An Important Announcement From OfficeNinjas Founders →We’re Taking a Hiatus

What You Need to Know to Work Productively with a Disorganized Boss

OfficeNinjas Disorganized Boss

Editor’s Note: This article was written in collaboration with Post-it® Brand.

Picture this: your desk is spotless, organized, and the very definition of pristine. Clear spaces equal clear minds—but when you step into your boss’s office, you see nothing but disarray and clutter. Even worse, it’s displayed for all the company to see.

Think a messy desk is just a messy desk? It’s not.

According to research by the Post-it® Brand, disorganization is more than just an eyesore. It can lead to decreased morale and productivity—plus, 3 out of 4 office workers believe disorganization is the result of deeper company issues. Yikes.

Though empathy, decisiveness, confidence, and optimism are all signs that you’re working for a great leader, a few other qualities affect that person’s reputation. Most (like 96 percent) office workers also believe that a clean and organized desk is also symbolic of great leadership.

how a disorganized boss affects the organization

If you’re laboring under a disorganized exec, chances are you’re all too familiar with multitasking overload—and performing your fair share of fire drills. Prioritizing is second nature to you of course, but handling conflicting priorities is challenging for anyone. To make office life better for you and your team test out these seven office-tested hacks for coping with a disorganized boss.

Be a Problem Solver

Screen Shot 2016-04-01 at 12.38.53 AM

Reflect on how your boss’s disorganization impacts you the most. Then, create solutions to improve that particular aspect of your job.

Problem: The only kind of clockwork your boss commits to is telling you she needs a report first thing in the morning—just as you’re grabbing your keys to head home.

Solution: Schedule a reminder to check in with your boss 30 minutes before closing time. Creating a daily habit will get your boss used to thinking of all the last minute things needed from you. Congratulations! This will secretly train your boss to be more organized, especially toward the end of the day.

Ninja Tip: Once the habit is fully formed, designate a certain colored Post-it® Notes for jotting things down throughout the day. Then, all you have to do at 4:30 PM is swing by and grab the green stickies.

Get Everything in Writing


Sometimes you get assignments thrown at you as the boss is running to his next meeting—or worse, through vague voicemails. Help your boss organize his thoughts by sending an email confirmation promptly after the fly-by task. Make sure it’s clearly written and restates exactly what he said.

Sum Up the Small Efforts


It’s easy for anyone to get overwhelmed with excessive emails or notes. Embrace the office digest format and propose sending one summary email at the end of the day. By minimizing the disruptions, you minimize the chaos of dealing with a disorganized boss.

Ninja Tip: Create your own Kanban system with Post-it® Super Sticky Notes by writing each assignment or task at the start of your work day. Stick them on a whiteboard that you and the boss can both see. As you move through your work and complete tasks, remove the corresponding note so you can see how small efforts contribute to the success of your day.

Help Them Delegate


Why wait for your boss to reach crisis mode? Be proactive and stay one step ahead of disaster by asking what you can take off the head honcho’s plate. They’re often overwhelmed by too many 10-minute tasks, or they have trouble delegating. If writing email templates will save the boss an hour a day, do it—then help fill the time slot with something that keeps the productivity momentum going.

Stack & Sort

One of the must-have desk items on any organized Ninja’s workspace is stacking inbox trays. Set some up for your boss so she has one for action items, pending items, and one for items that are ready to leave her desk. It’s simple, low-key, and easy to maintain—which means she can keep the clutter to a minimum and make a physical pipeline.

Plan for Emergencies

The best Office Ninjas are always thinking a few steps ahead. If your boss is notorious for last-minute emergencies or regularly asks you to find misplaced items, plan for this surprise. By adding a 30-minute buffer in the morning or in the afternoon, you’ll avoid derailing your schedule when a crisis pops up.

Bonus: If it’s a good day and there are no crises to be had, you’ve got a well-deserved breather. Leave the work behind for a few minutes and try a fika for an added boost of happiness and productivity. There’s a reason the Swedish are the happiest workers on the planet!


Set the Example

Let’s face it, your boss probably isn’t trying to be jumbled. A great way to help them be more organized is by being organized yourself. Act as a pillar of support and lead by example. After all, you are the average sum of those you spend the most time with.

“The best thing I did was to remove coffee cups and food containers. Nothing is worse than spilling a drink or food that you’re not even enjoying anymore. I always leave my desk clean when I leave, even though it can get slightly messy during the day. I definitely use my Post-it® Notes to keep piles of paper in order. This also lets people know where to drop things on my desk. I make sure to keep extra Post-it® Notes handy for others to use to leave me a message if I step away, too!” – Melissa

Post-it Notes

At The End of the Day

Start small when trying to handle your disorganized boss—let him adapt to little changes gradually until you can ease them into a more consistent organizational system.

Remember that you can’t change your boss’s personality, so if you find yourself getting frustrated by the disarray, focus on strengths. If your reorg attempts are futile, try the weekly “dig out” method. On Friday afternoon, spend 15 minutes with your boss sorting through any piles to set you both up for a fresh start on Monday morning.

Off to you now, Ninjas! What are your tricks for dealing with a disorganized boss?

For additional information on Post-it® Products, including where to purchase, visit You can also connect via Twitter, Facebook, Pinterest and Instagram. Be sure to check out the infographic and key findings below from the Post-it® Brand Office Organization research study.

Post-it Brand Office Excellence Infographic-page-001

*The Post-it® Brand Office Organization survey was conducted by Wakefield Research ( among 1,000 full-time U.S. office workers in 2015, using an email invitation and an online survey.


  1. Thanks all for your comments. Very helpful. Currently writing my essay about the leadership challenge and messy and chaotic boss is my thesis! wish me luck

  2. Unfortunately NONE of these suggestions would work for me. She constantly forgets even if you email her. She promises to write things down but never bothers to look at it again and you could remind her today… write things down and give her things and she misplaces it. Even if she claims she has set aside a space for things she’ll get it messy anyway. I don’t have the energy or patience to spoon feed a fully grown adult with grandchildren. Just like you’ve been reminding her every now and again about a scheduled meeting, remind her the evening before and she’ll reach to work the day of the meeting and forget. On many occasions she has had a clash of meetings. She procrastinates constantly no matter how you try to convince her to do things ASAP and shes stubborn and pushy and manipulative. As a result she leaves everything last minute and throws everyone off their schedules. After doing a personality type evaluation over a month ago that indicated that we are both entirely different when it comes to approaching things and reading this I’m convinced now more than ever to send out resumes. The facilitator of the workshop pointed out she was bossy, controlling and manipulative. How does a person run an organisation without any analytical skills at all and not see the need for it? How can you undervalue the need for precise data to make decisions? This is what I’ve been dealing with for almost 3 years and I have chosen to look for something else.

    1. Dana, if you’re going to start looking, check out Liz Ryan’s articles on LinkedIn – her information on today’s Human Workplace got me moving in the right direction and really helped my preparation and mindset when I was job-hunting.

  3. I was born with highly-developed organizational skills – and my boss reaps the benefits! I’m the first EA he’s ever had who always (even when he’s on vacation) sends him an end-of-day summary so he doesn’t miss out on anything. He has a good stack of different post-it notes at hand, along with a reporter’s style coil notebook (narrow so it sits nicely between his phone and computer, always at hand)-I have one too. And I set up a mesh file box on his desk with labelled hanging folders for his to-do (but no on fire today) items. I use transparent coloured sleeves to hold hard copy items, by priority to grab at the start of the day (red=right now, yellow=next, green=it can wait a bit), along with coloured pens so I make notes as tasks are updated or completed. There are lots of great organizing resources at the office supply store – I can’t tell you how many times the boss has come back from an off-site meeting and told me that others were so impressed when he pulled out his ultra organized folders – his last Christmas card said “you make me look good, and I never forget that”.

    1. This sounds like an EXCELLENT system. Do you use a template for that EOD summary? We’d love to peek at it…

    2. Michele, Would you be willing to share an example of your EOD email. Come help me and my boss get on the same page, lol

  4. I actually do a lot of these and the post it note idea for your boss to write down what he needs – HE DID!!! We can train them even without them knowing what we’re doing…LOL

    1. You got it, Peggy ;) Glad to hear some of these tips worked for you!

  5. Wow, this article is timely! Please share any and all tips. I’ve got one, too!

    1. Yikes! Hope this helps—and be sure to let us know if YOU discover any magical solutions

  6. I love the ninja tip on leaving post-it notes next to your boss for him to write down items throughout the day. Then I can pick them up at the end of the day from him and we both stay on task. This article was extremely helpful!

    1. Thanks for your feedback Carrie! Let us know if you try the Post-it Notes tip :)

  7. I work for a Trauma Surgeon in his research laboratory. His office is a wreck but I tidy it gently every time he goes out of town on business. He’s got a lot of irons in the fire at any given time and his calendar is difficult to manage. He never finds notes or emails because there is such a deluge. I’ve taken to putting all notes to him in the body of a calendar event every week. So he know all he has to do is look at that calendar event and notes about what I need from him or where we stand scheduling meetings are right there. I’d love to hear more about how others manage these things.

    1. It sounds like you’re doing a great job, Carol! Let us know if you try any of our tips :)

    2. Carol I have the same issue with my GM. His office is very messy and unorganized. Whenever he’s out of his office for an extended amount of time, that’s when I tidy up.

  8. Over the years, I have discovered that some people are “File-ers” and others are “Pile-ers”, meaning they either File or Pile.

    Some people visually “mind map” what’s on their desk and amazingly find things amid the clutter. I’ll admit that I am a Pile-er. If it’s out of sight, it’s out of mind. My tip is to eliminate horizontal places to pile paper. Get rid of credenzas, book shelves, side tables, etc. that create a dumping ground for paper.

    My current struggle is with digital filing and email overload. The paper is almost easier to deal with…

    1. We feel you!! We’ll try to share tips on digital filing and email domination soon, so stay tuned :)

  9. These are terrific tips and I would love to hear more about how to work with a disorganized boss.

    1. Thanks for your feedback! Are there any other topics you’d also like us to cover?

Comments are closed.