Quite a few readers have written in asking what to do about ‘disorganized’ bosses. It can be quite a challenge trying to do your job well when your boss’s organizationally-challenged work habits keep getting in the way.

In order to deal with it, you first have to identify why your boss is disorganized. There are a number of factors to consider. For example, ‘disorganized’ behavior is very common with highly creative people. Very often it can be a symptom of being overworked, or pulled in too many directions. It is also possible that what you are classifying as ‘disorganized’ is just your boss prioritizing his work differently than you would. And, of course, we can’t over look the possibility that he’s just…well… a slob.

Here are a few things you might try:

1. If your boss is simply overworked, the most valuable contribution you can make to him and the company is to cheerfully pitch in to pick up the pieces as he lets them drop. Your boss will greatly appreciate your support, and things will run much smoother. Scolding him or complaining won’t lighten his workload – it will only darken his mood.

2. If your boss is highly creative and just has a hard time remaining focused, don’t be afraid to put your foot down (in a nice way). Most creative bosses appreciate people trying to bring order into their lives – as long as they aren’t made to feel stupid or not respected.

3. If your boss has different priorities than you, then it might be a worthwhile exercise to explain what your priorities are, and why you think your way is better for the business. He may disagree with you – which he’s allowed to do – but at least you’ve tried.

4. If your boss is just a slob, try presenting things to him in a cost/benefit format. And have a little fun with it. e.g.: “Hey boss, you do know that we’d save about a thousand person-hours a year if we didn’t have to do an archaeological dig every time we needed to find something in your office…”

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