9 Ways To Manage Your Difficult Boss

“Life at work is just impossible. My boss is the most difficult manager I’ve ever met!

This clown thinks that his only important function is to criticise”.

In all likelihood, most of us have had similar thoughts. Some managers do project “compulsive, counter-productive, or just plain odd” behaviours. And yet, since most organisations have a top-down flow of authority and evaluation, it may seem very unnatural to think about managing your boss. But the alternative is unpalatable – a good manager is not doing him or herself, the boss or the company any good by continuing meekly to endure a problem boss-subordinate relationship.




Difficult implies hard to manage, hard to satisfy or hard to comprehend. However, before addressing the individual, you must identify whether the boss is merely acting out the philosophy of the company. If it is the company that is difficult, start looking elsewhere! Assuming it is a good company and your boss is unusual, you must identify what, specifically, is difficult about the boss. As applied to the work environment, a difficult boss is incongruent, inconsistent or unpredictable on at least one of three levels.

Difficult individual. The problem may be the boss as a person. The boss may march to a different drummer, and his or her personal idiosyncrasies drive subordinates crazy. Directives, responses and moods may all appear unpredictable and unpatterned. Your boss is known as a “real character” to some; to others, your boss’s personality inconsistencies would rate the label schizophrenic.

Difficult relative to you. The problem may be the relationship between you and your boss. The signals and directives you receive are varying and often conflicting. One day you are told to do one thing, the next day you are informed that the task was never requested. Similarly, the boss may be your pal and mentor in the morning, but your inquisitor and tormentor in the afternoon if things go amiss. In short, interpersonal conflict abounds because of poor communications. As the subordinate, you become increasingly frustrated because of the resulting role ambiguity or role conflict.

Difficult relative to group or organisational culture. Finally, the problem may arise because the boss does not behave in the manner expected in your organisation. Work groups and organisations amass symbols, rituals, and values over time; not unlike tribes, organisational members operate in cultures with distinct leadership and communication styles, judgements of performance, rewards and punishments, and even ways of approaching decision making. For example, the organisational culture may value its bureaucratic structure, autocratic leadership styles, and status perks like separate executive offices with elaborate furnishings. Your boss is difficult in this setting if he or she favours open communications, participative decision making, and a team spirit that discourages badges of status.




Your boss is difficult for many of the same reasons that others in the organisation, sometimes even including you, are “difficult”. Difficult people, whether bosses or not, leave those around them frustrated, drained, and hostile. Difficult bosses are often perceived as being negative, argumentative, frivolous, incompetent, non-committed, over-zealous, belligerent or fickle. Whatever the issue, they can drain energy and enthusiasm from everyone they encounter.

But labelling your boss as difficult because of personality conflicts is usually a great deception. While we each have different personalities, they do not necessarily clash. Most personality conflicts are, more

accurately, conflicts pertaining to goals, roles or values. Lack of co-operation, misunderstandings and bad feelings usually result when individuals pursue different targets. Personalities are usually only a small part of the conflict. The real conflict is different expectations about what we are trying to achieve, how we are trying to achieve it, and each person’s part in the activity. Thus, your boss may be difficult, not because he/she is your natural adversary but because your targets, methods and work distribution conflict. However, this does not mean you should excuse, ignore or even change your boss’s behaviour. It does mean you can take positive steps towards managing them.




You should ask yourself – can it be corrected? Is it worth the effort? For political reasons? Personal gain? Improved organisation effectiveness? The answer is “yes” on all counts. Whether intentional or not, your actions can affect your superiors, so why not be systematic in your impact!

A recent study implied that effective managers take the time and effort to manage their bosses and subordinates. After all, the boss is but another resource at your disposal. Just as some managers have more extensive financial resources at their disposal, some subordinates’ efforts at managing their bosses reap greater benefits for them and their organisation. A supportive and progressive boss is an abundant resource and a luxury most employees envy, but the supportive and progressive boss is at least partly the product of a subordinate’s efforts. The organisation and its participants also benefit when the subordinate and boss do not regard each other as natural adversaries.




One psychologist suggests that you “stand straight up” and listen when dealing with difficult people; however, when dealing with the difficult boss the problem becomes more sensitive. Although managing the difficult boss demands more skill than managing other employees, the task can be aided by the following suggestions:

1. Know yourself. Do you really know who you are, as an organisation actor? Within the organisational context, what is your role and how does it contribute to the organisation’s goal? With whom/ what are you interacting and how does it shape your view of the organisation? Does your job experience or training confound your view of your task? Do you think in terms of short or long-term goals? What personal values and goals do you bring with you to the workplace? Answers to these questions help you sketch your identity.

2. Know your boss. Do you really know your boss and what he/she does within the organisation? What is your boss’s role and how does it contribute to the organisation’s goals? What shapes his/her view of the organisation? With whom/what is your boss interacting and how does it shape his/her view of the organisation? Does job experience or training confound your boss’s view of his/her task? Does your boss think in terms or short or long-term goals? What personal values and goals does your boss bring into the workplace? Answers to these questions help you sketch your boss’s identity.

Awareness of roles and power relationships within your organisation provides a basis for management of your boss. However, managing your boss involves management of communications and power relationships.


3. Improve communication


The best planned message is lost if the source of the message is distrusted.

4. Build trust. Trust increases if you establish a history of honesty and dependability. Keeping your word and doing your job well may necessitate getting your act together, if you have not in the past. Introspection may reveal that your own work habits, and not the boss, have been the major contributors to a poor work situation. Moreover, you and your boss do not have to like each other to trust each other. An atmosphere of mutual respect is all that is needed to create a relationship characterised by loyalty, support, and integrity.

5. Adjust your communication style to complement your boss.

If your boss is a talker, become a better listener. If your boss is comfortable with “garden variety” explanations of technical operations, reduce detailed technical jargon in your messages to him/her. In short, adjusting your style can reduce the distance between you and your boss; however, “adjusting” your style does not equate with “changing” your style. A radical change encourages scepticism, not trust.

6. Open up lines of communications. Opening up lines of communications is important because it may increase the information your boss needs to perform his/her job and it may increase your boss’s awareness of you and your job performance. However, communications are not limited only to good news. You should never surprise your boss by allowing him or her to hear the bad news from others. When communicating with your boss, it is also essential to tell the story in his terms, within his framework. and in a way that links it to his personal and organisational goals. Demonstrate the same sensitivity with your boss that you would like to see shown to you by your boss.

7. Give Feedback. Step 7 relates to a common worker complaint; ‘my boss never gives me positive feedback’. Unfortunately, many bosses may lament that their subordinates are equally at fault. Rewarding and praising desired behaviour is as effective with superiors as it is with subordinates. Reinforce your boss by praising the behaviours you desire, and you may modify his/her behaviour. This doesn’t mean compromising your integrity; if you look hard enough, there is always something worthy of a pat on the back.

Another way of promoting positive feedback to your boss is to “share the credit” when good things happen. Cultivate the bond between you and your boss. As a rule of thumb, give credit where credit is due, but don’t forget that your boss is a team-mate and a helper. If your department’s performance hits a record high, all in the department, including your subordinates and your boss, deserve to bask in the glory.

However, communications is just one part of the puzzle of managing the difficult boss. Identifying and modifying power relationships are equally important.


8. Identify and modify existing power relationships


Organisations can be thought of as political arenas with organisational actors serving as power brokers with both individual and organisational objectives. Managing your difficult boss involves changing how you think as well as how you take action to change power relationships.

Regardless of who is or who is not dispensable to the organisation, make your boss think he/she cannot operate without you. Even though your boss may feel vulnerable and easily substitution, you can still let him/her know you are a team player and that you are a valuable asset to him/her.

In this case, be all that you can be. If you are a good performer – and your boss knows it – it works to mutual benefit. Enthusiasm and dependability are essential, but you must be your own salesperson. By enhancing your boss’s awareness of your performance, you are increasing your chances of being viewed as indispensable in his/her eyes.


9. When all else fails!


What can you do if the suggested strategies don’t bring fruition? Some bosses are hard cases and may not respond to subtle and caring actions. It may become necessary to adopt some more serious, yet sometimes necessary strategies.

(a) If you work for a large organisation, begin to look laterally in the company for a respected mentor and possible future openings. Build bridges and credibility with the desired boss. Become visible and exhibit your expertise when the opportunities arise.

(b) Start to document your activities and personal encounters carefully. In extreme situations, it may become necessary to prove your merit and your boss’s incompetence. A systematic, careful documentation of what you and your boss have been doing may be vital to proving your position.

(c) In some situations, going over your boss’s head may be in the best interests of you, the boss and the company. While going above is a serious move and should not be taken lightly, a competent, progressive company has top executives who are fairly accessible and honestly interested in problems that seriously hamper the accomplishment of organisational goals.

(d) If the above strategies do not prove effective and the situation is unbearable, you can always take the final, positive step and accept a position in another company. The opportunity costs can sometimes become to great to remain where you are. If you feel good about having tried the available options, it may be time to find a better environment. Life is to short to dread going to work every morning.




In summary, the difficult boss frustrates, antagonises, and, in general, tests an employee’s psychological and physical well-being. No-one should have to tolerate this forever! They should strive to manage the situation. Define what makes your boss difficult. Understand the roles within your company. Strive to improve communications and modify power relationships.

Finally, it may come down to the risky decision of going over the boss’s head or leaving. If you think managing the difficult boss is hard, consider living with the alternative!

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