Six Tips for Working With a Difficult Boss

A leader is admired, a boss is feared.
— Vicente Del Bosque
 

Mr. Burns. Michael Scott. Miranda Priestly. What do these three fictional characters have in common? They’re all examples of difficult bosses. 

Bosses can be difficult for a slew of different and varying reasons. Some are demanding. Some are disrespectful. Some are unclear in their expectations and/or direction. 

Whether or not you’ve had the (dis)pleasure of working for one, its certainly likely that you will come across one at some point in your career. So, how does someone deal with a difficult boss and remain professional?

Like anything, context is key. Here are some tips to make working with your difficult boss a bit more palatable.

  • Examine the Situation. The first step to clarity is asking questions that get to the core of the challenge. What makes the boss difficult? Is it certain behaviors or actions? Is it their communication style? Clarity is the first step in determining a course of action. Plans have the highest likelihood of success when they’re tailored to the personalities, culture, and context in which they’ll be implemented.

  • Take Initiative. Once you know the behavior that makes the boss difficult, then you can strategize. You can’t rely on a person, particularly a difficult one, to change their behavior. The only answer is to focus on actions that are in your own control. In other words, take it upon yourself to shift the dynamic. This includes either changing your actions, communication approach, or reactions. 

  • Communicate Clearly and Efficiently. Bosses can often be difficult for a variety of reasons, but I continually hear reasons that come down to the same thing: miscommunication. It’s a good idea to check in, confirm expectations, and over communicate at times. Also, if you hear something that doesn’t sound right, speak up early and often to get everyone on the same page. It’s also helpful to be concise, clear, and direct in your questions and communication to minimize the chance for veering off tangents and maximize the chances to stay on track for the meeting or interaction.

  • Keep the Emotion Out. It’s hard to stay calm and carry on with a difficult boss and sometimes emotions can get the best of us. My biggest piece of advice is the easiest, yet sometimes the hardest. Take a deep breath and pause before you speak. Remember, you don’t always need to respond in the moment; once you say something you can never take it back. Sometimes excusing yourself from the conversation, collecting your thoughts, and responding later when you’ve calmed down is the best approach, not only to keep the emotion out, but also to keep your messaging clear and chances of positive outcomes high.

  • Stick to the Facts. Another way to keep the emotion out of the interaction is to stick to the facts. Facts and logic are typically harder to argue, and can help conversations cut to the chase and minimize the chance for any heated debate.

  • Ask Questions. I often hear complaints about bosses that send employees from one analysis to another or ask for report after report, burdening the team with inefficiency. These situations can often be avoided by asking “what are you trying to determine from these analyses?” Understanding the intention behind a directive helps pave the way to collaborative and creative problem solving. 

Sometimes, seeking support is also key in navigating difficult and high- stakes situations. Whether a mentor, friend, or executive coach, getting an outside, unbiased perspective can be critical to success.

Are you having trouble navigating difficult personalities at work? If you’d like to explore how to approach these situations with greater confidence, more ease, and less angst, please reach out (link) to learn how Jaclyn Beck Consulting could help you and your organization.


If you’d like to explore how to better navigate your career, sharpen your skills, refine your performance and leadership capacity, please reach out to learn how Jaclyn Beck Consulting could help you and your organization.

 




Jaclyn Beck

Jaclyn Beck is an International Coaching Federation (ICF)-accredited (ACC) Certified Executive Coach and Certified Career Coach with 14 years’ experience working on Wall Street and commercial real estate investment.

She founded Jaclyn Beck Consulting to promote the power of self-awareness, emotional intelligence, and communication to enhance career performance, satisfaction, and success at work and in business. She is also the host of the podcast “Worked Up” which aims to help listeners navigate business and careers with more ease and less angst.

https://www.jaclynbeckconsulting.com
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