Difficult conversations workshop
Two hours. One name. An invite before they stand.
Independent facilitators invoice every week for a difficult conversations workshop. Managers walk in with a person they have been avoiding and a story wearing a fact costume. They walk out with an ask the other person could repeat, a 90-second opening in their mouth, and thirty minutes on the calendar this week. That is the product. A framework they will not use is not.
Length. 120 minutes including an eight-minute break. If you need three hours, you are stacking therapy onto a skills room.
Room. 6–12 managers or leads who brought one real name on paper. A room of people with no one to talk to is a book club. Reset the chairs.
Product. Name, three facts a skeptic would nod at, one ask, a 90-second opening practiced twice, four bans, a sent invite.
Steal the live kit. Start live · Print their pages · One-page run of show . No account. Not the twelve-minute film.
The 120-minute spine
10 + 16 + 14 + 14 + 8 + 20 + 10 + 18 + 10 = 120. Write before they talk. Phones in a bowl until the send block. You keep time. The hallway is not a tenth segment.
| Time | Min | Segment | Say | Do |
|---|---|---|---|---|
| 0:00 | 10 | The name you brought | Two hours. You leave with one conversation you will have this week. Fifteen seconds each: the name, then what you have been postponing, in one breath. Do not solve yet. | Board: NAME. ASK. THIS WEEK. Scribe first names. No name, they borrow one or they are a spectator. |
| 0:10 | 16 | Facts versus the story | “They do not care” is a story. “The Friday deck was late three weeks, and they did not tell me until I asked” is a fact. Left column: three facts a skeptic would nod at. Right column: the story, three sentences. You may only bring the left column into the room with them. | Silent 8. Pair 5: star one line that is still a story. Rewrite 3. Interrupt adjectives posing as facts. |
| 0:26 | 14 | The ask | If you cannot write the ask, you have a complaint. Complaints get postponed. Asks get dates. One sentence they could repeat: start, stop, or change, by when. “I just wanted you to know” is not an ask. | Silent 10. Neighbor reads the sentence aloud, 4. If they stumble, rewrite. Two asks means two meetings. |
| 0:40 | 14 | The opening ninety seconds | You get ninety seconds before they start defending. Purpose. One fact from the left column. The ask. No sandwich. No “do you have a minute.” No always-or-never. | Silent 8. Neighbor reads it to the writer once, 4. Cut 2. No group performances. |
| 0:54 | 8 | Break | Water, bathroom, stand up. Do not start the practice in the hallway. Do not coach your neighbor. | Visible timer at 8. Restart on time. Late people join the next pair. |
| 1:02 | 20 | Practice, round one | Pairs. Speaker uses only the ninety seconds they wrote. Other person: busy, a little guarded, not a villain. If you hear a sandwich, an always, or a second ask, stop and go back. | 8, swap, 8, 4 to write the line that opened and the line that died. No circle-share. Odd person rotates in as the other person. |
| 1:22 | 10 | What never belongs | Four bans. I start: the compliment sandwich, and always-or-never. You add two. If it needs a witness or a paper trail, it is a different meeting. | Keep four. Photograph. They copy and star the one they have been stuffing in. |
| 1:32 | 18 | Practice, the postponed one | Same pairs. This time it is the person they named. Opening, one fact if they ask why, the ask. If you apologize more than once, start over. | 8, swap, 8. Last minute of each block is the written ask. No third round. No group debrief. |
| 1:50 | 10 | Book it this week | Thirty minutes with the person you named. This week. One-line purpose on the invite — not the whole opening, not “quick chat.” We do not leave with “I should.” | Phones may come out now. Watch for unsent drafts and for “sometime next week” with no day. End at 120. |
The 90-second opening they actually say
Most postponed conversations die in the first minute because the speaker sandwiches, asks them to guess, or starts with the story. Write this on the chairs’ paper. Three beats, this order.
Purpose. Why we are talking, in one line. Not “do you have a minute.”
One fact. A date, a number, a sentence they said, a thing that did or did not ship. A skeptic would still nod.
The ask. A sentence they could repeat: start, stop, or change, by when.
Example, not a script to photocopy: “I asked for this time because the Friday client deck has been late three weeks in a row, and I found out when I asked. I need you to own that deck — in my inbox by 3 — and to tell me the same day if it will slip.”
Pre-work, or do not run the room
Send this 48 hours ahead. Twenty minutes on their side. Paper, not a tab.
- The person they have been postponing. First name is enough. Role if they cannot write a name.
- Three facts a skeptic on their team would still nod at.
- What they want the person to do differently, in one sentence. If they cannot write it, they have a complaint, not a conversation.
If someone cannot name a person, they tell you by noon the day before so you can reset the chairs. Partial attendance is survivable. A spectator with no name is not — they will turn the practice into commentary.
What never belongs in this conversation
- The compliment sandwich. They will only hear the bread, or only the meat, and they will not trust either.
- Always and never. You are handing them a story to fight instead of a fact to answer.
- Surprise performance news. If it needs a witness or a paper trail, it is a meeting you are afraid to put on the calendar.
- Other people’s gossip. You are not a hallway. If a third person is the point, they should be in the room or in writing.
- A second ask. You will get neither. Book a second block.
- “I just wanted you to know how I feel.” Feelings can live in the purpose line. They are not the product.
Keep four on the board. Photograph before they come down. The rest is a different room.
Mistakes that eat the two hours
- A lecture on psychological safety. They already know they are allowed. They do not have sentences. Write the sentences.
- Group share after practice. The notes are the debrief. A circle-share turns a skills room into a story hour and you will overrun the send block.
- Letting the hallway start round one. The break is bodies, not content. If a pair runs it in the corridor, send them out of the building.
- Skipping the calendar. A practiced opening with no date is a better complaint. The invite is the product.
- Two asks, or an apology loop. Start over. Thursday will not give them a rewrite.
A few lines you can actually say, as the facilitator
When someone has no name
“Borrow one from the side list or write a role. If you sit this as commentary, you are a spectator and I will treat you like one.”
When a “fact” is an adjective
“Checked out is a story. Give me a date, a number, or a sentence they said. If a skeptic in this room would argue, it is not a fact yet.”
When they want to process instead of write the ask
“The ask is a sentence they could repeat. If you cannot write it, you do not have a conversation. You have a complaint. Complaints get postponed.”
When practice slides into a sandwich
“Stop. Purpose, one fact, the ask. The valuable-and-also line is a ban. Start the ninety seconds over.”
The table on this page is the paper version. The console holds the clock, the talking points, and the chair prompts while you look up. Start live · print their pages · print the one-page run of show. See also the 1:1 agenda for new managers, the facilitator agenda template, and how to time a workshop.