THE LEAFLET

October 23 2025

build your bench of leaders, go-to questions for building up leaders, cheap structural changes to build leader thinking

BUILD YOUR BENCH OF LEADERS

There are specific tactical ways that you can delegate individual responsibilities to your people with great success (see last week’s issue for some of those). We think it’s even more important to embrace a mindset that leads you to delegate by default. Instead of delegating as an emergency measure when their calendar gets too full, an effective leader relentlessly builds the capacity of others on the team to lead. 

If you’re playing any kind of long game, that is, planning to chase a mission with this group of people for more than even a few months, the most valuable resource you can build and pass on is more effective leaders. 

This is a high expected value bet: you significantly increase the upside of the organization and incur minimal downside risk. With more effective leaders, you can scale the organization by cloning it at its current size (franchising). You can scale by ceding leadership of existing layers to those leaders you’ve built up and then take on new layers of leadership yourself. You can, if needed or desirable, step out of the organization altogether and hand the reins to an in-house successor. 

All of these transitions are frightening, high-variance propositions for most organizations. So often, that is because the bench of viable leaders that can lead those transitions and the work on the other side of them is far too thin. 

-eric

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GO-TO QUESTIONS FOR BUILDING UP LEADERS

One way to delegate by default and build your bench of leaders is to push those who report to you to do the hard thinking, with your support. Gradually, your people will come to realize that the social pressure and social reward in time with you comes from bringing their best thinking to hard problems, rather than asking you to dispense “genius” answers every time.

Here’s a list of things to say at the end of a meeting or 1:1 check-in that can start you down this path:

1. What did I say there that you didn't know?

2. What did I contribute to that we wouldn't have had otherwise?

3. Anything you took away from that that will make your future work more effective without me?

4. If you'd come to the same conclusion without me, what would you have needed to do differently/additionally?

5. [More informally]: any takeaways to stamp from this? Would those save us time in future?

-ben

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CHEAP STRUCTURAL CHANGES THAT BUILD LEADER THINKING

Doug Lemov observed outstanding teachers in action and created a catalogue of their go-to moves. This playbook is called Teach Like a Champion. One of the concepts he highlights is “think ratio”. Great teachers build lessons and uses lines of inquiry that give the students the chance to the do the important cognitive work instead of the teacher. In classrooms where kids learn a lot, the ratio of student cognitive load to teacher cognitive load is high.

These high ratio lessons sit in stark contrast to the classic college professor “sage on a stage” model, where the instructor has all the answers and simply gives them out, while students passively listen or transcribe. 

Workplace leaders who build their bench and delegate by default also achieve high think ratio with their teams. Here are a few cheap structural changes that nudge think ratio in the right direction, ie, get your leaders-in-training doing more of the most interesting cognitive work.

1. The leader enters meetings for only the last quarter of their run time to take recommendations and proposals arrived at in the first ¾ of the meeting.

2. The leader requires proposals and recommendations before a meeting with them can begin, limiting their time present to 2.0-ing those pre-sent ideas and highlighting their judgment and decision-making. Ideally concluded with questions and remarks like those in this post.

3. The leader encourages folks to give them no open-ended questions (only yes/no and multiple choice) throughout meetings. 

-ben

Read the rest here.

COMPELLING QUOTES

Creator and builder of things Kevin Kelly on the planning fallacy:

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

Poet and Ohioan Hanif Abdurraqib on mid-90s R&B:

By 1995, so much of the engine of R&B had become about the grand and urgent spectacle, being thrown into the chaos of the heart and surrendering oneself to whatever the heart demands. I love this, to be clear. In SWV’s 1992 hit “Weak,” I love the insistence that the feeling of a crush is akin to an Actual Condition, one that renders the person in the throes of the crush entirely incapable of language or movement. I will make my jokes at the expense of Boyz II Men, for all of their undignified pleading, however I also admire it, understanding that the loss of love—specifically if you are the type to not cherish it when it is in your palms and then ache for it when the wind carries it away—should leave you stripped of your dignity, on your knees, screaming into the rain.

Novelist Sam Graham-Felson on his son’s evolving masculinity:

I noticed that Saul was starting to imitate Pee-Wee’s mannerisms. He was also starting to sour a little on Teddy Roosevelt. Each night before bed, I’d been reading him a kid-friendly Roosevelt biography and there were things in it that didn’t sit so well with him. For one, Roosevelt’s penchant for violence. “I like the conservationist part of his story much more than the Rough Riders part,” Saul said, referring to the ragtag group of non-enlisted soldiers Roosevelt rounded up to fight in the Spanish-American War. “Why does anyone like the Rough Riders? They were basically just a weird gang.”

Keep going, keep growing,

Ben & Eric