How To Deal With A Difficult Boss and Not Die Trying 

How To Deal With A Difficult Boss the Right Way 

Wondering how to deal with a difficult boss or difficult people in your workplace but are embarrassed and afraid to ask around?

We know how frustrating dealing with difficult people can get and how lonely the journey is. But it doesn’t have to be this difficult! A lot of people have to deal with this situation every day.

In this Boostrappers episode, Gwenn shares her most valuable and effective actions when dealing with difficult people in any organization. 

Montreal Elite Unleashed

How Gwenn Deals with Difficult People

Gwenn found herself in a similar predicament with a client who was continuously arguing with his Virtual Assistant (VA). 

After years of experience dealing with difficult clients, Gwenn’s approach to this situation was both strategic and insightful.

She first attempted coaching both the client and the VA, trying to bridge the communication gap, but of course, difficult bosses rarely accept take this type of agreement. 

Listen to the full episode.

As this interaction unfolded, she quickly realized that she was dealing with a very difficult boss. 

So she stroked his ego, put herself in his shoes, and gave him a compliment while redirecting the conversation to the critical point to solve the problem. 

After this encounter, Gwenn realized that this happens too often in the business world, so she put together her must-follow strategies to deal successfully with difficult people:

Understand the Landscape

First, it’s important to understand the environment and the individuals you’re dealing with. Explore the parameters of your situation and strategize.

Ask yourself: Is initiating a conversation the right approach? Would involving others contribute positively to the situation?

These questions will help guide and navigate the situation, and its limits to handle it effectively.

This way, you can formulate an empathetic and efficient strategy, facilitating productive discussions even with the most challenging individuals.

Don’t take it Personally. 

When dealing with difficult bosses, remember one thing: It often doesn’t have anything to do with you!

Their behavior or comments often reflect more about them than you. When someone acts out or criticizes unnecessarily, it’s a manifestation of their insecurities or frustrations rather than a reflection of their abilities or worth. 

Don’t take it personally. Instead, consider it an opportunity to demonstrate professionalism. 

Your response to adversity and the results of your job will speak louder than any critique. 

Understand What They Want from You: Provide Clarity

In an ideal world, every supervisor and boss would clearly articulate their expectations. However, bad leaders usually don’t. 

So, how do you navigate this situation? 

Ask targeted questions to gain insights into their priorities and what they anticipate from you. Don’t hesitate to dive deeper if things seem ambiguous. 

Questions like, “What are your key objectives for this project?” or “How do you envision my role contributing to our team’s success?” can provide valuable clarity.

Set Limits

Many leaders don’t know boundaries! They will ask you to do things that might be out of your comfort zone or make you feel bad with their comments. 

How can you prevent this? Have heart-to-heart and specific conversations about what you are struggling with. 

Are you feeling drained or unmotivated? Perhaps the humor in the workplace feels inappropriate, or the working hours border on extreme? Whatever your concerns may be, they deserve to be heard and addressed.

After you express your concerns, set limits in a clear way and always provide a solution. For example, if you’re feeling overwhelmed by long working hours, propose an alternate schedule that allows for a better work-life balance.

Have Clear Communication

With clear, concise, and confident communication; you can navigate through the challenges with your difficult boss while building trust and fostering a productive work environment.

Here’s how you can enhance your communication prowess:

Document Everything

Keep a record of all important discussions, instructions, and processes. 

This will serve as your personal playbook, guiding you through tasks and decisions, and will provide clarity when someone asks you about the way you go about certain things. 


Don’t Ask Twice

Try to ask each question only once. Most difficult people don’t like to repeat themselves. 

This approach showcases your competence and attention to detail. Demonstrate your commitment to understanding and delivering on expectations.

Keep Your Cool

Maintain a calm and composed demeanor, especially during high-stress conversations. 

Your serene approach can influence the overall tone of the discussion, leading to more calm and effective outcomes.

Seek Help From Others

Remember that you’re not alone. Enlisting the support of your colleagues can not only validate your concerns but also pave the way towards collective problem-solving.

But a word of caution – this isn’t an invitation for workplace gossip. Instead, it’s about fostering a supportive environment where feelings are acknowledged, and solutions are sought together.


Learn From the Experience

Every challenge is an opportunity for personal growth, a chance to refine your communication skills, and a stepping stone towards resilience.

Remember, these experiences aren’t just building your character; they’re shaping you into a more empathetic, confident, and competent professional.

And finally, amidst all the hustle, never lose sight of what truly matters – your health and happiness. 

By following these simple tips, you can make your relationship with difficult people in the workplace work better for you and many others! 

Don’t be afraid to speak up and provide clarity. 

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