The Leaflet #125: good AI writing (it exists), insiders vs specialists, do you have to hire true believers?
The kind of writing task “AI writing” is already really good at
When you’re building projects or running organizations, the systems you need to get money or permission or attention from often want you to write something for them. At least, that’s what their website or grant application form or regulations say.
This is misleading. These systems rarely want “you” to “write” “for” them. They need words from your legal person that reassure their legal person (a lawyer, or the system itself qua legal entity). They need a box scratched in a checklist. They need a step completed in a process. For varying reasons, the checkmark has historically been paragraphs of prose rather than an actual checkmark.
But generating that prose barely counts as writing, in my view. I’m thinking of applications, pro forma legal documents, budget narratives. These are pieces that are supposed to bear minimal traces of the author’s personality or weirdness. They’re supposed to be nearly authorless. That way a system can digest them with minimal friction. That system doesn’t really want to “read.”
Doing this “writing” is often a bummer. It can be an especial bummer for a person who likes writing. The fun and curious and intellectually arresting bits of the job get stripped out.
As it turns out, many of the facets of AI writing I otherwise resent are assets for these authorless assignments. A chatbot writes sections of a grant application, an MOU, and an incident summary better and faster than I do in part because it’s a robot doing it.
-eric
Insider fit beats specialist fit
There’s a new kind of work your team or organization needs to deliver. No one currently on the team owns this kind of work or was originally hired to do it for you. No one on the team has a history of doing this kind of work.
In simplest terms, you’ve got two options: you can get someone you already have to develop a new specialty or you can hire an outside specialist who already has that specialty.
Very often, we see leaders assume that the outside specialist is the right default. They think it’s the smart, professional thing to do and think they should do it unless it’s injuriously expensive.
We tend to push leaders to flip the presumption. Your default should be to hire from the team you already have.
Three reasons we like this as the option you need a compelling argument not to do:.
Trust and context can outweigh the importance of specialist skill. This new chunk of work likely intersects lots of others. Partnerships needs the program team, fundraising needs the founder, government affairs needs everyone. The insider already has relationships and a lived understanding of your culture. The specialist has to spend time building that understanding. (Sneaky and important bit: building the understanding of a new culture and building new relationships within the culture are both skills unto themselves. There’s a good chance your specialist doesn’t specialize in those skills).
Specialists are good at their thing in the contexts where they’ve practiced it. They will inevitably make pattern matching errors. Sometimes they’ll insist on those errors (perhaps because they’ve overlearned lessons from earlier successes). Your org is a new context. Most senior specialists I’ve watched join early-stage orgs spend real time – sometimes as much as a year – unlearning the practices that earned them their title. Sometimes they don’t unlearn at all. Your insider doesn’t carry that baggage. They’re gaining status with their experiments in this new domain rather than risking status they’ve already accumulated elsewhere.
Promoting (or laterally challenging) someone with a new function tells the whole team that this is a place where people grow. Hiring someone from outside, especially a senior person, can convey a different message about the limits on advancement around here. In growing orgs, often this retention-and-promotion story has compounding value that outweigh the near-term value of the specialist skill.
The question is whether learning the work is harder for an inside person or learning the org is harder for an outside person. We’ve often seen that the second is harder, takes longer, and the failures hurt worse.
-ben & eric
Do you have to hire true believers?
Very often, it seems like folks on the team with a chunk of career years behind them have rationally adopted a skeptical, ~political take on almost everything leaders say and do. Their default expectation is that leader talk is lip service and that peer action is some version of self-serving or back-stabbing. At the least, they seem to think, one should always be on guard against these as latent risks.
Yet, the best cultures I’ve experienced have a minimal amount of this anti-social behavior and a commensurate lack of hard cynicism. But it feels unwise to make “ be a true believer” a default requirement for someone to join the team. Cynicism can be toxic but skepticism is super useful.
A suggestion: if you’ve hired a skeptic, don’t make it your goal to persuade them using more and more of your words and presence. You’re just helping them pattern-match you to others who have let them down. It looks like you’re optimizing for optics. And you kinda are.
Instead, do something more straightforward: keep your word. When you hire someone, you’ve made plenty of tacit and overt promises already. Fulfill those. You don’t need to add a bunch more.
-eric & ben
COMPELLING QUOTATIONS
AI chronicler Zvi Mowshowitz on getting AIs to write well:
My guess is that you could, with great effort, create an AI that ‘could write,’ but you would have to make that the deliberate focus. It wouldn’t be a model most people would want to call most of the time. Remember, most good writers are not actually great people to talk to in general and definitely not people you’d hire as assistants.
Philosopher Krista Lawlor on being reasonable:
If you are reasonable, you are open to the possibility that what matters to the other person does matter.
US Secretary of Education Linda McMahon on steak sauce:
A school system that’s going to start making sure that first graders, or even pre-Ks, have A1 teaching in every year, that’s a wonderful thing!
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