This isn't really an answer to your question, just food for thought: Two of the most successful entrepreneur CEO's, Steve Jobs and Larry Ellison, both started out as specialists in engineering who eventually (it seems) realized that they weren't and would never be the best engineers. Their strengths have been in finding the best ways to apply existing technology, not inventing it or writing its code. So, they slid into leadership roles by finding the best engineers who weren't necessarily interested in management (Steve Wozniak is a great example) and giving them room to be brilliant.
Meanwhile, someone like Richard Branson has never been a specialist in anything specific to his businesses. He's basically a professional manager who has a crazy ability to find and retain the best people in various fields. His original strength (according to his book) was that he was willing to do anything to succeed, including bluffing, lying, and (on one occasion) breaking the law. (Most of that was ultimately harmless, except the last part!)
He also works really, really hard.
I've worked with people in various leadership positions and seen all sorts of examples. I've seen a well-paid manager of a programming team voluntarily step down from his leadership position because he wasn't comfortable telling people what to do. I've worked for a well-known duo in the game industry where the charismatic designer became the manager and the programmer had no interest in doing so (with a team of 30 while I was at the company, probably 40 now).
So maybe the specialist/generalist question doesn't matter as much as your mindset. Successful people work hard, seek out information, and are willing to take risks. Some CEO's are more respected for their abilities than liked for their personalities, but obviously if you're just putting a team together and not starting from scratch you've got no room to be unlikable.
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This isn't really an answer to your question, just food for thought: Two of the most successful entrepreneur CEO's, Steve Jobs and Larry Ellison, both started out as specialists in engineering who eventually (it seems) realized that they weren't and would never be the best engineers. Their strengths have been in finding the best ways to apply existing technology, not inventing it or writing its code. So, they slid into leadership roles by finding the best engineers who weren't necessarily interested in management (Steve Wozniak is a great example) and giving them room to be brilliant.
Meanwhile, someone like Richard Branson has never been a specialist in anything specific to his businesses. He's basically a professional manager who has a crazy ability to find and retain the best people in various fields. His original strength (according to his book) was that he was willing to do anything to succeed, including bluffing, lying, and (on one occasion) breaking the law. (Most of that was ultimately harmless, except the last part!)
He also works really, really hard.
I've worked with people in various leadership positions and seen all sorts of examples. I've seen a well-paid manager of a programming team voluntarily step down from his leadership position because he wasn't comfortable telling people what to do. I've worked for a well-known duo in the game industry where the charismatic designer became the manager and the programmer had no interest in doing so (with a team of 30 while I was at the company, probably 40 now).
So maybe the specialist/generalist question doesn't matter as much as your mindset. Successful people work hard, seek out information, and are willing to take risks. Some CEO's are more respected for their abilities than liked for their personalities, but obviously if you're just putting a team together and not starting from scratch you've got no room to be unlikable.
Whew, long rant.