THE LEAFLET
November 13 2025
ceo & organization at cognates, using alter-egos to deliver feedback, LLMs for summary and structure
CEO & ORGANIZATION AS COGNATES
If you’re like me, the very phrase “strategic planning” gives you the willies. It conjures lengthy, directionless debates, often in the presence of an expensive facilitator/consultant. After all the talk and thin hotel coffee, you have a plan that may be laughably unrealistic, on one hand, or not so different from what you started with, on the other. Both of those are failures.
A thought experiment that can focus your exec team is creating the annual scorecard for your CEO. Sometimes thinking about the future and goals of the whole organization can spiral you out too far. Thinking more narrowly and concretely about measuring the performance of the leader – that one person, making decisions and taking action inside of their one human body over the next 365 days of Earth time – can zap the cloudy, aimless future into a sharp, present picture.
You find quickly when you start on this that there are way more outcomes that one person is responsible for than they can reasonably own all alone. Of course. This is why there are other people on the team. The CEO will often be responsible for managing the people who more directly own and influence those outcomes.
-ben and eric
Read the rest here.
USING ALTER-EGOS TO DELIVER FEEDBACK (TO START)
Sometimes an alter-ego can help you convey a difficult message. The message may be difficult for you; it might be difficult for the recipient. In both cases, the alter-ego sorta dislocates the feedback from you. It can allow you and the recipient to look at the feedback as a distinct, third thing that isn’t telling a story about either of you or your feelings. The alter ego lets the feedback be a thing that can improve the work and doesn’t assign it other responsibilities it can’t carry so well.
A couple of examples:
“Dumb, cheerful guy/gal/person”: Ben will often look at a problem that seems thorny and layered to the leader responsible for solving it. With the benefit of some distance and a lot of pattern-matching experience, Ben can see a relatively simple solution, one that might deliberately hold aside some of the brambly context. Hearing this kind of solution can be hard for the leader enmeshed in that context. So Ben proposes the solution in character, as “dumb, cheerful guy.”
“Savage cuts guy/gal/person”: When I’m editing scripts for Posters, I have a harder time than our lead writer and host does with cutting out material. I fall in love with the research he’s done and the jokes he’s written; I experience some stark loss aversion. But James needs me to hold a high bar for episode quality and duration. Without significant cuts to early drafts, we’d have super-long unfocused episodes that aren’t good. So I become “Savage Cuts Guy” and in the comments on the google doc, propose more dramatic changes than regular Eric ever would.
A better pattern to reach for is one where these personas aren’t necessary, where they take unnecessary time or words, and you can just say the thing directly, unadorned, as yourself. For some amount of time, the alter egos can prove out the safety and utility of the feedback to both of you. Ideally, you get enough reps with this kind of feedback that the alter ego can melt away. You, as yourself, offer the direct, simple solution. You slash the script to its valuable essence.
-ben and eric
Read the rest here.
LLMs for SUMMARY AND STRUCTURE
A common part of the workflow for Ben and me is a long-ish brainstorming conversation. I’m especially enthusiastic about the hazy, conceptual, anything-is-possible part of a project, when we can yammer at each other with a bunch of different ideas. Historically, I’m pretty bad at taking notes on these kinds of conversations and some of the things that seemed especially shiny or promising in the moment slip my mind by the time I need to act. In instances where I have been more disciplined, it takes beaucoup time for me to organize my transcript-like notes into something that’s logical, concise, and easy to act on.
Ben has taught me how to outsource this stenographer-meets-project manager work to LLMs. The basic workflow looks like this:
We have the conversation, usually recording it on Loom. Loom generates a transcript. If you don’t have or don’t like Loom, consider using Zoom or uploading a recording of the conversation to an AI transcription service.
We then upload that transcript to GPT-5 Thinking or Claude Sonnet 4.5 and prompt something like: “Take this transcript and make an organized outline / action plan based on what we discussed.”
I’ve found that this frees up thinking and opens the conversation in the moment, because we’re confident we’re not going to lose things and one of us isn’t participating halfway by trying to play notetaker at the same time.
-eric
Read the rest here.
COMPELLING QUOTES
Novelist Elmore Leonard on revising:
If it sounds like writing, I rewrite it.
Writer Yiyun Li on grief:
What is grief but a word, a shortcut, a simplification of something much larger than that word?
Poet Tracy K. Smith on love:
Is it strange to say love is a language
Few practice, but all, or near all speak?
Keep going, keep growing,
Ben & Eric