How to Talk About What Isn't Working

Most people do not avoid difficult conversations because they lack courage. They avoid them because the last three attempts went badly, and they have quietly concluded that the conversation itself is the problem.

It usually is not. What tends to be wrong is the opening, the timing, or the size of the thing being raised. Those are fixable.

Decide what you want before you open your mouth

There is a difference between wanting to be understood, wanting something to change, and wanting an apology. All three are legitimate. They are also three different conversations, and if you have not worked out which one you are having, your partner will not be able to either.

Before you start, finish this sentence privately: by the end of this, I would like us to have... If the honest answer is “I would like them to feel as bad as I have felt”, that is worth knowing too. It is a sign you need to let some heat off first, perhaps on a walk or with a friend, before anything productive can happen.

Raise one thing, not the pattern

The instinct is to explain the whole pattern, because the pattern is what hurts. But a pattern is almost impossible to respond to. “You never make an effort” invites a defence, and the defence will be a counter-example, and then you are arguing about whether the counter-example counts.

One specific instance is much harder to dismiss and much easier to fix.

• Pattern: “You always put your friends first.”
• Instance: “On Saturday you said yes to football before we talked about the day, and I had been looking forward to it all week.”

The second version gives your partner something they can actually engage with. It also keeps the conversation to a size that can be finished in one sitting.

Pick the moment on purpose

Almost nothing good gets decided after eleven at night, in a car park, or in the ten minutes before one of you has to leave. If the subject matters, say so and schedule it.

“There's something I want to talk about, and I don't want to do it badly. Are you up for twenty minutes after dinner, or would tomorrow be better?”

That sentence does two things. It warns your partner that something is coming, which stops them feeling ambushed, and it gives them a say in when it happens, which makes them a participant rather than a defendant.

Lead with your experience, not their character

The most reliable way to lose the next hour is to open with a description of who your partner is. “You're so selfish about this” is a verdict, and people argue with verdicts.

Describing your own experience is harder to contest, because you are the only authority on it.

Here is the same complaint, opened two ways.

A version that goes nowhere:

“You clearly don't care how much I'm doing around here. You just sit there.”

A version that has somewhere to go:

“I've been doing the evening clear-up on my own most nights this month, and I've started feeling resentful about it. I don't like feeling that way and I'd rather sort it out than keep swallowing it.”

Notice that the second version is not softer in content. It still says: this is unfair and I am angry about it. What it does not do is tell your partner who they are, so there is nothing to defend except the actual arrangement.

Say the thing you want in plain words

A surprising number of difficult conversations end with both people drained and neither of them clear on what was being asked for. Make the ask explicit and small enough to be agreed to.

Vague: “I just want to feel like we're a team.”

Specific: “Could we split it — you do the kitchen on the nights I do bedtime?”

You can want the big abstract thing and still ask for the small concrete one. The concrete one is what gives your partner a way to show you the big one.

Expect the first two minutes to be rough

Even a well-opened conversation often gets a flinch first. People hear criticism before they hear content, and the first thing out of their mouth is frequently the worst thing they will say in the whole conversation.

If you can stay in the room through that opening flinch without matching it, the conversation usually improves by minute five. Useful holding sentences:

• “I'm not saying you did it on purpose.”
• “I know you've had a lot on. I still need to say this bit.”
• “Can I finish, and then I genuinely want to hear your side?”

If either of you is too flooded to think, stopping is not failing. Name the pause and name the return: “I need twenty minutes. Can we pick this up at nine?” An open-ended walkout teaches the other person that raising things is dangerous. A pause with a time attached teaches the opposite.

When it keeps going wrong in the same place

If every attempt at a particular subject ends the same way, the subject is probably not the real difficulty. Something underneath it is — an old injury that never got properly addressed, a fear about the future, a sense of being the only one trying.

That is worth saying out loud, even without a solution: “We've tried to talk about money four times and it's gone badly four times. I don't think money is actually the problem.” And if a conversation leaves either of you frightened, or you find yourself managing your words to avoid a reaction, that is worth talking through with someone you trust or a professional who can give it proper time.

Where to start

Pick one thing from the past fortnight. Not the biggest thing — a middle-sized one. Write down the specific instance, your experience of it, and the one change you would like. Three sentences. Then ask for twenty minutes.

If you would rather see both sides written out before you speak, the Two-Sided Story tool is built for exactly that.