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A Checklist for Managing Your Boss

There will always be those who view the concept of managing upward as flattery and manipulation. Others hold the common belief that if bosses are wise, they don’t need to be managed and such efforts will be viewed solely as attempts to play office politics.

But managing upward is not about ambition, promotions or raises. It’s about the job and how to be effective at getting things done. How do you acquire the resources, information and advice you need, as well as the permission to keep moving ahead?

The answers always point to whoever has the power: the boss. Failure to make this relationship one of mutual respect and understanding limits your chances of succeeding.

Here’s a review of key points from a classic Harvard Business Review article originally published in 1990, and it remains pertinent today. “Managing Your Boss” was written by Professors Emeriti John J. Gabarro, PhD, and John P. Kotter, PhD.

Mutual Dependence

Two people can be temperamentally incapable of working together. Personality conflicts occur all the time. But when they happen between bosses and managers, differing personalities are only a small part of the true problem.

People usually have unrealistic assumptions and expectations about the nature of boss-subordinate relationships. They fail to recognize that it’s one of mutual dependency between two fallible human beings, so they avoid managing the relationship altogether or do so ineffectively.

Some managers behave as though their bosses are not dependent on them. They don’t see how much the boss needs their help to do his job efficiently; how their actions can severely hurt him; and how they truly need to be cooperative, dependable and honest.

Other managers see themselves as completely independent of their bosses. They gloss over how much information they need from the boss to perform their jobs well.

A boss can play a critical role in linking managers to the rest of the organization, making sure priorities are consistent with organizational needs and securing necessary resources. But some managers see themselves as self-sufficient.

Other managers assume the boss is a clairvoyant who will magically know which information or help is needed and magically provide it. This is dangerously unrealistic.

Managers must recognize that mutual dependence between two fallible humans requires two components:

  • Having a good understanding of the other person and yourself, especially regarding strengths, weaknesses, work styles and needs
  • Using this information to develop and manage a healthy working relationship—one that is compatible with both individuals’ work styles and assets, is characterized by mutual expectations and meets the other person’s most critical needs

Understanding Your Boss

Managing your boss requires you to understand him and his workplace context, as well as your own situation. Some managers aren’t thorough enough in this regard.

At a minimum, you need to appreciate your boss’s goals, pressures, strengths and weaknesses. Consider the following:

  • What are your boss’s organizational and personal objectives?
  • What are his/her pressures, especially from his/her boss?
  • What are your boss’s strengths and advantages?
  • What are his/her weaknesses and blind spots?
  • How does your boss like to get information: memos, emails, meetings, text or calls?
  • How does your boss handle conflict?

Without this information, a manager is flying blind and problems are inevitable.

Understanding Yourself

Developing a functional working relationship requires you to know your personal needs, strengths, weaknesses, and style or preferences.

You’re not going to change your (or your boss’s) basic personality, but you can learn which traits, habits or behaviors impede or facilitate working together. With awareness, you can take actions that make the relationship more valuable.

There are plenty of personality and work-style assessments available. By the time managers reach executive levels, they have more than likely participated in leadership development courses that include tests and surveys. Problems occur when the information gained in these training sessions is not used well. A coach or mentor can help leaders incorporate knowledge and increase performance.

A manager is typically more dependent on the boss than vice versa. This dependence inevitably leads to a degree of frustration and anger when one’s actions or options are constrained by the boss’s decisions. The way in which a manager handles these frustrations largely depends on predispositions toward those who hold authority positions.

The Counterdependent Manager

Some people’s instinctive reaction is to resent the boss’s authority and rebel against his or her decisions. A manager may even escalate a conflict to inappropriate levels.

Psychologists call this pattern of reaction to authority “counterdependent” behavior. The counterdependent manager sees the boss as the institutional enemy — a hindrance to progress and an obstacle to be circumvented or, at best, tolerated.

Reactions to being constrained are strong and sometimes impulsive. These managers strongly defend their sense of independence and self-sufficiency, making it difficult to accept orders, especially from a boss who tends to be directive or authoritarian.

Paradoxically, a manager with this predisposition is often a great leader to direct reports. These managers will go out of their way to support and go to bat for their departmental staff.

The Compliant Manager

At the other extreme are managers who ignore their anger and behave in a compliant fashion when the boss makes what they know to be a poor decision. These managers will agree and conform, even when a disagreement may be welcomed. Often, a boss wants push-back and would easily change a decision if given more information.

Such compliance is as much of an overreaction to authority as that of the counterdependent manager. Instead of seeing the boss as the enemy, these managers deny their anger. They prefer to see the boss as “father knows best.” Their expectations are unrealistic: They assume the boss is looking out for his/her career and limiting training opportunities in an effort to be irreplaceable, thereby protecting the “fiefdom” from overly ambitious peers.

The Passive-Aggressive Manager

A third style involves the passive-aggressive manager, who may appear to be compliant and cooperative, but holds counterdependent beliefs of anger and rebelliousness. This manager can be even more dangerous and disruptive because the reaction is covert. Instead of arguing and expressing resentment, he or she will sabotage in subtle ways.

Reactions to Authority

Counterdependence and overdependence lead managers to hold naive views of a boss’s true role. Both views ignore that most bosses, like everyone else, are imperfect and fallible.

Bosses don’t have unlimited time, encyclopedic knowledge or extrasensory perception, nor are they evil enemies. All bosses have their own pressures and concerns that are sometimes at odds with a manager’s wishes — and often for good reason.

Altering predispositions toward authority, especially at the extremes, is difficult without psychotherapy. But in most office situations, such behaviors can be modified through executive coaching interventions.

Obviously, such predispositions are rooted in one’s personality and family history. Even without extensive psychotherapy, however, awareness of these extremes — and the range between them — can be very useful. You need to understand where your own predispositions fall and the implications they have when you interact with your boss.

If you believe, on the one hand, that you have some tendencies toward counterdependence, you can understand and even predict what your reactions and overreactions are likely to be.

If, on the other hand, you believe you have some tendencies toward overdependence, you may question the extent to which your overcompliance or inability to confront real differences may be rendering both you and your boss less effective.

Developing and Managing the Relationship

With a clear grasp of your boss and yourself, you can usually establish a way of working together that fits both of you. Ideally, it will be characterized by unambiguous mutual expectations, which allow both of you to be more productive and beneficial to the organization.

Ultimately, the burden falls upon the manager to learn the boss’s expectations. Working for someone who tends to be vague when expressing expectations can be difficult, but savvy managers always find a way to overcome barriers.

Developing a workable set of mutual expectations also requires you to communicate your own expectations to your boss.

Effective managers recognize that they probably underestimate what their bosses need to know. Managing the flow of information upward is particularly difficult if the boss doesn’t like to hear about problems. Bosses often give off signals they want to hear only good news, but managers must find ways to supply critical information.

Many managers aren’t intentionally dishonest with their bosses, but it’s easy to shade the truth or to minimize issues. Dependability and honesty are crucial to managing the relationship.

Every request a manager makes of the boss uses up the resources of time and energy. Part of managing the relationship wisely is to avoid wasting time on trivial issues.

Here’s a summary of the key points:

Checklist for Managing Your Boss
Make sure you understand your boss and his/her context:
  • Goals and objectives
  • Pressures
  • Strengths, weaknesses, blind spots
  • Preferred work style

Assess yourself and your needs, including:

  • Strengths and weaknesses
  • Personal style
  • Predisposition toward dependence on authority figures
Develop and maintain a relationship that:
  • Fits both your needs and styles
  • Is characterized by mutual expectations
  • Keeps your boss informed
  • Is based on dependability and honesty
  • Selectively uses your boss’s time and resources

No doubt, some managers will react to this article with disdain, arguing their jobs are complicated enough and they shouldn’t have to invest time and energy in managing upward. They fail to realize how managing the boss can actually simplify their jobs by eliminating the potential for severe problems.

Effective managers recognize this part of their job is legitimate and that they’re ultimately responsible for what they achieve in an organization. As such, they must establish and manage relationships with everyone on whom they depend — most importantly, the boss.


Working Resources is a Strategic Talent Management and Executive Coaching Firm Helping Innovative Companies and Law Firms Assess, Select, Coach, Engage and Retain Emotionally Intelligent Leaders; Executive Coaching; Leadership Development; Performance-Based Interviewing; Competency Modeling; Succession Management; Career Coaching and Leadership & Team Building Retreats

Dr. Maynard Brusman
Consulting Psychologist and Executive Coach
Trusted Advisor to Senior Leadership Teams
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