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More Reasons to Have That Hard Conversation

Your Brain Is Not On Your Side

Joe Dunn
5 min readFeb 23, 2020

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Why Hard Conversations Are Hard — Short Version

I’d say the single most frequent issue that comes up in my coaching practice is the Hard Conversation. Perhaps a founder needs to reset the relationship with their co-founder; maybe a VP needs to be really clear with their GM that you can’t ship a product earlier with fewer people; or a Head of Product and Head of Engineering finally need to have that come to Jesus meeting.

The details (and the stakes) vary, but in the end we come to: “there is some really hard stuff I need to say, but I can’t find a way to say it”.

I’ve written before about what’s happening here. Telling another human being something that you feel may fracture the relationship is inherently scary. We are social beings. We feel social rejection almost as deeply as we feel physical pain. The Hard Conversation risks (in your mind) you causing the other person to feel rejected. You feel you are going to hurt them. You don’t want to.

And then there are the possible consequences: you Fear of the Bad Thing. They will quit, or be demotivated, or decide to reject you, hurt you.

“Worry is a way to pretend that you have knowledge or control over what you don’t–and it surprises me, even in myself, how much we prefer ugly scenarios to the pure unknown” — Rebecca Solnit

Often the Fear comes from a chain of Bad Thoughts: “if I tell X — a critical engineering person — that their behavior is bad for the team, they will quit”; “if they quit, the rest of the team will be demotivated”; “ if the team is demotivated, more people will quit”; “if they quit, it will be hard to find new people who are good”; “my company will become grey, staid and boring”; “I will end up a failure…”

So your brain, in attempting to be on your side, keeping you safe, is not doing you a favor. It’s telling you that your career, often your identity, is riding on this one conversation. In other words, you will be very unhappy. Your brain is almost certainly wrong.

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Affective Forecasting: We Don’t Know How We Are Going To Be

It turns out we have evolved a mechanism which doesn’t help us here.

Affective forecasting is the ability to predict our emotional state at some point in the future. We are bad at it. (The psychologists Timothy Wilson and Danial Gilbert published the definitive work on this in the early 2000s). We overestimate how intense our unhappiness will be and how long it will last when we experience breakups, job losses and illness (impact bias). We are pretty sure that good events (a windfall, a new partner) will change our life permanently for the better. Science (as well as folklore, of course) says it won’t.

“Our ability to simulate the future and to forecast our hedonic reactions to it is seriously flawed, and … people are rarely as happy or unhappy as they expect to be” — Daniel Gilbert

We also feel that keeping options open will make us happier. Nope. Once a decision is firmly made, we start to build meaning around it and move on. We come to terms with it. When the options remain open, we worry, fidget, can’t organize our happiness around it.

We weigh potential losses more heavily than the corresponding gains, which means we forecast poorly: we feel that a loss (“X will quit!”) will affect us more than the happiness we would gain in the alternative (the team starts to function properly).

So. You think if you have the conversation with X they quit and there will be a disaster and you won’t be able to cope. Probably you’re wrong all counts. You also think that if you continue in the current situation of keeping your (and X’s) options open, it will feel better than if you make a decision and have the conversation. You’re probably wrong about that, too.

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Have the Conversation

Humans are successful in groups because we share our truths: what we know, our experience, our ideas. The Difficult Thing will remain in front of you unless you have the Hard Conversation, and the likelihood of you overall success will be diminished, because you have not shared what you really think, and you can’t cooperatively solve the issue.

Your ability to predict the results of the Hard Conversation and the effect on your future happiness is poor, and biased towards the status quo, to staying quiet, saying nothing.

Take a good look at the Hard Thing you fear will happen if you have the conversation. Step outside your fear and look at it: will it really happen? and what if it does? what will you do the day after? Your life won’t be over, and it’s pretty unlikely your job will be, too. A lot of things will turn out to be good, and supportive on that day. You just don’t see them yet.

Take a look at some tools: Radical Candor (disclosure — I do work for the Radical Candor group), Crucial Conversations. People have been here before you, and their experience can help.

We have evolved strong mechanisms to avoid hurting ourselves and others. This is a good thing. But very likely they are turned up too high, and you are worse off in the status quo than you would be after the conversation (and, yes, there is a caveat: all the science is statistical, we’re talking about likelihoods here, not specifics).

Be wise and skillful, make your judgements whilst understanding your biases. Be compassionate (to yourself, and the other person), and have the conversation.

(If you are a founder, manager or technical leader and would like to talk further about decisions, difficult conversations or any other leadership topic, get in touch!)

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Joe Dunn
Tech People Leadership

Executive coach, working with execs and technical leaders in high growth companies in San Francisco. Ex Engineer, VP Eng from way back.