Once a company becomes an industry leader, its employees, from top to bottom, start thinking defensively. Suddenly, people feel they have more to lose from challenging the status quo than upending it. As a result, one-time revolutionaries turn into reactionaries. Proof of this about-face comes when senior executives troop off to Washington or Brussels to lobby against changes that would make life easier for the new up and comers.

Years of continuous improvement produce an ultra-efficient business system—one that’s highly optimized, and also highly inflexible. Successful businesses are usually good at doing one thing, and one thing only. Over-specialization kills adaptability—but this is a tough to trap to avoid, since the defenders of the status quo will always argue that eking out another increment of efficiency is a safer bet than striking out in a new direction.

Long-tenured executives develop a deep base of industry experience and find it hard to question cherished beliefs. In successful companies, managers usually have a fine-grained view of “how the industry works,” and tend to discount data that would challenge their assumptions. Over time, mental models become hard-wired—a fact that makes industry stalwarts vulnerable to new rules. This risk is magnified when senior executives dominate internal conversations about future strategy and direction.

With success comes bulk—more employees, more cash and more market power. Trouble is, a resource advantage tends to make executives intellectually lazy—they start believing that success comes from outspending one’s rivals rather than from outthinking them. In practice, superior resources seldom defeat a superior strategy. So when resources start substituting for creativity, it’s time to short the shares.

One quick suggestion: Treat every belief you have about your business as nothing more than a hypothesis, forever open to disconfirmation. Being paranoid is good, becoming skeptical about your own beliefs is better.

While there were undoubtedly people who came in for the food, worked 3 hours a day, and enjoyed their early retirements, all the people I met were earnest, hard-working, and wanted to do great work. What beat them down were the gauntlet of reviews, the frequent re-orgs, the institutional scar tissue from past failures, and the complexity of doing even simple things on the world stage. Startups can afford to ignore many concerns, Googlers rarely can. What also got in the way were the people themselves - all the smart people who could argue against anything but not for something, all the leaders who lacked the courage to speak the uncomfortable truth, and all the people that were hired without a clear project to work on, but must still be retained through promotion-worthy made-up work.

Another blocker to progress that I saw up close was the imbalance of a top heavy team. A team with multiple successful co-founders and 10-20 year Google veterans might sound like a recipe for great things, but it’s also a recipe for gridlock. This structure might work if there are multiple areas to explore, clear goals, and strong autonomy to pursue those paths.

Good teams regularly pay down debt by cleaning things up on quieter days. Just as real is process debt. A review added because of a launch gone wrong. A new legal check to guard against possible litigation. A section added to a document template. Layers accumulate over the years until you end up unable to release a new feature for months after it's ready because it's stuck between reviews, with an unclear path out.