The Leaflet #132: leader vacation, observation > 1:1, Claude reveals your preferences
Leader vacation as leadership opportunity
You’re taking real-for-real time off, right? You better. It’s good for you. It’s good for your people, too. Ideally, you’re modeling for them what healthy management of a life and calendar look like.
There can be a second benefit of your real-for-real time away that pays dividends long after you get back. Your vacation can be a leadership opportunity for others on the team.
To make that so, name it that way and set your expectations. Prep the interim leader(s), set a goal with/for them, and tell the team whom they’re supposed to go to with questions. This will be the most real-for-real leadership development if these interim folks get to make actual decisions without consulting you while you’re away.
The defaults the team might rely on otherwise could be more cautious or humble than you want. Folks who could excel and grow might play it small for fear of overstepping. Others might resort to calling / Slacking / emailing you and/or waiting around for your return.
-ben and eric
Consider swapping out a standard 1:1 for an hour-long observation
Whether you are a manager or a consultant, you may be much more helpful to your report/client as an observer than you are as an interlocutor. In other words, watching what someone actually does can get you both a lot further than just talking to them about it post-hoc.
You don’t have to toggle all the way to observation and totally scrap discussion. But if the current proportion of your management time is something like 95% discussion - 5% observation, consider recalibrating.
You can target this observation, too. Sit down with your person and ask them to walk you through the most painful, energy-sucking part of their work. Sometimes you’ll be able to tell them right there that they don’t even have to do this part of it at all anymore. Sometimes you’ll be able to code or outsource it away. Sometimes you’re an expert at this noxious task and you can upskill them relatively fast. They might not like the task but with greater skill to dispatch it, they may not need to dread it anymore.
You can also ask them to walk you through the part of their work they love and draw energy from. Your vantage point, a little removed from the direct doing, can allow you to see places they might be able to do more of this thing they love, to their satisfaction and the good of the team.
-eric
Using Claude to unearth your revealed preferences
Wouldn’t you know, we’re now in the back half of 2026. Earlier this week, I had Claude put together a review of the first half of my year. I shared my calendar, the transcript of my other Claude conversations (which amount to a sort of daily journal), and a long list of financial transactions from credit card and bank statements. I had Claude connect to my Strava account and gave it access to this very blog.
I told Claude in a few sentences what my intentions and goals were coming into the year. Then I asked for a review of all that data to get at what my revealed preferences are. I wanted to know: Where is there a gap between intent and execution? What does the actual allocation of my time, attention, and cash show about my true passions? What’s inaccurate in the story I tell myself? What near-term moves could I make that would make that story truer?
Here’s a lightly edited version of the prompt I used, in case you want to try:
Today is June 30, so the halfway point of 2026. I want to do a searching review and assessment of the first half of the year, in part as a reflection and self-awareness exercise, in part to set up a maximally satisfying and effective second half of the year. I’d like this to encompass all of my projects and workstreams: my running, my work, my pro bono projects, my personal life (family, therapy, dating, friendships, etc). I think it’s probably most effective if it draws from Claude conversations, my calendar, my email, Strava, my writing at thisistheleaflet.com and any other data basins you might be able to draw from. I’m looking in part for revealed preferences that might surprise or sober me - where am I actually spending my time, attention, and energy, despite what I say or believe? What am I committed to or interested in but gets comparatively little time and investment? This is the first time I’m prompting the creation of an artifact like this but I could see myself wanting to set it up as something like a quarterly review-and-look-ahead in the future. I’m also conscious that the second half of the year will have some special events: [event, event, event, event.] Rather than one-shotting this, I’d like to think with you about approaches to design and delivery, marshaling any new connectors or plug-ins we need to, then running it. Based on this, what do you advise?
-eric
COMPELLING QUOTATIONS
Practitioner of surrender Sasha Chapin on introspection:
The proper end of introspection is not being filled with facts about oneself. Your introspection is successful if it is finite, if it leads you towards direct contact with experience. Get out of the way of your becoming.
Author Ian Bogost (via Rob Walker) on gratification:
The more I worked on understanding gratification, the more I tried to deemphasize the idea that feeling gratified requires work. We’re so used to thinking that feeling good must require effort! But the good feeling of your senses connecting to the world is weirdly effortless. It happens all the time. I’m touching the keys of my keyboard as I type these sentences. My forearms sense the smoothness of my desktop. In another room, I hear the tink-toss of a garment careening around in the clothes dryer. So I’ve found it helpful is to think of gratification as something the world gives and that you accept. The keyboard is offering me smoothness and clickiness; the dryer is tendering tink-toss sounds. To enjoy the momentary delights of the physical world, all I have to do is accept the sensory gifts it offers.
Sculptor and scholar of charts Edward Tufte on information
Information consists of differences that make a difference.