How can an inexperienced "tech guy" help his organization IT-wise, if outsourcing isn't on the table?

As an unwittingly frequent mentor to technical hopefuls, it's hard to draw the line between "sure just follow these steps" and "it's over your head, outsource if at all possible." How do you distill half a decade of experience into an email? Here's a case study:


A few months ago I got a message from Roger, a member of the Spiceworks tech community I am active in, and "the sole IT person at a growing church." He described himself as having "been in IT for many years" but "mostly in software systems design & project management before this." What followed was a big technical implementation question, so I knew that the big omission here was any actual hands-on administration experience. As an IT Manager, I'd probably consider him a software guy not an IT guy.

He described his church's technical setup, and finished with "so we have 5 servers and are adding 2, upgrading from Server 2003 & Exchange 2003 to Server 2008 & Exchange 2010, and adding a network data storage array. Not sure how to blend all this together and can't find a network how to? Can you point me to a 'Best Practice' or design template?"

For those readers without IT experience, this is the computer equivalent of a 16-year-old calling his dad at work and saying "I figured out how to pour the oil down the tube by removing the dipstick, but how do I get the old oil out? Is there like a Porche manual somewhere?"

My first reaction was to wonder if he should even attempt to be helpful lest he destroy something; my conclusion was that some help is better than no help -- and if I don't help educate this person who will?


I finally replied:

Hi Roger, I'm flattered that you'd consider me an authority on such things. As far as I know, however, each network is unique and the IT industry is so rapidly-changing that there isn't one overarching template or howto. Architecture planning and server implementation are usually done by someone with years of experience and blood/sweat/tears."  I went on to encourage him to take a Microsoft Certified Systems Engineer (MCSE) training course, or to self-study the training materials and do the hands-on labs. Don't just train for the test, I cautioned.

Regarding documentation:

Generally speaking, documentation is written (sometimes poorly or not at all) for an idealized world devoid of reality. All the tech you see around you is purely the blood/sweat/tears of under-trained technologists like ourselves. My only advice is to get good partners/mentors and try not to break things outside of a test environment. (You DO have a test environment, right?)" -- this is important. As an IT student, I figured that the industry must have evolved to a point that you could "become certified" and know everything there is to know, or that Reading the F'ing Manual was the gold standard of knowledge. Both of these things are mostly untrue. The vast majority of people working in IT don't know how to fix the problem they're faced with, and there are no certifications or manuals that just give you the answer. The inescapable conclusion is testing and hard mind-bending work. Professors don't tell you these things.


I recommended against upgrading in-place from 2003 to 2008/2010, and also that he lock himself in a room long enough to get a general understanding of the concepts involved (all the way from IP addressing and DNS to Active Directory and Windows 2008 with Exchange 2010) and then sketch out his ultimate business goal ("get more storage space?") and finally outline each step along that path.

No battle plan survives contact with the enemy, but you should also know at what point you'll be implementing each step and in what order, and thus "eat the elephant one bite at a time." There will be occasions where you need to do 3 things simultaneously, and it'll be convenient to know WHICH 3 things it is you should be doing to ensure a smooth transition (there WILL be downtime, plan for it and mitigate it.)

I also added a few links so that he could better operate in the IT field, by asking "smart questions" of people online and by looking into the most complete IT handbook I know of:


Having not received a response for a few months, I followed up. Roger completed his "lockdown," recruited a few volunteers, and made a plan to install the new servers and migrate slowly and stably. He's armed with TechNet documents and partners at Dell, and just finished an Exchange training course with an instructor who's been helpful to him.

I hope to follow up and see what things look in retrospect, but this seems like a great success so far. He's gone from asking general, vague questions about complex IT topics, to developing a conservative plan and using all the right resources to their fullest.

Hopefully this is a good path towards IT enlightenment that other newbies can take advantage of to deploy technology beyond their current understanding.