Prioritizing When You Have Many Bosses

If you have multiple bosses, it can be tricky to figure out how to prioritize your time and keep them all happy. Get-It-Done Guy has the tricks to juggle several bosses without losing your mind.

Stever Robbins
4-minute read
Episode #253

Prioritizing When You Have Many Bosses

Listener Kaitlin has a problem. She writes:

“I provide administrative support for three bosses. Prioritizing is hard. How do I schedule my time, when they don’t have neat, equal workloads for me every week?”

Kaitlin, Kaitlin, Kaitlin. They say a man cannot serve three masters. Fortunately, a woman can, and you’re either a woman, or a man named Kaitlin.

When you serve only one master, prioritizing is easy. Your boss gives you 5,000 things to do. You say, “Boss, I can’t do 5,000 things at once. Which do I do first?” “All of them.” You reply, “Of course. I understand. And which one would that be?” Eventually, your boss will have to answer.

With three bosses, however, there’s no one authority on how you should spend your time. Except you!

Prioritizing by Urgency

Especially if your bosses aren’t all around at the same time, it can be really tough to prioritize tasks between those bosses. Let’s say your bosses are evil geniuses, scheming to take over the world. One is raising a zombie army–of course. Another is teaming up with space aliens to destroy Washington, and the third is plotting to destroy all human intelligence by forcing us all to watch the ninth installment of the Twilight series.

The urgent/important time management matrix popularized by Stephen Covey would have you do the important tasks first. But how do you know whether ordering brain pouch-equipped vests for the zombie army invasion next month is more or less important than preparing vats of green slime for the alien ambassador reception in a week? The projects belong to different bosses, so you can’t really compare them.

The answer lies with a fascinating observation by time management expert Mark Forster. He says that if something isn’t important, it shouldn’t be on your task list at all. So importance is irrelevant when choosing which task to do first.

Instead, since everything on your task list is important, you should do them in order of how urgent they are.

Urgency is the Start, not the Finish

“But won’t I spend my life in a frenzy of stress-filled last-minute catch-up, trying to finish what’s due in ten minutes?” you cry. It’s a reasonable concern.

The zombies will be marching on Washington in 4 weeks or 28 days. The alien ambassadors arrive in 7 days. Normally, we would say the green slime is more urgent, and we would start mixing it first.

According to Mark, we misunderstand urgency. We think that what’s most urgent is what has to be done the soonest. Nope. What’s most urgent is what has to be started the soonest.

Zombie vests require custom brain pouches, so they have a lead time of 24 days—21 days preorder plus 3 days’ shipping. To meet the 28 day deadline, they must be ordered in 28 minus 24 or 4 days. Green slime is needed in 7 days and can be prepared just 2 days in advance, so preparation must start in 7 minus 2 or 5 days.

Normal urgency would have us start the green slime first, since it is needed first. But then we would be totally squeezed and panicked because we would be late on the vests. When we determine urgency by start date, we know we need to order the vests first and we have time to get everything done. We’re prioritizing by urgency, with no panicking involved.

Set Boundaries When Prioritizing to Balance Your Load

Some weeks, one of your bosses may use you less, giving you more time to devote to your other bosses. If so, do the extra work. But make sure they don’t come to expect it! Say, “Boss #1, I have extra time this week because Boss #3 doesn’t need much of my time. So unless #3 gives me more work, I can give you a full 50% of my time to work on zombie army logistics.”

That “unless” is important! If Boss #3 comes to you on Wednesday and says you need to get Robert Pattinson on the line to review dialogue for Twilight 9: The New Moon After the Eclipse, you need to scale back on your zombie army efforts.

Let your boss choose how you scale back your work.

Give Your Boss Choice

Don’t just go to Boss #1 and say “Boss #3 needs me so you don’t get as much of my time this week.” That will remind Boss #1 that they don’t have absolute control, and will damage their fragile, world-dominating ego. Instead, rebalance your work by giving Boss #1 the illusion of control.

You can scale back in two ways:

#1 - Do less work

#2 - Do lower quality work

Tell your boss the implications of each choice and let your boss choose. “Sorry, Boss #1, but Boss #3 needs me to work on the Twilight project. Do you want me to delay zombie army logistics until next week, or would you prefer that I research less thoroughly, risking battlefield confusion when we deploy?”

Call a Boss Meeting if Needed

You may be the mastermind doing the work of world domination, but your bosses may still think you’re just their pawn. If they won’t respond to your prioritizing by boundary setting, pull out the big guns: the bosses themselves. Convene a meeting and say, “I am your innocent pawn and gladly do your bidding. But we need to figure out how to deal when you all need me at once.” Ask them to agree among themselves how to divide up your time when all three need you.

Serving three masters is tricky. Prioritize by urgency, the urgency of when things need to start, not finish. Set boundaries when you’re given work, and if your workload changes, let the boss who is losing some of your time decide how you should scale back. If all else fails, let your bosses fight it out among themselves. The worst that can happen is that they destroy themselves in the process, leaving a power vacuum for you to fill. I wish you the best of luck Kaitlin…Your Most Awesome Eminence. (I want you to think well of me, just in case).

This is Stever Robbins. I coach high-potential leaders in strategic thinking, strong interpersonal skills, and world domination. If you want to know more, visit http://www.SteverRobbins.com.

Work Less, Do More, and have a Great Life!


Three Bosses and Overworked Employee images from Shutterstock

About the Author

Stever Robbins

Stever Robbins was the host of the podcast Get-it-Done Guy from 2007 to 2019. He is a graduate of W. Edward Deming’s Total Quality Management training program and a Certified Master Trainer Elite of NLP. He holds an MBA from the Harvard Business School and a BS in Computer Sciences from MIT.