Have difficult conversations

Despite all the excuses you'll make for avoiding them

Photo by Hans Heap on Unsplash

This one I know, but I still struggle to follow …

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Difficult conversations

It is astonishing how resistant most of us are to talking to people about difficulties we have with them—or to having any difficult conversation. We worry it’ll go horribly wrong and leave things worse than they were, so we say nothing (or, worse, complain behind their backs). Sometimes the problem does go away. But often it festers, and the consequences of that can be a car-crash. If we do try to raise a problem with someone then, when we’re not practiced in doing that, we’re nervous and self-conscious and it comes out wrong—reinforcing our avoidance next time.

Disagreements aren’t things to be navigated around: they’re great. Opinions are sincerely held and working through differences grows teams, improves decisions, and brings people closer together. You don’t always have to agree: you just have to listen, think, and have your own perspective heard. Only then can you genuinely sign up to a decision that may not be the one you’d have made. It ain’t easy, but this calls for a culture that encourages respectful conflict. (There’s more on this in a wonderful, short book by Patrick Lencioni called The Five Dysfunctions of a Team: A Leadership Fable.¹)

So Thumper, the baby rabbit in Disney’s 1942 Bambi, was wrong to say “If you can’t say something nice, don’t say nothing at all.” It would have been less cute, but he should have said “If you can’t say something nice, say it nicely (and be damn sure your motivation’s good).”

There are cultural differences—I’m sure I wouldn’t find this quite as uncomfortable were I not English²—and nice people often find the necessary frankness particularly difficult. The problem’s everywhere: I’ve seen it as much in pugnacious lawyers as in GPs. Yet there are some, often the most kind-hearted souls and even some who are English, to whom this comes naturally, doing it with assurance, grace, and good results.

Here are the rules they follow. They’ve become a sort of preparation checklist for me.

The rules

a) If there are concerns about someone, it’s in their interests to know, and it’s therefore someone’s duty to tell them.

If you have a colleague who’s driving you up the wall, they’re entitled to a mature and respectful conversation about it before the situation explodes, or you unwittingly make the atmosphere uncomfortable for them. (We’re most of us easier to read than we think.)

If you manage someone and you have concerns, they’re entitled to the opportunity to do something about it long before anything disciplinary happens.

And if you have a trainee and you have concerns, they’re entitled to the opportunity to do something about it long before you write a report at the end of their time with you.

b) If you’re stressed, first sort yourself out.

If you’re stressed, your perspective’s unlikely to be fair, and you’re at real risk of handling this in a way that worsens the situation. Be honest with yourself about how you are and where you’re coming from and, if something’s amiss on your side, sort yourself out first.

c) Begin with the intention of doing this gracefully, and of learning from the conversation you’re going to have.

Be calm, open-minded, and positive. You’re likely to hear unexpected truths. Allow that you may be part of the problem. On occasion, we all are. Remember that strengthening the relationship, not winning (whatever winning would mean in this situation), is usually the best result.

Remember too the principle of charity: the duty to give people the benefit of the best possible interpretation of what they’re saying or doing.³

d) Chew it over first with someone whose objectivity you trust.

This is especially important if you’re feeling frustrated or resentful, or if someone’s pressing your buttons. Consider your motives.

e) Prepare.

Think in advance about what the point is, or the points are, that you want to raise. Think about any important specific examples: you’ll almost certainly be asked for them. Make sure you’ve got your facts right, and that your evidence isn’t cherry-picked.

Consider, too, anything that, in your darkest moments, you may think, but that you must never say. If there’s any risk of your going into this wanting to score points, you’re not in the right frame of mind to do it.

Think about what your opening words will be, so you don’t become flustered from the start. You’ll need to hear the other person’s perspective, so a question can be a good opener. “I’m a bit concerned we’re not working together so well. How do you feel about it?” “I’ve noticed a recurring disagreement we have, and I wanted to hear your point of view.” “Something that happened in that meeting this morning … Are you someone who likes feedback?”

Think too about the words you’re going to use to describe the problem. If you aren’t clear and candid about it, the person you’re talking to won’t get it. But don’t write a script: you need to be yourself.

Think about what an ideal outcome would be. But this will be a conversation. So, unless there is only one realistic outcome—in which case you’ll need to be honest about that—be prepared for things to go in unexpected directions.

f) Make time, and do it somewhere appropriate.

Don’t do this when you’re in a rush. It may take several times longer than you think possible. And it needs to be at a time and in a place that’s right for the other person, too—unlikely in front of colleagues.

g) Be frank about the problem.

The urge can be overwhelming to sugar-coat the problem. But that’s not fair, because it makes your point unclear. Gird your loins and be candid. If you’re not, expect no improvement.

Like sugar-coating, the shit sandwich is a metaphor for an approach to giving people negative feedback: say something nice, then the criticism, then something nice. It’s a terrible approach, confusing people with distracting information.

What does often help is to describe, fairly and objectively, what you’ve observed—not faults—and how you or others have felt. That means “You said this and, when you did, I felt ….” Avoid “You made me feel …,” which is manipulative. (And remember, It’s the reaction, not the stuff.)

h) Convey concern, kindness, and a desire to work this out with the other person.

i) Don’t throw your weight around.

… even if you’re the boss. There are respectful, courteous ways even of laying down the law.

j) Spend at least as much time listening as you spend speaking.

Don’t make assumptions about their perspective. Ask about it. Then listen.

k) Be open to changing your perspective on the problem.

l) Raise nothing extraneous in this conversation, or the point you want to discuss will be lost.

m) Look for shared solutions, plans, ways forward.

Seek out points of agreement, shared concerns, and things you can build on.

n) If it goes wildly wrong, abort—and then make a rescue plan.

One rescue plan when it becomes unexpectedly awful is to involve someone else, preferably someone who has the confidence of both of you.

o) Afterwards, take opportunities for normal, friendly communication.

Dissolving any awkwardness relies partly on you.

p) It’s harder, but probably more important, to do this with your equals than it is with people you supervise.

q) For most of us, having these conversations gracefully takes practice. Start practicing.

1. San Francisco: Jossey-Bass, 2002.

2. And it’s interesting that, of all the places in the world I could have chosen for an extended work adventure, I picked Canada: a stereotype of Canadians, with some justification, is that they’re just so nice to everyone, sometimes at the cost of good communication.

3. Blackburn, The Oxford Dictionary of Philosophy.