Trying to Manage Your Manager? Use the “BOSS” Acronym

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In my work training hundreds of leaders over the past seven years, many have wondered the same question: How can I manage my manager? And how can I challenge them when I disagree with one of their ideas?

This process is often called “managing up”: creating a strong, mutually beneficial relationship with your manager in which you can work productively together while also respectfully challenging them.

Many leaders fear pushing back on their boss because executives and senior managers can occasionally be intimidating, opinionated, and stubborn.

But managing up is an important career skill to build because it can help you grow in your career, increase your job satisfaction, and minimize your work frustrations because you’re able to collectively discuss difficult topics.

I use a 4-step acronym called “BOSS” to help leaders remember four elements of managing up:

1. Build the relationship

All strong relationships begin with a foundation of mutual respect. Get to know them on a personal level and allow them to do the same with you. Talk about both work and non-work topics (if they’re open to it).

Specifically, it’s helpful to learn what makes them tick — what motivates them. Try to learn the following things about your manager:

What are their hobbies outside work?
What types of things are they passionate about (family, faith, friends, etc.)?
What is their career goal? How can you help with that?

Strive to become a thought partner who helps them achieve their goals. If you can help them achieve their goals, they’ll help you achieve yours.

2. Observe their preferences

Every manager has preferences: Do they prefer to communicate via email or phone or Zoom? Do they prefer to read a bunch of prep material before each meeting or show up and wing it? Do they expect you to bring them fully-baked ideas or do they enjoy brainstorming half-baked ideas together?

For example, one executive I worked with loved to talk one-on-one on the phone after big meetings. We’d finish an All-Hands meeting, and he’d call me to get my immediate thoughts on how the meeting went. He was a highly relational leader who wanted immediate feedback on what landed from his talking points and what didn’t.

A CEO I worked for didn’t like to be asked any spontaneous questions in meetings. He was brilliant but didn’t think well on his feet, so he requested people to post their questions in advance so he could think deeply about them and come to a meeting prepared with a thoughtful response.

Pay attention to what your boss pays attention to. Then proactively provide that information.

It’s your job to learn your boss’s preferences. Study their style and try to answer questions like the following:

What values seem most important to them? Why? (Usually, these values were carved by prior life experiences of theirs — good or bad.)
What are their pet peeves? How can you get in front of those and ensure you and your team don’t make those mistakes?
What type of information have they asked you for multiple times? How can you proactively provide that information next time before they ask?

The final question above is one of my favorites because every manager loves receiving pertinent information before they ask for it. One prior boss asked me on two occasions for updates about my largest, most strategic clients. After the second time she asked, I realized that she probably wanted that type of update on an ongoing basis, so I created a calendar reminder to send her a proactive client email update once per month. Voilà! No more questions, and it made me look like a mind-reader.

Pay attention to what your boss pays attention to. Then proactively provide that information.

3. Support each other

I’ve heard a lot of leaders denigrate their boss and describe them as an enemy. That type of “us vs. them” mentality will only cause you problems.

Your goal should be to view your boss as an ally. Find ways to support them, and they’ll do the same for you.

If you can help them achieve their goals, they’ll help you achieve yours.

Specifically, look for tasks and projects you can take off their plate. One of the ways I’ve done this is to tell past bosses things like, “You shouldn’t have to waste your time with that type of admin work. Do you want me to handle that for you?”

This approach does two things. First, it shows that you value your time. And second, it shows you’re willing to be a team player to help them out. Even if they don’t take you up on your offer, they’ll remember that you asked.

In addition to asking how you can support them, tell them what they can do to support you. Here are a few examples of what that could sound like:

“I’m having a hard time making inroads with the Marketing team. I know you’re close with some of the Marketing leaders. Any chance you can help me get this ball rolling by talking to Jeff or Sarah?”
“My ultimate goal is to become a Controller, but I need to improve a lot of skills before I can achieve that. Can you let me know if you hear of any strategic finance projects I could take on that would help me learn more about X, Y, and Z?”
“I’ve been wanting to develop my public speaking ability. Do you mind if I step in to give the department update in your stead when you’re out of the office next week? I think I could learn a lot from that.”

As another method of supporting them, find ways to make them look good in front of their peers and their boss (your boss’s boss).

Advocate for their ideas in meetings. Represent their thoughts and opinions even when they’re not in the room. Avoid bad-mouthing them to colleagues. All of these little things add up to make a strong partnership.

4. Speak up

The first three steps above are all about building your relationship. The stronger that partnership is, the more latitude you’ll have to respectfully stand your ground and share opposing opinions whenever you disagree with one of their ideas.

There are many situations where you may want to challenge your boss on something. Here are a few examples:

You believe one of the quarterly goals they set is unrealistic.
You feel like they’re micromanaging you or not giving you enough room to make decisions.
Their style is quite a bit different than yours, and you want to discuss how you can find a middle ground between the two approaches.

Let’s say your manager just asked your team to take on a big project, and you’re not sure whether you’ll have time to complete it amidst all of the other priorities you’re working on.

Here are three tactics you can use to respectfully challenge them:

Explain your current priorities & ask where this stacks up: “Right now, the team is working on [XYZ objectives]. How does this project compare in priority to those?”
Ask questions: “I want to be sure I prioritize this appropriately. What impact do you expect this project to have on the company?”
Educate them: “The last time the team did a project like this, it took them about 20 hours to complete. Do you think it’s worth that time investment?”

Tactics like the ones above can help you persuasively but gracefully challenge your boss’s directive.

Ultimately, any manager/employee relationship is only as strong as the conversations you can have together. Those conversations should be filled with mutual support as well as productive pushback on both sides.

Don’t make the mistake of thinking that feedback or pushback can only flow top-down. Strong partnerships include two parties who can both express themselves candidly and considerately.

Use the four steps of the “BOSS” model to effectively manage up: