How to manage a difficult conversation

The art of creating connection despite a controversial topic or strong differences of opinion

I don’t know about you, but as I try to understand how to bridge the gaps and make connections with people who hold opposite views, I can easily fall prey to listening and losing the gumption to press on with my own viewpoint. Too much or too little and the exchange dissipates or disintegrates. It’s a balancing act to hold a strong opinion and learn to understand, if not accept, someone’s contrary viewpoint. Insofar as you are reading this Dialogos and wish to explore how we can engage in more meaningful discussions and debates, it’s incumbent on us all to make certain efforts, look at how we can adapt, rather than focusing on how the others should change or relent. I’m not proposing we all acquiesce to the other’s perspective, but if we could spend more time on learning about and understanding the other person’s viewpoint, without jumping in with immediate judgment, there’s a chance we may yet find some common grounds. But it’s a tango for two and, ultimately, both sides need to make an effort.  

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I have participated in and listened to many arguments over the years. I can hardly claim to be a perfect example of how to argue. I am not a negotiator nor a seasoned debater. However, through my experience and having studied deeply the art of conversation, I have come to understand how to enter a difficult conversation such that it goes as best as possible. What do I mean by “difficult”? I divide them into two sorts. The first is where the subject itself is tricky or sensitive. It’s the kind of subject where people can get very quickly heated. An example in many western countries might be around abortion rights or gun laws. The other example is when two or more individuals have opposite entrenched views on a topic in which both have an emotional attachment. In such situations, there are many barriers to allowing a connection to happen. As in figure 1, these can be the different, subconscious fears we harbor, more or less conscious biases, our past experiences, our beliefs and convictions, and so on. To the extent we are aware of our own baggage, this can help to surpass the barriers. However, it also depends on your sparing partner’s attitude.

Figure 1 - Conversations on Hot Topics

One of our challenges is having good examples for public consumption of heated debates that are well handled. On the one hand, when the subject is explosive, the Internet has a way of distorting or gaslighting content. If good examples – from which we can hope to learn -- are hard to come by, that’s because it’s very difficult to do. On the other hand, many of these heated exchanges lead to nothing. Especially when the conversation borders on highly sensitive, emotionally charged topics, there is inevitably a challenge in remaining present, understanding the dynamics, keeping the arguments in mind, holding your own emotions in check, and fully appreciating what the other person is saying and/or feeling.  At the core, it’s about knowing what kind of posture you have going into the discussion. Is it about ‘winning’ or convincing? Or is it about learning and co-forming a new understanding? The further apart and more entrenched the positions, the more challenging it is to hold a constructive dialogue. And the tighter the channel through which a connection (“the vortex”) can be made.

Figure 2 - The Vortex of Connection

So, how does one go about dealing with a difficult conversation? How does one expand the channel for a better connection? The short answer is that it isn’t easy.

Setting the context

Often times, an argument seems to come out of nowhere. Have you been at a meal or in a meeting and been surprised as an argument erupts in the middle of what was otherwise a reasonably relaxed atmosphere? In these situations, there is no time or option for setting of rules of engagement. We go into these exchanges with our repertoire of thoughts and skills and, typically, our emotions run less controllably. This type of spontaneous outbreak rarely has an explicit objective, except that each side is likely seeking to beat down the other. It sort of feels like the wild west, where anything can happen. I believe that there are two very important levers for holding a difficult conversation, noting that nothing guarantees success (because that would sound contrived, in any event). The first is whether the conversation is being moderated. For example, if the discussion breaks out at a dinner table, will someone else take the role of overseeing the ebb and flow of the conversation, ensure that all parties get airtime, and help spot the patterns or misunderstandings? The second lever is whether the conversation is being (knowingly) recorded. In other words, is the debate (or could it be) for public consumption? The RECORD button has a strong effect on the tenure of the chat, bringing the public into the discourse and providing an external perspective, if not judgment. This creates the following Difficult Conversation Matrix.

Figure 3 - The Difficult Conversation Matrix

In this matrix, the un-moderated, non-recorded conversation typically has the greatest potential to run wild. If it’s moderated but not recorded, depending of course on the moderator, there’s a chance it will be tamer. If it’s recorded, but not moderated, the key question becomes who or how it is being recorded. Specifically, who is the host? Where will the conversation will be published? In my experience, the chances of having a more compelling debate is generally greatest when it is both appropriately moderated and recorded.

The power of the record button

I’ve been hosting a podcast on which I have done well over 600 episodes (in French and English). I’ve also been interviewed on several hundreds of shows over the years. What I’ve observed is how incredibly powerful the record button is. When you’re speaking while the red “recording” signal is flashing, you know that what you’re saying will be put out there for all to hear. While it may not be available forever, unlike a book for example, the fact that it remains available – “on the record” as we say – is impactful. Just because it’s recorded, however, is no guarantee of a successful conversation. For starters, what does success look like? Or, to quote Bret Weinstein, is it productive? In a 2-hour vidcast hosted by Bret Weinstein on his Dark Horse podcast, he invited Robert Wright (author of Nonzero and The Moral Animal) to ‘have it out’ over a set of barbed public exchanges (tweets) they had had. This was an un-moderated discussion. As far as I was concerned, it wasn’t a pretty example. I felt that Bret, as host and thus ‘running the show’, was a bit of a bully. He used snarky terms like “cute” and regularly answered Wright’s question with a question, a well-known Socratic technique. In the end, I was not satisfied as there were too many different doors opened that rendered the debate too open-ended. There was a butting of heads with little conciliation. As the vidcast ended, Weinstein made a good point after Wright offered to have Weinstein in turn as a guest on his Nonzero podcast. Weinstein asked about whether hosting conversations with all views on display is productive? How does one gauge the success of a debate, if not by the number of up and down thumb votes? There’s no really satisfactory answer to that question, especially since the platform on which it’s published will inevitably contain a bias. If you watch this Weinstein/Wright discussion, I was certainly struck by how Weinstein keeps a level tone with his grave voice.

Having the mindset

Some people are far better equipped than others to enter into a conflictual conversation. Knowledge (with an on-tap memory) is a powerful tool. If you have a full grasp of the facts – even more impressively, when it’s on both sides of the argument – you are well positioned to state and back-up your position. But the question comes back to whether the purpose of the conversation is to win or to co-form? What’s your mindset coming into the discussion? Are you willing or seeking to meet, beat or grow with the other person? The key point is whether you are set on promoting your point of view or you are willing to listen and learn, with the potential to adjust your own perspective?

Creating debate

As I am writing about improving our abilities to hold more meaningful and robust conversations on difficult topics, I am allowing here for some prescription. And to extent there’s room for preparation, there some useful ways to create the space to hold the debate. If you’re wishing to up your game in having civil and vivifying conversation, let’s start by looking at what we can do on our side.

How to keep it civil?

How you go into the discussion is key. For this piece, I’m going to provide some guidelines for when you are having a difficult conversation on the fly. In other words, you’ve got a particular topic in mind that you know is high in priority for you. It could be that you hold a position that is controversial, or the subject matter is, by definition, sensitive. In all cases, it’s good to consider what are your expectations for the discussion? What are you wishing to achieve? Do you have clear (and even possibly shared) objectives? The second consideration is where and how you plan to hold the debate or launch the discussion. The context is important. Of course, you can’t plan everything. An argument can just erupt (as described above).

Things you can do on your own – LOFACC’R

• Link – be explicitly aware of your personal attachment to this subject

• Objectives – be clear at least to yourself what are you wishing to achieve

• Factual – brush up on your facts and sources

• Clarity – express your ideas clearly, being aware of your emotions

• Concision – practice brevity, to keep your arguments tight and to allow the other person to speak

• Reformulate – active listening should include, whenever possible, reformulation of what you heard the other person say, without being judgmental (or worse, adding snarky comments!)

Time, Gentlemen!

When you hold a space for a conversation that becomes testy, time (not to mention the timing) is an important factor. It may be counter-intuitive, but it can be a good idea not to have an exact time at which you expect to end. I’m not calling for an endless discussion, but it’s generally better to allow the time for the conversation to evolve and for each to feel that there’s no pressure (i.e. no deadline) on having to ‘get in’ all one’s arguments.

Things you can work on in advance with your ‘adversary’

To the extent you’ve identified an individual with whom you would like to have a debate, the nature of the preparation changes. Have you discussed together what are the objectives of holding this conversation? Who will be host? Where will you host it? What format will you use for the conversation? Will it be moderated or not? Length of time allocated? Will you have a timekeeper or not? Will it be recorded? What agreements do you have in terms of publication (including permission or not to approve and/or edit)? The more formal the format, the more unnatural it becomes.

Opening the pathway

Figure 4 - Opening the pathway for connection