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Pre-Scripting Difficult Conversations is Futile. Do This Instead.

In Which People Are Not Unexploded Bombs

Too Much Planning Is Not Your Friend

When smart, diligent people prepare for a difficult conversation there tends to be a lot of planning, which amounts to a doomed attempt to “pre-script” the exchange.

“If I say this, then she’ll probably feel defensive, so I’ll say something nice before I say the tricky thing. But she might spot that as a tactic, so I won’t say something nice, I’ll just get right to it, and if she gets defensive, then I’ll back off a bit. Or maybe she won’t get defensive! I’ve seen her be reasonable if people really give context, so I’ll start off with a ton of how this is necessary for the company and the team and all that, but that’s a little dry, so I’ll add how much I admire her work on the XYZ project and…”

Our complicated conversation tree

We attempt to build a path through the conversation which will avoid difficulty, emotion, or conflict. If we were to draw it, it would probably look like a rather knotty tree structure, with each branch assigned some probability (“he’ll probably be irritated”) along with our response (“I’ll tell him about the new office”), and then a guess at how that will be heard (“that’ll calm him down”), and then our response (“etc etc”), and on and on.

This planning can go on for hours, days, weeks sometimes, during which the conversation doesn’t actually take place.

If you’ve ever done this, and finally had the conversation, your experience was probably that you were surprised: “It went amazingly well!”, you will say. Or, “my God, that was terrible!”. All your planning went out the window, and what happened, happened.

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The Inconvenient Fact That We Don’t Know What’s Inside People

Difficult conversations are usually difficult precisely because we don’t understand the other person. If we did, the conversation wouldn’t be difficult, even if with a pretty significant disagreement. So basing our approach on the assumption that we do understand the other person is somewhat silly.

This is worth repeating: we don’t know what’s happening inside other people. It takes vulnerability and courage to find out. Once we find out, we can have a conversation. Attempting to finesse the result before we discover the other persons’ state just delays, or worse, indefinitely postpones, having the actual conversation at all.

What we are attempting is essentially manipulation: we are trying to get the other person to a specific result before the conversation has even started.

Why We Try and Manipulate the Result — Fear

Approaching a situation we don’t understand is scary. Uncertainty produces anxiety. In addition, we tend to expect the worst: the other person will break down in some explosive emotional way; they will storm out of the room and quit; they won’t quit, but they will sulk and be unhappy and cause everybody around them to become unhappy and demotivated; they will think less of us, maybe even won’t like us (the horror)!

Much more often than not, the worst doesn’t happen. I can’t persuade you of this in a blog post, because the fear of Bad Things is wired into us fairly deeply, but it is the case that the Bad Thing rarely happens. People don’t like quitting their jobs. People do become emotional, but, you know what — that’s fine. It’s a bit of a mystery to me that we don’t expect strong emotions in our work. The work is hard, intense, consuming, creative, uncertain. Why on earth would we not be emotional?

And emotions are temporary states. They pass. People come back to center. So, sure, maybe you’ll have an uncomfortable twenty minutes. Maybe you’ll have an uncomfortable few days. Maybe you’ll have to come back to the conversation later. You’re dealing with a human being. It happens.

That person is an unexploded bomb! Anything could happen!

People as Unexploded Bombs — A Metaphor

I love those movie scenes where an intrepid disposal expert has to defuse an unexploded bomb. They have to be soooo careful, gently unscrewing the cover, pulling it slowwwwly away, peering inside to figure out the trigger, choosing the right wire to cut (blue! no, red!). It’s tense work.

People are not unexploded bombs. They are not that fragile, and not that dangerous. They are deeply complex. They all love something, usually many things, and they all want something. Usually some of what they love and what they want is present in their current job, otherwise they wouldn’t be there.

In a difficult conversation, part of your job is to find out. If you treat them like unstable ordinance, you won’t.

Photo by Wynand van Poortvliet on Unsplash

What To Do Instead

Say what you want to say! Spend some time practicing, saying it out loud, maybe in front of a mirror, maybe to a trusted partner. Once you’ve said it out loud a few times, you’ll find you can shorten it, get it down to its essence.

Say it in a way which is respectful. But say it.

Then listen, carefully, with the intention to understand. And take it from there. Give up your plans — they won’t help. Be right there, in the conversation.


Our logical mind is not our friend in these situations. It is not possible to map out the ridiculously complicated tree of “what ifs” for an upcoming conversation.

Your truth, clearly and respectfully stated, will start the conversation. Listen and respond with clarity and compassion. You’ll do fine.

(also: if you are a founder, manager or technical leader interested talking about coaching, get in touch!)