The example which comes to mind is actually Apple and Jobs - Apple had a huge fiefdom problem in the 1990s, and Jobs had to deal with it when NeXT reverse-acquired Apple. But you don't get the political capital to rock the boat that much unless the company's in trouble (which Microsoft isn't) and you're a figure like Steve Jobs (which Nadella isn't).
NeXT's acquisition of Apple is one of the major inflection points in the tech industry. It eventually resulted in Michael Dell's most quotable quote, when asked what advice he'd give to Steve Jobs: "Shut it down and give the money back to the shareholders".
It sits alongside Palm's Ed Colligan concerning the iPhone: "We've learned and struggled for a few years here figuring out how to make a decent phone. PC guys are not going to just figure this out. They’re not going to just walk in".
There are an endless supply of statements from Apple's detractors over the years, predicting the imminent downfall of any and all of the fruit company's products and services. One of the most recent being Pat Gelsinger calling Apple a "lifestyle company", meanwhile Intel rehashes Justin Long's character from the archaic "I'm a Mac, and I'm a PC" adverts, showing that Intel is definitely keeping up with the times. Thing is, I think Steve Jobs might have taken the lifestyle remark as a compliment.
That is always going to be the great "what if" scenario, if Jobs had survived. The Apple of today is different than it was back when Jobs was CEO; it's much larger with additional pressures. He didn't care for the day-to-day operations of dividends and buybacks, nor the patience for politics required when running the world's most prominent and profitable tech company. Tim Cook was hired by Steve Jobs for his abilities in wrangling the supply chain and herding Apple's fickle suppliers. However, a modern tech CEO has to be comfortable as a skilled political negotiator, while walking a tightrope, not just with both major political parties in the United States, but around the world, as well.
I'm not certain that Steve Jobs would have had the patience to chart a passage through such stormy waters; his mercurial nature was in opposition to such circumstances. Also, Jobs was always on the hunt for the next big thing, which sometimes meant that older product lines would stagnate for far too long. The Mac had occasional moments of apparent lifelessness under Tim Cook, but Jobs seemed to become disinterested after the switch to Intel. I'm not certain whether the Apple Silicon endeavor would have been implemented under Steve Jobs, but fortune favors the bold, something that I believe Cook learned from Jobs, but he applies it in a more measured, judicious manner. How many times have we heard critics say "Apple can't do..." and then they go and do it?
I think Tim Cook deserves credit for putting considerable resources into an overhaul for the company's eldest product. Staying with Intel was the safe bet, Apple Silicon could have backfired for many reasons, yet has been an astounding success, allowing the Mac to outshine the mediocre offerings from the PC companies.
I suspect that if Steve Jobs had survived longer, he would have taken on a CTO role, while handing over the day-to-day operations to Cook. Still, that's entirely speculation on my part. Despite the Apple is Doomed™ and Tim Cook needs to be fired crowd over at MR, I think it's remarkable that Apple has been as successful as it has been, despite losing its genius co-founder, while facing strong headwinds from competitors, global events, government regulators, and endless frivolous lawsuits. I think Cook understands his limitations and delegates to employees who excel in those fields, while fostering a cooperative atmosphere that prevents the formation of fiefdoms. Apple is by no means perfect, but Cook seems suited to the role handed to him, and his leadership is a likely reason that Apple has continued to prosper as it grew in size and power.
In an alternate timeline, they purchased BeOS to replace classic Mac OS, and Apple was subsequently acquired by IBM. That would make for a much different technological landscape.
