Ask Unclutterer: Working with a messy colleague

Reader Laura submitted the following to Ask Unclutterer:

I know that several people have asked about living with a messy person but I have a question about working with one. I work in a fast paced coffee shop as an assistant manager with my direct boss that is completely disorganized. As a tidy person, I understand the benefits of cleaning and clearing on a daily basis, especially with paper work. She, however, seems so stressed out that everything gets lost. I am constantly amazed when she can meet a deadline because she is so all over the place. This work environment is starting to stress me out and break down our communication! How do I handle this, noting that it can be a tense work relationship? Is this something
that I should just get over and deal with?

Every employee brings something different to a business. In fact, the more diverse the employees at a company, the better the company is at responding to its needs. What your colleague lacks in organizing skills, she might make up for in people or management skills. For instance, I am bad at brainstorming, but amazing at follow through. If you want something to get done, you come to me. If you want someone to generate the next multi-million dollar idea, you talk to somebody else. You’re likely in the position you are at your company because your boss sees your organizing skills as highly valuable and complimentary to her skills. You have something she lacks, and she needs your organizing talents to do her job well.

Instead of being frustrated about her lack of skills, find ways to help her develop her organizing skills. Start by asking her if she wants some help in a nice, friendly “I genuinely want to help” manner. If she does, work together to find ways you might be able to streamline parts of her job to make things easier on both of you. If she doesn’t want your help, try your best to lead by example and maybe she’ll eventually change her mind. You can’t force her to become organized, but it never hurts to politely ask someone if they could use some help.

I’ve been the extremely disorganized employee in the past, and I would have loved for someone to have offered me help. I constantly felt like I was underwater and that I was letting down my co-workers. Your boss might feel the same way, and giving her a helping hand will likely make things better for her, you, and everyone else at your coffee shop.

Thank you, Laura, for submitting your question for our Ask Unclutterer column. Good luck!

Do you have a question relating to organizing, cleaning, home and office projects, productivity, or any problems you think the Unclutterer team could help you solve? To submit your questions to Ask Unclutterer, go to our contact page and type your question in the content field. Please list the subject of your e-mail as “Ask Unclutterer.” If you feel comfortable sharing images of the spaces that trouble you, let us know about them. The more information we have about your specific issue, the better.

Posted by Erin on Nov 13, 2009 | Comments | Tweet This

20 comments posted

  1. Posted by infmom - 11/13/2009

    Years ago I worked part time in a camera store. My boss was one of the nicest people I’ve ever met, but I don’t think anyone in the world was more disorganized. He’d created a whole bunch of totally unworkable systems for himself and since they were time consuming and complicated, nothing got done. He didn’t bill the customers for months at a time, to the point where some of them were coming in day after day and begging for a bill. He’d try to send out mailings about the store, but the database he used for customers was ridiculously complicated to enter anything into, and it only existed on his computer so nobody else could help. The front of the store was neat and attractive (you can bet I saw to that) but in the back it was like a bomb went off in there. It would have only taken a few minutes to enter the daily charges into the accounting software, but day after day he’d take the paperwork (also needlessly complicated with a four-part NCR form) back to the back and set it down and it’d be gone till the next frantic paper hunt.

    At one point, I offered to deal with it all for him. I’d straighten out the billing, enter all the data, clean up the junk on his hard drive and re-do the tape backup settings so that everything could fit on one tape (he bought a tape drive only half the size of his hard drive) and make a start on cleaning up all the papers strewn all over the back. I figured that would take me two weeks, tops, if he let me work my full shift doing that and not standing behind the counter.

    He refused. I hung in there for two more months because I genuinely liked the guy, but after he spent a week hiding in the back while an irate customer demanded to know where her irreplaceable antique photo of her grandmother had gone, I gave notice.

    The business didn’t even last a year after I left. Not necessarily cause and effect, of course, but when your business model can’t work, the business can’t either.

  2. Posted by Plain Good Sense - 11/13/2009

    “Every employee brings something different to a business. In fact, the more diverse the employees at a company, the better the company is at responding to its needs. What your colleague lacks in organizing skills, she might make up for in people or management skills.”

    This was a good reminder for me, Erin. Thank you! I often get frustrated with my unorganized (and just plain messy) boss just like Laura. When it comes to administrative duties, there is no way she could function without the rest of us picking up her slack. However, there are definitely things that she excels at, which is why she is in the position she is in.

    Thanks for reminding all us “unclutterers” to not compare our greatest strengths with others greatest weaknesses! :)

  3. Posted by Kathryn Fenner - 11/13/2009

    Married to a computer science professor for almost 20 years. I am organized. He is a total flake. He really cannot help it beyond a very limited point. I manage what I can for him and try not to nag. He helps keep me sane when the workmen leave the house in unnecessary disarray.we work together as a team.

    On the other hand, my former boss-from-hell was disorganized and highly resistant to any help, and prone to blaming others for foul-ups caused by her disorganization. I finally realized this was a situation I could neither change nor accept easily, so I left.

    You have to figure out which type you have.

  4. Posted by Dawn F. - 11/13/2009

    I think the “I genuinely want to help” approach that Erin mentioned is the best assuming you like/love the job enough to want to stay.

    Teaching by example, showing her your processes, procedures and tools and then giving her a pat on the back when she makes progress could possibly do wonders for the scattered boss or co-worker. Mentioning how relaxed you feel when everything is in its place and how confident you feel knowing that everything has a “home” in the office might motivate them to want to have the same feelings.

    Perhaps helping that disorganized person set up a daily routine could help in the process, too. Maybe if that person set aside at least 30 minutes each day reviewing, purging, trashing, etc. the papers, folders, packages and mail (or whatever that business deals with) that they receive could get them on track. It sounds crazy to have to help out a manager in this way, but it might make your life better (and theirs).

    TGIF!

  5. Posted by momofthree - 11/13/2009

    I work on a part time as needed basis for my local school district. I can work in one of three capacities: School Secretary, Nurses’s Aide or Library Clerk.

    I am overwhelmed by the sheer chaos that some desks, desk surfaces, and desk drawers are in. I one desk alone I counted four letter openers and more pens and markers than my local Staples had!

  6. Posted by Michele - 11/13/2009

    I think there’s a big difference between working with a messy colleague and working for a messy boss, not to mention being the boss of a messy employee. And I think each situation has to be approached differently.

    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).

  7. Posted by Lori Paximadis - 11/13/2009

    Be careful: “messy” is not necessarily equal to “disorganized.” I am notorious for my chaotic-looking desk and project shelves, but I KNOW where stuff is. I’m an out-of-sight-out-of-mind kind of person. If you make me start shutting stuff away in files and drawers, that’s when things start falling through the cracks.

  8. Posted by Rosa - 11/13/2009

    Yeah, what Lori said – I am a pretty messy person, but not disorganized. I also need current projects out where i can see them, if I am going to multitask, and a big visual calendar.

    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.

  9. Posted by Sandra - 11/13/2009

    A tip – a boss may refuse help because they feel guilty and don’t want to take advantage of an employee. If you try to offer help and think this is the case, you can say something like, “If you feel funny accepting my help, you can make up for it by . . .” and then ask for something that’s easy to grant like “let me take home a slice of pie now and then.”

    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.

  10. Posted by Chloe - 11/13/2009

    When I was a medical intern working nights I was totally stressed, resentful and disorganised running from one page to the next, backwards and forwards all over a huge tertiary hospital. It seemed that I never got a moments rest over the 13 hour shift. I will never forget the covering intern who took over from me who noticed how stressed I was and gave me a tip that when I was in each ward to ask for all their jobs when I was there, and do them right away if there wasn’t an emergency happening elsewhere. It saved an amazing amount of time but in my sleep deprived anxious state I had never thought of it.
    I actually ended up getting to lie down on the beds they provide for night shift on call doctors a couple of times!
    She wasn’t even especially careful or nice about how she told me. She wasn’t that sort of person. Just matter of fact, but I will be eternally grateful.

  11. Posted by Jurgen - 11/14/2009

    If your boss is very bad at paperwork, and shows no REAL interest in improving this, then there are two things you can do.

    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! ;-)

  12. Posted by Jurgen - 11/14/2009

    Oh by the way, I described your boss as a ‘he’ instead of a she. I guess i’m a male chauvinist pig.

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

  13. Posted by Kathy - 11/14/2009

    My only word of caution… like in every other situation where someone does something in a way differently than you do… unless they recognize the issue and are feeling the pain and ASKING for help, you should always tread lightly with your offer. There is certainly the potential for the person to feel judged (especially on a known weakness) and resent the judgment more than appreciate the offer. The fact is, if she DOES get things done, in spite of herself, the system may not be so bad as to have an intervention in her mind. Good luck!

  14. Posted by Louise - 11/14/2009

    I worked with a man who was incredibly messy in his office, but knew exactly where every paper was. He could reach into a stack 18 inches high, and pull out the report he wanted from somewhere in the middle. His cubicle looked terrible, though, and management constantly hounded him to clean it up. As a co-worker on another project, it didn’t bother me.

    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!

  15. Posted by Maryann - 11/14/2009

    I used to work on my with at least one inch of papers covering the entire desk (talk about “spilled liquid risk”!) I’m a visual worker & I need to see my stuff. My boss put up with it because I was the best one in the company.

    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.

  16. Posted by Christine Simiriglia - 11/14/2009

    When working with a disorganized co-worker or employee, there are two questions to be asked. 1) Is this person’s disorganization affecting the quality and quantity of the work they are able to produce and 2) is their disorganization and/or mess reflecting badly on the company (if you are in an open office with lots of visitors for example) or infringing on the karma of their co-workers?

    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.

  17. Posted by rachel - 11/14/2009

    @ Louise: Wow, thanks for that story! Lots of good reasons for me to continue to try to conquer my clutter. It’s such a shame that his clutter kept his true interests from being known by others who could have appreciated them.

  18. Posted by Beth - 11/15/2009

    I work in a unique situation where I visit clients’ offices on a daily basis – sometimes 2 clients in one day. I am an organized person and while I am working on a project, my desk may look like a bomb went off – it is always clean when I leave. This is due to 2 reasons -

    [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.

  19. Posted by Ellen - 11/16/2009

    The key word here is ‘compromise’. Just because you feel your way of working is ordered and uncluttered, doesn’t mean it is… I work for someone who believes she is incredibly organised and has set-up various intricate systems for everything. If it’s not done her way, she becomes a very negative person. The truth is that her systems are suffocating everyone else. Everyone has different ways of working but that doesn’t mean that they’re necessarily the right way. Sit down with your colleague and discuss the situation, you may discover that she’s written a ‘my colleague is too organised and its stressing me out’ question to a clutterer blog, lol!

  20. Posted by Joan - 11/16/2009

    Ellen hit on an interesting point – what to do if you’re the boss and your employees are “cluttered.”

    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!

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