Paralegal Life: Working For A Difficult Boss

Tips for Improving the Situation When You Work for a Difficult Boss

As paralegals, we often get difficult cases and even more difficult opposing counsel. However, when your boss is more difficult than either of those, it is time to reflect on the situation and what can be done to make the predicament better.

We all know that paralegals work in an industry where stress is par for the course.  We deal with deadlines, court rules, and client demands, adding to daily pressures to perform.  But, sometimes, that stress is ongoing because it comes from working with a difficult boss.  This difficult boss can be an attorney, office manager, or maybe even a paralegal manager. Sometimes it is just a co-worker who is a bit on the bossy side. But, no matter who the person is, we need to find ways to maneuver through the difficulties and work with the person I shall call “Bossy Pants.”

In my career as a paralegal, as well as an educator, I have faced many difficult individuals and supervisors. On more than one occasion, I have found myself paired with attorneys (or other supervisors) who have gone through multiple employees prior to my hiring. And, you guessed it, I did not find out until after I was hired that the individual I was hired to work for was the company Bossy Pants. I have also experienced being hired on to a firm only to have a switch in attorney support. Because of that shakeup, I was assigned to an attorney who had been through many paralegals and legal assistants in a short period of time.

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Instead of exploding and reacting negatively, here are several ways that I have used when working through those difficult situations and coming out on top.

Paralegal Life: 8 Tips for Paralegals When You Work for a Difficult Boss

1. Take a breath.

One of the easiest things to do is take a deep breath. It may not solve the issue at hand, but it will allow your body the ability to relax, even if for a few minutes. Now, I do not mean the audible *huff* which can signal your annoyance and frustration to Bossy Pants and escalate the situation. Let the person walk away, then close your eyes and breathe.  Better yet, find a quiet place if you do not have your own office. Take a few minutes away from the person or incident to breathe, let your body relax, and gather your thoughts.

2. Brush it off.

I have found that what works for me is just brushing it off.  What is the phrase – like water off of duck’s back? Sometimes the best thing you can do is just let things go.  I start each day with fresh eyes and a fresh perspective. Positive self-talk is used often, and I remind myself that I should not take the behaviors personally. By brushing things off, I do not let the situation weigh on me nor cause my usually chipper demeanor to sour.

3. Listen.

I have learned over the years that people just want to be heard and feel that their issues and concerns matter. This may mean you have to refrain from speaking back to the person.  This can be difficult when what you really want to do is explain your side of the story or respond. Just take that deep breath and allow Bossy Pants to vent. There will be a better time for you to respond. If you do have to speak, say something like, “I hear what you are saying. It sounds like . . .”

4. Talk.

Sometimes the best thing you can do when there is tension within the workplace (or any relationship for that matter) is to talk it through.  Schedule a time you can meet privately with the individual with who you are having difficulties. Sometimes the difficulty is just a misunderstanding between the parties. Sometimes Bossy Pants is not aware of how you perceive the way their behaviors or words affect you. Very calmly explain to the person what you are feeling.  Be prepared with an example or two of those behaviors.  Make sure you do not allow your emotions to get the best of you so that you come off confrontational.  It is also a good time to ask for feedback. But, remember when you do – go back to being a patient listener.

5. Approach from a positive presupposition.

Do not jump to conclusions or assume Bossy Pants is always coming at you with negative intentions. Always try your best to be positive and allow your boss to see you will tackle challenging situations with a great attitude.  If you do make an assumption—assume that your boss wants the best of you and the firm even if they do not know how to express it.

6. Build the relationship.

Relationship. Relationship. Relationship. Get to know your boss. I do not mean becoming social media friends and going out to pubs with Bossy Pants. I am talking about taking a genuine interest in your boss’s life.  Look for opportunities to discuss common interests.  Sometimes having a shared interest can help break down walls. Let your boss see you as a real person also. Be honest with your boss and allow them to see they can trust and depend on you. Do not forget to let your boss see you are committed to the position, working together and working as a team with him or her to build a great working relationship in order to meet the goals of the firm. Once you get to know and understand your boss better, you may better understand why he (or she) behaves and reacts the way he does.

7. Ask why.

Stopping and asking yourself why your supervisor is acting in such a difficult manner can help determine how to fix the situation. More often than not, I am not even the cause of Bossy Pants’ anger and frustration. Outside factors can often have an effect on people. I have worked with individuals who had spouses with terminal diseases, individuals going through a divorce, and even individuals who were getting pressure from their superiors. Without realizing it, they were bringing their own fears and frustrations to the office. When I stop to understand why people may be acting the way they are, I am better able to look past that behavior, and sometimes I can even help solve the problem. This also becomes easier to do once I have begun building a solid working relationship.

8. Leave.

Sometimes we can work through all of the suggestions, and no matter what we try, we just cannot make the situation better.  That is when it is time to reevaluate your position and if it is the healthiest place for you.  This decision should never be made in haste. However, we all deserve respect, and if the situation is genuinely unhealthy, it may be time to look for a position elsewhere. If this is the route you choose, do so in a way that you are not burning any bridges. The legal community is a small one. If your boss is truly difficult, other attorneys and other firms already know it. Take the high road and refrain from bad-mouthing your (now) former supervisor.

Hopefully, you never find yourself working in a situation with a Bossy Pants. But, if you do, maybe a few of these tips will help you work through the situation for a much better working environment and relationship.

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Meet the Author – Mary Mendoza

Mary Mendoza is a remote paralegal for the firm of Johnston Clem Gifford PLLC in Dallas, Texas which specializes in representing financial institutions and corporate plaintiff litigation. Mary has worked in the legal field since 1999, with an 11-year break from 2004 – 2015 when she taught for school districts in Texas and Washington.

Recent article from this author: Tips for Working Remotely


  • Claire R. November 5, 2021 at 3:03 pm Reply

    Really great article! I thought all the tips provided for how to deal with a difficult or toxic boss or other co-worker were great advice too! I would also add that as paralegals we are also often taught that the attorneys or supervisors we work for should be allowed to “unload” or “vent” on us as we are there to provide support but there is fine line between being supportive and/or being a “punching bag” so finding that line which allows you to still get the respect you deserve can also be critical.

  • Bob Haensel November 7, 2021 at 12:20 am Reply

    Great insight and positive thoughts and possible answers with non-threatening for either person. Yes, take that deep breath and reflect. Like you state “take time to fully understand and evaluate. Keep writing and publish.

  • Ronda November 8, 2021 at 7:58 pm Reply

    Great article. I have 30 years of experience as a paralegal and legal assistant and as a business owner in the past, but I choose to stay on the legal assistant side. I find it is less stressful and when you reach over 50, you definitely don’t need any additional stress in your life. We “oldies” are winding down toward retirement, not ramping up our careers. LOL.

    I agree to always take the high road and never let them know you are put off by their actions. We really do not know what is behind those actions. Some attorneys and even the co-workers have personal things going on and this is their only way to vent. I see co-workers with less experience feel very threatened by those of us with much more experience in diverse fields, so my advice on that is to always stay humble and never be a “bossy pants” ourselves. You cannot always control how others take your take you, but we can control how we come across. Humbleness always seems to pay off in the long run. Those who have to pretend to be more superior or knowledgeable are true signs of insecurities that we cannot control so don’t try. They will get their sense of security once they have some road mileage on them, just as we had to do. These days we are living in are filled with so many outside stresses we do not want to add to them for others. Be humble and kind. There is always a better way to get your point across if you need to without being bossy or hoity toity.

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