3 Ways to Make Your Difficult Boss Love You

How to build a more positive working relationship with your manager.

Always own up to mistakes, and be open to feedback.

When working with a difficult boss, it can seem like nothing is in your control and like you don’t have the power to effect positive change in your working relationship. But nothing could be further from the truth. Instead of being reactive or passive, use these three techniques to make your boss love you:

1. Stop trying to prove yourself. When you’re being put down or are not receiving the feedback you want, it’s tempting to try to show how good – no, great! – you are. Resist the temptation. And it’s hard, but try not to be defensive to your boss, even when you think his or her words are unfair. You don’t want to be at war when you’re on the same team.

Instead, change your mindset, and go from closed to open. Rather than retreating or advancing when things don’t go your way, try to stay present and put yourself in a learning mindset. Leadership – both managing up and managing down – is about empowering people to be their best. When you realize that, it takes a lot of pressure off and makes the adage “make your boss look good” much easier to execute. Every project or interaction can be an opportunity to expand your influence.

2. Write sample scripts between you and your boss. Always say the wrong thing? Wish you said something else? Can’t think of anything to say at all? When we’re put in difficult or conflict-oriented situations, it can be nerve-wracking to stay in control and ensure the conversation goes in a positive direction.

Use the script technique to imagine past and future conversations with your boss and ideal ways to respond. Start with writing down past conversations that you think didn’t go well, and then rewrite your response. Using your learning mindset, brainstorm ways to respond in a respectful and open manner. Here is an example script:

Boss: "You seem overly quiet in most meetings."

Your past responses:

"OK … Um …" Or: "Really, it's just the meetings you are leading – because you are leading them. I do my best to learn from your example, then I use some of your style in meetings in which I am the lead or facilitator."

Your new, better response:

"OK, that's good to know. I really appreciate the feedback, and I'd love to learn from these conversations. What are the best ways I can be responsive during the meetings?"

Do you see the difference? In the first response, you are retreating. In the second, you are advancing. In the final response, you are present and open to learning. Most of us think these types of negotiations have to be heavy-handed, but research shows the opposite is true. Positivity combined with a proactive approach is much more successful.

Once you’ve finished scripting past conversations, practice your proactive responses out loud, and see how you feel. Then repeat the process, imagining future conversations and what you would like to say. Practice out loud once again, and continue to do so until the words feel natural.

3. Own up, and show up. Own up to the fact that you don't know everything, and that's OK. Own up to yourself, to your team and to your boss. Own up to the fact that you will make mistakes. Once again, write out a script to own up to something that’s been bothering you. Here’s a sample script from someone who is having trouble finding his or her confidence as a full-time employee after months of working on a consulting basis:

"I'm excited to be full-time and look forward to rocking out [xyz]. I'm still new at this and will be testing different ways of doing things. Some of those things will work out, and some won't. As we move forward, I'm excited to work together and get your feedback to make this project a success."

And then you show up and do the work. You show up. You don’t worry or hold back. You show up and work on what matters. If something goes wrong, own up again: 

"Just wanted to let you know that I know that didn't go too well today, but I've already got a plan on how to do it better next time. If you have additional feedback, let me know."

The "own up, and show up technique" puts into practice both your learning mindset and your sample scripts. As you move throughout your workday, you’ll practice being both positive and proactive.

Each technique on its own will produce powerful results, but when combined, you’ll find they'll give you a huge edge in dealing with your difficult boss and conflict-oriented situations. Instead of feeling powerless, you’ll regain confidence and enjoy work again.

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