The Case of the Miserable Boss

By Allan R. Cohen

Tolstoy started Anna Karenina with the classic line, “Happy families are all alike; every unhappy family is unhappy in its own way.” Probably every person who has had or is having difficulties with his or her boss feels that no other boss has been so miserable in exactly the same way. When your boss is giving you a hard time or letting you down, it isn’t much satisfaction to try to squeeze that person into a category, or be told that a simple formula will cure all that ails you.

In this article, we will provide a way of approaching your boss or other higher-ups you need to influence, but we also will insist that you take a close look at your own behavior to see how much of the problem resides in you. This might be uncomfortable, but it is the nature of relationships that both parties bring their histories, beliefs, attitudes, and behaviors to the interactions so that improvements seldom will come only from one party.

We are optimists about the possibilities of converting the most problematic boss–subordinate relationships into something that more closely resembles partnerships, even though we know that you may be in a situation where that seems highly unlikely if not impossible. To begin this apparently perilous journey, we start with a report of the struggles of Mary Quinn with her boss, Kate McNaughton. Their names and the name of the company they work for have been disguised, for obvious reasons, but the events described are very real, and as difficult as they sound.

Mary Quinn was at her wit’s end. She didn’t think she could continue working for the nasty witch who had been her supervisor for the past year. She wrote the date May 15 on the white board in her office, which was the day she would receive her bonus check. After that she could resign.

After college, Mary had worked as the internal audit manager for a large consumer goods company for six years, then moved to a fast-growing software company as a business applications specialist for the next five years. She had done very well at the company until it was acquired by SuperiorSoft, a very large company that had specialized in systems software but wanted to form a new business application division. Kate McNaughton, a longtime SuperiorSoft employee, was named vice president of development for the division, and Mary reported to her. Kate resided in New York but her direct team was spread around the U.S. with a software manager in Nevada, integration manager in Scotland, and three people developing and servicing ERP packages in Cleveland and Seattle with Mary in Boston.

Mary’s experience with Kate had been dreadful. Most of the time, she dealt with her by phone, in conversations inevitably abrupt and unpleasant. Kate’s clipped, critical style and snapped-off orders had led Mary to feel that she was dealing with a corporate bully.

Kate obviously had never heard the maxim, ‘praise in public, criticize in private.’ I would suggest something, and there would be no response. Two minutes later another direct report would say the same thing, and get highly praised. At national conferences, she would ignore me, hang out with the three tech guys on staff. I would hear from others that ‘Kate can’t stand you.’ She heard good things about me, but was not favorable to me.

Although Mary received praise from customers and others she dealt with in the company, Kate criticized everything she did, and clearly disliked Mary. Kate was particularly critical of Mary undertaking many activities to work closely with clients without ever asking Kate’s permission or even informing her.

I was berated about not asking for permission to hold design review meetings with customers, grilled about who was coming into Boston, about why I made decisions to reduce features in order to ensure quality while meeting delivery dates. As I had for years, I collaborated with our clients in pre- and post- product acquisition meetings. I would even invite them into design meetings, or attend user group meetings. That aggravated her, because she had never done it. Why was I doing it without her permission? It confused and aggravated her.

In Mary’s view, Kate was a bright, hard-working, excellent programmer who had worked on the systems side of the house, was highly respected for her technical expertise, but a controlling, workaholic single person in her late 30s, who intentionally lived across from her office to be near work.

Mary on the other hand, was in her early 40s, with a 1-year-old child who attended the company day care center, and proud of her warm, personal style. She liked the connections among people and figuring out what made them tick. An independent person, she was used to being appreciated for her competence and interpersonal skills.

Kate’s background was entirely in systems programming, which could be conducted with very little direct contact with customers. Mary, however, was doing business applications and dealing with accountants, manufacturing managers, buyers, planners, and inventory managers, so had to understand their needs. Early in their time working together, Kate had frequently asked Mary “the most basic questions about business processes that demonstrated her complete lack of understanding about business applications software,” so Mary had concluded that there was no point in consulting with Kate about how to do her job.

I had really good programmers working with me so we were putting out good code. I was very close to the users group, so features we put in were what they wanted, but the process was very different from what systems programmers go through. Kate thought it was inefficient; that I could get done even quicker. The company was very much about tight deadlines, and she bought into that.

Although Mary had set a target date for leaving the company, she very much liked her direct reports and the people she worked with at her location, and enjoyed the customers, so she was reluctant to leave. In the meantime, Mary’s group started developing add-on products, and when Kate’s boss heard about it, he invited Mary to their headquarters to encourage her, and as a result she loved her work even more.

Finally, she decided to try to talk to Kate directly, and found that she could give speaking in person one try. She didn’t expect much, but wanted to at least have tried to do the right thing.

Before going on, you might want to think about Mary’s prospects. What kind of response was she likely to get? What approach do you think she should take? What should she say to Kate? If Kate were your boss, what would you do?

Here is Mary’s description of what happened:

In desperation, I stopped by her office for a heart-to-heart talk, and said, ‘Our relationship is not working, what can we do? I respect your expertise, I love my work and I want our relationship to work.’ She explained what aggravated her: ‘you go off and call meetings without me being aware; you do other things without asking, like take features out of an upcoming release to make the date without asking me.’ I acknowledged that what she said was true, but not meant to be disrespectful. I had just been trying to do the job as I had done it before.

Almost every conversation we had before that was virtual. Talking one on one and face to face seemed to make a big difference. Prior to that, everything from her was quick, snap-off comments. In that conversation she actually smiled for the first time and turned from an ogre into a nice human being. ... I saw her as more human, someone who was trying to please her demanding management; she did have people screaming at her to ‘get it done yesterday.’ So I became much more sympathetic and invited her to my next meeting. After that, she started to come to me with business application questions; she requested that when some customer had ideas for new products, I first should come to her. While I respected her expertise, two years of bullying was hard to forget, so we were not exactly friendly, but no longer hostile.

At the next users’ conference, customers were saying to me, ‘We have all the data in the world, but how do we get at it?’ I went to Kate for help, and she got all excited because she had good tech[nical expertise]. We would each write up a piece, meet to talk about it. It helped to have projects where the technical part was as important as the business piece; that helped bring us closer. ... In hindsight, I am sorry I waited so long to connect with her.

Does it always work to directly address difficulties with a boss or other higher up? Of course not. Your boss may be in your view far more miserable than Kate—nastier, less willing to give credit, more of a micromanager, fearful of conflict. In some situations, the best thing you can do is cut your losses, look for a way out as soon as possible, and resolve to learn from seeing the terrible effects of a really bad boss. The problem is that you might be as convinced of the futility of addressing the problem as Mary was, due to your history, your strong feelings, your vulnerability and fear of being fired or losing the relationship, or just your lack of knowledge and skill at working on a relationship.

When you were reading about the situation from Mary’s point of view were you convinced that there was no hope for her? Because she was so certain about Kate’s faults, her point of view was persuasive, even if not in fact totally accurate. Behavior she perceived as deliberate nastiness apparently had other causes. Mary’s independence and conviction that Kate had no technical knowledge to offer was making Kate quite uncomfortable, especially since she was trying to manage at a distance. Kate had learned to rely on technical knowledge and extensive hands-on work as a way of delivering, and didn’t understand how to lead when she didn’t have the appropriate technical knowledge. She also was responding to a macho company culture from people in jobs where relationships with customers were not so important. So while it might’ve been true that Kate really “didn’t like Mary” very much, and found Mary threatening and hard to control, she wasn’t necessarily a bad person who enjoyed attacking at every opportunity. If you were Mary’s boss, isn’t it possible that you would have been rather tough on her, too?

When you are in such a relationship, and things have deteriorated, it is hard not to attribute all the blame to the defects of the boss, or overestimate the bad consequences from trying to address the relationship. Once you have locked in on an explanation of what is wrong with the boss (or any other person you have to deal with), everything that happens tends to confirm your beliefs. Furthermore, since the boss does have the potential to affect your future, it can seem overwhelmingly threatening to initiate discussion on the subject.

To get ahead, often even to keep your job, you need to do more than just fulfill your formal duties. You must do these well, since no amount of relationship skill is likely to overcome the failure to deliver, but that is just the entrance fee. You have to demonstrate that you are willing to take positive initiative to solve problems and identify opportunities on which you can deliver.

Action Steps If faced with a boss who does not treat you the way you prefer, here are important steps:

1.Write a description of the problem; what you want, how the boss responds (or doesn’t), what you have done about it so far.

2.Read the description as if you are the boss, constructing at least two alternate explanations of the boss’s behavior. Think about how the boss’s role and background shapes what the boss cares about.

3.Try to differentiate between what you actually know and what you have assumed; you can then test your assumptions and not just act on them.

4.Prepare to directly discuss what you want with the boss. Frame the discussion in terms of how a new relationship will benefit the business and the boss. Do not accuse or attack; you are trying to problem-solve. “Here’s how you will benefit if you meet my request.”

5.Be ready to examine your contributions to the problem, and understand you may have to change some behavior to get something back.

6.Aim for a better relationship no matter what the specific changes that come out of the discussion. You don’t have to be close friends, but work to become a junior partner, who wants the boss, and the unit, to succeed.

This article is excerpted from a book in progress, Influencing Up, which Allan Cohen is writing with David Bradford.