Biglaw, In-House Counsel, Secretaries / Administrative Assistants

Inside Straight: How To Drive Your Boss Nuts!

Fair is fair is fair: Two weeks ago, I wrote about how to drive partners nuts. Last week, I wrote about how to drive associates nuts. Today, I’m continuing along the lawyers’ food chain: Secretaries (or “administrative assistants”) — it’s your turn: How can you drive your boss nuts? [FN1]

First: Your time after work is yours, to tend to your family, watch TV, go clubbing, or whatever. So you have to handle all of the other stuff — like making appointments, chatting with out-of-town friends, shopping, and the like — during work hours. Happily, the telephone and computer at your desk are all the equipment you need. So do all your shopping on-line during business hours. Talk to your friends, post stuff at Facebook, and surf the web from your office desk.

That does three things for you. It gives you more free time at home, to spend as you like. It helps to pass the time during work hours. And — best of all! — it’ll drive your boss nuts! Every time your boss walks up to give you a project, just click away from and whisper “gotta go” into your receiver. Your boss may not notice and, if he does, you’ve just pushed him one step closer to the edge, which is, after all, the name of this game. Use your time at work intelligently; use it to handle all of your personal affairs.

Don’t just fritter away your eight hours a day at the office. Also, nibble around the edges. Leave the office at 4:55 without telling your boss. Maybe she won’t notice, and she’ll surely never come frantically looking for you seconds after you’ve left. Sticking your head in the door and saying good night would just tip her off that you’re cutting out early; don’t do it!

Also, remember that Mondays and Fridays during June, July, and August are meant to be taken as sick days. If you take them regularly, your boss will get used to this, and he’ll become more efficient, doing all of his work between Tuesday and Thursday. He’ll probably thank you for this.

How else can you drive your boss nuts?

Here’s a good one: Do not keep track of the assignments that your boss gives to you. Your boss is a big boy (or girl). He knows what he asked you to do. There’s no reason for you to keep track of that stuff, too. Why do bosses exist anyway? If you forget to send out a document, return a call, or file something, your boss can always remind you to do it, and you can do it the second time around. (Better yet, the third. Or the fourth! It’s a good way to teach your boss to stay on top of things.)

It would be a pain in the neck to actually do all of the things you’re asked to do. And keeping a list of the projects on your desk would require extra effort. No one’s paying you for that.

You’ll probably remember everything you’re asked to do, and your boss will remind you if you forget. Think of it as teamwork; your boss will appreciate being made part of your team.

Here’s a third way to drive your boss nuts: Forget about deadlines. I mean, the legal profession is pretty laid back. If your boss misses a deadline, opposing counsel surely won’t make a stink about it, and clients are generally pretty forgiving. So if your boss asks to have a document back on Tuesday, don’t bother. Wednesday will do. Or Thursday. Or never.

If your boss says that something is “not a rush,” that actually means, “Throw it away.” (They teach lawyers those definitions in law school: “Collateral estoppel,” “res ipsa loquitur,” and “not a rush.” You have to learn the meanings of those legal phrases to be a good assistant, and now you’ve got one under your belt.)

Next way to drive your boss nuts: Don’t proofread anything. For heaven’s sake, your boss didn’t spend just four years in college; she spent three years in law school, too. With all that education, she should be pretty darn good at proofreading — probably even better than you are. So why should you bother? You can spend your time searching for good sales on-line, and your boss can proofread the document after you give it to her. It’ll make her feel needed, and she’ll feel better about herself when she finds some errors.

Here’s a good way to improve your boss’s proofreading skills. Put the correct inside address (the recipient’s address) on the body of the letter you prepare. But type a different address on the envelope into which you place the letter! Your boss wouldn’t naturally think to proofread both the letter and the envelope, so she’ll never catch that one. But she’ll learn over time! After letters come back for “addressee unknown” a half dozen times, your boss will check the letter, the envelope, and everything else that you do. That just makes her a more attentive boss, and she’ll appreciate the training that you’ve given her!

I feel good about this series of columns I’ve written: Partners can now drive associates crazy more easily; associates can drive partners crazy; and now administrative assistants can join the fun. Law firms (and corporate law departments) can be like shoot-outs in a saloon in one of those old western movies, with bullets flying in all directions and bottles shattering behind the bar.

Wait! I’ve missed one: How can lawyers drive their administrative assistants nuts?

Got it! If you know that your secretary catches a bus home at 5:05 every night, hold your projects until 4:59. Then unload ’em.

(This is so easy. I think I’ve finally found my true calling in life.)

[FN1] Here’s a secret. This column was actually meant to help passive-aggressive lawyers who are being driven insane by their assistants but don’t have the nerve to speak up. Just send your assistant a link to this column with a cover note saying: “I’m a sweet person, but isn’t Herrmann a jerk? Look at the way he criticizes secretaries in public, when he should be giving this advice as constructive criticism behind closed doors. We’re much nicer about these things, although Herrmann does make a couple of good points.” You’ll have delivered the message, and I’ll take the blame. It’s good for you, and I’ll never know. Got it?

Mark Herrmann is the Chief Counsel – Litigation and Global Chief Compliance Officer at Aon, the world’s leading provider of risk management services, insurance and reinsurance brokerage, and human capital and management consulting. He is the author of The Curmudgeon’s Guide to Practicing Law and Inside Straight: Advice About Lawyering, In-House And Out, That Only The Internet Could Provide (affiliate links). You can reach him by email at

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