Difficult conversations

How to plan a difficult conversation

Most hard conversations go wrong in the first minute. We open with a judgment, and the other person defends themselves instead of listening. This approach helps you plan words the other person can actually answer, and decide before you start what you will do after they answer.

What it gets you. Plan what to say in a way the other person can answer. Before you start, decide what you will do after they answer.

Start with what happened

Begin with one thing that happened and how it affected you. Leave what you think they meant until later.

When it helps
You expect the other person to get defensive quickly.
Where it stops
Careful words do not guarantee a fair answer. If the conversation could be unsafe, get support first.
For example
Say “the deadline moved twice and I lost my weekend”. Do not say “you are careless”.

Ask for their side

Ask how they saw it, and let them finish. You are checking your facts, not waiting for your turn to talk.

When it helps
You are already sure you know why it happened.
Where it stops
Listening does not mean agreeing. You can hear them out and still keep your limit.
For example
Ask what that week was like for them. Then repeat back the part you did not know.

Ask for one clear change

Say exactly what you want to change. Make it clear enough that they can say yes, say no, or offer something else.

When it helps
You know something has to change, but your request is still vague.
Where it stops
They can still say no. A clear request does not guarantee a yes, and you do not have to keep pushing.
For example
Ask for a short written update every Friday. Do not just ask them to “communicate better”.

Say what you will do

Set a limit by describing your own actions: what you can take on, and where you stop.

When it helps
Someone keeps asking you for more and more.
Where it stops
A limit is about what you will do. If you use it to control what someone else does, it becomes a threat, and they will hear it as one.
For example
Say which of this week’s tasks you can finish. Then ask which of the others should wait.

Pick the right time and place

Before you bring it up, decide when, where and how you will talk, and who else will be there. These choices matter as much as your words.

When it helps
A rushed or public talk would hide the real point.
Where it stops
Private is not always best. Some things should be put in writing, or taken to HR or a support service.
For example
Ask for a short meeting with time to talk it through. Do not bring it up at the end of a busy one.
An example, worked through

A colleague keeps moving deadlines at the last minute. You have lost two weekends this month.

  1. Start with what happenedOpen with the facts: “The deadline moved twice this month, and both times I worked the weekend.” Leave out what you think it says about them.
  2. Ask for one clear changeAsk for something they can say yes or no to: “Can we fix the date by Wednesday, and flag any change by Thursday noon?”

One next stepBook twenty minutes on Monday morning. Do not raise it at the end of Friday’s meeting.

In the Counsel app, you describe your own situation and choose this approach. It uses the one or two principles that fit what you wrote, and ends with one next step you can save.

Then practice the talk

Know what to say? Say it once before it counts. In nineteen practice talks, a mentor plays the other person and a coach steps in when a line slips. Start with asking for a raise, telling your boss you’re overloaded or telling your partner you’re not happy.

Try it on your situation

Difficult conversations, applied to what is going on for you.

Write it the way you would tell a friend. Leave with one clear next step.

Or ask the mentors

Prefer several views to one line of thinking? These mentors often read this kind of situation well. See all sixteen.

Other approaches

These principles were written and reviewed for Counsel in plain language. They are not quotes from a book. Counsel is for thinking things through. It is not therapy, and not medical, legal or financial advice.

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