So you may need to work on your connection to individuals on the team so that they perceive that you care about them. That makes it safer for them to have uncomfortable conversations with you in the context where you’re the leader.


So to summarize, if you want to get better at having uncomfortable conversations on your team, here’s a reminder that it’s super important to do it, because teams benefit from those diverse perspectives. On healthy teams, the conflict is a debate about ideas, not the value or worth of the individuals that are sharing them. And there are some great language patterns that, with practice, can help us do this more skillfully, both in one-on-one conversations as well as in teams and groups.

Finally, the more frequently we have these types of conversations, the easier it gets and the more safety we can build over time. And then (as a PS), leaders, you have an outsize impact on how well teams can do this. So mind your wake.

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