Quickest Way to Managing Up Tough Bosses Is Mastering These Top 10 Personality Types

Throughout more than 20 years of coaching and training in the workplace, these are the “top ten” types of difficult bosses I have seen. By mastering these personalities and tailoring your leadership and communication style to these, you can create the greatest impact:

1)The Indecisive. The person who cannot make a decision or tell you clearly what they want. Then, when you try to make a decision or take action, they get upset at you. With this type of boss, you want to make sure to confirm with them what they want, in detail and in writing.

2)The Favoritist. The boss who favors one employee over another. This is all too common. A survey conducted by Georgetown University’s McDonough School of Business found that 92% of senior business executives have seen favoritism at play in employee promotions, and about a quarter of the polled execs admitted to practicing favoritism themselves.[1]

Years ago, early in my career, I worked for a boss named Angela at a publicity agency. I was hired on the same day as another woman named Sarah. It started out as just the three of us in that office. Between Sarah and I, Angela favored Sarah. It was damaging to us as a team, and made it almost impossible for us to work collaboratively. Any project that Angela cared about went to Sarah. If something came in and Sarah wanted it, Sarah got it.

When it was just the three of us it was tough, and as our team grew it got even more difficult. Having a Favoritist boss is similar to being in a family where your mother favors one sibling over another. At some point you just can’t compete, no matter how much you try. The two of them would hang out late. I would get in around 7:30/8 am and leave at 6 pm, and they would hang out until 8 or 9pm at night.

One day I talked with Angela and told her that I really wanted to be developed and specifically wanted her help and support to become a better writer. We were working on a massive campaign, and I had been writing the announcement release. I came in one morning to find that everything I had written had been rewritten by Sarah and Angela—while they were hanging out at night together. I was so upset. After I calmed down, I had to consider how to approach Sarah. Since Sarah liked to be spoken to in a direct way, I asked her, “A few weeks ago we spoke about my development and specifically wanting to be a better writer. When I came in this morning I found everything re-written with notes to go with this current version. Can you please share what prevented you telling me what was off about the document and how I could make it better? Getting a complete rewrite doesn’t educate me, it doesn’t help me grow, and my intention is to learn and get better.” I did what I could to speak with Angela, to understand what happened and to learn how to mitigate this in the future. In the end, I had to leave the company because I realized that Angela was interested in growing the company, not the people and didn’t realize the interconnection between both.

If you find yourself in such a situation, all you can do, frankly, is your best possible work; and look to get the boss to see your desire to grow and request to give you opportunities.

3)The Screamer. Someone who loses their temper. If you have a boss that doesn’t provide that, then you must ask for it and even demand it. You can’t work in a place where you feel disrespected and unsafe. And if your boss is a bully, that’s a whole other story, and you may want to set a time limit for how long you will work for a bully before you find your way out.

4)The Workaholic. The person who works all hours, and intentionally or unintentionally implies that others should be doing the same. A woman was joking with me the other day and she said, “I work all the time. I’m stressing myself out. I know I shouldn’t send emails at 2am and on the weekends, and I know I should save them as drafts in my inbox and send them later.” Her tone and attitude made it clear she knew she shouldn’t be doing this, and at the same time she didn’t think it was such a big deal—she wasn’t fully aware of the impact of her behavior on other people. As someone who reports to this kind of boss, you may need to make them aware of how their actions affect the team.

I had a client of mine address this with their boss at an offsite we had. They approached it from the angle of, “We understand that you work different hours than we work, and so when you send an email at 2am, we’re not sure, do you want us to answer you then?” She was genuine and sincere. Framing it as a question may help someone see how they are coming across, and opens the door to address it, and to come to an agreement on what is and isn’t expected. In this case, the boss had the opportunity to say that she was unaware of the impact of her actions. She was committed to the team having more of a balance, and put actions into place that demonstrated her commitment to the team.

5)The Inexperienced. There are times when someone is hired as a supervisor who does not have analogous industry experience. I’ve seen this be incredibly positive for an organization, and have also seen this not work. It depends on the person, their experience, and how they are set up for success by the new company.

I had a client who was hired from outside the media industry into the media business, and it took a good 6–12 months for him to really know the industry and his job. He came from telecommunications, and although a few elements were similar, the TV business was very different. He leveraged his management assets and his skills of asking great questions and listening, and he built alliances and partners in the business. He was honest when he didn’t know what to do, and he won people over, including those who reported to him. He valued the people who reported to him who did what they could to educate him, and in turn they benefited.

If you are faced with such a boss, the smart approach would be to share your information and experience, to offer to help—and hopefully they will handle it well, as my client did.

6)The Youngist. The boss that is much younger than you. This is a common enough reality today, and this situation calls for you to help your boss and do what you can to make them look good. They were hired for a reason, including for their talents. Get to know what makes them unique. Keep in mind that they probably feel their age as much as you do yours, and while age may be a hot button for you, it likely is for them too. They may feel awkward and uncomfortable about being the youngest person in the room or on the team. Make an effort to help them reach their goals, and no doubt you can learn from each other.

7)The Micromanager. The person who is obsessed with managing every single detail, being involved in all the procedures and ins and outs. They are controlling, and they want to control you. If you work with a boss like this, it’s essential that you set boundaries. You need to come to agreements on what they will and won’t be involved with—what they will let you run with, and where they will review or approve your work. You might find it helpful to give them frequent reports and updates, so they know what is happening and where projects are at; if part of a micromanager’s issue is that they are anxious and worried that everything is being kept on top of, such updates may make them more at ease, and less likely to step on your toes.

8)The Playmate. The boss who also wants to be your friend. They want so much to be your buddy that it can appear they have forgotten that you work for them. They want to be well-liked, and their decisions can be negatively affected by this desire. You can be friends with people at work, and even with your boss, and with this type of boss you absolutely need to set some boundaries.

9)The Conflict Avoider. The boss who cannot handle conflict, and who is passive-aggressive. If you’re feeling the impact of someone’s lack of ability to confront conflict, you may have to step in and help negotiate or mediate. That’s probably not the job you want, and yet it may be part of managing up when you have a boss who cannot do this for themselves.

10)The Know-It-All. The boss who fully believes that their way is the right way, the only way, and they know everything. They don’t change unless there’s a life-changing reason why they absolutely have to. With a boss like this, you need to avoid falling into either the trap of giving in to them all the time, or getting into conflict with them all the time. Think about their values. Consider introducing them to new ideas at times, or even taking on assignments where you can position their idea to win. You need to be a bit more artful with some types of tough bosses, including this type.

Working with tough people is an art and science. When you can master it, it makes all the difference as to how you move through an organization and how you mange others. What strategies could you apply to make your interactions with a tough boss more successful – to achieve your goal of helping them do a great job while setting yourself up for success?

Esther Weinberg is the Chief Leadership Development Officer and Founder of The Ready Zone. To dive deeper into the ideas and strategies offered in this article, complete our Needs Assessment and we’ll schedule time to connect.

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