CTO dinners

Dinner protocol

One table. One conversation.

A room of CTOs will solve each other's problems by reflex. It feels helpful and it usually is not. Each dinner includes one facilitated conversation, and these are the rules we ask every guest to follow during it, so that people can speak openly and everyone leaves with something they can use. The rest of the evening has no rules.

  1. Rule 1

    One conversation

    The whole table talks about one topic together. No side conversations, so everyone hears everything.

  2. Rule 2

    Stories, not advice

    We share what we did and what happened. Nobody tells anyone else what they should do.

  3. Rule 3

    Nothing leaves the room

    What is said in the conversation stays there, unless the person who said it tells you otherwise.

The evening

How the evening runs

Every dinner is built around one topic and hosted at the home of a local CTO or engineering leader. The rules apply to one part of the evening only: the facilitated conversation, from when the facilitator opens it to when they close it.

  1. Before the dinner

    You get the topic for the evening and the address. There is nothing to prepare.

  2. Arrival and dinner

    Dinner is at the home of a local CTO or engineering leader. Drinks, introductions and food, with no rules. This is the time for the conversations you want to have one to one.

  3. The conversation opens

    The facilitator restates the topic and the rules. From here until the conversation closes, the three rules apply. We go around the table once so that everyone has spoken.

  4. One conversation

    The table picks up the threads from the opening round. One person speaks at a time, to everyone. If a side conversation starts, the facilitator will bring it back.

  5. The conversation closes

    The facilitator ends the conversation and reminds the table that nothing leaves the room. After that the rules are off and the evening carries on.

The conversation

How we talk to each other

During the facilitated conversation there are two ways to respond to what someone has shared: ask a clarifying question, or share an experience of your own. Advice is neither. If you disagree, tell the story that led you somewhere different.

Ask clarifying questions

A good question helps the other person think. It starts from curiosity, not from a view about what they should have done.

  • Keep questions short and leave room for the answer.
  • Start with "what" in place of "why". "Why" puts people on the defensive.
  • Do not hide a suggestion inside a question.
Instead ofWhy did you pick that vendor?
TryWhat made that vendor the right call at the time?
Instead ofHave you thought about just rewriting it?
TryWhat options did you look at?
Instead ofWhy hasn't your team adopted agents yet?
TryWhat has gotten in the way so far?

Share experience

Tell the table what you did and what happened. People remember stories, and they can draw their own conclusions from yours.

  • Speak as "I" or "we", in the past tense, about something that happened.
  • Leave out "you should", "I would" and "you could".
  • Skip the general lesson. Give the specifics and let others decide what applies to them.
Instead ofYou should freeze hiring until the pilot is done.
TryWe paused hiring during our pilot. Here is what happened.
Instead ofMost teams get this wrong.
TryI got this wrong twice before it worked.
Instead ofI would never let agents merge to main.
TryWe let agents merge to main for a month. This is what we saw.

Tone carries as much as wording. A well-phrased question asked sharply still lands as a challenge.

Confidentiality

What leaves the room

People only talk about what is really happening when they trust where it will go. Nothing said in the facilitated conversation leaves the room unless the person who said it tells you otherwise. They can do that in three ways.

The default

Nothing leaves the room

What is said in the facilitated conversation is not repeated outside it in any form, with or without names. Neither is who was at the dinner.

Looser, if the speaker says so

Unattributed

The person sharing can say that something may be used. You are then free to use it, but you do not reveal who said it or where they work.

Looser, with permission

"You can quote me"

If you want to attribute something or make an introduction, ask the person directly. Permission covers only what they agreed to.

Stricter, on request

"This stays at the table"

Anyone can say this before or after sharing something. It is then not raised again once the conversation closes, even with the person who said it.

  • No recording of any kind, by guests or hosts, at any point in the evening. That includes AI notetakers and voice memos.
  • Phones stay off the table during the facilitated conversation.
  • Photos are taken and shared only when everyone in them has agreed.
  • Actual follows the same rules. We do not publish who attended or who said what.

The facilitator

What the facilitator does

The facilitator is there to protect the conversation, not to lead it. If the facilitator interrupts you, it is the protocol at work and nothing personal.

  • Opens and closes the conversation, so everyone knows when the rules apply.
  • Keeps the table on the topic.
  • Brings side conversations back to the one conversation.
  • Steps in, kindly, when a story turns into advice.
  • Makes sure everyone is heard, including the people who speak least.
  • Reminds the table of the confidentiality rule at the start and the end.

Credit

Where this comes from

The format is not our invention. It borrows from two practices that have each worked for a long time.

  • The Jeffersonian dinner

    The format of one table holding one conversation around a topic set in advance is named for the dinners Thomas Jefferson hosted at Monticello.

  • The Chatham House Rule

    The unattributed level, where what is said may be used but not attributed, follows the rule Chatham House has used since 1927.