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Encourage Vulnerability At The Workplace With Dilemma Conversations

Dilemma conversations are something I’ve been facilitating (along with a colleague, at times) for small groups of managers or people who belong to regular teams.

Done in three rounds, over the course of a month, the dilemma conversation is essentially a Socratic dialogue that helps initiate a deep exploration into ourselves.

The most important aspects of a dilemma conversation are trust, safety, love and encouragement. These principles are all interdependent and a lot like the principles of Semco Style - we need to get transparent in order to share our vulnerabilities.

But first, we need to be our own leaders actively choosing to take part in a dilemma conversation. When you’re your own leader, you need to take ownership over what you share and how you react to someone else’s vulnerability.

The dilemma conversation is specifically unlike a group discussion because in group discussions, it’s more about who’s going to win; who’s making the cleverest points and whether the points we make are popular enough. When it gets competitive, it ceases to be a dialogue.

Stop Being Conversational Narcissists

Dilemma conversations usually involve groups that range anywhere between 4 to 10 members, with one or two facilitators who have nothing to do with the group. Although they are outsiders, facilitators are not outside the dilemma conversation because they bring their whole selves to the sessions.

Each of us wants to be trusting and we want to gain the trust of others. But before we can choose to trust someone, we need to ascertain if we’re safe in revealing our vulnerabilities to them. When we realize that we have the trust and safety to be vulnerable, we feel braver; our voices shake when we dare to share something, but aren’t sure how people might respond. So, the safer it is, the braver people get about being vulnerable.  

The central idea is to delay our judgements and to listen to others with an open mind. It’s important that we don’t jump to conclusions, assuming we’ve already understood the speaker’s problem. In other words, we need to stop being conversational narcissists.

For instance, assume someone’s sharing a story about their daughter, telling you how difficult it was for them to stay calm when their daughter kept arguing and doing things that annoyed them. When they’re sharing this story with you, and you too have a daughter, there are two ways in which you can respond. You can say: “Yeah, I totally understand...when my child was little like yours, I had to do...blah..blah..blah..”. Or, you can say: “Well, I think I understand your problem, but how was it for you? What is the most difficult part of the problem for you?”

In the first response, you’ve simply assumed that you understood their problem. In the second response, you’ve lead them into a deeper layer of the problem by asking a relevant question. You’ve set the stage for them to reflect deeply into what’s troubling them and enabled them to say, for instance, “Well, the most difficult part was that despite me being so loving and doing everything for her she was still arguing and yelling...well, I guess I felt like I was failing as a mother…”. With that, they’ve already gotten down to a deeper layer of the problem because you didn’t immediately assume that you understood what they were going through.

Building Your Tribe With Narratives

Dilemma conversations are a way to help people get to the bottom of a problem they’re experiencing and the goal is to understand the other person and know them better in order to make a connection.

The first time people enter into such a conversation, it will be quite exciting and intense. There will be fear because they aren’t sure what it would feel like to reveal their vulnerabilities... like how it feels to share with colleagues that their father kept beating them because nothing they did was ever enough.

Most people aren’t used to talking about their vulnerabilities and they need to learn via experience what it feels like. Of course, the deeper you get into your dilemma, the less comfortable you’re going to feel. But people do get used to the idea of sharing over time, just not at the same rate.

So how do you bring people out of their shell when they aren’t as brave as the others? Or, when they aren’t ready to believe it’s safe for them to share? You need to give them time and show that you’re trying to build a learning community through the narratives of the group members.

Dilemma conversations are, in essence, all about sharing narratives and that’s how we build learning groups; that’s how we become a good tribe that sits together around the fire, talking not just about our wins, but also our loses and moments of shame.

It’s important to understand that the things we talk about in a dilemma conversation is always rooted in the present and in some way related to how we perform our role at work. It’s not a place to discuss the issues you have with your mother - like her always breathing down your neck. Instead, it’s about how a certain manager reminds you of your mother constantly breathing down your neck and that in turn affects your relationship with the manager. The first step is to realize that the manager is not your mother. You feel like it’s your mother, but it really isn’t her. So, it’s all about what you can do to overcome that feeling, be strong and more effective at work.

Actively Choosing To Work Outside Our Comfort Zone

As a facilitator, I make notes throughout the three sessions and I also encourage group members to write down whatever they feel is important. For when we write things down, the left and right hemispheres of our brains work in tandem and we make deeper connections. When we just talk, the intensity of the moment is lost as soon as we’ve moved onto something else.

I also insist that whatever’s discussed in the group remains within the group - otherwise the group dies and you can’t build those deep connections anymore. In my experience, people have always made sure it was safe for the group since people who choose to participate in a dilemma conversation do so after making a conscious decision to offer trust.

Another important thing to keep in mind is that you can’t force anyone to join the dilemma conversation. We are all afraid of being vulnerable and we’re wired to protect ourselves and this whole process is about breaking those protective mechanisms.

The dilemma conversations are meant to stretch individuals, as well as the entire group, to move out of their comfort zone and work from a spot of difficulty. We may confront each other at times, but it’s always coupled with encouragement, trust, love and safety.

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