How do you get past the 'damned if you do, damned if you don't' type of boss.

How do you get past the 'damned if you do, damned if you don't' type of boss. I just started at a new firm a few months ago, 99.9% of the time I love it. My direct boss is fabulous, his boss on the other hand is horrible. I am good at my role, get here the information needed, I'm proactive and it's never right for her. If I ask her for information, it's all crickets, but when she needs something she is firing off Teams messages one right another. It is very frustrating, how do you handle this type of person? I am not going to let her chase me out, but I might seek another department to move in the near future.

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  1. Kimberley Ferretti Hammett

    It's a tricky skill to build but I've learned to "coach up". It might not work 100% of the time but the majority of the time I'm able to alleviate some of the stress by at least getting them to settle down.. and in several cases I've turned into the favorite. Essentially it's a way of taking control of the situation while letting them still feel like they are running the show.

    It takes some time because you first need to get to understand them better. If you have the opportunity to have conversations with them that are not directly about work you're involved in, get curious, ask questions about what they are focused on, how they like to work, how they got where they are.. it's like research. It gives you insight so you can figure out a better approach. One example is a leader I had similar to yours that was very demanding with high expectations but never seemed satisfied. She had trouble communicating what she wanted. Through some 1 on 1 chats (and with the help of Gallup Strengths because I work with that) I learned that she is action oriented and a maximizer which kinda just means she's a perfectionist. It's hard for her to feel like something is "good enough". So After some observation, I stepped in in a project meeting and started by kindof defending her to the group.. saying "I get it.. this is a really important project, I think the impact could be big. I see why we want to get it right" and then I'd address her action-oriented side by saying "but I think that's why we need to take a beat to understand where we're going better. We can get the details done, but I think we're having trouble with clarity.. this is clearly more than just a guide (we were working on a leaders guide), so what will this project accomplish at it's best? What impact should it have on the leaders who use it?" and then I continued to ask some questions, then relayed it back not only to her, but the group in a way that they could understand. Almost like a translator. I think showing that I understood her and I wanted to make it happen for her brought some of her walls down enough to get some answers out of her. Then basically guided her through guiding the team with my questions and because it worked and we finally got the momentum she wanted, she started really trusting me.

    Again, it takes some skill to build but if you can make someone feel seen and safe, you can get them to tell you a lot more. Not that that should be your job.. but you're obviously in this situation and you can't make her change overnight, but you can change the way you interact with her to try to get a different response.

  2. Anonymous

    It's 1% of your otherwise perfect job. Don't stress and just respond with what you would normally do.

  3. Anonymous

    Since your immediate boss is fabulous and you only have to deal with his boss intermittently, just do your job to the best of your ability and realize that you actually answered your own question; some people can't be pleased because they choose not to be. Just ask for clarification when needed and follow her directions to the extent feasible when you work with her. Don't leave a job that you are otherwise happy with . You may outlast the bad boss at the company; I outlasted a former boss who was so negative all the time that I thought surely they would fire me, but they didn't and they no longer work there!

  4. Anonymous

    Ask for a sit down, let her know what you need to do a great job. Manage the manager and let them know your goal is to do great work and make them look good to their upper level. Usually the skip level leaves it to your direct manager to deal with and that may be the reasoning for the general avoidance. If you cannot get direct time speak to your fabulous boss and ask them to broker a conversation for you.

  5. Anonymous

    Have you tried asking your manager's advice on how they deal with their boss? Maybe there are some ways that your manager has learned that they can share. For example, is there a specific way that the manager likes to receive information, or is there a preferred communication path or process? Understanding more about the way the manager rolls may help bridge that gap.

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