Stacking the Tech Support Deck in Your Favor

Leo Notenboom
Tech Ramblings
Published in
6 min readDec 9, 2017

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When you ask someone for help, stack the deck in your favor by painting a clear picture of the problem you’re experiencing.

In a recent Ask Leo! Tip of the Day, I suggested you should Provide Enough Information When Asking for Help.

Great, but that raises the question: what’s enough?

In fact, even more than that, which information?

While there are no hard and fast answers, here are guidelines to consider when asking anyone for help with technology.

It’s not about me

I’ll be talking about what I see, what I need, and what helps me get questions answered, but honestly, this isn’t about me. This is about anyone, anywhere, from whom you are requesting help. The concepts are the same no matter who you ask.

I just happen to be my own best example. 🙂

It depends

I will readily admit that there’s no magic formula, no checklist, no set of rules to follow when providing information to someone when you ask for assistance.

Asking for help about a webpage’s behavior requires different information than if, say, your computer suddenly starts blue-screening.

But there’s definitely some information common to all issues — both specific questions you need to ask yourself and have on hand to share with the technology gurus in your life.

“It doesn’t work” never helps

A surprising number of questions I get just boil down to “[fill in the blank] doesn’t work”.

That’s exactly zero information. I have nothing — literally nothing — to go on. All I can do is respond with some questions of my own to try to uncover more details about what’s going on.

To be brutally honest, these are the kinds of questions I have little remorse about ignoring, especially if I’m already busy.

More information is always better.

Just making the attempt to provide more information tells me you’re willing to work at it. Whatever you’re dealing with probably isn’t your fault, but working to get help on it is your responsibility. The more obviously willing you are to try, the more likely I or someone like me will make the time to try as well.

I’ll say it again: more is better. Too much information is better than not enough, and most certainly stands out when compared to no information at all (aka “it doesn’t work”).

The questions I ask in response to “it doesn’t work”

When I’m faced with an “it doesn’t work” style question, I have a set of questions I pull from to try and get more information. Answering these questions as part of asking the question in the first place really stacks the deck in your favor.

How did it not work?

By this question, I mean “Tell me what happened.”

Tell me the exact error message (if there’s a way, include a screen shot). “It said something about …” isn’t particularly helpful. The more precise you can be, the better.

“Tell me exactly what went wrong”, another way of phrasing it, also leads to my next question:

What were you expecting?

It’s not always obvious what success looks like, so tell me what you were expecting to have happen. Compare what actually happened to what you were expecting.

Sometimes it’s the expectation that’s in error, and knowing what you wanted to have happen can allow me to clarify if that’s the case.

“What would success have looked like?” is another way to phrase the question.

What exact steps did you take to get the problem?

While this doesn’t always apply, detailed step by step instructions to reproduce the problem you’re experiencing can help me understand what’s happening. Sometimes those steps are enough to identify a solution, but more commonly those steps are what I would go through in my attempt to duplicate what you’re seeing.

In other words, “How would I make this happen on my machine?”

What kind of things have you tried?

This is about saving us both time and frustration. And, yes, it’s frustrating to make a suggestion only to have the response be, “Oh, I tried that. It didn’t work.”

Let me know what you tried to resolve your problem before you contacted me. And let me know how each attempt failed — differences in the way things fail can often be important clues to resolving an issue.

“What else didn’t work?” might be another way to think of this.

Has anything changed recently?

People are generally pretty good about letting me know if a change “here” seemed to have a side effect “there”.

The most common case is “I updated X and now Y doesn’t work”, where “X” is often a system update. That helps a lot.

But it’s also a fairly clear case of cause and effect. Less clear cases count too.

For example, installing some software and then having some seemingly completely unrelated failure appear later is surprisingly common. Include changes that might not even seem related. As I’ve said many times, these are incredibly complex systems we’re dealing with here, and how seemingly unrelated things can impact one another is one of the ways this complexity becomes glaringly apparent.

“What else is new?” might be another way to look at this.

Tell me about your system

This is the one I understand the least. I get that sometimes the variations of “it doesn’t work” at least feel like a reasonable question, even if it’s lacking important details.

But it seems to me that what kind of a system you’re working on would be fundamental information to include. Sadly, while it’s not often, I’ve definitely had to ask, “Are you even running Windows?” to some questions (and received “Oh, sorry, no, this is my Android phone” occasionally in return).

This is pretty close to a check list of information to include.

  • Operating System (Windows? MacOS? Android?)
  • Operating System Version (10? 8.1? XP? Bonus points for including specific update level — see below.)
  • Browser (IE? Chrome? Firefox? When applicable)
  • Computer or device make and model (at least whether it’s a desktop, laptop, tablet, or phone)
  • Installed RAM and hard disk(s)
  • Additional hardware that might even be vaguely related to the issue at hand

You get the idea. And, absolutely, much of that information may not even relate to the problem at hand, but if you’re not certain, include it anyway. More information — even too much information — is better than not enough, and only serves to increase the odds of a successful resolution to your problem.

Two approaches can help automate some of this for Windows. Speccy (a tool from Piriform, the makers of CCleaner) can perform an inventory of your system that you can save to a file and include with your question. Even just taking a screen shot of your system properties (right-click on “Computer”, “My Computer” or “This PC” and click on Properties) will provide the details of your Windows version as well as useful information about your computer in general.

There are many more questions

There are many more questions that could be asked, but they quickly devolve into situation-specific questions best dealt with case-by-case. The person you’re asking for help will hopefully quickly narrow down the right set of things to ask for additional information.

The single best thing you can do with your question — again, regardless of who you ask — is:

  • Be as clear and complete as possible.
  • Ask yourself some of the questions above before you ask someone else.

I can’t guarantee you’ll get a response or an answer, even if you do provide all the information I’ve mentioned. But the answers may even help you resolve the problem yourself, and they’ll at least help paint a clearer picture to help people like me help you.

This article originally appeared on Ask Leo! where you’ll always find updates as well as the most vibrant discussion. For the latest, subscribe now to The Ask Leo! Newsletter and get a copy of The Ask Leo! Guide to Staying Safe on the Internet — FREE Edition. This ebook will help you identify the most important steps you can take to keep your computer, and yourself, safe as you navigate today’s digital landscape.

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Leo Notenboom
Tech Ramblings

Former software engineer at Microsoft for 18 years, now sharing my passions, answering questions & helping folks with technology. askleo.com (since 2003)