When I saw the topic I was given for this month, I immediately burst out laughing as I have (while never violating an NDA) shared more than a few horror stories, complaints and tales of woe (from the perspective of both employee, and boss) with my fellow Handlers. In retrospect, some were not as bad as they seemed at the time, and some are far worse. In the end, as someone who has held positions from helpdesk to CISO of a global company I have a broad range of experiences to draw from in giving you my opinions on how to handle those impossible requests. Christopher Carboni - Handler On Duty isc dot chris at gmail dot com |
Chris 140 Posts Oct 21st 2010 |
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Oct 21st 2010 1 decade ago |
Good article and pretty much spot on. Give them the initial feedback, gather additional details needed to further define the problem and solutions, tell them you will look into how to solve or work around any problems, and then come back and tell them what your stoppers are if they exist. Also, explain what other tasks might get delayed while you are working on this task.
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Anonymous |
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Oct 21st 2010 1 decade ago |
At my first serious job interview the interviewing manager asked me almost exactly that. I told him I'd try to explain why the task couldn't be done as formulated, and try to offer workable alternatives. He nodded and pushed on: "What if your boss insists you do it just like that?" My reply (ad.lit.) - "I document everything and do exactly what he wants, give him all the rope he wants to hang himself."
I was hired despite that, and found out later that the questions were plot-relevant foreshadowing on his part. |
Anonymous |
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Oct 21st 2010 1 decade ago |
When I get an impossible request, I usually find that it is because the boss has over-specified the task (getting into the technical details when they shouldn't). I then try to get them to just describe the business function that is trying to be achieved and tell them to let me figure out the technical details myself.
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Skip Carter 4 Posts |
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Oct 21st 2010 1 decade ago |
In my experience over the decades, I have encountered a few cases where the impossible request was because the boss was literally insane. While admittedly rare, something to keep in mind.
In one case, the president of the company apparently found the wiring unsightly, so he cut off all the cables in the PBX & server room with hedge shears. He demanded we (IT) get the phones and computers working again, but without "all those nasty wires." After some debate, and with trepidation, my immediate boss called the chairman of the board. That's about as go over your boss' head as you can get. While the chairman was doubtful, he did call the president, followed by a call to the police to take the former president into custody. Later, we discovered the president had ordered the janitorial staff to sweep the parking lot to "get rid of the ants before they got inside," and had made some bizarre requests of engineering, but no one had the courage to do anything about them. In another instance, the CFO demanded we "fix the database," since it showed the wrong balances, as they did not match his financial reports. As we discovered, he had been spending money based on his own projections, not the actual amount the company had received. That one I was able to report to the CEO's secretary. Sometimes you have to deal at a higher level of responsibility than the chain of command. |
Rastech 18 Posts |
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Oct 21st 2010 1 decade ago |
In my experience over the decades, I have encountered a few cases where the impossible request was because the boss was literally insane. While admittedly rare, something to keep in mind.
In one case, the president of the company apparently found the wiring unsightly, so he cut off all the cables in the PBX & server room with hedge shears. He demanded we (IT) get the phones and computers working again, but without "all those nasty wires." After some debate, and with trepidation, my immediate boss called the chairman of the board. That's about as go over your boss' head as you can get. While the chairman was doubtful, he did call the president, followed by a call to the police to take the former president into custody. Later, we discovered the president had ordered the janitorial staff to sweep the parking lot to "get rid of the ants before they got inside," and had made some bizarre requests of engineering, but no one had the courage to do anything about them. In another instance, the CFO demanded we "fix the database," since it showed the wrong balances, as they did not match his financial reports. As we discovered, he had been spending money based on his own projections, not the actual amount the company had received. That one I was able to report to the CEO's secretary. Sometimes you have to deal at a higher level of responsibility than the chain of command. |
Rastech 18 Posts |
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Oct 21st 2010 1 decade ago |
For the more normal impossible requests, the advice to think twice before responding is excellent. I have lost at least one role from a too quick response, which, on further thought, I could have handled better.
I have generally had success by incorporating a back-of-the-envelope ROI calculation with documentation of both the risks and benefits inherent in it, with a meeting to discuss and then a request to sign off on those aspects that are beyond my authority level. I have gotten resistance to that in some cases, but I then file the request further up the chain of command with a request to discuss. While that could have negative repercussions, I've never actually encountered any from the higher ups. As long as I express myself as trying to fulfill the business goals, with some concerns, I have been accepted at that level. I may be ordered to do the task anyways, but that's alright - I made my concerns known. If I succeed that's great, and if I fail, then I'll do a post-mortem with the boss on why it failed. I always stay civil, polite, smile and try to make the project into a joint effort to solve the impossible task, whether it fails or succeeds. Since I had a trial-by-fire wherein one of my staff was physically assaulted by a manager for attempting to do his job correctly, I refuse to kowtow to anyone, and, due to my earlier experience as noted above, I am willing to escalate matters as far as needed. Doing it with civility is key. |
Rastech 18 Posts |
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Oct 21st 2010 1 decade ago |
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