The Semco Style 5 Principles to transform the way we work

Having A Dilemma Conversation

A Socratic Dialogue

Human nature demands recognition. Without it, people lose their sense of purpose and become dissatisfied, restless, and unproductive– Ricardo Semler

In a Nutshell

When a small group of people, aided by a facilitator, get together to reflect upon universal dilemmas, like ‘what is happiness?’ or, ‘what is integrity?’ they’ve entered into a Socratic dialogue or a dilemma conversation. It is important not to confuse this with the philosophy of Socrates or Plato. Instead, the idea is to turn the gaze inward, onto the particular experiences of people, and to arrive at universal answers and truths.

A dilemma conversation might happen in a group, but it is far removed from the mechanics of group discussion. It isn’t a debate where witty, clever things are said for the sake of argument; and neither is it a contest to see whose opinion wins or is more popular. Instead, it’s a conscious deliberation on certain dilemmas, with the group striving towards decisions with clarity that eventually leads to consensus.

People who enter a dilemma conversation expect disagreements and over a period of time emerge into consensus. Since the dialogue is bound by time, the group may or may not arrive at a conclusion within the set time, but every insight shared, every question raised, every objection or observation made is deliberated upon by the whole group, until there’s consensus.

We don’t always have to get consensus. It would be nice, sure, but it isn’t necessary. What we need is understanding. So, that we can all at least agree to disagree, after we’ve all understood what exactly we’re disagreeing about. For, when we understand things better, we’re able to manage our disagreements better. And when the disagreement is really big, we know we have to say goodbye to each other – but in a respectful and loving way.

Such conversations on universal dilemmas are aimed at creating accord between people. It’s implied that participants need to be attentive, tolerant, respectful and patient towards others in the group. Emotions are allowed to wax and wane without judgement. And over time, participants begin to realize that they have safety, trust, love and encouragement from their peers and become brave enough to be vulnerable.


Create the time and space for teams to enter into dilemma conversations that help them gain each other’s trust. To do that, they need to first get to know each deeply; openly share each other’s vulnerabilities and understand why they respond to certain situations in the way they do.


Each of us have deep-seated beliefs that we’ve adopted without question while growing up. A woman, for instance, might have been told that she needs to be brave and independent; that she shouldn’t trust strangers, particularly men; or that she should trust only women; or, that she’d have to fight their male colleagues to rise within the ranks at work. And that might be defining how she interacts with her coworkers. When people are shown that it’s alright to be vulnerable and that it’s safe to reveal the beliefs that drive their actions, they are able to make deeper connections with others, receive and offer support, and help each other shine.


A dilemma conversation always has three rounds, spread out over the course of a month. If the group is small in size (4-5 people) then a single facilitator will be enough; but if the size is bigger (6-10) people, then an additional facilitator is required to keep track of the conversation and its layers.

The facilitator(s) need to be people who aren’t directly involved with the group, but they’re as much part of the dilemma conversation as the rest of the group is. They are simultaneously involved and not involved in the process: They are not involved because they aren’t part of the group. But, they’re subjective facilitators whose skin is as much in the game as the rest of the group. They come to the dilemma conversation with all of who they are.

First Round : The first round is meant to make people touch base with their vulnerabilities because the dilemmas they face at work often have something to do with who they really are. Participants begin exploring how they can share their vulnerabilities with their coworkers. They also learn how they can be more empathetic towards coworkers who are sharing their own vulnerabilities.

However, to engage in such deep sharing, people need to trust each other. More importantly, they need to feel its safe to be vulnerable at their workplace. In other words, they cannot be penalized for what they share within the dilemma conversation. This emphasis on trust, love and safety enables people to become braver and experience what it really is like to be vulnerable. They realize that people aren’t laughing at them for being vulnerable, but are in fact, touched by their pain and that makes for a deeper connection between people.

Second Round: The second round, which takes place about a week later, is all about deepening the trust and safety people experienced in the first round. The session begins with people sharing what they thought about in the intervening days; whether they talked about their vulnerabilities to a friend or a family member and so on. If there were some people who didn’t share anything in the previous session, they are encouraged to share in this session. They are asked about what things make them feel safe; or, to think of a time when they felt like it wasn’t safe enough for them to be vulnerable and to share what finally enabled them to overcome their fears and be more transparent.

The idea behind the second session is to deepen the conversation and enrich the dialogue; to make people experience trust, love and safety. In the end it’s all about breaking out of the ideologies we grew up with: Some of us are told that you can trust people until they show they can’t be trusted. Some others grow up believing that you can’t trust people until they show you they’re worthy of your trust. That’s two different approaches to the same dilemma conversation that aren’t obvious in a superficial exploration. Once people understand the deep-seated drivers in their coworkers, they can begin exploring how they can deal with people who are different from them.  

Third Round: About a week later, it’s time to draw conclusions that show each member of the group where they presently stand and what they need to do in order to get further. For instance, if a person says they want to learn something, then they can engage with the entire group about what they need in order to learn and how people in this group can help them do that. They can even take it a step further and figure out which person in the group will be the best-suited to help them achieve their goal and make a deal to help each other out. They simply ask each other, what they can give and receive from each other.

The third round is also the time when the facilitator shares (if asked to) with the group the insights they’ve gained. With the notes they’ve made over the three sessions, facilitators can share with the group the things they noticed and if the group agrees with their observations they can together decide what needs to be done next.



The best time to begin a dilemma conversation is when coworkers feel the need to clarify themselves or get to know each other in a deeper way. Since the dilemma conversations employ multiple principles of Semco Style, such as – trust, clarity, self-management and extreme alignment, we recommend scheduling dilemma conversations about three times a year. It’s not a good idea for people to take part in a dilemma conversation immediately after they’ve experienced a burnout at work.

Level to implement



Delay judgements and assumptions

Be brave

Offer trust, safety, love and encouragement

Be respectful when talking about colleagues who aren’t present


Discuss what’s shared with people outside the group

Hijack/ steer the conversation towards yourself

Don’t force people to take part in dilemma conversations


Fosters trust between coworkers

Bolsters clarity and deep connection

Helps experience personal bravery


People can get hurt if there isn’t enough safety offered

The organization already needs to be oriented towards trust

Everybody’s skin is in the game – nobody can be a passive observer

People need to be mentally calm to begin a dilemma conversation



The dilemma of vulnerability at the workplace and the conversation around it.

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 the 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. And, 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.

And, 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. So, 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


Expert avatar

Sas, John

Facillitator in learning and development processes for individuals, teams and organizations. I believe that everything starts with desire ..

Rotterdam, Netherlands


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