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Dealing with a disorganized boss

By TimMitchell ·
How does one deal with a boss who is a hopelessly disorganized procrastinator?

I really like my job. I work with some great people, and the environment is relaxed. However, as a results-oriented person, I am finding an endless source of frustration in dealing with my boss, who is the most disorganized person I've ever known. Further, he hardly ever communicates necessary information to our team, and he's a procrastinator who won't deal with issues until they become big problems. We frequently have end users who are furious at us - the tech staff - because of problems that he was aware of but did not notify any of us.

Don't get me wrong - my boss is not a jerk, in fact he is normally very pleasant to deal with. And it's not that he's lazy - he's a hard worker, though most of his work is trying to straighten out messes due to his disorganization. The ironic thing is that, he doesn't recognize these failings in himself - in fact, he tells us very often that 'we' - the tech staff - need to be as organized and efficient as possible.

I work for the sort of organization that requires management approval for EVERYTHING, and all my work must go through him. He's not a technical person, so he's a little paranoid about delegating too much control and therefore maintains absolute ownership of every aspect of our systems (he alone has the domain admin and root passwords, though he would have no idea with what to do with them). But getting results from him is next to impossible. Our small tech team is well-trained and experienced, but because of the leadership, we are inefficient and can't get a lot done. Emails and voicemails to him requesting permission for this, or clarification for that, very often go unanswered.

I'd be interested to hear if anyone else has to deal with this sort of supervisor, and if so, how do you get around this sort of chaotic management style?

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Disorganized or Overwhelmed?

by Oldefar In reply to Dealing with a disorganiz ...

It sounds like this supervisor may be in way over his head. My guess is that he knows this and is intimidated by his staffs' technical savvy. It does not sound like you are trying to have him replaced, so the focus has to be on working with him.
My first suggestion is to look at what isn't working - emails and voicemails. Try to do things on a face to face basis instead. Often times this will create the perception of an issue requiring immediate action.

Next, look at your approach. If you have been asking for technical decisions or clarification, you are hitting him at his most vulnerable. Instead of this, try giving him the answers you want. Make it a multiple choice thing with two or three simple selections, all of which will work. You will learn which choice he typicially goes with, and can position your desired solution to that choice.

People and businesses deal with five currencies - time, money, security, knowledge, and prestige. Make sure you are feeding him security, knowledge, prestige, or time with each meeting and he will welcome these meetings.

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by TheChas In reply to Dealing with a disorganiz ...

I suspect that your bosses problems arise from problems forced upon him from higher up.

To get quick action, you need to anticipate what the next 2 higher levels of management want to know in order to approve your projects.

For starters, you need to tone down technical details, and present a 'business case' for the equipment / projects that need approval.

If your boss can clearly understand what is needed, why it is needed, and how it will help the company make higher proffits, he willbe able to take it directly to upper management for approval.

He may be unwilling to admit that he does not understand all aspects of your projects as submitted, but knows that he does not have what he needs to take to his boss to get the projectapproved.


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