I'm thinking to change my career path and become the system administrator (Windows systems). I'm a proficient power user and would like to extend my knowledge.

I do realize that there is a long path ahead of me but I'd really appreciate if someone of you guys could give me some tips where to start.

The obvious questions are:

1) Which technologies/OSes (Windows 2003/2008) are the most crucial (ActiveDirectories, Group policies, Exchange, SharePoint)?

2) Any good books/websites/tutorials - but I guess something more like step-by-step guides rather then technical reference?

3) Any recommended certificates?

4) And generally, how to start - maybe someone could share with us his/her own story.

All answers are truly appreciated! Many thanks!

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This should be Community Wiki – Izzy Sep 30 '09 at 15:43
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See serverfault.com/questions/9766/… – Zoredache Sep 30 '09 at 16:40
Thanks Izzy, I didn't know about this functionality and wasn't sure what did you mean by community wiki. – karolek Sep 30 '09 at 17:08
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6 Answers

  • Pick yourself up a copy of The Practice of System and Network Administration, This will teach you not the 'how' but the 'why' of systems administration.

  • As for the 'how' of systems administration I would recommend anything and everything that Mark Minasi writes, many consider his "Mastering Windows Server 200X" books to be the "Windows Server Bible" of administration and this book will be a trusty reference.

These two books should give you a very stong foundation, now just fire up a copy of Vmware Server to practice the concepts and ideas from the books and you should be on your way to Junior level systems administration :-)

The rest you will learn on the job doing the profession, if you can find yourself a mentor within the company and learn from him and his past mistakes so much the better ;-)

On the note of certifications, I have never had much use for them, but they can make the difference in the hiring of an admin when two candidates have very similar resumes. So in short, your mileage may vary.

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Very good point on the 'why' and not the 'how. The 'how' changes often but the 'why' stays roughly the same through a system administrator's career. – Dave Drager Sep 30 '09 at 15:59
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One often overlooked area, and where a lot of sysadmins fall down, is developing good people skills. This can help lead into quality customer service, which is really lacking in this particular career field.

I don't really have any recommendations as far as developing people skills. But, I have worked retail and was a top salesman at a furniture store prior to entering this (I.T.) career field. I think it was here that I learned to develop and hone my people skills.

Where I actually started in this career field (not including what I did for it in high school or college) was work a support desk. All of our sysadmin duties were over the phone. So it became necessary to translate my good "in-person" people skills for phone usage.

You'll also be amazed at what you can accomplish in your sysadmin career if you just learn how to talk to people. It will be easier to free up money for what you need. It will be easier for your users to adapt to changes, etc.

So, beyond all of the technical information that you can absorb and learn, don't neglect your people skills.

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+1 to reading "The Practice of System and Network Administration".

I would also recommend setting up virtual machines on your local computer to experiment with the different technologies. Set up a Win2k3 SBS play with AD, Exchange, VPNs, IIS, and domain controllers. Try and cluster them as well and see how things are handled. Then try upgrading to Win2k8 SBS. Set up a Linux box (CentOS is good) and try to get it to handle SAMBA shares w/ the Win domain.

Essentially try to get your feet wet on a broad range of technologies. Employers will want to feel confident with you since so much of their business depends on technology. They can't afford to have any unscheduled downtime.

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I would advise learning the ins and outs of the Sysinternals tools and reading http://blogs.technet.com/markrussinovich/ which is Mark Russinovich's blog. Reading some of his stuff gives you a very good idea of how windows works on a very low level.

Techwise on Windows your going to want to know the OSes themselves, AD, GPOs and security.

Best thing is to practice and experiment. Just like professional atheletes, you get better, faster and more agile the more you practice.

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From a cultural perspective, I suggest you read Bastard Operator From Hell. It will teach you those all important 'soft skills'

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1) It depends. Know the OS well if you want to be a Windows-based system administrator, Exchange admin, sharePoint admin, SQL Server DBA, etc. So much of how those apps work is based on the OS. So get very comfortable with the desktop OSes Windows XP/Vista/7. And learn Windows Server 2003/2008. There's a huge 2003 install base that won't be migrating very quickly.

2) Don't just depend on certification books and sites. They won't give you the all around knowledge you're going to need. You're going to need to pick an area to concentrate in, and that really determines the site. For instance, on the SQL Server side, the first place to start is SQLServerCentral.com but there's a ton of other sites like SQLBlog.com, SQLTeam.com, SQLServerPedia.com. TechNet is a good site. Books? The how and why books that have been mentioned. And then focus on the subject you want to go into the most. You can generally use Amazon and other sites to get a feel as to what books are good. If you want to save some money, check out library sites like Safari (safari.informit.com).

3) This depends on the area you want to focus in. Probably your best bet to get in the door is as help desk/workstation support. In that case, A+ and MCDST are the first couple of certs you're looking to work as you gain experience. But as they say, certs aren't everything. You want to build up experience and couple that with your certs.

4) Most folks that get into system administration either start by doing it on the side, or by coming up through help desk or something similar. In your current organization, if you can lateral over to a technical team, that would be the most ideal situation, especially if there is time built-in for you to come up to speed. Otherwise, start looking for helpdesk and junior admin positions. Be honest with those interviewing you. If you have strong people skills and show a willingness to learn and be a team player, they may be more willing to take a chance on you than someone more experienced.

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