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THE LEAFLET

October 16 2025

delegation and micromanagement are not opposites, how to choose what to delegate, what about famous founders who hated delegation?

DELEGATION AND MICROMANAGEMENT ARE NOT OPPOSITES

Bold assertion here: delegation and micromanagement are not opposites of each other. In fact, selective micromanagement can be a great tool for delegation. In a good instance of micro-management, a leader provides vivid clarity about what excellence looks like in a narrow area. The team member can think model their work on that example in that narrow area and possibly translate that standard into other areas as well.

The goal of delegation is that somebody can successfully meet your standard without your assistance. This sometimes requires your reminders of what the standard is. Delivering those reminders (“here, watch me one time” or “not like that, like this”) can often seem like micro-management at the beginning of (and occasionally throughout) a successful delegation process.

-ben

Read the rest here.

HOW TO CHOOSE WHAT YOU DELEGATE

Pick a 2-3 week representative sample of your calendar/task list. This could be simply pulling the last two to three weeks of your actual calendar and task list (unless there was something unusually unrepresentative about those last two to three weeks).

  1. Write down every activity that you participated in from that sample and put each on a small post-it. You can use a shorthand or a headline, as long as you can recognize the activity by name.

  2. On a decent-sized whiteboard or a fairly large piece of paper, draw a 2x2 matrix. Label the y-axis "Impact on Mission" and the x-axis "Doesn’t Have to Be Me."

  3. Treating the "doesn’t-have-to-be-me" axis as theoretical or hypothetical (i.e., another person competent enough could take on this task instead of me in the organization, whether or not that person is currently with you), place all the post-its somewhere that makes sense to you within these four quadrants.

The things you should aim to delegate first are the post-its in the northeast quadrant: high impact on mission, doesn’t have to be you.

-ben

Read the rest here.

WHAT ABOUT THOSE FAMOUS FOUNDERS WHO HATE DELEGATION?

Founders podcast host David Senra loves to tell the tales of founders who refused to hand over control of detailed areas of their business. In Senra’s telling, Steve Jobs reviewed every word of copy for every Apple ad. Raising Cane’s founder Todd Graves personally approves every one of the chain’s 100+ new locations each year. Rockefeller adjusted the number of drops of solder used to seal an individual oil can from 40 to 39. 

Don’t these examples prove that delegation is for weak leaders who lack the drive and obsessiveness of the greats?

I don’t think so. Here are a few reasons why:

  1. Part of what makes these stories notable is selection bias. There are WAY more things the CEO is not scrutinizing to death. Jobs reviewed copy for every ad. He did not quality control every single iPhone that came from the factory. He did not ring up every single customer at every single Apple Store across the land. It feels a little dumb and obvious to point this out but it’s a truth that gets obscured in the romance of the detail-obsessed CEO.

  2. In at least some of these instances of crazy attention to detail, the CEO/founder is swooping in to give an object lesson and a reminder. This is what our global standard of excellence looks like in this very local domain. 10-time national champion coach John Wooden started each season teaching his players how to tie their shoes. He did not then tie each player’s laces for them the rest of the season. He didn’t shoot the ball for them either - he was the coach. He had to stand on the sidelines. He was illustrating for his players, in a memorable, granular way, “how we do things around here.” This early-season moment of (potentially jarring and patronizing) micro-management was a step toward the inevitable, necessary delegation that was ahead. 

  3. Often, these dives into the details are incidental learning opportunities for the CEO, not ongoing exertions of power. Exposure to the front lines and contact with the customer deliver special kinds of data that are hard to grok from a pie chart or spreadsheet.

-eric

Read the rest here.

COMPELLING QUOTES

Founders podcast host David Senra on learning:

Learning is not memorizing information. Learning is changing your behavior.

Writer and doctor Scott Alexander on perspective:

All human values disappear if you zoom out too far or zoom in too far - so what? So don’t do that.

Writer James Baldwin on children and responsibility:

The children are always ours, every single one of them, all over globe; and I am beginning to suspect that whoever is incapable of recognizing this may be incapable of morality. Or, I am saying, in other words, that we, the elders, are the only models children have. What we see in the children is what they have seen in us — or, more accurately perhaps, what they see in us.

Keep going, keep growing,

Ben & Eric