How I Turned My Nightmare Boss Into My Biggest Fan

On February 16, 2021

Early in my career, I saw a listing for a position that I considered to be a “dream job.” Full of more gumption and courage than experience, I sent a resume along with the world’s most ridiculous cover letter.  It was formatted to look like an invitation and began with the words “You are cordially invited to the interview of a lifetime” With who?  Me of course.  Applicant extraordinaire.  It ended with “Please RSVP for an opportunity you won’t want to miss .”

It was a bit much.  But truthfully, I can be a bit much, and I reasoned it would at very least let potential employers know what kind of candidate I was.  Surprisingly, the owner of the company was intrigued by my letter and asked me to meet with him.  Although I did not have the amount of experience they were looking for, I was invited to the next round of interviews.  The next round was a group interview with a half dozen members of the team.  The owner of the company looked at me and said “This job requires sales.  You have no sales experience.  We have had hundreds of applicants and you are perhaps one of the least qualified.  What makes you think you can do this position?”

I looked at the group before me, summoned all the confidence I could muster, and replied, “I am your least qualified candidate and yet I am the one sitting here.  Clearly, I can sell something, even if it is just myself.” Somehow, I won the position, but I was a long way from winning my boss’s respect or loyalty.  Based on my cover letter, I had a lot to live up to, and very little knowledge on how to live up to it. 

My new boss was notorious for being hard to work for, and before long I knew why, he was a nightmare boss.  He was not an easy man to understand and an even harder man to please.  

The truth is there is not a “one size fits all” strategy when dealing with your boss, coworkers, or employees.  Managing up can be an especially tricky thing.  It is a delicate balance.  You must earn enough respect and professional and relational equity to be able to speak into situations. 

Here are 5 tactics I employed to turn my boss into one of my biggest fans:

  1. Get to know your boss professionally.  Take the time to understand your boss’s vision for their team, what they view as their function within the team, and their goals and motivations. Watch how they behave in meetings and how they react to pressure and try to understand what their stresses are.  This will help you anticipate both their needs and their reactions to any issues that may arise. 
  2. Get to know your boss personally.  Are they married or single?  Do they have kids or pets?  What are their hobbies?  Where do they vacation?  What do they do for fun or on the weekend?  What makes them laugh?  What are they passionate about?   Employees often forget that their bosses are human.  While it is important to always keep a professional demeanor in the office, a little bit of small talk creates community and builds comradery.
  3. Earn Trust.  Trust is a critical factor for any relationship.  If you want to manage up it is crucial that you follow through on your commitments.  Your boss needs to trust that when they give you a task, you will finish it quickly, efficiently, and fully.  You must be on time for meetings and be prepared. Find out key information your boss needs and the best way to update them and do so often.  When things do go wrong, be honest.  Actively work to make your boss’s job easier by being exceptionally reliable and productive.  Trust takes time to build, but the rewards are long-lasting and long-reaching. 
  4. Be an expert but know your weakness.  Your manager is your senior, not your superior.  They hired you because of your skills and expertise, so don’t be shy about sharing your knowledge or offering solutions. Proactively work to find solutions to business problems.  You need to be thinking constructively to engage in a useful dialogue with your boss.  Along those lines, we are not all experts in all things.  To build a good working relationship with your boss you need to be upfront about your management flaws or the areas where you are not as knowledgeable as others on your team.  You can be an expert on knowing who an expert is and where to turn when faced with issues. Foster a collaborative environment and build trust among your colleagues.  A team is stronger as a whole. 
  5. Display the qualities that matter in all relationships.  Be a good human. It takes no talent or special skill to be on time, bring a good attitude to work, put energy and enthusiasm into what you do, support your colleagues, ask questions when you don’t know the answers, and be willing to work hard. Learn from those around you. Be empathetic. Be flexible. Be loyal, and do not bad mouth your boss, your company, or other employees. Many companies hire on the strength of these qualities, knowing that specialist skills can be learned along the way. 

Change doesn’t happen overnight, and HE ultimately wasn’t the one who changed

It did not happen overnight, but eventually, I lived up to my cover letter and earned my boss’s respect and friendship.  He began to seek my opinion about business decisions and marketing plans. He micromanaged less and began to trust more.  I got a promotion. And the next time there was a group interview I was right next to him, looking at cover letters and asking the questions. I had quite literally earned my seat at the table. Most importantly, my boss became a mentor during my career at his company and long after I left the company. 

Would you like more tips and tricks?  Join my Masterclass “Managing the middle” on February 25th at 11 am.

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Managing the Middle

Jamie Quickert
Passionate about people and outstanding customer experiences, Jamie helps our clients uncover the ways to best surprise and delight their customers.

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