Is your biggest problem your boss? Read this article for tips and techniques for managing the most important of workplace relationships.

The relationship with your boss is one of the most important in the workplace. Your boss has the power to recommend you for new assignments, stretch goals, high-profile teams, promotions, and raises. She can make your life miserable or help you achieve your goals. Yet, despite the importance of this relationship, there are many more books on how to manage direct reports than how to manage bosses. This article explores four factors—style, context, relationship, and urgency—to consider before giving up on the relationship with your boss.


Observe your boss’ behavioral and communication style. Are they fast-paced, and fast to make decisions? Are they slow to think about things and want time to process? The more you can match style to your boss when communicating, the more they will really hear what you are saying. You may have great information to convey, but if you don’t convey it in a way that your boss can really hear, it will fall on his or her deaf ears.

Think about the “what’s in it for me?” for your boss each time you approach them. What do they care about? What do you know about the view from their seat? Can you frame comments in a way that makes them feel what you are proposing, or doing, is good for them? Many senior people have told me they wish their staff understood more about the complexities they deal with, and the issues coming down on them. Put yourself in their shoes a bit before you ask them to understand you!

Be a proactive communicator. Find out your boss’ preferred method – email, in person drop-ins, or lengthy memos – and be sure to pass along information. Most bosses don’t like to be caught unaware. Even if your boss doesn’t ask it of you, tell them what’s going on; keep them updated. Most senior people like to know what’s going on – and if your boss is a micro-manager type, the more outgoing information you can convey, the less they will ask you about what’s happening.

Help to support their weaknesses. If you know you have a boss who is disorganized, instead of grousing about it, help them to be on top of things. If you know your boss is often late to meetings, offer to kick off the next meeting for them. If you know your boss is slow to respond, continue to work on a project while you wait to hear back from them. Will you be covering for your boss and enabling bad behavior? Maybe, but you are also giving them much-needed support to succeed and they will appreciate you for it.


Do the best job you can do. Too many times people will start to slack off, or lose interest or stop performing well because they feel entitled to do that with a bad boss. Don’t do it. Keep your mind focused on top performance. Most people do desire a good relationship with their boss, but if you don’t have one, invest the time and energy you have into doing the best job you can do. Don’t let the boss drag you down.

Keep a good attitude. Go home and complain to your spouse or friends all you want, but when in the office or workplace, stay upbeat and engaged. You never know who is watching or listening. Don’t get caught bad-mouthing your boss. It never goes well.

Remember that bullies get their power from those who are afraid. If your boss is a yeller, a criticizer or a judge – stand firm. If you are doing the best job you can do, keep your head held high and don’t give in to the bullying. Ask questions, seek to understand and work to defuse a difficult situation, instead of cowering or responding in anger. It takes practice but the results are well worth it.


Know where your boss stands in the company. If your boss is well regarded and well liked, they probably do a very good job of managing up, too. As a result, you will be considered the “problem” if you complain about him or her. If you decide you want to take action against your boss, weigh your options carefully before you do.

Share your ideas. Once you’re a “big-picture thinker,” as Baldoni puts it, and have established his three Cs necessary to become an influential leader – competency, credibility, and confidence – you can start sharing your ideas. In addition to establishing the exact steps for handling a recurring issue, for example, you can consider why the crisis continues to happen. And what impact does it have on not only the team but the company overall? How does the problem derail your business’s goals?

Lead your Boss: The Subtle Art of Managing Up 

Create standard procedures. Remember how you’re clarifying specific steps and deadlines on a project-by-project basis? Similarly, disclose exactly how you plan to handle common recurring issues and requests. In this situation, however, you can decide on the procedure once and then follow it – without nagging your boss for approval – in each recurring situation. “Take the initiative, and write out your own step-by-step-operating procedures, and run them by your boss,” Tulgan says.

Get specifics. “Could you take care of this?” – the six-word request that’s as vague as it is infuriating. Wait, how, exactly, do you want me to accomplish this? By what time on what day? Do you want me to stop doing that other thing so I can start doing this? “However, you want,” “as soon as possible” and “uh” are not good enough answers from your boss.

“When managers don’t spell out expectations, they think they’re empowering you, but a lot of times its false empowerment,” Tulgan says. “You end up wasting a bunch of time and doing things wrong.”


To save time and second-guessing, Tulgan suggests outlining the exact steps you plan to take to complete the project and then running them by your boss before beginning. Don’t worry about being high maintenance – you already did your homework and are simply asking for her blessing. “You’re not asking the manager to spoon-feed you,” he says. “You’re actually spoon-feeding the manager.”

And as for that ambiguous deadline: “Never accept ‘as soon as possible,'” Tulgan says. Get an exact date, and confirm the shuffling you’ll have to do with your other priorities. Speaking of which …

Establish ground rules. Get a few things straight with your manager, ideally when you’re just beginning the working relationship, says Bruce Tulgan, author of “It’s Okay to Manage Your Boss” and founder of Rainmaker Thinking Inc., a management and workplace research firm. He suggests you clarify the following big-picture items: “how you’re going to stay in dialogue, how you’re going to set priorities on a day-to-day basis and how you’re going to monitor, measure and document your performance.”

Lead up. John Baldoni, the author of “Lead Your Boss: The Subtle Art of Managing Up” and chair of the leadership development practice at N2Growth, a global leadership consultancy, says “managing up” is tactical, while “leading up” is strategic.

That’s all Managing is: Just coming up with the right questions and getting the right answers.

So, you’re set on getting your work done efficiently, setting priorities and establishing a working relationship with your boss. But when you lead up, you also have to think big. “Your perspective is that of a CEO,” Baldoni says. “You’re looking at the holistic point of view for what your department does and how it relates to the rest of your firm.”

To lead up, you must be a student of the company and learn as much about it as you can. What is its vision? What is its mission? What are its strategic goals? Ideally, your manager should fill you in on these important points, but Baldoni says they often skip the important explanation.

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