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I am not Afraid - Negotiating with Difficult Bosses in the workplace

Negotiating with a dominant or aggressive manager can be one of the most challenging situations in a professional environment. But you can do it!


Challenges in Negotiating with Difficult Bosses in the Workplace


Negotiating with a boss who exerts a dominant or aggressive management style presents unique challenges. These managers often wield their authority and assertiveness in a way that can be intimidating. They may have a tendency to dominate conversations, dismiss opinions, and push their agenda aggressively. The goal here is to ensure your voice is heard and respected without escalating the situation.



Rubik's cube indicating complexity
Photo courtesy - Unsplash

Understanding Dominant and Aggressive Managers


Difficult bosses often exhibit traits like assertiveness, impatience, and a strong desire to control situations. They may also be results-driven, which can lead to a disregard for the process or the people involved. Recognizing these traits helps in strategizing your approach. Each individual will have a unique reason why they are seen as difficult. The important thing is to have a strategy going into any conversation with such a boss.


Key Negotiation Principles and Strategies

  1. Your Want Portfolio: This is a list of all the things you want to ask for. This list should be ranked in order of priority. Having this list front and center will help you focus on the critical things.

  2. Assertive Communication: Communicate your points clearly and confidently without being confrontational.

  3. Listen Actively: Show that you value their perspective, which can make them more receptive to yours.


Identifying and Managing Conflict during Negotiations


The key is to identify potential conflict points early and manage them constructively. Use techniques like reframing the conversation, focusing on mutual goals, and employing 'I' statements to express your viewpoint without aggression.


If your boss employs aggressive, hardball negotiation tactics, then it's important to shift to direct and frank speech, indicating that you will not be intimidated. This could be as simple as:


"I appreciate that you don't like this "ask," however, based on XYZ evidence, let's keep working on it to find a win-win solution."


However, all of this is easier said than done. So, focus on building your resilience ahead of time.


Building Personal Resilience in Tough Negotiations

Negotiating with dominant, aggressive bosses can be draining. Spend time preparing ahead of time.


Building personal resilience is essential. This involves:


  • Staying Confident in Your Abilities: Believe in your skills and worth, irrespective of the pushback you receive.

  • Remember your North Star: Generally, these are values. And next your Want Portfolio.

  • Remind Yourself: Understand that it's often a reflection of their management style, not your performance or your personality.

  • Take a Break. If you feel your emotions are getting ruffled, say in an even tone, "I see you may need more time to consider my request, I am happy to discuss next week. Shall I find a time that works for the both of us?

Encountering difficult people and navigating challenging conversations are inevitable aspects of both personal and professional life.


Employing the tools and techniques mentioned in this post can significantly improve your ability to handle these situations effectively.


It's important to acknowledge that if assertiveness does not come naturally to you, developing this skill will require patience and consistent practice. This is not a quick transformation but a gradual evolution in your communication style and confidence. Over time you will feel more at east with negotiating with difficult bosses in the workplace


Start by applying these strategies in less intimidating, everyday scenarios. Engage in assertive communication during team meetings, or practice negotiation skills in regular interactions, like making a purchase or setting up appointments. Each of these instances provides a valuable opportunity to refine your approach and build your confidence.


Over time, as you become more comfortable and skilled in these techniques, you'll find yourself increasingly prepared to face even the most challenging bosses or daunting conversations.


You can start with the free training on negotiation here.

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