Questions worth exploring with a prospective senior hire
In senior hiring over the years, I keep seeing that leaders tend to reprise the locally shaped roles they’ve held before. Somewhat counterintuitively, they even do this in cases where they struggled or failed in those prior roles. I’ve done this, too. Despite ourselves, we try to do again what we have already done.
So one useful goal for an interview with a senior candidate is something like “identify the weird geometry of this person’s recent leadership work” because chances are they’re going to force that geometry on your organization / their role at your organization, even if it’s subtly and over time rather than all at once. It’s hard to recreate oneself for a new context, especially once you’ve logged 10-15+ years in a career.
Similarly, accomplished, senior folks will have schema for how a professional, well-run effort operates. They will expect that your organization will have/offer xyz conditions or supports by default. Part of your team’s core strategic bet or cultural weirdness/beauty might be a deliberate choice NOT to have/offer xyz.
So it’s good for you to flag these potentially aversive, dealbreaking conditions and then ask about their past experience working within similar conditions. A risk for both sides is a faulty pattern match fueled by shared desire to achieve a match. A scrappy entrepreneurial person takes a job built for a steady technician (or vice versa) and everyone is dissatisfied.
-ben and eric
One way to use AI and talk about it with your team
AI polls remarkably poorly. Data centers in particular have become the rare contemporary issue that earns bipartisan scorn. So you may manage a team of folks who sit somewhere between wary of- and outright hostile to- use of AI at your workplace.
An approach that might cut through the angry politics and shaky reporting on this:
Well-deployed, AI tools can protect human judgement. That protection comes from taking on the tedium that normally gobbles up human time and attention. The tedium isn’t usually what your wonderful people have gotten into the game to do. Smart hustlers find ways to get relatively good at that tedium; they build workarounds, they hack together google sheets, they make a template where there was a mess. But smart hustlers usually have a whole intuitive, hard to replace, head-and-heart-and-hands set of skills that they’ve refined during their careers and maybe their whole lives. Those skills are the ones you need maxed out and the ones those hustlers really enjoy flexing. In tough cases, they get to do that less than half the time because of the mountain trail of tedium they have to hike every day.
So, if you want to unlock better work from your people and a better work experience for your people, consider using AI as judgement-protector instead of person-replacer.
Who’s to say why, really, but I’ve found “I want to protect your judgement and offload the most annoying parts of your job” is more palatable than “Me and GPT gonna drink your milkshake.”
-eric
Small task: map the universe
When you are in an early design phase, sorting out what your team or project is even going to do, the perceived vastness of your options can daunt you. You could be so many things. How to choose?
One worthwhile approach to shrinking this problem sounds like it might do the opposite: map the universe. More specifically, map your universe.
Your current constraints, including any design choices you’ve already made, set the bounds of the universe you’re mapping. Solo operator vs co-founding team of 5; making money vs giving away resources; a skillset you already have vs one you’re interested in relying on or developing. Any of these can be constraints that delimit the options you map next.
Once you’ve established those boundaries, make a list of all the alternatives available within those boundaries. Aim to keep the alternatives at a common level of altitude and detail. When in doubt, keep the altitude high and the detail light.
This list of alternatives is your map. It’s the hazy romantic expanse of The Universe distilled to the judge-able, tractable shape of Your Universe.
From here, you can weigh the alternatives against one another with any heuristic you like. Sometimes intuition alone is just fine. Sometimes you’ll find value in a more sophisticated rubric.
You can also repeat the exercise, this time within the bounds of the alternative you like best from your first map. Map the universe of options that exist within that first option.
-eric
COMPELLING QUOTATIONS
Writer Ava on safety and aliveness
If you want to know if something is alive, ask yourself: does it thrill me?
If you want to know if something is safe, ask yourself: do I intuitively feel I can depend on it in every realm that matters?
If you care too much about safety, you’ll be terrified of risks that lead to more aliveness because you’re so indexed on what you might lose: This is good enough.
If you care too much about aliveness, you’ll struggle to create a solid foundation from which to experiment and grow, or the intuitive sense that you are fully held.
Writer Adam Mastroianni on speaking vs reading:
Without any formal instruction, approximately 100% of humans will learn to speak, and approximately 0% of humans will learn to read. Talking comes easy and early, enabled by ancient mental structures that hoover up words and extract the meaning behind them. These are the original LLMs, and still the best in the known universe. Reading, on the other hand, comes late and laboriously, piggybacking on bits of brain that were never meant to decode squiggles on paper, let alone comprehend Finnegans Wake.
So when thinking about any human ability, it’s useful to ask: is this more like speaking, or is it more like reading? Is this an ancient capability that we get for free just by living long enough, or is this a modern skill that you can’t get without working for it?
Writer Sam Kriss on the reverse panopticon:
We’ve built this reverse panopticon where the gaze of a hundred million people converges on a single point, and it turns out all those concentrated eyeballs have the force of a ten-kilowatt laser, they start stripping off the skin, they peel a man like an orange. Put anyone you like in the machine and turn it on—vicar, imam, sweet old widower tearing up bread for the ducks with his trembling hands—and before long you will discover something that retroactively justifies putting them in the machine. But it will never be you. You get to watch as today’s subject is slowly ground down to a nub, a thin film of dust covering the bright clean mirrored room, and didn’t we see some crazy stuff inside that guy when we opened him up? Wasn’t that cool?