​By Gabrielle Naglieri

We all know that boss. The one you just can’t get along with. The one that causes an uneasy feeling in the pit of your stomach. The one that no matter how much you deliver, how much you perform, how organized and on top of things you are never seems satisfied with your work. 

For some of us, the first thing we do when faced with a bad boss is look for an exit strategy. And for others staying put and dealing with the stress is the only option. But a challenging boss doesn’t have to be an either/or situation. There is a third way, managing up. 

The phrase “managing up” doesn’t mean taking your issues with your boss to a superior or politicking your boss out of his or her position. Rather, it is a conscious effort on your part to work with the boss you have to create the environment you want. Don’t think of your boss as a boss, but as a client you need to manage and work with to close the deal that will propel your career forward. 

Your relationship with your boss is one of mutual dependence. Without you, your boss cannot do his or her job effectively. The work you do allows your boss to achieve the higher level goals and strategies set by corporate. And as much as your boss needs cooperation, honesty and diligence from you, you need your boss to provide you with information and direction so you can get your job done. This recognition is of vital importance especially when the relationship with your boss has impacts across the organization.

Once mutual dependence is recognized you can start the process of managing up. This begins with understanding. Examine yourself and your boss closely. What are each of your strengths and weaknesses? What work styles do you each favour? How are both your needs similar and different? What motivations drive each of you? 

Understanding yourself and your boss will allow you to formulate new channels of communication. If your boss prefers informal drop-ins to long memos, mimic that behaviour. What if you prefer the long memos? Compromise. After a drop-in, pull together a summary email of the meeting and send to your boss. You’ll both have a record of what was discussed and you will meet your need for documentation. 

Adapting to some of your boss’s preferences isn’t a sign of surrender; it is a form of leadership. Leading from behind by silently managing up will strengthen your relationship with your boss and allow you to develop the fundamentals of negotiation.

One of the more contested strategies for managing up is ensuring the success of your boss by working around his or her weaknesses. The immediate reaction is “No way am I going to cover for my boss’s incompetence.” But in this situation we are not talking about incompetence. Incompetence speaks for itself and can rarely be covered up. What we’re discussing here is fallible human behaviour: disorganization, lateness, slow email responses, etc. 

If you know your boss is disorganized, offer to help in ways that will allow for the smoother facilitation of tasks. For example, maybe your boss is late to meetings and the meetings he or she runs tend to wander with little resolution. Volunteer to create meeting agendas and designate yourself as meeting manager. Keep everyone on topic and guide the conversation. 

For larger projects where a disorganized boss may struggle with the details, organize your workflows so your boss can easily follow each stage. Create a pipeline if your boss is visual or set-up quick catch-up meetings with your boss once a week for project re-caps. 

The more you work with your boss’s weaknesses, the more success you and your boss will achieve. If your situation with your boss is dire and you do need to leave, the bigger your successes the easier it becomes to find a new position. By creating success you build a personal brand others will notice.

Sometimes the issues with your boss cannot be fixed by reactive behaviour. These situations require a measured vocal response. Set-up a meeting with your boss to explain your concerns. While this may seem like a daunting task, engaging in an open conversation with your boss may make him or her aware of issues never considered before. Keeping quiet can seem like the safest option, but if your boss does not know how his or her behaviour affects you, there is little that can be done. 

Come to the meeting prepared with examples that demonstrate your position and be ready to respond to counter examples your boss may provide. In addition, have a few solutions or compromises you can discuss with your boss to help foster a better working relationship. If you come to the meeting with just a list of complaints, your boss will be less open to your arguments. Try to be constructive but also honest about your concerns.

Unfortunately for some, managing up will do little to pacify the challenging boss. If it is clear the environment you are in is toxic and it is affecting your health, finding a new role is a perfectly reasonable option. But before you jump ship, make sure you know what you’re jumping into. 

Do your research. Learn as much as you can about the culture, leadership, and management style of any potential employer. Speak with current and past employees by reaching out through LinkedIn. If the company you are considering is a major player, chances are the press have written about them. Read as many articles from as many media sources as possible. During the interview ask questions about the work environment, cultural ethos, and expectations. And as you walk through the offices take note of the morale and how people are interacting with each other. Small details can provide big insights.

Remember to always keep your head in the game. No matter your decision, to manage up or get out, all success is built on experience and without challenge nothing is gained. Finding the right balance is key.​