20 Things I've Learned from 20 Years in IT

Veteran technician and project manager, Scott Matteson, shares tips and insights from his 2+ decades in the IT field.

IT Career Tips Advice

Working in the field of Information Technology means more than fixing computers or troubleshooting email issues. Thriving in this career requires you to sort out an intricate tangle of problems, priorities and people on a daily basis. Keeping your technical skills relevant and up-to-date is always a challenge, but one that’s well within reach if you train on the job, enjoy learning new things, and keep your thumb on the pulse of the tech community.

However, it’s harder to figure out how to deal with “back end” tasks like juggling priorities, managing stress and developing positive working relationships with peers, customers and managers. In fact, handling interpersonal relationships can be more challenging (and rewarding) than managing the tech itself – and it’s essential since the technology goes hand in hand with the people who use it.

IT roles are changing; support may be located remotely, systems might be off site, and some jobs will disappear entirely. However, there will always be pain points, pressure and personalities in the field. I've worked in the IT space since 1994, primarily in the realm of support and implementation. Along the way I've made a few observations with accompanying advice which I want to share with you. Many of these apply to my role as the “go-to” guy who can get things running, but I think they are universally relevant to any role where you're seen as a resource or a decision-maker on which other people depend to do their jobs.

So without further ado, here are 20 things I've learned in my 20 years in IT:

  1. You’ll be a Pizza

    Think of your daily schedule as a pizza divided into slices (it’s a fitting analogy since IT people eat more pizza than any other group I’ve seen except perhaps pizza shop owners). Everyone is going to want a slice of your time, maybe more. Divide your day up into separate components then figure out who gets what: break-fix work, projects, training or handling email. However, keep in mind there’s only one pizza to go around each day: don’t over-schedule or get bogged down with commitments you can’t keep.
  2. Know how to Apply & Reinforce Limits

    Problem severity and importance will vary depending on user or system impact… or the views of those involved. An email server outage is obviously far more critical than a user not being able to print to a certain printer (while others work OK). Throughout each day you’ll have to assess what you’re doing to make sure it’s the most relevant work that can be done at that moment and limit the non-essential tasks. They say Nero fiddled while Rome burned. If you don’t use limits to keep yourself focused on what counts you might be doing the same.

    How to apply limits? Be clear up front with users about the time you have to devote to their issues. Reschedule minor issues for slow days. Provide workarounds to allow them to do their jobs (use Firefox instead of Internet Explorer to access a site for instance). Simply put, people will use you if you don't set limits.
  3. Nice Guys Finish Last

    This is not meant to advocate rudeness or being unhelpful. However, it goes hand-in-hand with the prior two concepts. Users have a tendency to return to the last IT staffer who helped them, even if it's for a completely unrelated issue. IT newbies often want to be as helpful as possible, and dive into any problem they’re requested to help with even if someone else typically handles those issues. You may need to learn how to diplomatically state "that's not my job " or else your actual job will suffer due to ad hoc requests. Redirect tasks to appropriate personnel (if applicable).

    Here’s an example: Several years ago an intern was leaving our company and wanted all his personal contacts – which he had loaded into Outlook – exported to a file he could then load onto his home computer. HR approved the request, but it took some time since he added all the company addresses into his Contacts folder as well; we had to comb through these one by one. Then he wanted detailed, written instructions on how he could load his personal contacts onto a mobile phone (which he hadn’t even selected or purchased). I had to firmly state “Sorry, that’s not my job” and get back to work.

    Be mindful of situations where you may be asked to provide free support for home equipment and ensure the boundaries of work are respected. In another instance, I worked for a company that gave out old equipment to employees, and this led to entanglements whereby we were asked by coworkers to support said equipment for their personal use. One even kept coming around asking for memory for this system! We had to reinforce the “As is” notion after people approached us with blue screen issues on former company equipment.
  4. Interruptions are a Way of Life

    You will be interrupted -- stay focused on the big picture. Sometimes concentration will seem impossible; other times the very threat of being interrupted might hover over you and impact your work. You'll be grabbed walking down the hall or while you’re eating lunch, just like in the Bob Dylan song "Everybody Must Get Stoned." You may need to retreat to the server room or a network lab to accomplish tasks.

    Some interruptions will be legitimate, and others will have to wait for more opportune moments lest you feel like a marionette on a string. Plan for the interruptions so they don’t derail your day. Know your schedule and book meetings with people to handle the additional workload they bring you so you can do what you set out to do each morning (or as much as you can).

    Our society is becoming more and more expectant of instant gratification. Considering the fact many companies now operate 24x7x365 and shopping, online banking, and tech support might take place at 2 pm or 2 am, it’s not hard to see why many people want their problems solved immediately rather than waiting in line. It might be difficult to even communicate to a user that you’re tied up at the moment. I was once approached by a person who was receiving a minor error when getting his company email on his phone. I explained I was fixing the phone system at the time and would check in with him later, but he just blinked, shrugged and kept on talking about his phone problem like I’d never even spoken. I had to repeat myself, a little bit louder and more firmly, adding that the phone system was currently down and nobody could call in or out of the company. He got the point, though not without asking how long I thought it would be until I could look at his phone. I just had to shake it off and keep working on what was the most important thing at the moment.
  5. Stress will be a Factor

    A famous Maytag commercial once showed a repairman sitting around the office all day, bored with nothing to do because Maytag products were supposedly too reliable to break. Your job won’t be like that. You will be stressed – and you need to factor this into your life and accommodate for it. Get some exercise, get out for lunch, ensure you use your vacation time and stock up on hobbies and outside interests not related to IT. I've had vision troubles that were stress-related for instance – don’t let the job take a physical or mental toll on you. A walk outside at lunchtime can work wonders.
  6. There’s No Such Thing as Multi-Tasking

    I tried for years, but finally concluded there is no way to truly perform several tasks at once in an effective manner. Splitting your time and attention between 4 or 5 things just means each process gets less of your focus than you can meaningfully provide at that moment. Stuff gets dropped, forgotten, or delayed when you juggle things; eventually all the balls will fall. Furthermore, your concentration and attention to detail suffers. Now my mantra is “one thing at a time.”
  7. People will Surprise You

    I have found that very few people have fixed personalities; these may change on a given day or within any given scenario. Something about technology – and our dependency thereon – makes a very interesting ingredient in the recipe of human interaction. I’ve known people who seemed congenial on quiet days then turned into Gestapo nightmares during a system outage (one such person, a VP of Customer Service, marched over to my area to bellow “Do you understand how important email is?” during an email server outage we were struggling to fix). I’ve also known people who seemed unsympathetic or ruthless who turned out to be calm and helpful during those same situations.
  8. Keep your Friends Close…

    If you're on a team of IT staffers, maintaining good relations with them is critical, since they will be the ones in the trench with you at 2 AM Saturday morning. However, keep in mind your team might also be your #1 source of interruptions. Quite likely that will be easier to handle since as fellow IT folks they’ll understand how hard it can be to stay focused on a single task, but you should consider setting up official training and knowledge transfers to help orient them to things you do and vice versa, so that they require less of your time.
  9. …but Don’t Keep your Enemies Closer.

    “Enemies” shouldn’t be a word at all. Don’t get involved in Machiavellian office politics, grudges or battles between IT and users. Simply put, everyone is there for a reason: to get their jobs done. However, there are some hard truths to learn about your encounters with the user community. You may make lots of friends and help people with numerous computer issues, but you won’t get along with everyone you encounter. Some people just won't care what you think. They might be pushy, self-centered or egotistical. Don’t take it personally.

    You're going to have to make hard choices at times – namely, who to please on any given day. Remain polite and professional, but stick to your guns and develop a thick skin to handle any personality conflicts which might arise.
  10. You'll be Invisible to some who see you as Just the "IT Guy/Girl."

    The fact of the matter is that some people will only talk to you (or even say hi) if they’re having a computer issue. You’re the IT person, not an actual human being with a family, hobbies, and life outside the organization (at least that’s how it will seem). In a way it’s like how kids view teachers – I remember being surprised when I saw my third-grade teacher at the grocery store with her kids; I didn’t think she had any children but lived only to instruct those of other people!
  11. But you’ll be a Hit at Parties!

    If you’re ever bored at a party or need a conversation starter, tell someone you work in IT. Immediately they’ll light up at the notion of a captive IT audience to ask questions of. Whether it involves mobile devices, internet access, tablet problems, Word complaints or wireless anxieties, you’re sure to find more conversation than you know what to do with. This is why it might be best to be vague when strangers ask what you do for a living (I hear lawyers and doctors do the same).

    More challenging than dealing with strangers, however, will be dealing with family or friends who know your line of work. Are you prepared for that Sunday night phone call from an in-law whose computer won’t turn on and they think you know some magic solution to get it to boot up from 400 miles away? Maybe it won’t bother you or be unmanageable, but it might also turn into a problem if you’re seen as a resource for others to abuse at will. Think about how you can handle these types of situations – maybe turn them into a “quid pro quo” arrangement whereby they’ll repay your time with expertise of their own (for instance if your sister-in-law prepares taxes can you ask her to prepare yours in exchange for computer advice?) Do you charge them an hourly rate so they’ll value your time? Do you refer them to another resource such as Geek Squad? The answers will vary depending on your personality – and theirs.
  12. You’ll Be What You Support

    Whether you’re a Windows, Apple or Linux tech you’ll be seen as the physical embodiment of what you support. This means you’ll be expected to know everything related to the subject… and you’ll also be seen as responsible for that crazy incoherent Internet Explorer error.

    It can be thrilling to be seen as a god or supernatural being, but more likely it will be to your detriment. If necessary, make it clear you work with these products but you didn’t program them nor do they always make sense even to you. Don’t get dragged into holy wars with other tech aficionados who may think that because you work with one operating system you automatically love everything about it as well as the company that provides it. Life’s too short to waste on “my OS is better than your OS” arguments; no one changes their mind and it just breeds animosity.
  13. The Early Bird Gets the… Surprise Assignment

    I’ll let you in on a secret: getting into the office early to get caught up on a pile of work can sometimes lead to even more work. If you beat your coworkers into the office and someone shows up looking for one of them, guess who’s going to get hit with their request? Maybe you’ll know how to handle it; more likely you'll wind up playing receptionist to find the person in question.

    Some of this stuff is unavoidable and simply the nature of the beast. I’m not staying don’t come in early or stay late since you might end up grabbed, but have a plan of notification and escalation in place. If I need to reach a coworker on something urgent I can page them on their smartphone; all of us are set up in the system so we can be reached any hour of any day. It works well since we have an “on call” rotation where someone is the primary contact for emergency issues each week, and others can refer issues to them if needed.
  14. Switching Roles will be a Challenge

    If you move from one group to another (help desk support to system administration) make sure to do so with an accompanying company announcement, preferably from your manager. Not only does it welcome you to the new role, but it informs company staff you’re no longer the go-to person for your prior responsibilities.

    People will still come to you with requests related to your old role – especially when those who handle those requests aren’t available – but don’t let it overload you. You will have a new set of responsibilities to adhere to, and while an occasional step back to your former position isn’t an issue, you also don’t want to be seen as the patsy people approach to make an end run around official processes or “first come first served” policies.
  15. Keep Track of Everything

    Document everything you work on, including ad hoc work, interruptions, last minute requests and so forth (especially this stuff!). Whether you record items in an official ticketing system, on paper or just keep notes in a text file on your computer, you’ll want a running log of what you’ve been doing so you and your manager can plan work and assess trends. This can come in handy for acquiring training for users, hiring additional staff or setting boundaries to limit interruptions.
  16. Bend with the Wind or You’ll Break Before It

    It’s not just users who may dictate your workload and priorities: managers can also be guilty of “drop this and do that!” In fact, as project priorities change you might be told that the system which was so critical to rebuild last week will now have to wait because something more important which just came up.

    If you’re the meticulous type who likes to finish each task before going onto the next, this can be a major bone of contention. However, you’ll need to be flexible and remember that departmental priorities take precedence over individual ones. For better or worse, adhering to management requests is the core responsibility of your job.
  17. IT can Eat Into Your Personal Life

    It’s great that now we can work from home, get company email on our smartphones, borrow laptops from the office to use on trips, or enjoy any of the other benefits that make it easier to do our jobs. However, sometimes it’s a little TOO easy to blend our personal and work lives, to the point we may feel like we’re constantly on duty. Resist the urge to check email every five minutes or log in late at night to fix some minor issue.

    Timothy Leary coined the famous countercultural phrase “Turn on, tune in, drop out.” The modern day equivalent is “Shut down, turn off, step away.” Recharge time is essential for you to maintain your enthusiasm and energy level.
  18. Technology can Burn You Out

    It happens to everyone who works in IT at some point; you get fed up with hunting down problems or dealing with inexplicable failures. Sometimes even the professionals find things way too complicated. For instance, I have wrestled with the concept of streaming media to get movie files to play from my PC to my TV over a wireless connection and time and again I’ve walked away in disgust and resorted to using USB flash drives to play content instead. I know I should be able to find a reliable solution but thus far it has eluded me, leading me to the point I’m reluctant to invest further time on the topic.

    It’s natural: when all you see are the problems you can develop a negative viewpoint and steer clear of the things which annoy you. I have a friend who is a police officer and he reports a similar experience since he sees the worst sides of humanity. However, you need to hold onto whatever thrills led you into an IT career (I hope you didn't pursue it for the fame and fortune!) to stay upbeat and engaged. Success echoes more loudly than failures, and if you've been in the IT field for a while chances are you have way more accomplishments than setbacks under your belt.
  19. You'll Develop a Love-Hate Relationship with Vendors

    Most companies settle on specific brands for use in the organization: Dell servers and workstations, Cisco switches and routers, or VMware virtualization products. These brands and the vendors behind them will be like family in a sense: they’ll support your way of life and you’ll become intimately familiar with them, but they will also aggravate you at times. Whether it’s dealing with bizarre Windows errors, trying to troubleshoot display driver problems on a certain type of Dell laptop, or researching what should be a very simple function in a Cisco VOIP system, you’ll want to pull your hair out at times over a vendor’s shortcomings.

    All products have issues from time to time. Most support sites aren't very helpful, and poor documentation simply seems a fact of life. That’s just the way it is. The good vendors will be the ones who guide you out of the forest when you’re stuck, by helping provide solutions (or replacement hardware if need be). However, others may get under your skin and fester. After almost 20 years supporting Microsoft Windows, I have significant issues with some of their product decisions; hiding necessary folders and files, nagging users with unhelpful prompts and forcing unwanted changes upon people (new interfaces or menus). In short, it’s hard for me to get enthusiastic about new versions of their software due to the headaches I've had. I have used this to my advantage by learning alternative operating systems such as Linux and Apple, to make sure I can separate what’s native to (and annoying about) Windows from what’s universal across all computers (missing functions, maddening error messages and system failures). Trying to mount a USB drive in Linux, for instance, is a lot more challenging than in Windows, which makes me appreciate the latter’s functionality.
  20. You can Write Your Own Ticket

    Hands down, the best thing about working in IT is that chances are you’ll get back what you put into it. Unlike many traditional fields of work like medicine or law, if you learn as much as you can on your own you can build a solid career. There’s plenty of information out there on any given technology topic, much of it for free. Books and PDFs can be acquired and studied, test labs can be built in your home, and there are plenty of online communities to discuss concepts and problems with. Information technology is about information, after all.

    When I interview potential IT staffers I’m less interested in their academic backgrounds than what they know about the job they’re interviewing for – as well as how enthusiastic and independent they are. I’ll take a candidate who only finished two years of college but writes PERL and Python scripts and experiments with Puppet for fun over the person who just got a four-year degree and can recite buzzwords and corporate jargon.

    A good work ethic and the willingness to help out/volunteer will take you a long way. Take the on-call pager for a colleague for a week while they’re on vacation or grab that ticket with the problem user that everyone avoids. Remember #2 and #3, of course, so that you don’t overextend yourself, but make sure you’re an asset to your group and company by leveraging your skills and knowledge set as best you can.

I hope these tips will be useful both for those seeking to enter the IT field and those who have worked in it for years. IT has its ups and downs: it can be a rewarding field to work in and provide for you and your family, but it also requires skill, stamina and patience. Conflict and pressure are part of the game, so you’ll need to manage the struggles before they manage you, and know what to expect so you can plan accordingly.

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