Advice from Your IT Director

Crowd of cell phones
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Speaking to you with direct advice to manage your technology life, as if I were your personal IT Director.  Which, by the way, I'm not.  So please don't ask me to fix your technology.  ; )


Disclaimer: All the ideas expressed in this article are my personal statements and opinions, and do not reflect the opinions/statements of the City of Urbana.


Technology is difficult. Unfortunately, that can’t be fixed because it’s a basic law of the universe that complex things have more problems.  As annoying as this can be for the casual user, imagine how painful it is for IT support teams who spend their days dealing with the technology problems of everyone else. (P.S. Systems Administrators Appreciation day is at the end of July.)

In my day job, I manage one of those IT teams for a City government, but I’m speaking to you here as YOUR director of IT, helping you manage your personal technology use. (Footnote 1) Professional IT teams do a generally good job shielding their organizations, but individuals don’t have the same protection. From observing so many people have personal technology issues, I was inspired to write this to share some best practices, presented along themes I’d use to make recommendations to any organization.

So here is my advice to keep your technology use safe, simple, and hassle-diminished…

Security - You're not paranoid; you ARE under constant attack

Let’s start with the bad news. Security is a race against an opponent who’s faster, smarter, and constantly evolving. You’re never safe, so focus on basic defenses...and how to recover from problems. Some recommendations:

  • Keep your devices up to date. This includes operating systems, anti-virus, and phone apps. It's easy if you just accept updates when they’re offered, but you’d be surprised how many people don’t! (Apple people are especially biased against updates.)
  • Use a password manager, and (this part’s important!) allow it to generate complex - and different - passwords for every site. The password manager keeps them organized for you behind one single password, which should be a new password that you do not use anywhere else (or have ever used before). See Footnote 2 for more on this. 
  • Backup your stuff. Follow the 3-2-1 rule: have at least three copies of your data, store the copies on two different media, and keep one backup copy offsite. If you back up your computer to a hard drive, buy a second one, rotate the copies, and keep one drive offsite. I think that’s a lot of work, however, so I strongly recommend using an online backup service instead - it does it all in one simple step. (Actually, I have a more specific recommendation in Footnote 3.)
  • Treat suspicious e-mails with care. Generally, you'll see two kinds of attacks. One is an e-mail with an infected attachment or a malicious web link ("hey, check this out ...") often from someone you know. Opening the e-mail isn't harmful, it's the attachment or link that is. When you see these, pause: are you expecting this person to send you something? If you're not sure, CALL them - don't respond to the e-mail. The other common e-mail attack is phishing (spear-phishing, whaling, etc.) This where the person asks you to do something, like go to a website and fill in your user ID and password ("your bank account was compromised, click here to reset...") or to respond to them by e-mail because they need you to buy gift cards, transfer funds, etc. If you follow the link and sign on, you're seeing a fake site and you're giving up your user ID and password. If you want to confirm that there's no issue, go directly to the real website (not from the e-mail) and sign on to see if you have any notices there.

Branding – Managing your online identity

Entities struggle to define their brand and use it consistently across different platforms like marketing, websites, and social media. Individuals have it easier, but it's important to separate your work and personal lives, and to separate your public online identity from your private one.

  • First, maintain separate e-mail accounts for home and work. Never use your work e-mail for anything you might want to access after you no longer work there. Never use your home e-mail for work. If you’ve broken this rule already, fixing it is just a matter of going back to different web sites and changing the e-mail account associated with it. (Following the Security guidance, you’ll need to visit them to change your password anyway… do them both at once!)
  • Create a third e-mail account for online use (like website registrations) that is separate from your home e-mail. This is your primary online identity and this account will absorb most of the unimportant e-mails that clutter your Inbox now. Meanwhile, your home identity can be used for truly personal communication, shielding that from your more exposed online account. For most people, it's too late - any home account you have is hopelessly drowning in a deluge of unimportant offers. If that's you, then please see Footnote 4 for steps to clean this up.

Procurement – Buy the best solution you can afford and adapt to it

Helping my employer buy technology wisely is a big part of my job. Purchasing rules are not as critical for individuals because the transactions are smaller, but here are some suggestions based on how we manage our IT spending.

  • Stay in one ecosystem to keep things simple. Organizations make everyone use the same technology because it makes IT management easier – and I suggest you do the same. Apple has created a masterful “walled garden,” but Android shows that there are alternatives. Things are simpler if you stay in the garden and let these apps move you along from one action to another (like opening a map from an address someone texted you). You may use a different ecosystem at work, but that’s fine because you should keep your home and work identities separate anyway.  
  • Know what you want before you go to spend money. Let’s assume you’re replacing your phone. Your phone should match your ecosystem, so you know you’re getting an iPhone. Now, which version? This is where it gets hard - and it’s worse for Android, with a huge array of phone makers!  So, decide which features are most critical to you and judge based on those. For a phone it might be storage, physical size (I hate huge phones), camera pixels, etc. Use these key features to whittle down your choices without regard to price, until you have some finalists. Then…
  • Consider all the buying options. With a phone, consider signing up for a phone plan to spread the cost of the device over several years.  Or consider buying an older model; instead of the X, how about the X-1? What about refurbished or used equipment? In many cases (printers, monitors, PCs) I think refurbished equipment is fine. (But please see Footnote 5) Truly used equipment (bought from Craigslist, eBay, etc.) is more of a crapshoot and not recommended unless you research the seller and they do a large volume of these transactions AND have good reviews.

Communication - How do you spell “Huh?” in hexadecimal? (Footnote 6)

One of my most important roles as an IT Director is translating between IT people and non-IT people. Here's some advice on communicating across this divide.

How to communicate with us

The most common situation when you’ll talk IT to an IT person is when you need help. This should be easy – you want your problem fixed and IT people like to solve problems. But of course, it’s not easy… that’s why IT Directors have jobs!

The support person you’re dealing with didn’t create the problem, and they may be very limited in their ability to fix it. Your goal in this communication is to get them to understand your problem and acknowledge that there is an issue, so they can resolve it or escalate it to the next level. If they don’t understand your problem, or agree that the product isn't working correctly, neither of these will happen. 

You want to clearly show them what happened, with as many details as possible - so that they can recreate the problem, or at least see and understand your description. This is essential because most support people start with the assumption that the user did something wrong and is blaming the software for their own mistake. (Sorry to tell you this, but that is the default attitude!) Providing details speeds up the interaction; they can bypass the standard questions because you have already presented them with what they need to know.

I like to send an e-mail with an attachment. (More details are in Footnote 7.) This is a better use of my time than a chat session (they take too long, and it’s hard to multitask) or phone calls. (So painful!) Usually a detailed e-mail gets detailed responses, or specific questions – which can rapidly achieve the goal of showing the problem. Plus, they can be forwarded to other support people without you having to explain it all over again.

How to understand us

In case you haven’t been reading the Footnotes, like many IT people I prefer numbered steps to describe a sequence of actions & events. This is our communication style in action – we like specificity, order, and structure. In short, many IT people think like computers... it's a good model to keep in mind when you're dealing with us. Present us with a mass of extraneous information and you'll overload us, getting a blank stare that's our equivalent of "Does not compute."

Another example of thinking like computers: when answering a question, we are precise, but may stop when we’ve answered the original question, without telling you other information you probably need to know. We do this to be accurate, but I understand how frustrating it can be. Be patient with us and ask more questions or open-ended ones.

Finally, be prepared for a little smugness from us when you talk to us about IT things. As I started with, technology is difficult. IT people have made a career out of specializing in some aspect of it - and we may take some pride in that. Also, there's a certain amount of "oh, so now the class president who wouldn't talk to me in high school needs MY help to save their presentation" resentment that can bubble up at times. Some praise and a thank you e-mail to the person (with a copy to their manager) go a long way and might earn you better assistance next time - or at least a little less attitude. And don't forget about Systems Administrators Appreciation day!


Footnote 1: There’s great irony in me advising on IT, because I consider myself a Neo-Luddite (see my blog on that here: and I truly regret that we live in this screen-focused world. My negativity helps, however, because my goal is to minimize the effort of technology while maximizing its benefits.

Footnote 2: Passwords are something that even IT people are lazy about. Here’s the problem: let’s say you’re like most people and you’ve used the same password + e-mail combination to register on different websites. Now if one of those websites is breached then bad actors could get the list of e-mail & password combinations. Next, they use software that attempts to log in with those combinations against a bunch of other web sites, hoping you used the same ones. This is why you need a different password on every site. That’s also why you should use a brand-new password for the password manager, in case your favorite password is floating out there. Seriously, if you really want to keep it simple just use the password manager! And one final benefit, you can grant emergency access to someone else in case you're incapacitated, and they can access your accounts, so you don't wind up in this unfortunate situation:

Footnote 3: My recommendation is to use a cloud service AND to turn on File History (for Windows users or Time Machine (for Apple users  File History and Time Machine give you easy access to prior versions of a file if you have an "oh crap!" moment and want to undo changes, and your cloud backup will save you if your whole hard drive is toast.

Footnote 4: First, create a new “home” e-mail account and give that to friends and loved ones, but don’t use the new account for online accounts. Now turn your old home account into your online account. Monitoring two accounts will be more work for a while, but it gets easier over time - and it pays off in keeping your real life and web identity separate. Here are some steps to help managing two inboxes easier:

1) In your online account, mark as “junk” any sender you don’t want to ever see again. This will make a difference in time saved. Unsubscribing is effective, too, but more work. I recommend selectively unsubscribing when you want to receive SOME types of e-mail from a reputable sender (e.g. order confirmations) but not others (like online deals). If you want no-emails from them, mark them as junk.

2)     When your online account gets emails from real people you want to stay in touch with, respond with a “Here’s my new e-mail” note. (But don’t use a permanent auto-respond; it would be easy for some spammer to scrape your new e-mail from your response.)

3)     Consider adding a fourth e-mail account – a “junk” e-mail account. Use this for any one-time items, or when you are forced to enter an e-mail but don't want to ever hear from them. I rarely check my junk account, and when I do it’s usually just to do a mass delete.

Footnote 5: Refurbished means it was inspected and repaired. Always try to get a warranty on these - and think twice before buying if you don't. As long as you buy refurbished from somewhere you can easily return, it’s a good way to save some money.

Footnote 6: 48 75 68 3f

If that made no sense to you, then just know that hexadecimal is a base 16 method to represent binary numbers, because computers think in binary - and "Huh?" in binary is 01001000 01110101 01101000 00111111

And if that made no sense to you, then just know that hexadecimal is a magical tongue that lets you speak to unicorns.

Footnote 7: Here are some steps to follow to document your problem.

1) Can you repeat the steps and get the same problem? If so, awesome – you’re 80% done – see step 2. 

  • If you can’t get your problem to repeat, and your thing now works… then great, you’re done – your thing is working! 
  • If your thing is inconsistently not working then keep going to step 2, but you need to capture an example when it's not working, even if that takes you a few tries.

2) Now you need to show & tell your problem.

  • My favorite method is a video capture. You can use free capture tools to record (with or without audio) a movie file that shows the problem occurring.
  • Next best are pictures and words in a document. I use a Word Processor to write numbered steps of what I did and add screenshots, which are tremendously helpful.
  • The third option is just the numbered steps with no pictures. As long as the steps are accurate and detailed, that's enough.