You have rehearsed that conversation in the car and in the shower, and by Thursday it has moved to after the holidays.
After reading this, you will know how to start a hard conversation with words you can say out loud, and what to do with each answer you get.
Picture a man who hears from someone else that his brother sold the family truck. He says nothing for eight months, because speaking up might make it worse. By month eight the silence has already cost him the closeness he was trying to protect. The steps below follow him, and they work the same for a boss or a friend.
1. Decide what you want when it ends
Before you say a word to anyone, finish this sentence on paper: "When this is over, I want ___." The blank holds a request, and a request gives the other person something to answer. For the man with the truck it reads: "I want my brother to know it hurt, and I want us to agree that big family decisions get a phone call first." If you cannot finish your sentence, take what you have to a friend or a notebook first, because the person across from you will hear a list of complaints as an attack.
If you are still angry, wait a day. The conversation needs your calm voice, and your first voice is rarely that one. If the other person has power over you, such as a boss, or controls something you depend on, such as housing or money, get advice from a mediator or HR before you speak.
2. Pick the place and ask for the time
Choose somewhere private where nobody has to leave. Many people find a car or a walk easier than sitting face to face. Skip the holiday table and skip a day when either of you is rushed. Ask for the time by phone or in person, because a text can leave them guessing for hours.
“I want to talk about something that matters to me. Do you have twenty minutes Saturday morning?”
If they ask what it is about: “It's about the truck. I'd rather say it in person.”
3. How to start a hard conversation: open with why you are here
Your first sentence sets the tone for the next ten minutes. Say that you care and say why you are raising it now.
“I'm bringing this up because you matter to me, and I've been avoiding it for too long.”
4. Say the one thing plainly
Use three parts in a breath: what happened, how it affected you, what you are asking for. Include your own part, because it is usually true and it makes it easier for the other person to listen.
“When I heard about the truck from someone else, it hurt, and I went quiet for months, which was my part. I'd like us to agree that big family decisions get a phone call first.”
Bring one subject. The next one waits for another day. For a friend who keeps cancelling, the same three parts sound like this:
“When you cancelled the third time, I felt unimportant. I'd like us to pick a date we both keep.”
5. Stop talking
After your sentence, stop. Let the silence run. Silence often feels longer to you than to them, since they may be choosing how to answer. If it goes on, offer a way in.
“Take your time. I'd like to hear your side.”
I wrote more about that silence in The Pause Before the Answer.
6. What to do with the answer you get
If they agree or open up. Say it back, then agree on one concrete next step with a day attached. Saying it back shows you heard them, and the day on the calendar keeps the agreement from fading.
“Let me say it back: you thought I'd be upset, so you put off telling me. Is that right?”
“Can we try a Sunday phone call for the next month and see how it feels?”
If they say you are right and nothing else. Agreement with no next step often fades. Ask for one small thing.
“Thank you. What's one thing we can each do this week?”
If they ask why you are bringing this up now. Tell the truth in one line.
“Because I've been thinking about it and I'd rather say it than let it grow.”
If they get defensive. Set the facts aside for now and hear their version first; people who see that you are listening tend to defend less.
“Tell me how the sale looked from your side.”
If they answer with a grievance of their own. Agree with what is true, then offer them equal time.
“That's fair, and I want to hear it. Can we finish this one first and then give yours the same time?”
If they go quiet or start to leave. Do not chase and do not add more points. Give them a way back in.
“Let's stop here. Can we pick it back up Thursday?”
If they say not now. "Not now" asks for a different time. Name a second date and stop.
“Okay. Would it be all right if I asked again Sunday?”
If they get angry or cry. Slow down and lower your voice. Raised voices or threats from either of you end the conversation for today.
“Take a minute. I'll wait.”
If voices rise: “Let's stop for today and talk tomorrow.”
If they deny it happened. Say it once and let it stand.
“That's what it was like for me, and I wanted you to know.”
If the answer is no, or they end the relationship. You still said it, and you now know where you stand. Thank them for listening and leave the door open with one sentence. Wait a few weeks before you try again.
“I hear you. If that ever changes, I'm glad to talk.”
7. What to avoid
- Do not text "we need to talk" and then vanish. If you must warn them, name the topic in one sentence.
- Do not use always and never. "You always cancel" starts an argument about the word always.
- Do not bring in other people's opinions. "Everyone thinks you've changed" turns one conversation into a crowd.
- Leave old grievances out of it.
- Do not demand a decision on a big request in the room. Ask for a time to answer.
- Do not keep going once either of you has stopped listening. Close it and name the next time.
- Apologize for your own part, and for nothing else.
8. Follow up the same day and the same week
Send a short message the same day.
“Thank you for talking with me today. I know it wasn't easy.”
Within a week, do the one thing you agreed to do, and check in on theirs.
“Checking in on what we talked about. How's it going on your end?”
A second sitting is normal. If the first one ends with nothing settled, you still spoke, and that counts.
9. When it is serious
If at any point the other person says they want to die, or that they do not want to be here, set the original topic aside. Ask in plain words, "Are you thinking about suicide?", and stay with them. In the US, call or text 988, the 988 Suicide and Crisis Lifeline. If you are the one having those thoughts, the same number is for you. If they have a plan or the means, call 911 and stay with them until help arrives. A veteran can call 988 then press 1, or text 838255, for the Veterans Crisis Line.
If you feel unsafe, leave, and call 911 if the danger is immediate. For domestic violence, the National Domestic Violence Hotline is 1-800-799-7233, or text START to 88788; if you think someone might check your phone history, call from a different phone. For other serious conflicts, bring in a pastor or a counselor, and for a legal or business dispute, an attorney.
The words for the man with the truck take less than half a minute to say. Eight months is how long he waited to say them.
More conversations like this on Next Level Thinkers.
What is the first sentence you would say, and when will you ask for the time?
“Say the true thing kindly, then give the other person room to answer.”