A Blueprint for Working with a Difficult Boss

Steven C. Owens
7 min readMay 11, 2023


There is a right way and a wrong way of navigating your career through a difficult boss. In my 30 years of experience I can tell you I made mistakes.

Working with a tough Boss can be challenging and rewarding.

We all have horror stories of bad bosses and a few good ones. However, whether they are good or bad has nothing to do with the way you deal with them. What?

“Well it’s not my fault that they are terrible communicators and have no personality”

That is you first mistake. Making excuses. You are correct, “No” it is not your fault but you need to still be an effective communicator who is prepared and knowledgeable in your job. A bad boss will seek the weakness in your lack of knowledge and exploit that weakness to demoralize you. Do not let this happen! There are ways to at least keep you on an even playing field if not give you the advantage.


There is no better defense then a great offense. One of those cliché's that is still true after many years of perhaps being overused. A difficult boss will always look for ways to trick you or ask that one question that you didn’t think of. Therefore, you need to be prepared and know your product like knowing your lines from a script on shoot-day.

Knowledge is learning the material thoroughly. Similar to an actor understanding their lines from a script rather than strict memorization without feeling.

Acting is all about the depth of your knowledge of the content and not the idea of reading your lines from a cue card. A difficult boss will exploit your lack of depth quickly to dominate a conversation especially in a meeting and in front of others. Suddenly anything he/she does not understand about a particular topic becomes your fault. You didn’t explain it well or you are not knowledgeable enough to explain your topic.


Super bowl winning New York Giants coach Tom Coughlin, had a saying about attending his meetings;

“If you are 5 minutes early you are 5 minutes late.”

Tom Coughlin

This has always been one of my steadfast rules. I expect everyone to be on-time if not early to a meeting. This is how you show you are prepared and ready to be productive. When you are facing a Boss who is looking to grab the upper hand, timing is everything. Arriving early will catch him/her off guard and can give you the slight edge to work your offense.


A director in a movie will always rely on authentic props to highlight their movie sets. You need to have a folder with all your information printed rather than just a laptop. Huh? I know in today’s electronic age most show up to meeting with their laptops and nothing else. There is nothing more effective then to show up with a folder and all your e-mails and charts pertinent to your meeting. Including copies for your Boss with highlighted information so he/she does not need to search. This allows you to steer the meeting in the direction you want it to go.

TEAMS Meetings and remote work will eliminate the paper handouts so be ready to share your screen with the participants with the same charts and literature. Sending copies in an e-mail ahead of the meeting is also effective. Send no more than 2 hours before the meeting. Enough time for the participants to review the material but a short amount of time where they do not have time to write endless lists of questions.


Once you are in the meeting room and you have handed-out the copies of your material begin speaking. You can start with pleasantries thanking the attendees for meeting but don’t linger. Direct your Boss and attendees to the material you handed-out and go to the highlighted portions. You have now taken off the runway and are gaining altitude.


As you start cruising at 20,000 feet your Boss will now begin his/her questioning and point to areas he/she may not understand but will always frame it as “tell me why this number is higher than last year’? This is where your depth of knowledge is being tested. Never say “I don’t know?”, but do not make up an answer. It is alright to pause and look at your information even your laptop and give your best educated answer. When you do not know or cannot provide a partial answer your answer should be:

“You are correct. Last year we came in lower a that number so I will research the descrepensie and send a response with supporting information after our meeting.”

Move on quickly but don’t run over your own sentences and go to the next highlighted item. Your Boss may feel that they have gained some advantage with their question and look to continue to stay on the negative.


Your posture and body language are important. Even on TEAMS calls. Your tone and positive personality keeps you at a high altitude with a Boss that wants to drag you down. High energy but not annoying like you are overloaded on caffeine.


Know the landscape of your job and see 3 steps ahead. A difficult Boss will look to blame you for any and all mistakes or unexpected issues that could make them look bad. Always memorialize your anticipated findings in an e-mail or electronic memo to keep a trail. Do not look for positive acknowledgement and look at no response as a positive. If they are not reacting it means they cannot be on the attack or find fault. Keep them informed with e-mails but do not over due it. They will find this annoying and look for another reason to come at you.


No you cannot. So often we do this in personal relationships where we feel like we can change a person into who we want them to be. Do not try to change a terrible Boss into someone you love. Chances are they were like this before you reported to them and will be for the rest of their career. If they want to change they will on their own. This is business and not personal.

Keep the urge to change your difficult boss to strictly business.


Difficult Bosses should know their limitations of tough business versus harassment. Understand your rights and if they are pushing past the limit of their authority allowed from your employer then you need to contact your Human Resources Department. Employers will not allow any kind of bullying or inappropriate behavior that goes beyond the border of respectability.


We discussed the actions necessary with a difficult Boss but have not forgotten the great Supervisor’s that we are lucky enough to work with. The same game plan of being prepared and early to meetings apply. A good Boss will love your enthusiasm and knowledge and use these points to promote you. Where as a difficult Boss has little history of pushing their employees to their next level. Great leaders make it their mission.


When you report to a less than desirable Boss your time with them will feel like an eternity. Everything has its Season and as long as you are striving to do your best this bad season will pass either way. This may result in a job change or a transfer to another Department but a change is always a welcomed challenge and rarely did I regret having to push through a difficult time.

“If you do the right thing long enough you will eventually come out on top”

This is a edict I have lived by and created myself. Having 30 years experience in the corporate world has taught me many things. It is easy to take the quick root or try and stab someone in the back. The difficulty is waiting for the tide to change in your favor but this will only happen if you protect your integrity and continue to work hard. Always be aware of your surroundings even when walking in the hallway of your place of business. The person you pass today can be your next boss tomorrow. Smile and say “hello”.




Steven C. Owens

Writer of life lessons sprinkled with meaningful sports and history editorials.