3 Steps to Thrive While Working for an Unreasonable Boss


Maybe you’ve fantasized about quitting, but you’re not ready to give up your steady paycheck, 401k, or insurance?


There is a quit alternative.  Transform your current job into a job you love by engaging with it’s full potential, marshaling the resources around you, and seizing the opportunities that are there for the taking. 


You can even do this with one of the most difficult challenges in any workplace: an unreasonable boss, as I explain in The Quit Alternative:  The Blueprint for Creating the Job You Love…Without Quitting. 

Dealing With an Unreasonable Boss Without Getting Into Trouble

Pursuing what you want when working for an unreasonable boss is a challenge. No matter how hard you work, the unreasonable boss is never happy and always demanding more—a slippery slope toward burnout for you.


No matter how much past success you’ve had, you may begin to question your ability and find your confidence shaken. But if you can learn to thrive while working for an unreasonable boss, you’ll be able to thrive anywhere

Finding a Way to Work with an Unreasonable Boss

When I moved to Manhattan, I started off on the wrong foot with the boss, and things got worse fast. I put in long hours without results coming very quickly.


My boss began to come down on me about the lack of results, and directly questioned whether I was cut out for the job. He threatened to demote me and even lobbed insults about “the way they do business back in Alabama.”


First, I pushed back, but then gradually I resorted to survival mode, going through the motions and staying out of his way. I approached HR but nothing seemed to happen. As the berating escalated, I called every recruiter I knew to find an escape.


I had to make a change, so while he was on a trip to Europe, I quietly lined up another job in the same company at an office across town. The evening before he returned from Europe, I packed up my office under cover of darkness. My office was vacant when he arrived the next day. I sealed the deal by sending him a “Dear John” email concerning my new position.  (By the way, better not to deal with your boss with a “Dear John” email.)


He was furious, and our future interactions did not go well. My new boss offered me protection, but it was still incredibly awkward when our paths crossed.


I pushed myself to the limit working for that unreasonable boss, but learned invaluable lessons that enabled me to thrive under the next unreasonable boss I encountered a few years later. And that second experience shaped my career.


Through experiences like these, you can become more self-reliant and creative in negotiating for what you want. Even though it’s painful, you come out the other side wiser, more confident, and much smarter about what not to do.


3 Steps to Thrive While Working For an Unreasonable Boss

I learned these strategies the hard way.


Step #1: Clarify their interests first. In the heat of the moment, it is natural to start the conversation with what you want—but not effective. You’ll come off sounding whiny and needy, and the response you get will often translate as “suck it up” or “you go figure it out.”


Expose their interests first, and address them.


Looking back, I never understood what motivated that boss or even the pressure he was under. Most employees assume that the boss will tell you, but that’s a dangerous assumption because without that knowledge, you’re flying blind.


Clarify your boss’s concerns by finding out:


  • Why does your boss work in the first place?
  • What are his or her annual goals? How are these measured?
  • Are you and the group performing to those goals?
  • What pressures is the boss under?
  • What is his relationship with his boss?

It may seem forward or out-of-the box to ask these questions directly, but answers will help you a lot. If you choose not to ask the boss directly, ask coworkers or the boss’s peers.


This knowledge will help you craft conversations in a way that considers the boss’s interests, along with yours.


Step #2: Learn to speak their language. The cold truth about conversations with the boss is that it doesn’t matter what you say; it only matters what he or she hears.


With that in mind, speak in a way that resonates. Notice when she speaks if she refers to dollars, headcount, savings, feelings, relationships, or hypothetical situations, and then consider incorporating similar examples when you speak with her.


Even if this strategy differs from your usual approach, it will ensure your words are heard. The boss will be more likely to listen and to understand. Looking back at my situation, I was talking processes and prospecting, and this only irritated the boss further. He wanted to talk about closing deals. Discussing that first might have enlisted his support.


Step #3: Be clear about what you want. Does the boss know what you want in your work day? Many employees never make this clear and leave the outcome up to chance.


The happiest employees articulate in detail what kind of job and work day would be ideal, and they share it with the boss. Of course, that doesn’t mean everything falls into place immediately, but over time, this information becomes part of the decision making process about organizational changes and work load.


The Courage to Get Clear and Make the Ask

We’d spent weeks preparing for my client Janet’s annual review. Although she’d been through 11 already, this one was different.


She’d had a banner year at work and decided that what she most wanted wasn’t a raise or promotion, but a more flexible schedule. She wanted to work from home two days per week.


She wanted to ask to work part-time for a while so she could be at home more with her family. Originally, she had come to talk with me about planning her exit strategy, but now she wanted to figure out a way to stay. In our discussions, she realized how much experience and value she brought to the organization. She’d generated a lot of trust, strong relationships, and proof that she could get the job done. She figured she would work from home two days a week, become even more productive, and be at home when her children came home from school. She could use the occasional break to tidy up the house and actually cook dinner for her family.


She clarified her boss’s interests first. She spent the time in advance anticipating what concerns her boss might have and what benefits the new situation might confer on her boss and coworkers. She knew her boss was under a lot of pressure to deliver big results the following year, and several of her projects were crucial to that goal, and so her project timelines couldn’t slip.


In her annual review, she made her request to work from home and began by speaking her boss’s language with her plans to ensure her projects would succeed on time. She explained how much more she could concentrate at home and how this time would contribute to the overall process. She also addressed how communication would occur on those days.


Then she was clear about what she wanted. Janet’s boss agreed to one day at home per week for the first quarter and, if everything was running smoothly at that point, he’d consider adding a second day.


Although Janet had good annual reviews previously, she was most proud of this one because she’d had the courage to ask for what she wanted while addressing the concerns of her boss and company—truly a win-win-win strategy.


Now Try This Quick Exercise

Here’s a quick exercise that will help you clarify what you want, so you can better articulate it to your boss.  As follow-up, I recommend taking a casual approach to the conversation to see how open your boss’ might be to further discussion.


The ideal workday exercise — With a sheet of paper and a timer, brainstorm for 10 minutes what your ideal workday would look like. What work activities would fill your day? What time would you arrive and leave? With whom would you work? Take one or two nuggets from the brainstorm, and integrate them into your next conversation with your boss.



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This article is an excerpt adapted by Ben Fanning from his forthcoming book, The Quit Alternative: The Blueprint for Creating the Job You Love….Without Quitting. Ben will be giving away a limited number of digital copies at launch time. To get notified when they’re available, sign up at http://benfanning.com/getnotified