Glenn Kelman from Redfin wrote about how MSFT people are upset about one of the job posts on Redfin that has the phrase "You don't need big money to do something big. Don't apply if you've worked too long at Microsoft, Amazon or an agency" for a Marketing job post.
Do I agree with Glenn? For a Marketing, Biz-Dev or Sales person I wouldn't hire someone from Microsoft that was more than 2 years there. So, the answer is yes!
For engineering, PM'ing, testing I'd be open to someone that has worked 20 years at Microsoft, as long as they didn't work on a single product while they were there. I even wrote about this last month.
So, is it bad if you worked too long at Microsoft?
Well, it depends, if your next career move is to join a startup or found your own company, yes it is. Me and dozens of others ex-Microsofties that left have felt the pain first hand. First, you have to go through detox to learn a lot of things again. Then, you have an uphill battle with the entire startup community (other entrepreneurs, investors, potential employees and partners) to prove that you know what it takes to execute on a startup environment.
Now, if you plan on joining Google, Amazon, Yahoo or another Fortune 500, having worked at Microsoft for a long period of time is an immense amount of prestige and an invitation card into those jobs.
The answer to the title of this blog post, like for many things on life is: maybe.