How to Build a Healthy Relationship with a Difficult Boss

Ask Yourself These Three Questions to Figure it Out

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Credit: Shutterstock

is a key priority for millennials when deciding whether or not they want to stay with a company.

Yet not all organizations can meet this need. Rigid corporate structures, an older generation of managers far from retirement, and a bureaucratic mentality mean that climbing up in an organization can become a tedious slog for many young workers.

What makes things worse is that Millennials are finding it hard to navigate having a boss, especially one that they think is difficult.

Managing a difficult boss, for example, could do wonders for your career, especially if sticking it out in your current role could boost your career prospects down the line, add to your professional network, or even build soft skills that can be used down the line.

If we want to truly succeed in our career we need to learn how to manage these bosses better. So to handle that difficult boss, and to create a healthy professional relationship, ask yourself these three questions.

Do you know your boss — the human?

There are :

There’s the one that tries to be your buddy.

The one that is a bit self-centered and thinks he can do no wrong.

Or the one that forgets stuff, placing the blame on you, and constantly wanting you to remind him when to eat lunch.

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Even if they think they’re the world’s best boss, every boss is a human and figuring out what makes them tick will ultimately be to your benefit.

Does she expect things to be done a certain way?

Does she invite feedback?

Are you expected to “run with things”?

To be truly successful you’ll have to learn how to get on her good side while avoiding the bad. Remember, your boss isn’t perfect and they’ll have their own idiosyncrasies.

Are you building trust?

Effective workplace relationships are .

In the 7 Habits of Highly Successful People, Stephen Covey says this about trust:

“Trust is the glue of life. It’s the most essential ingredient in effective communication. It’s the foundational principle that holds all relationships.”


“The ability to establish, grow, extend, and restore trust is the key professional and personal competency of our time.”

Trust is essential, and building that in a new or existing role means honoring the rule and duties that are expected of you.

That means:

  • Staying longer if you have to.
  • Going beyond the call of duty if you can.
  • And especially taking responsibility for your mistakes.

Doing this will show your boss you mean business, which personally is better than just mere lip service.

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In my first job out of undergrad, I remember keeping a mistake log that was publicly visible in my cubicle. My boss saw it one day and asked me what that list was. I simply said it was a reminder of all the mistakes I had done so that I would make sure not to do them again. He was shocked that I would so publicly show my mistakes but he respected why I did it; taking responsibility for my mistakes, he said, was a “marker of maturity”.

Bosses want to you know you’re mature, and can take on more responsibility.

Ultimately, this lead me to getting more advanced projects and duties that I later used as the basis for an increase in compensation, which I got. But, had I not cultivated that trust, I never would have grown in the position and been able to ask for a bump in compensation.

Do you have good professional boundaries?

Remember when you originally applied for that job and read its job description?

The duties listed there are a starting guide, but as your role evolves you take on more responsibility that goes beyond what the position initially entailed.

Depending on your industry though, you boss might ask you to do something that goes beyond your job description. It’s just to you to figure out whether or not that is something you’re comfortable doing.

For example: say your boss texts you off-hours to respond to a work email that he think is an “emergency.” You don’t think it is, and you would rather she not interrupt your Netflix and chill time.

So what are you to do?

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You learn how to have an adult conversation about it and what appropriate work-life boundaries are.

It’s that sweet spot in the middle, where both your space and what is demanded of you in your position is respected, that creates a fruitful relationship between you and your boss. If you cannot vocalize your needs, then resentment will build, you’ll intentionally sabotage, and eventually leave, without anything positive to say about your employment.

Ultimately, everything at work is a negotiation, including what is demanded of you beyond your initial job description. If a difficult boss is asking too much from you, learn to have that difficult conversation to find a solution that works for both of you.

Bottom Line: building a professional relationship with your boss should be that painful of an experience. Get to know him as the human that she is, especially her quirks and what makes her happy, build that trust, and, should you have an issue, learn how to have a health exchange that is respectful and maintains proper boundaries. And if your boss is truly that big of a nightmare to deal with, you probably should find a new job.

Want to add something to the advice I gave? I’d love to hear your take on it. Comment below.

Bryant is a certified mediator and coach based in Los Angeles, CA. His company, , helps startup entrepreneurs, freelancers, and Millennials navigate the ups and downs of working life through self-inquiry, practical strategies, and expert help. He has a Master of Science in Negotiation and Conflict Resolution from Columbia University, is an avid traveler, and is a first-generation Mexican-American fluent in Spanish.

I help founders and business leaders negotiate agreements and resolve disputes. Columbia University Educated 🎓 . More at

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