The Leaflet #120: questions a new exec should ask; making use of a rough patch; AI for navigating bureaucracy

1. Two questions to return to as you become an executive

   1. Does this need to be me? This question helps you recognize that you’re the bottleneck on many things. At a certain size and reach, the organization is no longer necessarily most benefited by you just strapping down and doing it yourself.

   2. “What are we getting done as a team/organization?” Ask yourself this rather than “What am I getting done as an individual?” When you’re making the transition from IC to manager or manager to executive, your value is increasingly in what you do, not how much you do. It’s challenging but necessary to switch your default from high-ownership, reactive problem solving to high-mobilization proactive problem solving. You’re doing better by the organization over time by building capacity in others than fighting every fire yourself.

-ben

2. Making good use of a rough patch

I’m thinking of a rough patch as a period of time where things don’t go well and most people can tell. You might fail to hit your goal and that failure is clear and measurable and everyone is bummed about this. You might achieve your goal or stay on target but the way it happened was painful and unsustainable.

As a leader, a rough patch, especially the first one, is really useful. That patch carries data about what works and what doesn’t for this team in this context. There’s operational information in it. The rough patch also affords the leader a storytelling and identity-forming opportunity. Think about what made this patch rough - what went wrong and why. Draw a distinction between the right kind of challenge, the right kind of stress, and the wrong kind. Then walk the team through your rough patch analysis and the decisions you’re making based on that analysis.

It’s useful to be able to say, “We’ve seen what happens when we do x. We want to avoid that. So this time, we’re doing y.”

It’s even more useful to be able to say “Around here, we’re the kind of team who does y when x happens. X just happened. I probably don’t have to remind you how painful that was. So here’s how we’re going to do y. That’s what we’re here for / what our values demand / the kind of team we are.”

-eric

3. AI for process insight - what’s happening over there?

One frustration of navigating bureaucracy is a lack of information. You may be told where you sit in a queue relative to others. You may be shown where you sit on an approval pathway. You may have a mere rough estimate of how much time you have to wait before you hear back from someone else in the bureaucracy. In any of these situations, I can feel passive and powerless and quite frustrated.

When bureaucracy gets opaque, I have found Claude to be a useful navigator and clarifier. When I describe the goal I’m trying to achieve, the context I’m in, and the latest message I’ve gotten from someone in the bureaucracy (public permitting office, hospital, etc), I can ask Claude what the the heck is happening over there (in the bureaucracy) and get useful insight that the bureaucracy won’t or can’t give me. I can also get a reasonable indication of how much I can push and where I should apply the pressure. When the bureaucracy is one I don’t have much experience with, there’s a chance there’s a whole category of person in that bureaucracy whose job is to help someone in my situation. But there isn’t someone in the bureaucracy who tells me this. Claude can do that instead.

If you’re stuck in a 2026 Kafka short story, it’s worth a try.

-eric

COMPELLING QUOTATIONS

Writer George Saunders on connection:

These days, it’s easy to feel that we’ve fallen out of connection with one another and with the earth and with reason and with love. I mean: we have. But to read, to write, is to say that we still believe in, at least, the possibility of connection.

Writer Imani Perry on prayer:

Living as prayer. I think that is when I am at my best. Because seeing through prayer provides a remarkable clarity. Not in the doctrinal sense, but because it is, at best, the lens of a love for every tattered inch of this earth.

Butterfly enthusiast Vladimir Nabokov on art and nature:

I discovered in nature the non utilitarian delights that I sought in art. Both were a form of magic, both were a game of intricate enchantment and deception.