8 Ways I "Manage Up" My Unorganized Boss While Working Remotely

My boss is many things. She is a hard worker. She is fair. She is considerate. She is passionate, inspiring, kind, and great at what she does. I genuinely love her – but she is also the most unorganized person I have ever met.

Many people work for an unorganized person who constantly drops balls and blames others. If that is true for you – run. That is a lousy boss. That is 100% not this case for me, though. In this instance, my boss is a visionary, and she is disorganized only because her mind races in every direction, at light speed, every waking moment. She always has the “next best thing” teed up and ready to go. But there is so much to be done before we can get to that part. Sound familiar?

Who am I? I am the administrator of Woodard Institute and assistant to the Director.

I am also a planner. I plan everything in advance. On Sundays, I plan what I am cooking each night of the week, what I will wear each day of the week, and what my backup plan will be for each of my plans. I am so much of a planner that I’ve got my calendar filled in for the next 2+ years (true story). In my social circle, I am the vacation planner, the reservation maker, the Murder Mystery party purveyor, and the hostess with the mostest!

My boss and I are in a long-distance relationship. It seems that this is a perfect recipe for disaster, doesn’t it? We don’t see each other. We communicate via Microsoft Teams and a short virtual meeting every morning. There are times when this can go wrong: animosity, frustration, declined productivity. Because I am not privy to what is going on every minute of her day, I might feel that I am not important, or I may think she’s being short with me when she is just busy.

For some, these things might make them stray and look for employment elsewhere.

But I will not quit. As I said, I love my boss. More importantly, I love the company I work for, the people I work with, and the work that we do. That is the trifecta of the perfect place to spend eight hours a day, five days a week.

So here is my dilemma: How do I do my job while maintaining a great working relationship and accomplishing our goals? She is the boss for a reason. She is good at what she does, and she built this business her way for years before I came along. I often wonder how much more she could accomplish if she were organized – and that is where I come in.

You can learn from my experience. Here are the things I do to “manage up” that you can deploy to keep your own team on track.

8 Ways to Manage Up

1. Accept Them for Who They Are

I have to attack this issue the way a football coach would. A good offense makes the best defense, right?

I have accepted who my boss is and who I am. My job is to make her job easier, not to change her fundamentally. She will never know what her plan is two days from now, two weeks from now, or two years from now. With that foundation set, I can turn my attention to the tactics that make our daily work more efficient.

Tip: Think of it as job security. Just like you will never be them, they will never be you. If you do your job properly, they need you.

2. Set Boundaries – It’s Good for Both of You

Especially if you work from home, set boundaries. Often, visionaries are the type that will be at their desks until 11 p.m. It is easy to respond to them when your computer is fifteen steps from your couch.

I used to be that person, but I am not anymore. Not because I don't love my job, but because I love my family life more. I will give 100% every single day to my job. But outside of work hours, I will give 100% to my family. So, I’ve set boundaries and I have work/life harmonization.

In fact, my boss says I am her role model, and she is starting to have a social life, too. I love adding up all the small wins!

Tip: Don’t only set boundaries within your own mind. Instead, verbalize it to your boss, “I only answer work calls after hours if it is an emergency. Please contact me via Teams, or text if necessary, and I will respond as soon as possible.”

3. Prioritize for Yourself and for Them

My boss and I have a limited amount of time together because of the nature of our work. We also work remotely, so I cannot just pop into her office and ask a question.

If there is something urgent, I will send her a message via Microsoft Teams. If she does not answer, I repost it marked important. I only escalate it to urgent when it is time sensitive because I must always be respectful of her time and her capacity.

Outside of these urgent matters, I keep a Word document open on my computer and jot down notes throughout the day: questions, comments, or issues. These are the things I will go over with her the following morning during our daily sync. We organize those conversations like this:

• Projects that are necessary
• Projects that are nice-to-haves
• Projects that might happen one day

We always cover the “necessary” list in our daily sync. If we have time, we talk about the things that would be nice to have and the things that might happen.

In a perfect world, we could talk about all three every day. But we are not living in a perfect world.

Tip: Like many people, myself included, sometimes my boss becomes overwhelmed. Before I came to work for her, she had non-stop, back-to-back appointments. She could not even get up to use the restroom. Now, I block out a time for lunch on her calendar every day.

When the overwhelm sets in for your boss, put a 15-minute block on their calendar and allow them to use this time to monotask on something they can complete in under 15 minutes.

4. Communicate – And Then Overcommunicate

Overcommunicating does not mean you need to speak constantly. That would take too much out of both of your days. Instead, communicate expectations, timelines, deadlines, clearly defined goals, and results. This will keep both of you organized.

Tip: Repeat your understanding of a project to confirm you are on the same page: “You need to accomplish this task by this date. Immediate action items are this, this, and this to be completed by this date.”

5. Always Strive for Clarity

There is a fine line between clarity and convolution. Sometimes too much information just makes a disorganized brain too crowded. Understanding exactly what she needs me to do is paramount. To accomplish this, I ask clarifying questions to make sure we are both on the same page.

Tip: If you are sending a message, use bullet points to quickly get to the heart of your query. It is easier to read, easier to understand, and cuts right to the chase.

6. Keep Yourself Organized with a Task-Based Management System

I was the quintessential “sticky note” person. I had sticky notes of every color, shape, and size on my desk and all over my computer monitor. Sometimes, those sticky notes were not so sticky, and they fell off and ended up in the trash. Whatever that task was, it was never completed.

Now, everything I do goes into my task list, with a “to be completed by” date. Every day I will look at my upcoming tasks, prioritize them, and mark them off as they are completed.

Anything I need my boss to complete becomes a task in my task list, so I can follow up with her. Checking off completed tasks is so satisfying, and it helps keep her organized and focused on the goals she needs to accomplish.

Because she can see my task list, it also allows her to know what I have completed each day without micromanaging me. On the other hand, she can see immediately where I might be falling behind and need some help. It is a win all the way around.

Tip: If your boss has tasks that you can do for them, reassign them to yourself. Keep them focused on the tasks only they can do. You can do the rest – that’s your job.

7. Be Proactive, Not Reactive

I love being a problem solver. Because I am a planner, I do not want to be surprised by something that may not be on my radar. I check her calendar daily and make sure she has all the information she may need for any upcoming meetings or events. We share a “general info” inbox, and I read and respond to all emails so that she doesn’t need to look at them unless I bring them to her attention. This takes a huge amount of work off her plate and allows her to focus on bigger things in the company. I also plan out all our classes a year in advance, and I put them on her calendar so that she does not double book herself.

Tip: Schedule everything – including vacation time and lunch. Otherwise, it will not happen. Everyone needs to be able to step away from their desk and eat, go outside for ten minutes of sunshine, or just regroup and think about what needs to be accomplished next.

8. Focus on Their Strengths

One of the things my boss is great at is helping our clients decide what path they should take in their educational plans. She truly understands their needs, and she can guide our clients down the path that is perfect for them to reach their goals. These are the calls I route to her. She is the strongest link in this part of the chain.

That said, I am always respectful of her capacity and her schedule. I cannot overwhelm her with one-on-one client meetings (although she would happily take them all). Instead, I only send her the clients who truly need her guidance and knowledge. I do my best to manage her day so that she has as few interruptions as possible. This leaves her with the time to focus on the things that only she can do.

Tip: If your boss steps in and does something you can manage, gently remind them that they need to let others do what they do best. (My boss is getting better at this; I expect to have her fully trained in the next few months!)

A remote world is new to me, to our company, and for much of the world. It takes some getting used to. There are ways to work together to get all the goals we set for ourselves accomplished. Organization is key and makes us more productive. Productivity makes my boss happy. A happy boss makes me happy. Remote life is good!