Bosses: How I’ve Learned to Distinguish Between Good & Bad Ones

If you’re in the work world long enough, you most likely will experience both good and bad bosses. Most of us have witnessed all the iterations in fiction, on the screen and in the news. These days there’s buzz about Senator Amy Klobuchar (D-Minnesota) and whether she really has been a terrible boss who berates her staff and yells too much. Furthermore, does that make her a terrible potential U.S. President? I’m not sure since I don’t know how much is true or simply hype that comes from disgruntled staff members. 

However, since we’re first talking bad bosses, let’s tick off a list of those on the big screen. Who can forget Miranda Priestly, the perfectly coiffed and dressed terror at a fictional version of Vogue magazine who was awful to sweet, cute Andy. Fortunately, since this is Hollywood, Andy (aka Anne Hathaway) got her comeuppance by the end of the movie, The Devil Wears Prada, when she left Miranda (aka Meryl Streep) and the magazine.

Later, in another movie, The Intern, Anne now playing Jules, the head of fashion startup, About the Fit, masters more lessons about being a boss when she gets to order around much older widower Ben Whittaker played by Robert De Niro. In a clever twist, this time it was Ben, decked out in his Paul Stuart-style debonair sports jacket, tie and pocket square, who ended up teaching the much younger staff a thing or two about working as a team and being loyal. 

Let’s move on to real life and what I’ve learned in 47 years of work for a variety of bosses, including myself. I’ve now run my own writing/speaking company for the last 31 years but still basically work for others in my assignments. I have many masters, as I like to say. As a result, my many writing projects and experiences engender ideas for our weekly blogs on lifelessonsat50plus.com. Today’s piece was inspired by attending a lovely lunch to toast my first and favorite boss before he and his wife moved from their New York City apartment to a retirement community on Long Island.  

Like me, the guests were all current or former magazine writers and editors at glossy shelter publications, the kind you might subscribe to or have subscribed to since some have been closed and now are in “publication heaven.” We were all at the lunch to share wonderful “Lou” stories and echo one another’s sentiments about what a great boss he was. It was almost sickening how much we all adored working for him and our time at magazines when they were thick with advertisements. That’s when we could write thousands of words of copy about a favorite house, new starchitect, color or home furnishing trend—kitchens as the hearth of the house!

I shared with a few guests how great it was to have a boss with a wonderful, optimistic spirit, who let me pursue stories that piqued my interest, and which often meant travel to see and touch what I was writing about (Amish quilts and others that reflected regional differences, the crafts of New Mexico and Oaxaca, Mexico and the American antiques collections at the White House and State Department). Lou demanded quality work, but his critiques were always constructive and kind. His eye for good design was so superb that we all went to him to arrange our furnishings according to his rough floor-plan sketches. He also taught me about several masters of modern furniture such as Charles and Ray Eames and George Nelson and both of us learned about furniture maker George Nakashima.

He and I shared a love for a certain burger place near the office, stitching needlepoints and sharing recipes (his cold carrots are still legendary among my friends and family). The only reason that I stopped working for him after eight years was because my then-husband took a job in St. Louis. 

I next learned about the difficulty of working for unkind bosses, including an editor, who chose to be far tougher on the female members of our department at a major daily newspaper. Yet, the editor let me return after a maternity leave for four rather than five days a week, which was a big deal back in 1982. This editor—I prefer to avoid gender--let me take a leave to write a book about family business with Margaret Crane, who would later become my writing partner. While in that same job, there was also a very senior editor who didn’t back me up on one story I wrote about a national furniture manufacturer that had entered our local market and was using an 800-number to offer discounts. This infuriated the local furniture retailers (most good advertisers). It was my first experience where the editorial side bowed to its advertisers, not a hallmark of good journalism standards. 

A move next to Chicago spurred me to start my writing business since I had young children and working from home made more sense economically. I would also get to decide which assignments to take on, though my problem was that I never said “no” to work. I soon found I was writing for dozens of editors at a slew of publications as a full-time freelancer. Most were wonderful, especially one at The New York Times, who remains the most demanding boss I’ve had. He questioned every fact and word, nothing got by him. It was a great learning experience. Also, while living in that city, I worked under one editor who convened meetings of freelancers and often was mean during show-and-tell sessions. “What were you thinking?” I remember this editor asking me in front of others. Tough love? Maybe, but repeated incidents spurred me to seek advice from a business psychologist about how to deal with this type of boss. He advised me to make a friend of the editor. “Find things you like. Ask the editor out for coffee, tea or wine,” he suggested. I reached out and over time we became casual friends who cared about each other. 

Then, years later back in New York, I found that a one-size-fits-all approach to a boss doesn’t always work. I began working for a boss who was as mean as Miranda. We worked together on multiple magazines each year. I tried hard to befriend this editor, asking about family, vacations, anything to trigger conversation! Nothing worked. Fortunately, I learned that I wasn’t the only one. Others who worked full-time had asked management to change them to another publication since the company owned multiple titles. The editor never seemed content with anyone’s work, was dismissive when you had an audience in person, and was extremely rude in comments whether anybody else was present. “These rooms are all terrible,” I remember the editor saying over the phone one day after I had turned in 50 different kitchens. “All 50?” I remember asking. “How about if you look at them again?” I softly asked. The editor agreed and decided several hours or days later that only a few wouldn’t work. I stayed calm but remember being nervous each time after that when submitting possibilities. I was ready to quit after several more incidents, but the editor made my “job” easier when someone else was brought in to replace me. I had received my first pink slip, so to speak. 

I was fortunate that I never allowed the nastiness of a boss to affect me physically—headaches, stomachaches, back aches. However, I did recognize the difference in working for someone who appreciated hard work and creativity versus someone who was perennially unhappy. And though it’s tough to predict what a work relationship will be like over time, these are a few common threads that I try to detect before I take on work for someone new. As the cliché goes, life is too short. 

What have I learned about good versus bad bosses through the years? Here are 8 lessons:

1. They may show their hand during the interview process. One potential boss who pursued me for a job in public relations’ damage control work kept me waiting for more than one hour. There was no emergency I learned, just her own self-importance. I did some intense research about her style of being a boss after the interview. When I was offered the job. I turned it down and felt I had dodged a bullet.
2. They provide clues in what they say--or don’t say--over time. Do they ever offer compliments? Ever say thank you? Maybe not in my case for each article but occasionally is nice. One editor always says “thanks” and appreciates greatly when I turn in an article ahead of the deadline. This editor may be the kindest person I’ve worked for. I’ve also learned that some bosses or supervisors just can’t seem to part with a “good” or even “great job” for whatever reason. That’s says more about them than your work.
3. They offer good instructions or marching orders. They are very clear in what they want, in terms of my work—number of words, content, any specific type of sources, artwork and even what they don’t want in terms of subject matter. If these specifics aren’t spelled out in advance of an assignment, ask. Pin them down, even asking multiple times. If there is pushback or ambivalence, think about turning down the assignment.
4. They frame criticism and suggestions kindly. My goal is always to learn, and the tougher the boss in terms of standards the better. I still value making any article or book better and am always willing to revise. Not everyone is, I’ve learned. At the same time, I finally learned it’s not worth trading a paycheck for outright meanness. How things are presented and in what tone matters a great deal to me. It may not matter to others, however, I recognize. When one daughter had a very mean boss in her first “real” job and wanted to quit, we all advised her to stay. We felt everyone has a mean boss at some time and should learn how to deal with it firsthand. She did, stayed a year, and then went on to much better experiences.
5. They ignore age and other differences. I now generally work with much younger editors. We celebrate our differences. Some could even be my kids! I love their excitement and knowledge about social media, appreciation of new real estate and home furnishings and real estate trends (my overall subject matter). Viva la difference may be another cliché but the best reflect this, too.
6. They encourage staff to take on more responsibility and move up. They want to see you succeed and grow. A good boss in my book wants staff to be successful, maybe not take their job but take another position with more responsibility, even if this results in eventually leaving. Not all do this, especially graciously.
7. They care about you enough to connect beyond the work. You don’t have to become a friend and have them know every detail of your life—what type of diet you’re now on or where you ate dinner last night. You also don’t need to know about their life out of the office and what their children’s homework assignments are. In fact, it’s better if you don’t share too much, at least initially. Let time direct where a possible friendship might go, too. Yet, occasionally it’s nice if they ask, “How was your weekend?” or “How was that vacation?” One boss whom I didn’t work with directly but oversaw the magazine where I worked, never asked anything about me or it seemed of anyone else. I remember this editor established what I felt was a terrible office culture by expecting everyone to be at their seats at a set time. The editor often strolled around the office to check. There was almost no chit-chat among staff. The silence was deafening, a shame since it was a great team of hard-working, fun, smart colleagues.
8. There are countless books and resources about good and bad bosses online. Two examples: Good Boss, Bad Boss by Robert I. Sutton (Hachette Book Group, 2010) and A Survival Guide for Working with Bad Bosses by Ginny Graham Scott, Ph.D. (Amacom, 2006).