Do You Feel Like You're Babysitting Your Boss?

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Help me, Rhonda!

My boss is a mess. She is so disorganized, it’s driving me crazy! She forgets meetings, leaves things undone and creates more work for me because I have to fix her mistakes. I want to go into her office and clean everything up, but I’m afraid to. I feel like her mother, constantly having to remind her about everything. It’s a huge waste of my time, and it keeps me from doing the other things that need to get done.

I Don’t Want To Be A Parent At Work

Dear “I Don’t Want To Be A Parent At Work”:

There is no question that having to constantly keep your boss organized disrupts your own time management. However, cleaning your boss’s office is not the answer (unless she wants you to do that for her — which I sincerely doubt).

The first step towards a solution that works for both of you is to put yourself in her shoes.

Understand that she probably doesn’t feel that she is unorganized. She got to where she is with some type of ability, right? So telling her (or showing her) that you feel she is disorganized will backfire and create tension in your working relationship.

You can’t make her put her things away. You can’t make her organize herself the way you want her to be organized, the same way she is not going to convince you that chaos is best.

Stop trying to rebel against her system and instead, find a system that works for both of you.

Here are a few things that you can do to help keep her on the right-track without making you feel like her parent.

Keep it simple. Be concise and clear. Don’t send one email with 10 reminders. Instead, send 10 reminders. Often people see an email but don’t open it and read it all the way through. They look at it on their smart phone or in the reveal panel on their computer, and don’t scroll down. Put your reminder, your message, your question in the first line (or better yet, in the subject line).

For instance, send an email with the following subject line:

REMINDER: Board meeting at 10 a.m. Monday (today!)

In the body, say:
Boardroom A, should be over by noon, your board documents are in the red folder on your desk.

Any more information is probably not going to get seen, let alone read, so don’t continue to frustrate yourself. Give her what she needs in the folder, and let her work in her own style.

Make it easy. Are you able to program reminders in her computer or smart phone? I love using reminders where the little bell warns me of something 15 minutes in advance. I am organized, but it’s easy to forget an appointment when you are in the middle of something else.

If you can use a system where you install those reminders, then you know they are set up and that she will receive automatic reminders (perhaps a few times) and you can keep your focus on your own tasks. Using the same tip as above, instead of creating a reminder that simply says “board meeting,” create one that says “Board Meeting 10 a.m., Room A, red file on desk.”

Use colour coding. I realize that to many people this is a basic strategy, but it might not be basic to someone who needs organization. If you are consistent with colours, it allows her to prioritize. Things to be signed are always in a green folder, information for meetings in red folders, FYI in yellow, etc. Put big labels on them (especially at first) so everyone understands the system.

Visual is best for those who thrive on chaos (notice I didn’t call her unorganized). That’s why the email reminders, folder and even wall charts, if you have them, should feature different types of appointments marked in different colors.

Stacking up your boss’s information into one big pile shows her there is a lot to do, but it won’t allow her to visually prioritize her work. Everything in its place is probably not the best organizing method for her. Perhaps her motto is “out of sight, out of mind,” so going into her office and putting everything away for her won’t work. She likely needs to see it, and believe it or not, some people work better in chaos than in a pristine environment.

Be a blocker for her. Block interruptions if possible, the phone if possible, and be the first line of defence on her email if you can. It is possible that the reason she seems so unorganized is that she is overwhelmed with requests coming at her. See if you can’t get a few of them out of the way for her, because in the end it does make it easier to do your job if you help her do hers.

Focus on the positive. She does have good qualities. I’m sure there are many things you can focus on instead of focusing on what she doesn’t do well and what frustrates you about her.

You’re a team, so work as a team. The easier you make her life, the easier things will eventually be for you as well.

You shouldn’t need to parent your boss, so stop thinking that way, and instead think of how your strengths (such as organization) can allow her to maximize her strengths.

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