Q: The new IT director at my large, international office is a rude, condescending jerk. We’ve been through years without any IT leadership — the previous ones quit or disappeared — so our infrastructure has run amok, and he has a big job to do.

But he lacks serious people skills, at least around me. In conference calls, he has openly accused me of various transgressions, like how my large files are supposedly causing backup problems. He laughs at my serious comments or questions. And he has threatened to delete my folders or charge me an outrageous cost to put them in the cloud. I have told his staff how unpleasant this is for me, but they shrugged it off.

What do I tell HR — that he’s just a lout? I suspect upper management doesn’t want anyone rocking the boat after years of IT chaos. The problem is, this guy wields huge power over my work and data. If I don’t have IT, I might as well just go home and do analyses with my calculator. — Washington, D.C.

A: This is why they call them information technology pirates.

Actually, no one calls them information technology pirates, but I do, because good ones — as you have discovered the hard way — are difficult to find on the open corporate seas and can be wont to hold you, or at least your data, hostage. This is because everyone needs an IT pirate, and the demand is growing every day, what with China stealing everything in sight from random hotel chains. (They are the IP pirates.)

Because look, nothing against information technology pirates, but if you do well in your college computer science classes, what would stop you from becoming a computer programmer pirate? Those pirate jobs pay better and people such as yourself don’t go around treating computer programmer pirates like back-office drones. In a way, I can’t really blame your IT pirate for trying to take ransom on your data.

That said, if you want to have an easier time with your IT pirate, try talking to him honestly and one-on-one. Reporting someone’s abrasive personality to HR can backfire badly. Say you understand that it’s hard to be an IT pirate but that you cannot do your job without IT. The worst thing that can happen is he acts the way he always acts, and you wish that you could make him walk the plank.


If you can’t bear the thought of any of this, you might also seek out one of the IT pirate’s more competent direct reports and ask this nice person to assist you with your projects.


Man overboard

Q: I am a 64-year-old software engineer who was forced to change jobs because of a layoff. I was with my previous employer for several years and had hoped to retire from there when I turn 65 at the end of this year.

Fortunately, I received and accepted an offer for a position at a new company. I am working with several friends and colleagues I have known for many years, and I believe that their advocacy was a big reason I was given the job. I considered this a true blessing, as I had been unsuccessful in interviews with a few other companies.

But I still plan on retiring at 65.

Is there an ethical imperative for me to give my new employer a heads-up about my plan? If so, how much notice do you think I should give? Should I feel guilty about the fact my friends helped secure me the position? — New Hampshire

You have no need to worry. Unless they asked you explicitly in the interviews or when they extended you the offer that you commit to a particular duration of employment, you can retire at whatever point you like.

The reason employers tend not to like short tenures is because they want to amortize the hassle of hiring, training and everything else that goes into bringing a new employee on board. The fact that you are highly experienced and already comfortable with so many of your colleagues ameliorates this issue to some degree. There is also the possibility — common with employees at the end of their careers — that you keep working in some capacity for this company as a consultant.


I am not sure from your question whether you plan on taking on part-time or contract work once you retire, but if you want to make yourself feel a little less guilty when you quit, include in your resignation letter a sentence or two offering to freelance. Benefits typically add about 30 percent to the cost of a salaried employee. If you end up working for this company part-time after a year or so in-house, this might be an even better deal for the company than they had bargained for originally. It might even qualify as “a win-win”!

As for notice: Ideally, you want to give them as much as they would need to find and train your replacement. A month would be a nice amount.

Severance includes the word ‘sever’

Q: I’m middle-aged in a youth-dominated technical industry and beyond burned out. A few months back, I went to HR to explore alternatives to full-time, in-office work. There were none, and during the conversation I hinted I was thinking of leaving. Mistake. I was naively under the impression that HR people were like lawyers and bound by silence — but soon after, word came down from above asking me “when I was planning to leave.”

I gave them a date, because I’d decided to leave by that point, but part of me feels hard done by. I’ve put in some good years, but as soon as I asked for help — or, it seems, showed my lack of company devotion — I was basically shown the door.

Should I stick around and force them to fire me, as all my friends counsel? I say forget it, I’m done. But some bitterness remains. — G.F., New York City

If you see some way to get severance out of this, I say take it, even if you have to sacrifice a little of your self-respect. This is because they have already belittled you, so why not get some compensation for your troubles? Also, for most established companies, an ounce of severance is worth a pound of lawsuits. Or something like that.


Work Friend is a cheeky New York Times advice column to help with careers, money and the sometimes grim, sometimes hilarious maze that is the contemporary office, from a rotating cast of advice-givers.