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From the Career Files: How to Supervise a Secretary or Assistant

Ed. note: This is the seventh installment in a series of posts from the ATL Career Center’s team of expert contributors. Today, we have some great advice for newly minted attorneys from Joshua Stein, the principal of Joshua Stein PLLC, a prominent commercial real estate law practice in Manhattan.

When you start out in any professional career, you will probably soon have someone to help you do your job, such as a paralegal, a secretary, or other assistant. Having that assistant can make your life easier, and help you do a better job — especially if you know how best to work with your new assistant. Here are some suggestions for working with any assistant, but particularly a secretary or a paralegal. Many but not all of these suggestions also apply to working with junior associates or other professionals who report to you.

A. Clear Instructions.
Your assistant doesn’t know what’s in your head. You have to tell them, at least until you’ve worked together long enough that your assistant develops a good sense of what you need done and how you like it done. Until that happens, make your instructions as clear as possible. Think about where things might go wrong, where your instructions might get misinterpreted. What steps did you forget to mention? Prevent problems by foreseeing them. Even if you can legitimately say the problem was “someone else’s fault,” it’s better if you can prevent the problem through foresight and by taking even more care than you might strictly think necessary. And make sure you define the project you want your assistant to complete. Don’t leave them guessing. What exactly do you expect them to accomplish, beyond “please take care of this”? What’s the “deliverable”?

B. Involvement.
Let your assistant know what projects you have on your agenda and what goals you want to achieve. Let your assistant know something about the people involved, especially if you or your assistant will interact directly with those people. This will all make their job more interesting, and ultimately help your assistant do a better job for you, than if you just give them individual discrete and disjointed tasks – little pieces of projects as they arise – with no understanding of their context. It may take a little more time to give your assistant a broader view of things, but it will pay off quickly. By knowing more, your assistant will do a better job. If you make a daily to-do list (not a bad idea in any case), you might go over it with your assistant at the beginning of the day, and let them know how they will fit into the things you’ll do that day.

C. Who Does What.
Just because you can do some project that needs doing, that doesn’t mean you should do it. To the contrary, if it’s something you can have your assistant do, ask them to do it. The first time you do that, it won’t be efficient. You’ll take more time to figure out exactly what you want your assistant to do, explain it, review it, and maybe even redo it, than if you had just done the job yourself. But the great power of having an assistant comes up the next time you have a similar task – and there will be such a next time, usually a few hours later or the next day. The next time your assistant helps you with the same task, they should have an idea of what to do. The third time, they should have mastered it. After that, you’ll always be able to have them do the job smoothly and successfully. And through the learning process, they will also gain skills and knowledge that will help them do other projects for you.

D. Consistency.
Try to come up with systematic ways to define and delegate the pieces of your job that come up again and again. Do those pieces of your job the same way every time. Keep it simple and consistent, without exceptions and variations, even if this sometimes results in a bit of work you might have avoided. By doing similar tasks the same way again and again, you will prevent mistakes and save time. Once you’ve figured out the right way to do these things, you might want to create a checklist and ask your assistant to use it. But checklists have a habit of getting longer and longer over time. Details get added. Options and alternatives creep in. Before long, the checklist can get out of control, causing confusion rather than clarity. So keep checklists short, simple, and focused on just the “main event” elements of what you do. And the more organized you are about your own work, the better you will do in assigning parts of your job to an assistant.

E. Getting Coffee.
Asking someone to get coffee for you just has too much baggage to it, whether your assistant is female or male. Therefore, if you want a cup of coffee or anything else to drink, get it yourself. You can probably use the walk.

F. The Whole Project.
If you can delegate an entire project, try to do that. You’ll get better work than if you delegate little pieces here and there every time you see an opportunity. But also make clear how and when you plan to review and check your assistant’s work.

G. Be Nice.
Your assistant is probably the most important of your various co-workers. Treat them nicely. Smile. Praise them – as often as possible – when praise is due, even for little things. In some sense, regardless of age, we are all just kindergarteners anxious to earn our next gold star. Your assistant is no exception. Hand out those gold stars! And if you’re having a bad day, don’t take it out on your assistant.

H. But Don’t Be Too Nice.
It’s good to have a nice friendly working relationship, but don’t get too close. Usually, you should maintain some professional distance and not share too much personal information. Plenty of exceptions exist, of course. Some lead to marriage. And some lead to litigation.

I. Questions.
Encourage your assistant to ask questions if they don’t understand what you want. If you don’t encourage questions, your assistant may hesitate to ask, perhaps out of terror or embarrassment. When your assistant does ask questions, make it clear you appreciate the questions. Don’t get annoyed. Answer the questions quickly and completely. Make sure your assistant “gets” the answer, and if they don’t, be patient. Asking and answering questions can be a great way to prevent problems and mistakes. Both you and your assistant can learn something. In my experience, there’s no such thing as a dumb question. But you may want to encourage your assistant to “save up” their questions and not constantly pepper you with questions, except when they can’t go any further without the answer.

J. Encouragement.
Help your assistant feel competent and confident. In most cases, it will play out to everyone’s benefit.

K. Personal Stuff.
If it will free up time for you to spend more time on your job, then it makes sense to have your assistant help with minor personal chores, such as handling personal correspondence, sending personal packages, or filing paid bills. That’s especially true if your work demands so much of your time that you don’t really have “personal time” for your personal chores. On the other hand, some organizations want your assistant to help only with work-related assignments. So find out what the rules are. If they allow you to delegate personal chores, do it without hesitation, at least for work your assistant can do without leaving their desk.

L. Timing and Deadlines.
Let your assistant know your timing needs. If something is an emergency, tell them. Don’t be subtle about it. Don’t assume they know. Remember they don’t have ESP. And don’t make everything an emergency. When your assistant helps you with an emergency, try to leave them alone for other projects. If they don’t finish the emergency project within some reasonable time, check back.

M. Micromanagement and Review of Work.
Once you’ve assigned a project, resist the urge to “check in” all the time. Let your assistant take the project as far as they reasonably can. In most cases, you should review it completely, especially with a new assistant, before it goes to someone else, but wait until your assistant has reached the point where that makes sense. When you do review it, don’t hold back on comments or changes just because you don’t want to hurt your assistant’s feelings. But recognize that they probably have pride in their work and you may hurt their feelings. If they did a good job but you just want to do it differently, or perhaps you changed your mind about something, you have the complete right to do that. But acknowledge you’re doing it. Make sure your assistant realizes they didn’t screw up.

N. Keeping Your Assistant Busy.
What if you don’t have anything for your assistant to do? Don’t worry too much about it. It’s fine if they take a break. Don’t make yourself crazy feeling you need to keep your assistant working every minute, for fear of wasting a company resource. Over the course of a day or a week, your assistant will do plenty of work. In the meantime, they can have light spells. But if you can come up with some long-term projects for those light spells, that’s good too.

O. Outside Communications.
One barrier to good delegation arises when you think about tasks that involve communicating with other people. You may think you need to do those tasks yourself, so that those other people see you, know they are dealing directly with you, and don’t get their feathers ruffled because you had your assistant communicate with them. But try to get past that, where appropriate. If communications are routine and your assistant can handle them, don’t insist on “taking them back” and handling them yourself. You can often freely use your assistant to carry routine messages to other people, and no one will care. Of course, sometimes they will care. Use your judgment.

P. Computers.
The prevalence of computers means we have all become our own computer assistants. It’s so easy and quick to do something on the computer that we just do it, rather than ask our assistant to do it. But that doesn’t always make sense. Even with computer-related tasks, you can make your life easier by delegating projects to your assistant. Some examples: updating your calendar and contacts; editing documents online if you feel like printing them out on paper and editing them on paper, which is a great idea for anything important or complicated; making corrections received from others; making documents look better; filling out online forms; sending out distributions; and other routine tasks. These tasks add up to a significant amount of time. Once you’ve trained your assistant on how you want them done, you will save time by delegating them.

Q. Older Assistant.
What happens if your assistant is older than you, maybe a lot older than you? How does that change the dynamic, and what should you do about it? The answer is: Not very much. All the same principles apply, including the importance of treating your assistant well and making them feel appreciated. For the most part, you can prevent or solve problems by being serious, professional, business-like, and nice. Don’t hesitate to ask your assistant to do the same things you would if they were ten years younger than you. An assistant who is significantly older than you may be more inclined than otherwise to try to make you feel like you don’t know what you’re doing – and may come to believe that you work for them rather than the opposite – but you just need to ignore that and go about your work. And if your assistant has worked at the same organization for a while, then they may know much more about the workings of your organization than you do. Take advantage of that knowledge.

R. Reverse Delegation.
If your assistant has lots of trouble with things, can’t find information they need, and asks lots of questions, you may feel the urge to take a project back, based on the “logic” (discussed above) that it would be easier and quicker for you to do the project yourself. Resist that urge. Answer the questions. Show your assistant how to work through the problems themselves. Teach them how to get the information they need. It’s all part of training. Don’t let them reverse delegate the project back to you, whether that’s what they intended or not.

S. Office Politics.
Sometimes your assistant will have problems with other people in the office, and will try to enlist you to help solve those problems. Stay away from that morass. It usually has no upside for you. It soon becomes an exercise in nursery school supervision. In most cases, both parties are to blame – both are behaving like unprofessional jerks – and you just don’t want to get dragged into investigating a situation that usually has more complexity and sad history to it than you ever might have imagined.

T. Mistakes.
Your assistant will screw things up. Maybe more than once. When they do that, don’t wait. Let them know right away. Use it as a teaching opportunity. Don’t use it as a screaming opportunity. You may have much more fun if you yell and scream – it feels really cathartic – it’s a great show of how angry and serious you are – but it ruins relationships and does you no good in the long run. When you criticize or correct someone, do it only in a gentle way, in person, and never with anyone else in the room.

U. Lots of Mistakes.
If your assistant keeps making the same mistake again and again, or just doesn’t get it or doesn’t seem to care, then maybe it’s time to think about finding a new assistant. If you think you may have reached that point, then before you say or do anything at all, speak confidentially to whoever handles staffing in your organization. Let them control the process. In most organizations, any termination or reassignment is slow, difficult, and bureaucratic. You don’t want to find yourself stuck for a long time with an assistant who knows you want to get rid of them. Also, if you are dissatisfied with your assistant, they are probably dissatisfied with you and may start complaining about you. If they do, then whoever receives that complaint will in all likelihood give it more weight and seriousness than it deserves, for fear that it will escalate into a claim of discrimination or some other illegal employment practice – or may even lead to litigation. As a matter of internal politics, if someone is going to start complaining about the relationship, you should try to beat your assistant to the punch. That way, you define the agenda rather than react to someone else’s agenda.

For more expert advice and insight, please visit the ATL Career Center.