Dealing with a difficult boss at work?

Many people have had the unfortunate experience of dealing with a boss or supervisor they perceived as a bully or as inconsiderate. Dealing with such a problematic relationship is sometimes made all the more difficult by the imbalance in the power or authority that each person in the relationship has. On the one hand, a certain amount of “bossiness” or authority comes with the territory of being a supervisor or employer. On the other hand, and as with many situations in life, being in a position of authority does not entitle anyone to abuse it. In either case, everyone is responsible for their own actions, and deciding whether to avoid or stand up to your boss is your decision.

When should I stand up to my difficult boss?

  • When your anger or stress builds up as a result of not expressing feelings or needs.
  • When you start taking it out on your family, or start acting unprofessionally to get back at your boss
  • When you need or want to maintain a good relationship with your boss (i.e., you value your boss’s role in your career)
  • When you feel there is a threat to your dignity or your rights
  • When making the effort to be assertive takes less effort than suffering the consequences of not asserting yourself.

How to become more assertive

Confronting one’s boss can be a tall order. Let’s remind ourselves that we are not suggesting either open hostility or being too passive like a doormat. Instead, we are talking about something much trickier: assertiveness. Here are some guidelines from a very well-known researcher and psychologist, Marsha Linehan (Linehan, 1993). She developed these assertiveness recommendations as part of a treatment for helping people deal with what she termed “invalidating” environments – environments where we feel criticized, given double or inconsistent messages, or where our values and self-concept feel constantly undermined. Without going into too much detail, there is pretty good scientific support behind these ideas, meaning that relationship functioning and people’s self-esteem appear to be improved when the guidelines are used. Linehan developed the ideas combining Cognitive-Behavioral Therapy principles with acceptance and mindfulness skills.

An easy way to remember Linehan’s assertiveness skills is to remember: the words “DEAR MAN”


Describe the problem situation when necessary. Stick to the observable facts and do not use judgmental statements. “I’ve been working here for 2 years now and haven’t received a raise, even though my performance reviews have always been positive” Or “I consistently meet deadlines and complete tasks required of me. Despite this, you tell my colleagues my work ethic is poor.”


Express your own feelings/opinions about the situation clearly. “I believe that I deserve a raise.” Or “It feels hurtful that my respect of deadlines goes unnoticed and instead I get reprimanded behind my back.” Expressing your feelings helps the other person see that you take responsibility for your own actions and reactions.


Assert your wishes. Ask for what you want. If needed, say “no” (or “that’s not possible”) clearly and repeatedly. Don’t tell your boss what you think they “should” do. “Based on the positive evaluations, I would like a raise. Can you give it to me?” Or, “Given that I consistently meet deadlines I would appreciate not being told my work is always late in front of the team.” Asserting takes responsibility for your stuff and invites the other person to take responsibility for their own stuff.


Reward your boss when he or she responds positively to you. Another possibility is telling them the positive effects for them of listening to your side. “I will probably more productive if I get a salary that reflects my value to the company.” Or “if you could mention to the team when my reports are done well or are on time, team spirit would increase. That would increase everyone’s productivity.”


Keep your focus on your objectives in the situation. Be respectful and stay calm. Maintain your position. If your boss does not appear to listen or to respond then keep asking, saying no or expressing your opinion…over and over and over. Keep a calm and even tone of voice….your strength comes from maintaining your position. In a disaster scenario where you feel humiliated or attacked, ignore your boss if he or she attacks, threatens or tries to change the subject. If you respond to these attacks, you have allowed the other person to take control of the situation (and your feelings).


Use a calm, confident tone of voice. Don’t be condescending or cocky, even if the other person is acting badly. Have confident physical manner: don’t intimidate, back down or slouch. Use appropriate eye contact: don’t avoid or stare menacingly. No stammering, whispering, staring at the floor, or pounding desks. This gets easier with practice.


Be willing to give to get. Offer and ask for alternate solutions. If it helps (and you are willing), change (or even reduce) your request. Or, maintain your side but offer to do something else or solve the problem another way. “What do you think we can do?”  “I am not able to say yes, but you really seem to want me to. What can we do here?” “How can we solve this problem?”

A really difficult boss?

Sometimes, using the above assertiveness skills is easy. However, with a difficult or bullying supervisor, it can be quite challenging. Remember that your boss may have really good (or manipulative) interpersonal skills too, and may keep refusing your legitimate requests, or pestering you to do something you don\’t want to do. In this case, here are some suggestions.

1. Describe the current interaction: “You keep asking me over and over again even though I have already said no.”

2. Express your opinions / feelings of discomfort about the interaction: “I’m not sure that you understand what I am asking” “I’m starting to feel upset about this.”

3. Assert your wishes: “I would prefer to discuss this further at another time.” “Please think this over and get back to me.” “Please stop.”

4. Reinforce: “I am not going to change my mind on this one. Maybe we should agree to disagree and just end this conversation.”


Linehan MM (1993). Skills Training Manual for Treating Borderline Personality Disorder. New York: Guilford Press.

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Photo credit: Tom Holbrook