THE LEAFLET
September 04 2025
turning a cliche into self-awareness and habit change, five birds and one crumb with a scorecard, celebration as one-to-many communication
TURNING A CLICHE INTO SELF-AWARENESS AND HABIT CHANGE
Recently I re-encountered the old chestnut: “How you do anything is how you do everything.” This felt to me a little too much like high school football coach wisdom – something that holds true when the rules are clearly defined, there’s a literal level playing field, and the game is time-bound. In other words – great for sports, maybe a little shaky for the vagaries of real life.
Then I thought about it some more and was like, “let me not be so smug. Let’s at least test the proposition.” Then I ran a rough version of the test below, which I’ve now turned into an exercise you can do, too. This can be a pump for your self-awareness that can spark habit change or habit deepening, as needed.
1. Choose one of your current endeavors. I loosely define “endeavor” as “something that requires inputs from you over more than a few days.”
Things that count: a work project, a hobby, a big international trip.
Things that don’t: a meeting, one instance of disciplining your child, making dinner.
2. Now break down “how you do [endeavor you chose]” by completing the prompts below that are relevant to your endeavor (there might be some that don’t make sense):
A) Operational Moves
When I start, I naturally…
I postpone ______ until ______.
My default with tools/tech is…
My pattern of communication and updates to others looks like …
I decide I’m done when …
B) Relational Moves
With collaborators, I usually…
When conflict looms, I…
My go-to way of contributing to relationships with collaborators is…
My interaction with my broader network or community tends to look like …
C) Decision & Resource Moves
My budgeting approach is…
My risk appetite is…
…and I can see that because I …
I’ll happily spend time and/or money to …
I’m very reluctant to spend time and/or money to…
I learn and grow by…
E) Energy & Boundaries
When I get busy, I drop…
I protect time by…
I draw energy from…
I feel enervated by…
3. Transfer to other projects
Now you can pressure test the cliche in your other endeavors. For each of the moves you identified above, ask yourself:
Where else does this move appear in my life?
Is this move helping me or holding me back?
As a follow up to 2: If I really “overdid it” with this move, like 10x’d it, what, if anything, would break? What would get super duper good?
As with any exercise like this, you can feed data, like emails, calendar events, and google docs you’ve written, to a state of the art LLM like Claude Opus 4.1 or GPT 5 Thinking and have that LLM take a crack at this for you. The AI version can serve as a point of comparison with the version of the exercise that you write on your own, helping you see some things that may escape you when you’re looking in the mirror.
-eric
Read the rest here.
FIVE BIRDS AND ONE CRUMB (WITH A SCORECARD)
Clear thinking upfront about what a role on your team is for can solve four or five challenges that new managers and founders often grapple with. These leaders can waste loads of time and confuse their people with bespoke approaches to
the weekly 1:1 check-in with a manager
the (semi)annual performance review
promotion decisions
the performance improvement plan (PIP)
and regular, relatively lower-stakes feedback
Instead of cooking up five processes – a slow and painful approach, even when you have great people – you can get five birds with one crumb. To do this, we recommend an exercise we call “CEO of x” or, more simply, “creating a scorecard.” Each role on a team is "CEO" of something: "CEO of x". X is the function or outcome this person owns. Here’s the exercise:
State what "x" is as concisely as you can – try to doit in <5 words, rather than a big gnarly sentence.
Example:
Terrance is CEO of Business Development
Non-example:
Terrance is CEO of developing relationships with potential clients in current and prospective business lines for the company and he handles some of the ops stuff, too, since Julie left.
2. Imagine a year from now (or maybe 6 months), you decide to fire this person and/or dissolve the role entirely, not even rehiring to fill it. Holding aside cases of lawbreaking or egregious abuse, what went wrong? What did this person do or fail to do that led to you letting them go? Identify the 3-4 specific and most important things.
Example:
Pipeline of future clients is thin or non-existent. We’re in a sort of “all eggs in one basket” situation.
Promising leads that CEO and others are sourcing rarely make it all the way through to a closed sale
Systems are leaky, inefficient, or remain unbuilt - it’s a handmade, confusing process for T and anyone who is chipping in to help
3. Take the 3-4 items from the previous step. Flip them to the positive versions of themselves - the opposites of the failures, which make this role and person a big and vital success for the team. Attach a measure (even if binary yes/no or more qualitative survey response). These flipped failures, once they have metrics, are the measures of success for this role.
Those measures of success are the ingredients you use in all five of the recipes. They are the crumb that gets you all five birds. Use them as the agenda items or prompts for discussion in weekly 1:1s, performance reviews, feedback delivery, performance improvement plans, and promotion decisions.
-ben and eric
Read the rest here.
CELEBRATION AS ONE-TO-MANY COMMUNICATION
Leaders self-handicap, often, by skimping on award-giving and other forms of celebration of work well done. This is one of those cheap incentives you control when you’re running the little nano-economy of your team.
One mistake leaders can make is thinking that an award is mostly or even solely about the feelings of the recipient. Some leaders refrain from giving awards or celebrating because they think the recipient will be embarrassed or doesn’t like the spotlight. These leaders can overlook the fact that they are communicating to the whole team when they celebrate and award. Even an award that recognizes a single person, rather than a team or the whole org, is a one-to-many message, not a one-to-one message that everyone else gets to eavesdrop on.
Whether these words are printed on a plaque the recipient gets or not, you’re saying to the whole crew: “this is the kind of thing we value around here. We’re the kind of place that cares about x.”
By default, your people want your approval, even if the idea of accepting an award in front of a crowd gives them the howling fantods. They want your approval, even if they have a Gen X slacker / Millennial self-doubt / Gen Z stare sort of take on Your Whole Deal – those same skeptics, of whatever generation, often understand the nanoeconomics that surround them. They want security and they want to get ahead. They see the incentive underneath the award.
Style, delivery, tone of the celebration - those can all be customized to your team and culture. Some places get a lot of mileage out of awards that are deliberately ugly or low-status.
The part that’s important to nail with at least some part of your incentive economy is celebrating specifically. You’re awarding a discrete choice or move that all the other observers can make, too, in their own contexts. If “what we care about around here” is something that is impossible for others to do, like “being Ben”, your one-to-many message will be a frustrating, enervating one. If “what we care about around here” is something others can do, too, like “enacting our shared value of [truthseeking] by [redteaming the hell out of a proposal from the exec team]”, that message can directly motivate others to do that thing.
-eric
Read the rest here.
COMPELLING QUOTES
Doer-of-many-interesting-things Kevin Kelly on where you work:
Don’t ever work for someone you don’t want to become.
Organizer Dean Spade on disillusionment in movements:
Many people joining resistance groups hope they will finally meet people who understand them and believe in the same things. When differences inevitably arise, they feel betrayed in a way that is proportional to their overblown hopes for belonging. This can be particularly acute if we have often been excluded from groups because of our identities, and we think we have finally found “our people.”
Writer Adam Mastroianni on our modern moral circles:
Although the circumference of our moral circle is theoretically infinite, the extent of our efforts is not. We can care about all eight billion people riding this rock with us, but we can only care for a tiny fraction of them.
Keep going, keep growing,
Ben & Eric