Organizing @ Work: The Disorganized Boss

My first Organizing @ Work post featured how to deal with disorganized co-workers. However, what do you do when your disorganized co-worker is your boss?

This is where things can get sticky. Your boss, after all, controls your destiny – raises, promotions, stretch assignments and references to name a few.

First, you need to determine if your boss is disorganized or “just” overwhelmed. By design, the boss has more on their plate, and those responsibilities vary depending on if they’re running a department, a division or the entire company. It seems everyone is trying to do more with less, and that can take a toll on the entire office.

When you get down to it, it doesn’t matter whether you think your boss is organized or not. What matters is how you work with your boss, no matter the situation. Here are some ways you can do that:

Be organized yourself. You can’t help your boss if you can’t help yourself first. By being organized yourself, it trickles up to your boss and co-workers.

Manage information you send them. Ask how they prefer to receive information. Do they prefer email or paper? Do they prefer one-on-one meetings? Do they want a summary or a lengthy report?

Don’t add to the problem. One way to make the boss glaze over is bringing them a stack of stuff to read about your latest project. Give them a one-page summary (shorter the better) and email a link to a longer document via Box, Dropbox, Sharepoint or a shared server. This eliminates extra paper on their desk, and if they want to read the entire report, they have access to it.

Have an agenda for your one-on-one meetings. Keep a running list of items you need to discuss with your boss, and put them in order of priority so you can discuss the important stuff first in case you run out of time. If you need to get their signature on something, this is a good time to do it.

Make it easy for them. If you’re working on a project together or need your boss’ approval before turning something in, give gentle reminders about deadlines. It’s better to say something, such as, “This is the report I have to turn in Wednesday to the finance department, and I’ll need your approval before sending it.” Or “I have completed these sections of the report, and whenever you’re ready, I can plug in the sections you have.”

Ease them into a digital life. It’s hard to break the paper habit, but you can lead the way. Before our office move in mid-August, I used the move as an opportunity to go digital and eliminate paper files in my file cabinets. Throughout our institution, we use Box, a cloud-based service, and several of us showed our boss how to set up Box files and share folders and documents.

Make them look good. Always make the boss look good, and never let them be surprised by any issues. Don’t let them miss a deadline – especially one with their own bosses.

Learning to manage your work with your boss will help you both in the long run.