How to Properly Care for and Feed Your Secretary/ Assistant

Darling! You know how over New Year’s I always clean and sort – and found this long forgotten dear example of aunt-esque affection. Remember your cousin Eustace, from your Father’s side of the family, the one who lives in New York with the unfortunate haircut and the significant other who talks about the price of everything. That Eustace. Well, when you were just a tot, he got an MBA (as I am sure you always suspected, those ill-fitting trousers and the way he always under-tips), well, to resume, when he graduated and found himself a quite respectable job, I, the devoted aunt that I am, sent him a present worth more than rubies – this missive of advice, which he completely ignored. He was “let go” in a “restructuring” within 6 months. Oh, one does what one can with the younger generation, but if they will not listen, there is nothing to do but go to Helsinki for a week and then try again with another offspring of a sibling. [Eustace, poor thing, found another job quickly, made pots of money, then at 36 decided to ‘find himself’ and went to Nepal. That ended rather badly, as do all attempts to use foreign countries for one’s personal aggrandizement. He slunk home, became gainfully employed and acquired a partner who asks me how much I paid for my purse. Every Time I Visit.] But in the interest of preventing you from similar pitfalls – I shall, note my infinite kindness, recycle this for you.

A Paean to a Paragon

Do you ever wonder why Sears, Pan Am and Enron sank but nobody has been able to take down the Mafia? Companies have secretaries, the Mafia doesn’t.

Business schools don’t teach you that secretaries rule the world. This is not that big of a problem because if they did teach you this, your professor would have merely shown you a six slide PowerPoint presentation establishing this fact. The presentation would, of course, have been created by his or her secretary from a half a page of illegible scrawl which the professor handed to his or her secretary twenty minutes before the class started. The secretary would have turned the scrawl into an insightful, authoritative presentation, complete with moving graphics, transparencies for the professor and double-sided, three-hole punched copies for all the students. But the lecture would not have helped you because, if you were even listening rather than surfing the Internet for i-touch upgrades, you wouldn’t have believed it. And the lecture would not have gone far enough.

Luckily you have me. Now, of course if you don’t believe that secretaries rule the earth, I can’t help you. Stop reading immediately. Go live your blighted, soon to be ill-fated, if not already miserable, life. Walk through a large public space screaming into your cell phone. That will help take the sting out of your coming public humiliation and devastation. And don’t keep reading this because you think I will prove that secretaries rule the earth. It’s like religion, for those who understand the truth, no explanation is needed; for those ignorant heretics, no explaining will suffice.


* Ideally you need a secretary who puts the fear of God into you. Be very careful about secretaries who think you are wonderful; they are much more dangerous than ones who think that you are a prize twit. Subordinates who think you are God, who devote their lives to making your life better, will invariably trip you up. The problem is that because they think you are so marvelous, they can’t imagine that others won’t adore you as well. They won’t tell you not to do something, won’t warn you that your presentation is incoherent, won’t tell you not to try for that account or that job because you aren’t good enough yet. The ones with a very clear view of your shortcomings will be able to help you overcome them. Think of secretaries in old movies, grey-haired battleaxes who knew everything and managed everything brilliantly by keeping their bosses in their place.

Even secretaries who think you are worthless will be better for you than a relentless cheerleader; they may take you on as a ‘project,’ to prove that they can make a success out of even the roughest material. Remember that no one likes to work for a loser; your secretary wants you to do well, if only so she or he can brag that it was all her doing.

* Every secretary has some flaw. Figure out what you can and can’t live with. It doesn’t matter if you are the grand Poo-bah CEO of Allied-Algamated-Everything, your secretary is going to have at least one characteristic that drives you crazy: come in late, leave early, talk on the phone all the time, chew gum, make lousy coffee, screw up the web-page. Tell him straight out what two or three things are verboten, wait to see what his flaws are, then see if you can live with them.

If he or she has kids, he or she will take days off with no notice when the kids are sick or might even need to bring them in. But that will also mean that if you are understanding, he or she will be willing to go extra miles for you when you need it. If she is in school, then she will try to sneak in studying at work. But that means she will stay at her desk most of the time, not running off to go shopping or meet friends for lunch. It’s always better to know the parameters. If she’s single, it means she could easily move to another city on a whim. There is no ‘best type’ – there are types mesh with you and those who don’t.

STANDARD CARE, a.k.a. Enlightened Self Interest

* You, maybe not so much with the talking. The hardest part of being a secretary is the incessant, feigned interest in someone else’s life. Do you think anyone is deeply curious about your kitchen remodeling, second home decorating, new car buying, and fancy restaurant visiting? Don’t yap about a $500 espresso machine to a person who can’t afford a Starbucks cappuccino. Faxing, doing airline schedules, answering the phones, copying, coordinating meetings, ordering supplies, and arranging catering is the simple part; pretending that you care about boss’s new handmade shirts when you buy your clothes at Target is a talent granted to few.

* Try very hard not to indulge your fantasy that you are more important. You double-schedule yourself for a meeting, say that you need tickets to Albuquerque when you meant Alberta, lose an important file, or enter the wrong function into the excel spreadsheet, and the reason is because you are so busy, so stressed, so over-worked. Your secretary double-schedules you, gets you tickets for Albuquerque when you need to be in Alberta, loses an important file, or enters the wrong function into the excel spreadsheet and the reason is she’s not concentrating enough, she’s letting standards slip, she’s not working hard enough. So you feel it necessary to give a little lecture, perhaps indulge in a little temper tantrum.

This is a dangerous trap, a most dangerous trap. You think that the fact that you make five times as much as she does and work much longer hours allows you to be sanctimonious. You make mistakes because you have so much work; she makes mistakes because she isn’t focusing. But the fact of the matter is that you don’t really know very much about your secretary. Maybe you’re the type who stops to ‘chat’ but very, very few people know anything about their secretary’s life, although you can be damn sure she knows all about yours. As you give your little lecture, have your little temper tantrum, she is debating whether she should tell you that you have spinach in your teeth and perhaps you ought to get it out before those five people show up in your office for the meeting. She’s debating whether she should tell you that when she called your house last night to say you would be working late, it was not your husband who answered the phone, but a woman. She’s debating whether to tell you that Edwin, your arch-rival, has been receiving faxes from a real estate agent about 2 million-dollar homes, homes he could not afford unless he was sure he was getting a big promotion.

You rage on about how important it is to be detail-conscious and she looks at that large piece of spinach stuck in your teeth and nods vigorously and promises to do her best. You, self-satisfied, go back into your office and make a complete fool of yourself.

* Remember that secretaries fly under radar. You’ll never see a chapter on secretaries in a book on management; they are never on your business’ “org chart.” When you speak of them they are always pared to the person they work for, “oh that’s Mary, she’s Culpeper’s assistant.” No one remembers that before she worked for Culpeper, she worked for Haselton, and before that for Thatching and that Mary knows where a lot of bodies are buried and that your CEO always wears red ties on the days that he is going to fire someone.

Secretaries are invisibly plugged in. They know the people who deliver FedEx packages, the copier repair people, the cleaners, the guys who move furniture, other secretaries, the guards, the cafeteria workers, and the people who bring the mail around. They know who is getting a lot of mail, or not much, who is re-doing their office, who is getting empty boxes delivered, who just got a shredder, who stays late, who eats lunch every day with an attractive accountant and never calls his wife. Think of it this way. You probably don’t talk to your secretary, you say, ‘good morning’ and start giving orders (hopefully couched as polite requests). Yes, you may ask ‘how was your weekend’ but you really don’t want a ten-minute answer to that because you have things to do. So he has to talk to someone, and as he runs to legal to get a document for you, walks to the front desk to give the receptionist something to be picked up, goes to HR to find out how many sick days he has left, he talks and people talk to him.

Secretaries make odd lateral and vertical alliances. If yours knits and the secretary of the CFO knits and they happen to see each other with bags of yarn and get to talking, you may get to learn something you didn’t know before. Unforeseeable alliances and hatreds grow up over time; if, and only if, you are pleasant to your secretary you will be able to benefit from this knowledge.

* On a related theme, many people assume that secretaries are stupid, and thus don’t realize that the invisibility issue can back fire on them. All the simple, routine tasks secretaries do gives them a chance to see what others are up to. They open the mail, answer the phone and sometimes even check your e-mail.

Even lowly fax machines are a gold mine of information: clubs confirming membership, airlines confirming reservations, someone asking you to sign a release, sign a document. But, you say to yourself, this doesn’t apply to me, fax machines are old-fashioned and I don’t have one. I live the paper-less life. Ha.

Your printer will break, you cell phone will get dropped, your computer will fuzz out, your i-whatever will sulk. Machines need to be fixed and you don’t have time to oversee that what with your webinar coming up. Your assistant will be calling the repair people and the repair people will chat. But, you protest, I have given my assistant specific instructions not to ever… blah blah blah. You say that information can’t be communicated to a larger audience because you have decreed it should not be. You see yourself as Greeks at the Thermopylae, “They shall not pass.” They passed. E-mail and smart phones make it less probable that your whole life will be on view to your assistant, less probable, not impossible.

* Think of yourself as a truffle-hunting pig. You have a sharp brain and are highly trained to do one thing very well. But you can only do one thing very well. Your secretary can do many, many things well. So never, ever try tactical maneuvers or end-runs. If you two don’t get along, if she isn’t what you want, bite the bullet and get her transferred or (worst case) fired. Always remember, you don’t have any free time and she has a lot of it.

Case in point: Annabelle wasn’t happy that her secretary Max didn’t run errands as quickly as she would like. One morning Annabelle put a package on Max’s desk that needed to be express mailed by 4pm. Annabella expected it to be mailed right away, but at noon, it was still on Max’s desk. So, with Max at lunch, Annabelle asked Ginger, another secretary, to take it to the post office. When Max returned from lunch and asked what happened to the package, Annabelle explained that there was a 4pm deadline and that she had asked someone else to handle it. When Max explained that he had planned to do it at 1pm along with several other errands, Annabelle merged shrugged.

A week later, she put another package on Max’s desk to be mailed. When she came back ten minutes later to see whether Max had finished typing some notes, she discovered that Max had left. He didn’t return for forty-five minutes and, as no one could discover where Max had left the notes, Annabelle was both late and unprepared for her next meeting. Questioned later, Max explained that since Annabelle had been so unhappy with him last week that she got another secretary to mail the package, he had immediately gone and mailed the package as soon as it had touched his desk. Annabelle had an instant decision to make: get rid of Max or play by his rules. She capitulated. The two of them set out guidelines for completing tasks and Annabelle never tried another end-run.

* You need to be thoughtful. Now this does not mean you have to give presents for all major holidays, including his birthday (ask HR if you have to), Christmas/ Hanukkah (if she’s Muslim, at Eid al Fitr, when Ramadan in over), although it’s a good idea. It means that if you do give presents, that you give presents that he will like, not that you think he will like. When he starts working for you spend a concentrated ten minutes at some point figuring out if he likes chocolates, flowers, Star Trek, bee-keeping etc. This will not only help you in the short term, he’ll be grateful for a day or two, but will help you in the long run. Let’s say he leaves the company and it’s time to find you a new one. So a secretary who already works for the company sidles up to your secretary and asks, “So what’s it like?” Your secretary can say “well, she’s late for meetings so you’re always calling people to make excuses, and she’s having an affair with her pool boy, so you have to do call hotels to reserve rooms, but she doesn’t yell too much and that annoying body order has cleared up. And she is thoughtful.”

Now imagine you are complete jerk. When your secretary leaves he will insure that her replacement is a miserable, inefficient hag. Why allow a good person to work for such a twit as yourself?

Every day there are dozens of small decisions that he can make that will make your life easier or more difficult, decisions that you don’t know about and couldn’t affect, even if you did know about them. I once worked for a man who did nothing for Christmas or Secretary’s Day but brought in lavish bouquets on May Day from his own garden and shooed me out of the office at 4pm on Fridays in the summer. I also worked for a woman who brought me chocolates back from every country she visited, more than six times a year. They didn’t just get everything they needed, they got every important scrape of office gossip I accumulated and mail runs twice a day. I suppose it sounds like I would sell my soul for a pound of good chocolate and some French tulips but think of it this way: the more information you have, the better decisions you can make. With your secretary thoughtfulness always equals information.

Tragic example: cute guy whose secretary always took lunch from 12 to 1, would come out of his office at 12:15 needing something and saunter over to Alicia’s desk. He was so smooth, so charming, such a great smile, she would willingly put down her book to help. Until she realized she was missing about a third of her lunch time and getting nothing but a charming smile in return. So she figured out when his next big afternoon presentation was and invited the file clerk for lunch that day. Out he walks at 12:15, no Alicia, the file room locked, he takes his charming smile around the office and finds that every other staff person is gone or terribly busy. Bad presentation and Alicia takes her lunch in another part of the building from then on. He gets mad at secretary, she retorts that she is allowed an hour for lunch. It all gets ugly. This could have been averted with a timely, thoughtful gesture. Other people may pay you $150 an hour for your presence and expertise but your secretary doesn’t think you are that interesting and that smile isn’t going to get you far.

* Allow yourself to be trained. Yolanda used to have a boss who would ask her if she had finished something “Yet.” She told him as soon as she completed each project, so the repeated questions drove her bananas. Finally, in retaliation, each time he asked she would start in on a long-winded answer about how Marcie’s sister just had a baby so she was organizing a baby shower so she couldn’t look up the file he needed. He would stand by my desk, twitching with exasperation (please note that she never started with a simple, ‘yes’ or ‘no’). He learned to stop saying “Yet” in two weeks.

Another boss would arrive back from a meeting, take the message slips Wilhelmina handed her, glance at them, then ask Wilhelmina if a specific person had called. She simply couldn’t help himself. Wilhelmina would stand up, say “Let me check,” take the messages back from her hand, read them, hand them back and say, “No.”

After a few days, when Wilhelmina would make a move towards her boss, she would hold the messages out of her reach and say, “There isn’t a message from Flavia here, I was just wondering if maybe she called and you didn’t get a chance to write it down.”

Wilhelmina would ponder this for a moment, looking very thoughtful, and ask, “Have you or Flavia done anything to warrant me not telling you Flavia called, if she had, in fact, called because you know that I write out a slip for each call?” Her boss stopped after three days.

Secretaries talk about their bosses as if they were dogs in a long-term training program. If the boss misbehaves to a certain level, the secretary is judged as insufficiently strict. But if you are deemed “untrainable,” no good secretary will go near you.

* Allow yourself to be spoiled. Read previous sentence carefully, it doesn’t say “allow yourself to be spoiled because you deserve it.” You really don’t deserve it. There are many, many people smarter than you, who have worked harder, got better grades and test scores, have better mentors and contacts, but you were the one who got the job. So after all the labor of picking a good secretary, the chore of behaving correctly, the effort of not being condescending and the toil of getting yourself trained, do enjoy the benefits of a superior assistant, the kind who will give you advice on restaurants, ties, the boss’s mood and how charged your cell phone is.

Think of dear Siegfried who works for Ermengarde. He spends who a fair amount of every week educating his boss on the lay of the interpersonal landscape. He makes sure her calendar has the right month, her plants are watered, surfaces dusted. He shoos her out of the office at 4 pm to get take a break by walking down to the cappuccino machine. He reminds her which people to say ‘happy birthday’ to and to take off her ‘away from the office’ automatic e-mail when she gets back from vacation. She is on time and prepared for all meetings; her travel reimbursements forms are filled out correctly and the checks arrive promptly. There are no harassing calls from HR, legal, billing, or building facilities that she has to deal with. He has every size and color paper she might need, every kind of writing instrument, removable poster tape, plastic bags for when it is raining, cough drops, attractive Kleenex boxes, Vitamin C tablets, green tea, and an emergency supply of chocolate, all of which she has needed more than once.

That spring in her step, twinkle in her eye and recent pay raise, yes – all his doing. In return he have time each morning to drink his coffee in peace, no second-guessing his judgment, gift certificate to his favorite restaurant on Secretary’s Day, no boring recitations about her latest squash game and an occasional afternoon of novel-reading at his desk when it’s quiet. They work well together all day, then go home and forget each other exists. A rare and lovely partnership which is never mentioned, much less taught, in business school.

You can build a better mousetrap without a Wharton degree, but you won’t get anywhere without the secretary who can retrieve your mousetrap plans when you leave them in the bathroom at Penn Station.