Common mistakes when having risky conversations
- Mar 13
- 5 min read
We’ve talked about it before, risky conversations ain’t easy. We know they’re worthwhile because they can help us build trust and gain more accurate views of the people we hold relationships with but don't always disagree with.
So why don’t all (or even most) risky conversations feel like they’ve built trust and mutual understanding? How we show up in risky conversations can often lead us into ruts that are tough to recover from. Let’s unpack four of these mistakes that are very common
First mistake: Kicking off with a hot take
You’re scrolling through your news feed and come across a headline that makes your eyes roll. You blurt something out in exasperation, even though your brother, who couldn’t be more different than you, is seated on the other side of the coffee table. And the race is off! He’s not going to let that comment slide. You’re in a risky conversation now.
Maybe your scenario isn’t this careless. You’ve learned not to just let comments casually slip. Maybe you tactically brought up an opinion where you were positive there would be shared ground. You were so sure he couldn’t disagree with you on this, but he goes and surprises you.
When we kick off risky conversations by simply stating an unpopular opinion it can immediately put the other person on edge. Survival mode has switched on in their brains and they are figuring out if they are going down the path of fight, flight, or freeze. If they do stay engaged, they are already assuming the defensive posture. Without sharing a thorough viewpoint and how you got to it, you’re defending it against criticisms that aren’t even accurate or applicable.
Second mistake: We tell them what they should believe
When they come back at us with their point of view, the most common response is for us to shake our heads and reassert our point of view. When we do this we are essentially telling them what to believe. I don’t know about you but this has rarely worked on me. No one likes to be told what to believe. And yet we assume that if we can make it clear, a lightbulb should click for the people we disagree with and they can get on board.
This fails so easily because when we disagree we’re each walking into a risky conversation with different sets of values and frameworks for logic that only holds up our point of view. Imagine if you built a structure out of LEGO® bricks and they built a structure out of K’nex®. You try to take a few LEGO® and graft it into their structure, it’s not going to stick. The same thing happens when they try to adjoin their K’nex® to your LEGO®. The two frameworks behind what we believe work individually but are not compatible.
We get into this pattern of insisting at one another or what we at the School For Risky Conversations like to call a ‘reasoning rut’. Our conversation partner’s reaction when we do this, tell them what they should believe, is to focus on what we got wrong. They aren’t doing any introspection on their own logic and framework, they’re just trying to break down ours and we reciprocate in kind, as if we’re Godzilla vs. Kong.
Third mistake: We assume we understand their point of view and how they got to it
Let’s say your brother was the one who was scrolling and made the off-hand remark that got this risky conversation started. We jump in with our perspective and back to Godzilla vs. Kong.
Before we’re very far into the conversation we assume we know why he made that remark, we know all his views around that topic, and why he cares about this topic. We know because we’ve seen exactly three minutes and eighteen seconds of news clips from his preferred station in the last month. We’ve seen the tweets from the senators that rep his party that make our blood boil. And we saw that one gif he posted on facebook before we blocked him out for 30 days because honestly, you just couldn’t deal with that right now on top of everything else.
We feel like experts on the opposing point of view because we’re inundated by clickbait and outrage posts that compel us to experience strong emotions. We use that as a basis for assuming we understand someone else’s point of view before they’ve even fully expressed it themselves. We assume we hold the same definitions for the politically polarizing terms we both use. We don’t need to seek clarity or ask questions because we know exactly what they’re like. We stick a label of too immoral, too close minded, or too much of a sheeple, on them instead of recognizing that they might hold a more complex view of something that can fit into an 280 character post.
Fourth mistake: We don’t have a goal for our conversation (or at least a good one)
The conversation is off, it’s a little ugly, and we don’t know where it’s going or when it will end. That’s because we don’t have a goal for the conversation, at least not a good one. So we talk in circles until someone taps out.
In a dream world, your brother would realize the superiority of LEGO® over K’nex®, go Godzilla with you on whatever is left of his framework, and buy the two of you tickets to LEGOLAND® for the following weekend. But that’s not realistic.
Winning feels great but it’s a TERRIBLE goal for a conversation. It can feel rewarding in the short term to think you’ve out-debated and outsmarted the other person but, that’s probably not what actually happened. In all likelihood, they hit a wall and switched their survival tactic from fight to flight. They’re done talking with you about this or anything else risky, for a while. You’ve created a wider divide and they’re going to go seek validation from the people who already agree with them. Winning isn’t just a bad goal, it’s an anti-goal.
We also have to recognize that we can’t force people to change, especially not in a single conversation. If we’re being honest, the work we put into trying to change them is exhausting and not worth our time and energy. You may not be able to get them to join team LEGO® but you can build trust, understanding, connection, and over time build an off ramp for them. They might choose to take it, they might not, but it has to be their decision.
As Adrienne Maree Brown says:
Change can only move at the speed of trust.
If they ever decide to make a serious change to their opinion, they will need your support. And it’s important to remind ourselves, we don’t have to completely convert them to impact how they view the world around them. When we can avoid these pitfalls in conversations we see them as less unreasonable and they see us as less extreme. When we can avoid writing each other off, there’s always hope.
If you’re interested in more tactical ways to avoid these pitfalls, we highly recommend our two-class session, the Official Guide to Risky Conversations which takes from starting a risky conversation through to how we respond in risky conversations.
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