How can you develop empathy towards a difficult boss?

Accepting your boss is difficult and understanding if you want to address the situation or leave the organization, are the first few steps. Commit to what you decide. Often addressing the situation forms a bond that you'll cherish for years. When you start reaching out initially they might push you back and not open up, respect their space, and keep reaching out humbly. You'll find them eventually opening up. You could find a common hobby or sport that you both enjoy and may talk about that which will reduce their pushback. Understand why they are behaving this way and what are key triggers that are not allowing them to trust their team. Try to address them! Remember it's a process and we've to be consistent with it.

As I'll say more than once, empathy isn't about giving bad behavior a pass, but it is about recognizing our common humanity. Neither is it a manipulation technique, although empathetic communication is more likely to achieve my own goals. Often, the thing that triggers me from my boss is some shortcoming in my own life. He may not have intended any criticism, for instance, but his tone may remind me of the way my mother used to couch criticism. This isn't a time for psychoanalysis, but rather an opportunity to recognize the complexity of experience and the impossibility of mind-reading. Don't assume intent.

Most of us believe we listen actively, so it can be hard to catch ourselves getting more tied up in how we intend to respond, arguing internally, getting lost in our own reactions. One way to provide some psychological distance: instead of "what am I going to do about this?" say to yourself "I wonder what Donn is going to do about this?" (with your own name, of course). You can then listen from a less emotional space. Another part of this is simply to slow down. In fact, a powerful response in a conversation is to pause, say nothing for a few seconds. Often, the other person will start talking again, giving you more insight and information, and they will view you as giving thoughtful instead of knee-jerk responses.

Curiosity is one of my core values. It is a natural extension of something I said earlier, i.e., gaining some emotional distance. If I have stepped back with "I wonder what Donn will do?" I naturally ask myself other questions, such as "what has led my boss to behave this way? What are his assumptions? What kind of pressure might he be under?" That will lead to questions I can ask out loud, which will foster conversation—and that's almost always more affirming than passive listening or arguing.

The key in offering support is to foster the feeling that you and your boss are on the same side, that you are allies rather than enemies. When your boss senses that your goals are mutually beneficial, he is more likely to work with you. The old saying is that all else being equal, we like to do business with people we know, like, and trust. This is one of the best way to foster all of those.