Cut the Layer, Keep the Ladder: The Great Unbossing, Round Two

Block CEO Jack Dorsey says his ideal setup would be all 6,000 employees reporting directly to him. If he held monthly one-on-ones, that’s close to 300 a day.

He isn’t the only leader thinking along these lines. Uber cut about 3,300 roles to remove layers and flatten the company. Block cut roughly 40% of its staff, and Dorsey and Sequoia’s Roelof Botha argued that AI can handle the coordination managers used to do. In this episode, Jaime Peters and Cindy Goodwin-Sak ask the question those announcements skip: when a management layer disappears, what happens to the work it was doing?

They cover:

* Why Uber’s flattening is likely an AI story too. Uber’s memo never mentions AI, but Bloomberg reported the company had used up its annual AI budget by June.

* The “Great Unbossing.” This isn’t the first wave of manager cuts. It includes Gartner’s 2024 prediction and Bayer’s experiment with self-organizing teams, which cut its manager ranks by about two-thirds.

* What happens to employees and executives. In a Korn Ferry survey, employees whose companies cut management layers reported feeling directionless. Senior leaders doubt they can absorb the work that moves up to them. The hosts point out on air that these are survey findings, not proof of cause.

* How people end up as managers. Gallup finds most are promoted for tenure or for success in a non-management job, and most never get formal training.

* Where the next leaders will come from. Only 6% of Gen Z want to reach senior leadership, according to Deloitte. A flatter organization may give them even less reason to try.

Three takeaways for managers:

* Cut the layer, keep the ladder. If you remove a level of management, name who is now responsible for developing the next leaders.

* Let AI coordinate, not coach. Status updates and routing can be automated; developing people can’t. If your span of control is about to double, decide what you’ll stop doing before you give up one-on-ones.

* Track the coaching, not just the savings. Finance tracks the savings from day one, but almost no one measures whether people are getting meaningful feedback each week. Gallup finds that feedback is a strong predictor of engagement.

Next time, we step away from AI to ask whether elections matter to day-to-day business. We’ll talk about politics without talking about politics.

Keep your spreadsheets handy and your coffee strong.