Zen and the Art of IT Diplomacy
November 9, 2005 2:25 PM   Subscribe

Help! I'm so very stressed out. How do I convince my luddite of a boss that our office desperately needs a regularly scheduled IT person? I even have a perfect person in mind.

I have been working in an office for about 2 months and the woman I work for is one of the co-owners of the business. While she is excellent at the skills of our profession, she doesn't know anything about computers.

For example, several people have been hired recently and she purchased computers for them without knowing what she was doing. The computers are minimum configurations from Dell with very little RAM and most don’t meet even the minimum requirements necessary for the users. Also, there are about 20 computers in the office and many of them can’t access the network (internet or intranet) because no one has the appropriate privileges or settings.

She has made weak attempts to get some of these machines working and to repair some of the other technical problems that have arisen in the past few months by hiring a consultant. However, he's only in the office once every few weeks and doesn't seem to actually repair anything when he's there. In the 8 weeks I’ve been there he has yet to change it so that printing a file does not require me copying the item to my personal jump drive and using someone else’s computer in another office.

Money is not really an issue in this. The office is in the medical field and does pretty well for itself. The problem is the owners just don’t understand how hampered the employees are by these issues on a daily basis.

As it happens, I am in a relationship with a brilliant IT person who, with proper admin privileges, could fix this place up in no time. Additionally, he'd be willing to work at reduced fees because he's so sick of hearing me complain about the rampant computer problems in my office. My boss actually brought up the issue of having my partner do some work for them when I first started working there but decided to go with this outside consultant so I know it's not completely beyond the realm of appropriateness.

How do my partner and I diplomatically approach offering services to my employer? I know that his skills and availability would quickly allow the entire office to operate more smoothly and increase everyone’s productivity. I'm just not sure of the best way to approach the situation.

This is not about getting my partner more work. He’s got plenty of work and income outside of this. Right now, my boss is very over-stressed with other professional and personal demands so I actually think this would be a very helpful proposal. I want to make sure I don't over step my bounds or create any awkward situations. Any advice at all would be greatly appreciated.
posted by abbyladybug to Human Relations (12 answers total)
The problem is the owners just don’t understand how hampered the employees are by these issues on a daily basis.

It seems like this is the heart of the problem. Have you put together some sort of report about what the problems are, how they're impacting everyone in the office, and how things will improve once they're fixed?

Having a solid list of things that need to be improved might help make the problem clear to your boss. Perhaps your partner can supply estimates of how long each problem will take to rectify.
posted by clarahamster at 2:36 PM on November 9, 2005

Suggesting your partner is bound to appear to be a conflict of interest. If there's an open offering of the job, then he's at an advantage of getting in.

Mark down what sort of tasks and jobs are made more difficult by a lack of proper IT in the workplace. Find instances where valuable time is wasted, and work backlogs due to tech problems. Find out who can't get to what they need, and be able to show why this is hampering their work.

No need to overdo it, but if you can show a few very solid examples of why an IT professional would enhance productivity, your boss is likely to give this serious consideration. If your boss asks you for ideas on where to go to find a professional, you can suggest then. If the position is offered to the public, your partner has a reference from within the company, is fully qualified, and is willing to work cheap. Don't go too cheap though, or else your boss might get the wrong idea on IT wages.

I'm reading that your primary goal is to get an IT professional in there. Don't worry too much about who it is, as long as they're competent.
posted by Saydur at 2:42 PM on November 9, 2005

The boss is only going to listen to the bottom line. The phrase you want to use is "ROI": Return on Investment. If you give them good hard data, in dollar amounts, of how much money they are losing because of these problems, and that you could save money by supplying this expertise, then they will possibly listen. Or they will continue to be intractable, in which case you should quit.
posted by matildaben at 2:50 PM on November 9, 2005

matildaben said it so much better than I would have.
posted by mischief at 3:33 PM on November 9, 2005

Do write up a simple, plain english list of the productivity losses they are taking.

Do include dollar amounts where possible.

Do list the top [3|5|10] priority items, and (if you know) the technical resources needed for those bottlenecks to be eliminated.

Do not mention your boyfriend. Besides an appearance of conflict of intest having the unfortunate potential to backfire into prematurely dismissal of your serious findings, there are other dangers. Like when the owner's ignorance leads to grossly unrealistic expectations or communication problems, which result in less than 100% perfect bliss, which results in people unfairly pointing the finger at you and your "profiteering" boyfriend.

He's such a sweetheart to make that kind of generous offer. Maybe he could help you in a different capacity, like organizing that list and writing a decent job description for the position they need to fill? That'd be a huge contribution. 'Cuz convincing them to get real help is one thing, but the real triumph will be if you can get a technically-illiterate manager to correctly identify which techie has adequate and relevant skills to fit their needs.

Good luck!
posted by nakedcodemonkey at 3:33 PM on November 9, 2005

One thing I'm thinking about as I read this is that these are very businessy answers. Not to go into too much detail about the office environment, but we all have PhD's, and writing up a report about the technology deficiencies will certainly be viewed as a significant waste of time when I could be doing other more work-related activities. I have documented the problems that are occurring extensively. There is someone coming in. He's just never there. Also, hiring people they know is WELL within their comfort zone.

I really think that, given the situation, it's an appropriate question/suggestion. I just want to know how to do it. I know my boss doesn't want to be bothered with computer details. Whenever the IT person is around, she has him talk to me about what isn't working.
posted by abbyladybug at 3:59 PM on November 9, 2005

Hiring people THEY KNOW may be well within their comfort zone, but they've only known you for 2 months. If you don't know how to bring up the problem in a way that gets your boss' attention, then you aren't in the "in-crowd" yet. You shouldn't be suggesting your partner. It's not appropriate and could significantly backfire. All you should be doing is enlightening the boss to the someone who is never there. She's not getting what she is paying for, and she should be made aware of that. Or maybe she doesn't want to pay anything. Maybe the guy/arrangement she has is exactly what she wants, because that someone is someone else's "perfect person". She already didn't choose your partner so it's not work savvy to bring it up again. The problems yes, but let her figure out the solution (or not).
posted by dness2 at 4:17 PM on November 9, 2005

I would suggest asking others if they would approach the boss with the idea to get somebody in full time. Leave your partner out of it would be my suggestion.
posted by Megafly at 5:17 PM on November 9, 2005

abbyladybug, sound like you may be overthinking this. "Writing up a report about the technology deficiencies" isn't necessary unless the boss asks for more detailed info. But you've noted the boss is already busy, and this is (for her) not a simple topic to grok. So having some kind of written list in front of her will help give her digest the info and recognize the scope of both (a) problem and (b) needed solutions. You asked how to bring it up; well, a complex, tricky discussion generally needs a paper backup for everyone to refer to. That's all.

Also, any manager worth their salt would not look upon identifying major cost-saving measures as a "significant waste of time". You already know what most of the problems are, right? How long would it take to throw them all into a simple list, then move the biggest ones to the top? An hour? Two?? Unless the problems are very trivial, or your hourly rate is phenomenal (congrats!), big whoop.

I don't see that anyone's challenged the appropriateness of making suggestions for office improvements. Quite the opposite. But having asked about how to do so diplomatically, it shouldn't be surprising that you're getting answers that focus on business diplomacy. "Businessy", indeed--by design.

I wholeheartedly agree with dness2. If personal trust is so important to this boss, then no proposal is going to get far without taking that trust factor into account. Is there someone in the office who especially has the boss's ear, who also "gets" the magnitude of the problem? If you can team up with to raise the topic jointly, it's more likely to gain the boss's full attention and less likely to be greeted with

By the way, is there no hope the you and the current guy could collaborate to solve some of these problems, or that he could bring up the problem areas to the boss? Diplomatically-speaking, solving as many problems as possible through existing channels represents the path of least resistance. The boss has apparently delegated IT problem solving to you two, so accomplish as much as is possible then present a list of the remainder to her with a budget total. "We need to do X, it'll give good result Y, and cost only Z. Sign on the dotted line to authorize. Thanks!"
posted by nakedcodemonkey at 5:44 PM on November 9, 2005

I would try to get an estimate from your boyfriend on what it would take to fix things (time and dollars) and then waltz into the boss's office and say: "look, our computer situation is all fucked up; I can get it fixed by this time next week for $X, do I have your pemission?"
Your boss should be pleased to have a proactive and knowledgeable person volunteering to take responsibility for something she's uncomfortable with.
Your fella will have to be as good as you think he is and get it all sorted in the estimated time, and then you'll be everybody's hero. If not, you could be in trouble.
You don't have to be as foul-mouthed as me; I just like swearing at my boss.
posted by nowonmai at 10:49 PM on November 9, 2005

abbyladybug, you need to simply take charge of the situation. Your boss has no desire to deal with this. If you wait for her to deal with it you'll end up waiting until some IT disaster strikes. That could take years. You're the one who's affected most by it. The IT guy already reports to you so you already have the necessary "authority."

So, the next time the IT guy comes tell him right off the bat that he's doing a terrible job. Put your concerns in writing and be specific. After that, the IT person will either address your concerns or he won't. If he does, problem solved. If he doesn't go to your boss and tell her that you you're going to bring in your friend and try him on size because the current guy isn't working. You have documentation to justify the decision. Don't ask your boss. Tell her in your best this-is-what-we're-doing-because-I'm-the-IT-authority-and-I-know-what-we-need-but-you-should-know-and-do-have-any-questions tone. Really, I suspect your boss is just waiting for you to step up. She doesn't want to deal with it and any formal reports or the such will be glanced at and then forgotten.
posted by nixerman at 1:08 AM on November 10, 2005

After encountering the 2005 version of the screen of death, I go in to the woman who's apparently the one who's supposed to beckon the IT guy when there's a problem. I say, "Is IT-Guy coming any time soon?" She says, "No." I ask, "Why?" She says because there are no problems.

Huh?! I tell her that there actually are still several problems. She says she will send a message out to the office asking everyone what their IT problems are. I tell her I'll go make my list.

I return with this:
➢ NECESSARY SOFTWARE in the conference room always says “Licenses: 1, Current User: 1.” In other words, it's never accessible.
➢ The Dell that was purchased for me has not been networked to the Local Area Network. While IT-GUY did bring in a hub with network cables, this only allows me to access the Internet, not shared network drives or office computers. As a result, I use my personal USB drive to manually transfer files to other office computers in order to print.
➢ Microsoft Office on my Dell is expired. I can not use MS Word, Excel, or Outlook. As a workaround, I've installed Open Office Suite, but there is always considerable reformatting in order for documents to appear as they should in MS Word. I can not access my work E-mail without Outlook.
➢ None of the computers here are being regularly serviced to remove spyware, defragment hard drives, etc., and as a result, they are all running very slowly and crashing often.
➢ Hard drive is over-full on the computer in the conference room and the one on the office on the left. A screen pops up that says, "Disk free space has dropped below the minimum threshold..." These computers crash often, and the load up time after logging on and when opening programs is considerable.

That, and I have convinced my parents to get me a laptop of my own for a combined Xmas/Bday present. Yes, I'm 35, but I just finished a doctorate, and I still need financial support sometimes. I'm starting to get a little learned helplessness-y about this whole thing. Now if only they can network my laptop so I can actually print at work. Ugh!

I do want to take charge, and I'm doing my best, but it's so hard to talk to people who don't HEAR anything. Will keep you all posted...
posted by abbyladybug at 6:08 PM on November 14, 2005

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