Your 5-Step Plan For Converting A Nightmare Boss Into Your Best Ally

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Jenny Maenpaa
Jenny Maenpaa
June 15, 2024 at 12:5PM UTC
So you have your very own Miranda Priestly/Bill Lumbergh. Yikes. That sounds awful. Good luck with that. But more likely than those fictional nightmares, you just have a regular boss with whom you have trouble connecting. Maybe it’s making you feel like this job is not right for you or that this boss has it in for you. But before poisoning your boss’s coffee, try these strategies for turning an enemy into an ally.
1. Identify what is bothering you so much in yourself. Name it.
Naming emotions and frustrations morphs them from a nebulous blob lurking in your chest to a manageable, one-time nuisance you can deploy and then throw away.
2. Think about your own value system.
What core value is being threatened by your boss’s actions? For example, you might be irritated at their hesitation about making decisions. But if you dig deeper, you might realize that one of your core values is social justice, and when your boss takes too long to choose, the clients that you serve do not get the services they need. 
Maybe you value efficiency and effectiveness. When your boss makes decisions or creates systems that are inefficient and ineffective, you feel more strongly because it feels as though your purpose is being threatened. 
3. Think about your boss’s value system.
Do they value the same things you do? Maybe they value compassion over efficiency, and that leads them to hear every single employee’s input before making a decision. Do they value being liked? Maybe that leads them to seek consensus before moving forward. If they value improvement, they might spend more time than you think is necessary tweaking and making iterative changes.
4. Shift your mindset to be asset-based.
This is not the same as being a Pollyanna or washing over negative situations with a pink paintbrush. It means that in situations where you can assume the worst or assume the best, assume the best. 
If your boss always writes terse emails that put you on edge and never include praise or positive remarks, read them in your head as if every sentence ends with an exclamation point. Even if you know your boss would never speak that way, it instantly lifts your mood and improves your ability to receive their feedback constructively.
5. Take an honest look at yourself. 
How are you engaging with this person? Are you expecting that they are going to come at you with negativity, and setting up that situation to be the only outcome? Maybe you feel like every time you contribute in a meeting, your boss shoots down your idea. 
Unconsciously, you are likely walking into that meeting prepared for a fight. Your shoulders are hunched, your mouth is set in a line, your eyes are cold, and your boss knows that. They are now also prepared for a fight because that is the energy you are giving off. It is much easier to point to others than to look at ourselves, but only one of those people’s behavior is within your control.
Once you have done all of that, you may find that there are still issues. In that case, you will likely have to follow the standard protocol for conflict resolution at your office. You may have to start by addressing your boss directly. This is going to be an uncomfortable conversation for both of you.
One strategy is to enter the conversation by disarming your boss with an area of growth for yourself first. For example, you might say, “I noticed that if my project is not run by you a week before the deadline, you email me and copy my manager. This makes me feel as though you don’t have faith in my work, but I realize it could also be your way of simply asking for a status update. Would it help you if I sent you a status update one week before the due date to make sure we are aligned? It would help me feel that you have confidence in me and my abilities to perform if we did not have to include my manager quite so often.” 
This shows your boss that you are focused on growth and results, not blaming and finger-pointing. It also shows that you have thought about your boss’s motivations for their actions, rather than only focusing on yourself and your hurt feelings.
Bosses are humans, too, and most of the time they are not out to get anyone. Their bottom line is performance of the company, and you are an integral part of their metrics. It will cost your boss a lot more to fire you or have you quit, and then have to search for a replacement, hire the replacement, and train them to reach your level of proficiency than to get along with you. Remember that it is in both of your best interests to find common ground and successfully work together long-term.
Jenny is the founder of Forward in Heels Executive Coaching, which empowers badass women who want to excel at what they do, stand tall, and own their worth so they can light up the world. As a licensed psychotherapist as well as certified executive leadership coach, Jenny has been helping women make bold, lasting changes in their lives for over a decade.

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