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How to Organize a Disorganized Boss

Is your boss disorganized? Try these four tips to manage upward.

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Disorganization comes at a cost, especially for business leaders. Most CEOs work more than 60 hours a week, per a Harvard Business School study. Yet the National Association of Professional Organizers notes that the average executive can expect to waste six weeks annually due to poor organization. That’s where professionals like me come into the picture.

I was brought aboard our company to assist the CEO and the chief of staff. My primary role? Keep them free of administrative entanglements, informed of updates, and able to focus on urgent issues. That way, my bosses can concentrate on solving all those little surprises that come their way. In essence, I act as a point person, integrating with employees, departments, and outside contacts in order to save the CEO and chief of staff time.

Am I an organization expert? Not necessarily. But I’m a lifelong learner who’s passionate about contributing and evolving. I’m also becoming a stronger advocate for administrative personnel to learn how to organize their bosses.

Mastering Organization by Managing Up

Organizing a supervisor takes careful planning. In my case, it’s been a collaborative effort. From the get-go, I was tasked with giving our CEO and chief of staff security and peace of mind. They leave the routine communications to me, and I take gatekeeper responsibilities off them. They get to put creative energies toward mission-critical, high-level tasks, and I offer a space to answer more routine questions so people don’t have to move through multiple channels to get resolutions.

In other words, I manage up — and that’s good for everyone involved. Instead of a job, I have a relationship with my executive bosses. Take email, for instance. One of the CEO’s first priorities was to get her inbox under control. She gave me complete access, trusting me with something very personal to most people. In one afternoon, we hammered out the details of what emails she needed to see, what could be deleted, and what needed to be flagged for her every day.

Not only did our meeting end with her being relieved, but also it helped me understand how many directions she’s constantly pulled in. No shocker: CEOs get tons of emails. One study found that email takes up 24% of office time for most executives. Even stopping for a few seconds to get rid of an email costs professionals minutes they can’t afford to spare if they want to be at peak productivity.

At the end of the day, I see our partnership as a transfer of abilities and functions. I have been given time to spend so she has time to release. It’s a very balanced way of working together — and one I’d recommend. In fact, if you want to start keeping both you and your boss more organized, I urge you to try the following techniques.

1. Communicate relentlessly. Regular communication between you and your boss (or bosses) needs to be established right from the start. Talk about expectations and understand your supervisor’s communication style. Work together to create a communication system between you that promotes productivity.

2. Write everything down. I keep detailed outlines of everything from the current projects and to-dos on my bosses’ radar to the small items that could easily get lost in the chaos of day-to-day work. My documents are organized from broad to specific, by date, by relationship, and other points. That way, any of us can look at my outlines and see, at a glance, what’s happening.

3. Embrace existing and new technology. Our team incorporates the use of technological business tools to make organization simpler. If you don’t have a robust enough tech stack, you may find collaborating with your boss difficult. Ask for what you need and make a case for new software or systems when you believe they could save even more time.

4. Take everything in stride. Managing upward isn’t a science. It’s an art. And art can get a little messy. Hold yourself to a high standard of organization and communication, but know that challenges and misunderstandings will happen. And that’s OK. It’s all part of the self-development aspect of becoming a flexible, nimble, calm professional with a pragmatic mindset and empathetic heart.

Many executives are go-getters who try to do it all. However, your boss probably could use a helping hand to keep everything straight. Become a more powerful team player by offering to take on the overlooked but critical role of chief organizer.

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