Two "valid" concerns people will have about MSFT employees:

* MSFT is a huge company, and is run nothing like a startup or a small software company. They'll be worried that you're processbound.

* There's a perception that Microsoft is massive and loaded with middle management and that anyone with a "do-ing" role is pigeonholed very specifically, so you'll want to stake very specific and aggressive claims about the breadth of your get-shit-done experience.

These concerns would also apply to anyone from IBM, Sun, or Cisco.

Generally, compared to a recent CS grad, multiple years at MSFT doing real work is a huge win. My only big caveat is that 5 years is a long time to be at a BigCo.

Ditto. Similar to tptacek's processbound argument, I'd be very concerned that you'd be dumped into an environment with very little supervision and flounder. My experience at four startups has been that they really mean it when they say they need selfstarters and you tend to get very little direction as compared to bigger companies. Instead, you're expected to jump in and find work yourself.

Also, if you are interested in startups, remember that virtually none of us use MS tech anywhere in our stack. It's not a huge problem, but I generally prefer engineers that have put in a couple years somewhere else and aren't new to the LAMP/postgres/mysql/linux/java/ruby/rails environment. All the way from the different dev tools to the ethos of source distribution and the skills you pick up around installing and configuring software from source. As far as I remember, the MS stack generally seems to ship as binaries and have very little of the admittedly sometimes annoying issues that come with distributing software as source. That's a problem for you because I expect engineers to be able to install software from yum / rpms and deal with more common link / library / configuration issues that come up. Finally, it seems to me that MS typically has a blessed method of doing everything -- there is a preferred method to connect to MS SQL server, a preferred method of parsing xml, a preferred method of sending mail, etc. The open source / linux tech stack is nothing like that -- there are always multiple ways of doing anything and it's often an unwritten part of the job description to help sort that out.

Finally, again specific to startups, I think you'll be shocked how different a 15 person company, or even a 100 person company, is to a 30K person company. For instance, there will often be no review process, etc etc.

Depending on what exactly you've been doing at MSFT you should have some valuable experience, so don't be too pessimistic. Good luck.

I don't think there are negatives that you have to mitigate, but you really need to think about where you want to end up down the line.

Working 5 years at Microsoft says, "I'm perfectly happy doing solid software engineering/management work at an enormous company." If that's the image you want to project, then go for it. Just remember that the companies that are most impressed by that are the companies that are most similar to Microsoft.

That said, if you don't want to continue working for companies like Microsoft/IBM/whatever, you should probably start branching out now. Looks like you're finishing up 2 years by your linkedin profile. That's actually a great time to move on. As the grandparent said, what you get out of working for Microsoft for 2 years is basically what you would get from working there for 5 years. The difference is you have 3 extra years to improve your resume at other companies.