The Leaflet #138: who to hire first, graceful exits, AI usage in work tests
Who to hire first in start-up mode
If you’re in start-up mode, the radical advice is to throw away the reassuring and symmetrical org chart for your first few hires. Determine what the bottleneck is and hire the person who opens that up for you. Repeat that move.
The bottleneck is more serious than a pain point or a gnarly process. At the earliest stage, it’s work that, if it went undone or badly done, would sink you fastest. Sometimes it’s the product not existing. Sometimes it’s, “um, there is no money is coming in.” Sometimes it’s that you personally are the constraint on every decision.
This sounds obvious but it requires some real discipline and sometimes, a stomach for low-status moves. Maybe in good faith you want to do what a “real organization” or a “grown up organization” does. But that can lead you to hire a senior operator before there’s enough of an operation to run, eg, instead of getting someone less shiny who will chase clients for you like there’s no tomorrow.
At the start you don’t really have an organization. That’s painful in a lot of ways and freeing in many as well. Instead of an organization, you’re closer to the nakedness of a mission and a set of barriers to reaching that mission. Ideally each early hire loosens or softens the worst of the constraints, the most existentially threatening of them.
Eventually, a structure will emerge or the existential risk for your organization will be the lack of that structure. Then you address that problem, rather than pretending you can solve it before it’s there.
-ben
How a leader can make a graceful exit
A leader with a high sense of ownership and responsibility usually wants to make a deliberate and graceful exit from their organization. They’re not trying to cut and run. Yet, so often, the exit feels painful and protracted for everyone involved.
Making a transition like this go well starts way before anyone (including the exiting leader) knows it’s going to happen. Developing a strong default of building capacity in other leaders helps immeasurably. If the pattern of your own leadership has been prepping others around you to be on stage, make stakes-y decisions, and think about the medium- and long-term, your exit asks others to do something they’ve already practiced. That means your exit can likely occur quicker and sparks less anxiety on your board, among your junior folks, and on your leadership team. Chances are higher everyone has already seen what this looks like, at least in miniature.
In addition to building leadership muscle around you all the time, whether you’re planning to leave or not, consider these moves as well:
If you have an immediate successor already on the team, move as quickly as you reasonably can to having that person field questions, make decisions, and otherwise assume the responsibilities of the leader. If you’re a high-ownership person, this likely will feel like you’re shirking responsibility but it’s actually a gift to your successor and the team. Ambiguity sucks, for everyone. You getting off stage fast prevents one painful species of this ambiguity from taking hold.
When you have a rising star working for you and you’re not sure what feedback to give them or what to assign them, ask yourself, “What would worry me about having them step into my role next week/month?” Then have them get good at that thing.
-ben and eric
Two ways to address AI usage in work tests
A challenging, true-to-life work test can be a powerful part of inoculating your job candidates. Ideally, you’re giving them work to do that is very close if not identical to the work they’ll do on the job irl, including the abrasive unresolved parts.
We’re fans of making the rubric for these tests explicit. “Here’s what we’re looking for and why. Here’s what we’re not worried about / interested in.” A really good work test gives you evidence of the skills and values that really matter to you and doesn’t hide those skills and values from the candidate.
If “using AI tools well” is one of those skills, don’t just give candidates permission to use them. Say more and ask for more so you can learn more about your candidate. Two moves to try:
Include something like this in the instructions for the work test:
“Using AI tools well is a key part of the job. So you are welcome and encouraged to use AI tools to help you complete this test/task/assessment. If you do use these tools, we ask that you write a concise summary of
Which tools you used
How you used them and
Why you used these tools in this way”
Then, before you grade any candidate work, feed your assessment to a frontier model (as of this writing, Fable 5 or GPT 5.6) and have that model complete the assessment in one shot. You can use this one-shotted sample to cross-check the work you’re getting from candidates and get a sense of how much of their own taste and judgement shaped the output they got from the bots.
-eric
COMPELLING QUOTATIONS
Economist John Maynard Keynes on purpose and cats:
The “purposive man” is always trying to secure a spurious and delusive immortality for his actions by pushing interests in them forward into time. He does not love his cat, but his cat’s kittens; nor in truth the kittens, but only the kittens’ kittens, and so on forward forever to the end of cat-dom."
Critic Henry Oliver on ideas in literature:
Every novel is a novel of ideas, not in the sense of being a novel that explicates and sermonises but in the deeper, broader sense that nothing can be written that is not founded on some belief, some worldview, some ideology, or some instinctive understanding.
Advocate of clinical trial reform Saloni Dattani on medical progress:
Medical innovation has transformed our lives, but hardly anyone realizes it. You can tell people that global life expectancy has doubled in a century and watch it fail to register – it just sounds like an abstract number, and numbers don’t convey how different life used to be. So let me describe it another way.
If you collapsed with a heart attack in 1950, hardly anyone around you would know how to help. CPR wouldn’t be invented for another decade. If you reached a hospital, a doctor would likely give you morphine, tell you to lie still and hope for the best: the prevailing view was that once the heart stopped pumping, nothing could be done.
That changed in the 1970s. Cardiologists began to understand that with each passing minute, more heart muscle would be starved of oxygen, and once dead, it wouldn’t be able to recover. But doctors could limit that damage by swiftly restoring oxygen supply with a clot-busting drug or a balloon catheter, opening blocked blood vessels and rescuing heart muscle.
In other words, the idea that a heart attack is something you could actively treat is only about fifty years old. Since then, the share of patients who have died within a month of having the most severe type of heart attack has fallen by two thirds.