8 Secrets to Working for a Disorganized Boss

Have you ever worked for a boss who was bad at time management?

Or disorganized to the point that it was affecting your job?

You know, constantly late. Losing paperwork. Not responding to messages.

It can make your job twice as hard.

And a lot less rewarding.

What do you do when your boss is sabotaging your work and that of others?

The Boss Disorganized

When I reported to my first duty station in the Navy I had to opportunity to witness my future boss interacting with my predecessor. (You don’t always get this chance, especially in a corporate environment.)

It was an eye opening situation.

My future boss was yelling, frantic, and generally disorganized. He was missing papers, not sure if an assignment was done, and unaware of the status of the latest divisional project.

My predecessor, another young Naval Officer, was on the receiving end of a Jonah Jameson-style reprimand.

And I was about to step into this mess.

He was about to be my boss.

I vowed right then and there, that I would not endure what my predecessor had.

But how was I going to do this?

Staying One Step Ahead of the Mess

I remember the first time my new boss yelled, “Jarrow! Where is that report…?”

Before he could finish the sentence, I had handed him the status report he was looking for.

“OK! Then, when will the inventory be done on…?”

“Already done, Sir. And verified by Chief Smith.”

“And the Captain’s walk-through of…?”

“Scheduled for next week. Details are in your inbox.”

I think that first conversation ended with my confused boss snapping, “OK, then. Get out of here, Jarrow!”

Secrets to Working for a Disorganized Boss

I have worked for my share of good and bad bosses. A good boss can make all the difference. And a bad one, one that inflicts his or her disorganization on their direct reports, makes life worse for everyone involved.

Here are just a few of the secrets I have learned over the years working for a disorganized boss:

1. Stay One Step Ahead – As I did in my first duty assignment, one of the best ways to work with a disorganized boss is to always be one step ahead of them. Ensure that your work is always done before they reach the crisis stage of asking you for it. You will quickly get a reputation as a solid performer in this type of situation.
2. Find the Best Way to Communicate – Tired of your boss not reading your emails? Or losing the status update your put in their inbox? Determine the best way to communicate with your boss. Some are good at email. Some are better with in person updates. Figure out which methods are best for your boss and stick to those communication channels.
3. Plan for Problems – If your boss is the type that invites a crisis, then prepare for it. Be ready for last minute fire drills and projects that run up against deadlines. Leave extra slack time in your schedule and check on the status of projects on your own.
4. Don’t Wait for Lateness – Is your boss always late or missing meetings? In the corporate world, this is often played off that the “executive” is busy doing important things. However, it is usually just that they are bad at managing their time. Here is my tip: Don’t wait. Go on with your work and day. It is easy for your boss to track you down at a later time via phone, text, or email.
5. Don’t Assume…Anything – If your boss is disorganized, don’t assume that your boss read that report. Don’t assume that he knows that a deadline is rapidly approaching and you are awaiting their approval. In fact, don’t assume anything. Check facts yourself, and don’t be afraid to approach your boss if they are not aware of something that should be on their radar.
6. Finish Things Even that Much Further Ahead – If your boss is bad at meeting deadlines, that means that you have to be better. Maybe doubly so. Ensure that your work is finished well ahead of schedule and leave some slack time for your boss to catch up.
7. Bring Solutions to the Table – The disorganized boss doesn’t need more trouble. They need answers. Bring your disorganized boss solutions to their problems. They will appreciate this approach in a big way.
8. What Can You Take Off Their Plate? – Many disorganized bosses are in their predicament because they have taken on too much work. Perhaps, they are bad at delegating and are trying to do everything themselves. Ask yourself, “What can I take off my boss’s plate?” Just as a good leader removes obstacles from their team’s path, and a good team ensures that they are getting the work done for their boss.

Keeping Ahead of Your Boss

Working for a disorganized boss can be a trying situation.

However, with a little effort and some smart tactics you can stay one step ahead of the situation.

You can keep things operating smoothly in spite of your boss’s disorganization.

If they are good leader, you just might earn their respect for helping them out of their mess.

Have you had to work for a disorganized boss? How did you deal with the situation?