“What was your biggest challenge?”

“What was your biggest challenge?”

Just now coming up on the one year mark of being unemployed, and having gone to about a dozen different interviews now, one of the most common questions I hear is “What was your biggest challenge?” or “Describe a time when you had a particularly difficult challenge and how you resolved it.”

In order as I think of them:

  • Apple and it’s lack of Enterprise support
  • Node locked software on a machine that just died, it out of warranty and the company refuses to return support phone calls or emails.
  • The user who doesn’t understand that going to certain web sites pretty much automatically means the machine is getting a virus.
  • Being asked to deploy non-existent machines to user who were hired only a few hours earlier and are scheduled to start the next day.
  • Explaining what “Corporate Standard Software” means, and why I can’t simply give you a license number so that you can install at home “to learn”
  • Complaints about machine slowness and weird problems to find that the uptime is 45 days.
  • User who upon being told “Those computers are too old, you will not be happy with them when I’m done,” buys new computers (from someone else,) the next day and then expects them to be installed for free after I’ve already done all the work.
  • Users who do not contact their IT support at all when there is a problem, then go home for the day because they “can not get any work done.”
  • Being expected to install a 15 computer network within 8 hours, never having done so ever before (it’s harder then it sounds)
  • Users who expect something done their way when it’s technically impossible.
  • The above, but when it’s illegal or unethical
  • Explaining to your direct supervisor why you REALLY don’t want to see the Midget Porn Website they found
  • Yeah. All of those.

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