From Eric -> Larry:

- "More wood behind fewer arrows". This was actually a Steve Jobs principle that Larry adopted: kill off all your insignificant products to focus on just a few key areas.

- More willingness to take on moonshots; less tolerance for projects that might be good for a small segment of the userbase, but don't appreciably move the needle.

- Seemingly less collegial atmosphere. Eric tolerated a lot of "You'll do your thing, I'll do mine, and it's okay if Google has half a dozen products that all do slight variations of each other." Larry insisted on more product discipline, but that often meant more of a scarcity mentality among execs, which led to more turf wars and infighting.

- More top-down culture. Eric had few opinions on what Google should be doing, he just wanted to make sure we were doing it well. Larry had very definite opinions on what Google should be doing, and if you didn't share them, go start your own company.

- More chaotic management style. I got the sense that Larry didn't actually know what was going on with the company, on an individual-contributor level, and so when he made decisions, they often made no sense to the rest of the company. Eric didn't know what was going on with the company either, but he was okay with that, as long as the money kept coming in and we didn't do anything illegal, so he made fewer decisions that weren't a direct reaction to an issue that was brought to him.

From Larry -> Sundar. Keep in mind that I left before Sundar became CEO, so this is all second-hand:

- Hierarchy and top-down culture has persisted.

- Collegiality seems to have returned. Just my perception, but Google seems a nicer place to work now than when G+ was seemingly taking over the company in 2012.

- Sundar is generally more informed and, well, sane, as perceived by the employees.

- Sundar is a caretaker: the core areas of Google are explicitly designed not to require massive company-changing innovation, instead relying on incremental improvement to existing products that can be driven by middle-management, and all the innovation is shunted off to the rest of Alphabet where Larry & Sergey have a more direct role in shepherding it.

I think all 3 CEOs were strong in their own way, but the CEO transition made me appreciate how oftentimes a leader's biggest strengths are often also their biggest weaknesses. Larry is insane, for instance; IMHO he's insane in a good way, because we outright wouldn't have Google otherwise, but that same oddness of perception made him a maddening CEO to work under. Similarly, Eric was a great peacemaker and good at quickly making decisions that pleased as many people as possible, but that same ability to compromise made him a poor innovator and unlikely to have the moral courage to bet the company on crazy ideas.

It also convinced me that Paul Graham's thesis, that big companies are constitutionally incapable of innovating, was correct. The reason is precisely that duality above; in order to innovate, you need someone whose personality is insane, but who then has to directly butt up against reality, and experience that resistance first-hand. It doesn't work for someone insane to direct lots of not-insane employees who get paid to build the product, because the type of creative insights that come from facing contradiction directly can't survive outside of a single mind. The innovator has to do the work directly.