THE LEAFLET

November 06 2025

the second 90%, risk reps instead of risk reduction, too much humility and a little self interest

THE SECOND 90%

A couple weeks ago I quoted one of Kevin Kelly’s bits of Excellent Advice for Living.

“Be prepared: When you have 90% of a large project completed, finishing the final details will take another 90%. Houses and films are famous for having two 90%s.”

Of course, the way this math works out, he’s telling you that ~half of the work lies in that last mile / post-production / paint-and-cabinet pulls phase. Embracing this is helpful for avoiding the planning fallacy.

Beyond films and homes, I’m thinking of applications of this idea to teams and people management. Here are a few other examples, with the familiar, visible 90% and the hidden, second 90% spelled out. 

• Hiring: 

• First 90%: writing the job description, posting the job description, interviewing, offering, negotiating, hiring

• Second 90%: onboarding for the first ~month

• Presentations / trainings:

• First 90%: Choosing what you’re going to say and putting that in pretty slides or a crisp memo 

• Second 90%: Sending pre-work, practicing all the tech transitions (launching Zoom breakout rooms, eg), sending follow-up survey and email, doing live observations of folks using the material from the presentation and giving them feedback. Aka “making sure they actually learned and used the stuff and you didn’t just talk at them for 40 minutes”

• Event planning:

• First 90%: Drafting the run of show, choosing vendors, signing contracts

• Second 90%: Relentless follow up with everyone involved in the first 90% to confirm that the actual physical object or human body is actually in the location where it is supposed to be ahead of showtime.

• Random bonus one: planting trees

• First 90%: Buying the trees, digging the holes, filling the holes

• Second 90%: Watering the trees regularly until they are well-established. This is easy when it’s one tree in your front yard. It gets dramatically more complicated if you’re planting >5 trees anywhere else. 

-eric

Read the rest here.

RISK REPS INSTEAD OF RISK REDUCTION

If you want a muscle to be strong, flexible, and reliable, you have to tear it. Not the traumatic tear of injury – the micro-tear of training and recovery. The strength comes from repetitions over time, repetitions of gradually ascending difficulty. This is a metaphor for building up skill and confidence and feedback appetite on your team, too. 

A good-hearted desire to make people feel safe can lead to reductive moves that freeze or sap people’s strengths. You try to achieve safety for them by reducing the risk of negative feelings. You don’t put people on the spot, on the stage, or up for (earnest, pro-social) public critique. You shield them from risk instead of exposing them to it.

The teams where I’ve seen the most consistent growth approach this very differently. They promote repetitions of the risk instead of reductions of it. Around here, people speak to the whole team all the time. Around here, we ship rough drafts and embrace the direct critiques of those drafts. Around here, we pitch an idea and workshop it on the spot. Around here, we move in a circle and give each other a piece of criticism and praise in 30 seconds. 

When you do this, you’re not asking everyone on the team to become a charismatic salesperson. You’re insisting that they build, ship, and revise like a good leader: with a focus on outcome more than appearance.

-eric

Read the rest here.

TOO MUCH HUMILITY AND A LITTLE SELF INTEREST

Managers often get positive reviews from their reports and feel good about themselves when they are stunting the growth of their reports. These managers care about their people and want to achieve the team’s goals. The way they enact this is to make their people reliant upon them.

Managers in this mode fail to model and teach their own thinking. They remain “answer-havers” rather than “prompt-givers.” Often these same managers are striving not to condescend to anyone they manage with hands-on teaching and coaching.  

I suggest that this whole approach can be rooted in a) misdirected humility and b) self interest. Having the answers and sharing them when you’re asked for them feels good. You feel needed. Your expertise is affirmed. And refraining from preaching or teaching or coaching feels appropriately humble. You never risk implying that you know better and the discomfort that can arise on both sides from that implication.

But a great manager doesn’t focus on safeguarding egos and equanimity. A great manager focuses on achieving the team’s mission – doing the thing the team exists to do – by building the skill and autonomy of everyone else. That building is slow and unpredictable, if it happens at all, when the manager is the “answer-haver.” It can be fast and consistent when the manager is the “prompt giver” instead.

-ben

Read the rest here.

COMPELLING QUOTES

Rocker and poet Patti Smith on artmaking:

The artist seeks contact with his intuitive sense of the gods, but in order to create his work, he cannot stay in this seductive and incorporeal realm. He must return to the material world in order to do his work. It's the artist's responsibility to balance mystical communication and the labor of creation.

Writer Yiyun Li on unreality:

Death is one reality, life is another. The two realities are rarely compatible. Sometimes one reality obliterates the other, or, worse, banishes the other into the realm of unreality.

Poet Ben Lerner on open heart surgery:

What people report, the nurse explained, is that it feels like mice scurrying in their chest. Wait more than one patient has said this thing about mice? I asked. Yes, she said. A lot of people have told me that.

Keep going, keep growing,

Ben & Eric