Here’s the thing. I’m the boss. Three of my employees are “cluttered.” However, one is cluttered in a way that’s fine – the papers that I need to find on her desk are always where they belong, and she knows where everything is and is not late with assignments. So she gets left alone.

The other two, though, are cluttered in a way that’s not fine. They know where everything is (well, most of the time, anyway). But when a customer comes in looking for something and they aren’t here, and it’s not filed where I’ve asked it to be, then I’m stuck rooting through a desk piled high with papers.

Also, they’ve both missed deadlines because they misplaced an assignment. I’ve tried helping them set up systems that work for THEM – but they just plain don’t follow through.

The bottom line is, while they think their “system” is fine, as their supervisor, I need to be able to make the best use of my time and ensure deadlines are met. It’s unfortunate, because I gave them a chance to make it work on their own, but now I’m going to have to put my foot down, because it reflects badly on our whole department when their work is not done by the deadline.

So I guess the point is this – I’m not crazy enough to say everyone has to use color-coded folders and not have a paperclip out of place. But when you work for someone, it’s your job to do your work on time and to keep papers that need to be accessed by your coworkers and supervisor in the appropriate place. My employees joke with me about being anal and crazy, but I keep trying to help them see the big picture – if I’m not wasting an hour hunting for something, I can spend an hour on staff development and training.

So please, please, if you’re an employee, don’t assume that your boss is just a crazy neat freak. Maybe he or she understands some of the needs and workings of the company that you don’t and has a REASON for the systems you’re asked to follow!

[1] Many times I am working on a desk that is not my own – I share with someone. I aim to leave it better than it looked when I started – even wiping down the surface and computer screen. Its just the respect I would want shown me if someone was working in my space.

[2] My boss and I have to know how each other works because we often share or cover clients. This can mean having a “working info folder” at all clients with contact phone numbers, passwords, etc. to making sure files are labeled correctly.

She set the expectation very early on that this is the way we were going to do business and we have been successful for 9+ years.

If the answer to either question is “no”, then leave it alone.

If the answer, however, is yes. Focus on one particular thing and offer to help. Use “I” phrases such as: “I’ve struggled with maintaining my calendar in the past and tried several things; maybe one of these will work for you”. Showing empathy while one offers help sometimes works like a spoon full of sugar with medicine.

If the person’s messiness boarders on hoarding, you may want to read this: http://www.organize-more-stres.....arder.html

I hope these comments are helpful.

Now that I’M the boss, I’ve “cleaned up” (pied up, actually) quite a bit because I realize it looks very unprofessional.

If the work is getting done though, sometimes you have to just live with it until the person changes. Hopefully.

He was such a nice guy, I introduced him to a very close family member and they got married. The messy guy became one of my relatives! And he remained truly messy, filling his home office with huge piles of paper. Again, this didn’t affect me, since it wasn’t my house. He was a very quiet, unassuming person, and quite shy.

Several years ago, messy guy died, and the task of clearing out his office fell to me. It took me a solid week to throw out old papers, sell off old (and often brand-new in the packages) electronics buried under old papers, and cull out the 10 or 12 truly important things from his office. The piles were literally waist-high. It was very sad, and yet oddly satisfying.

What I learned in this process is that he really was quite organized, but when he became very sick, his system completely fell apart. It took only a short while before he simply gave up trying to find things in his office and let it become chaos. I also found, buried in the piles, evidence of many hobbies that interested him that I never knew about. I wish I had known he was so well-versed in archeology, astronomy and photography. If his office had been neat and orderly, I would have seen the books and projects proudly on display and had a chance to ask him about his trips and lectures. Instead, they were hidden in the mess until he died and it was too late.

I know this doesn’t really help anyone with a messy co-worked, but the question brought up a flood of memories for me. Thanks for letting me share them!

Hope you still like my suggestion, though. Keep up, J.

one: as suggested by others, you can quit your job.

two: you accept that your boss will never become organised with papers. Therefore: make sure your boss does not have to do that paperwork in the first place – have him *delegate* it to someone who is organised.

That someone might be you, it might be somebody else. It doesn’t really matter, just make sure the paperwork is no longer your boss’ responsibility. Let him concentrate on what he is good at and loves doing.

Make sure that you suggest this to him a positive manner. Describe a vision, an outcome how great it would be if he was relieved of the burden called paperwork but still have everything organised – by simply delegating it to someone who is better with papers and likes handling them.

Make it appealing to him and he will understand the benefits and relief. Because the real reason that your boss is disorganised, is that he doesn’t like to do the paperwork in the first place.

I hope this will work out for you – and your boss!

A few years ago I had health problems and was offered help by some students, which I was very grateful for. In return, I gave them each several children’s books since they refused pay. But it may not occur to the boss that she can feel okay about accepting help if she’s able to reciprocate in some way.

I shared a cube and a job with a person who was the absolute opposite of me – he needed everything clear so he could think, but his drawers & files weren’t organized at all.

We worked out a system that we could both use, pretty much – but it was a kludge for both of us. Neither of us would have been able to survive using the other person’s system.

It’s a lot easier to set boundaries and communicate your expectations of neatness with a colleague, i.e., someone who’s an organizational equal, than with a boss. In both cases, it affects your work — “when a report gets buried and misplaced on your desk, boss/colleague, I can’t get my end of the task completed on time” — but a colleague is likely to be more understanding and respectful than a boss is.

At least in my experience. Last time I worked for a messy boss, there was only so much C.Y.A. I could do for myself before my boss figured out it was always my fault, anyway, that we blew a deadline or lost some paperwork in his office. Eventually I figured out that my time was better spent in polishing my resume than in cleaning up his messes (both the paperwork messes and the professional fallout it caused).