5 Proven Strategies to Master Negotiating with Difficult People

Negotiation: How to Successfully Navigate Difficult Conversations

Negotiation is a skill that can be applied to multiple aspects of life, from high-stakes corporate deals to everyday disputes. It can create win-win situations that are beneficial for all parties involved. However, in the midst of a pandemic where tensions are high, it can be challenging to negotiate successfully, especially with people who do not play nice. To help navigate difficult conversations, here are some expert-backed tips on how to negotiate effectively.

Before Negotiation Begins

One of the most important aspects of negotiation is preparation. Before any discussion with the other party, it is essential to think through possible solutions so that you arrive at the negotiation table prepared. Try to anticipate how the conversation could go and prepare for possible outcomes.

For example, if you are seeking a promotion but your boss says it is too soon to consider it, you should highlight your contributions to the team and the value you have created. By doing your homework ahead of time, you will feel more confident, and you will signal to your counterpart that you are invested in the outcome.

Before difficult negotiations, Susan Hackley, Managing Director of Harvard Law School’s Program on Negotiation, recommends considering the following questions:

– What are your hot-button issues?
– What is essential to you?
– What is unacceptable?
– What are you likely to hear from your opponent?
– How will you react?

By preparing ahead of time, you are setting yourself up for success.

Be a Giver

Instead of heading into negotiations focusing on what you stand to gain, try to start from a place of generosity. Research has shown that being generous while negotiating may be a sign of intelligence. Additionally, people who exhibit generosity during negotiations tend to make their counterparts better negotiators too. These smarter individuals who focus on how to meet their counterpart’s needs and not just satisfy their own tend to form stronger, long-term relationships.

During Negotiations

After you have done your preparation work and have a solid understanding of the issues, it is time to move into the negotiation process. Here are some effective strategies for navigating conversations that are both difficult and contentious:

Ask Questions to Uncover Hidden Motivations

When individuals head into negotiations, they tend to focus on their objective and what they want to say. However, according to experts, listening is even more critical to discovering the best solution for both parties. Former FBI negotiator Chris Voss explains: “We like to say that the key to flexibility is don’t be so sure of what you want that you wouldn’t take something better. If you’re focused on the number, you’re not seeing the other possibilities.”

By asking questions and listening, you can convey to the other party that you are invested in finding a mutually satisfying solution. This approach can also help you understand the other party’s concerns and underlying motivations. It is only by gathering this information that you can effectively come up with a solution that works for both sides.

Involve Your Counterpart in Finding a Solution

When dealing with hard bargainers, changing the game “from face-to-face confrontation into side-by-side problem-solving” can be highly effective. This approach involves restructuring the alignment of typical negotiations. Instead of trying to convince your counterpart to agree with your proposal, try presenting a few options and work through the reasoning behind each of them.

By allowing your counterpart to participate in the problem-solving process, you are creating an environment where they feel respected and heard. This process can build trust and rapport between parties, leading to a more positive and productive outcome.

Keep Aggression at Bay

Aggression has been shown to not only be unproductive but can also hamper the negotiation process. Instead, try to remain calm and collected throughout the negotiation process. William Ury, co-founder of Harvard Law School’s Program on Negotiation, suggests taking yourself mentally to a place where you can look down objectively on the dispute and plan your response. Removing your emotions from the situation can help to diffuse high-stress situations and lead to a more productive conversation.

Last-Ditch Efforts

Even after all of the preparation and effective strategies, sometimes negotiations can still be difficult. Here are some last-ditch efforts that might help:

Loop in Others

If you can’t seem to make any headway, sometimes it can be helpful to loop others into the process. Whether you CC relevant people or invite third parties to the meeting, you are creating documentation of your good-faith efforts to come up with an agreement. Additionally, holding the other party accountable for his or her actions can help to change the tone of the conversation. People are less likely to act unreasonably or disrespectful when there is another set of eyes on the situation.

Preserve the Relationship

Negotiation is not just about accomplishing what you came to do; it is also about preserving the relationship. Even if an agreement is not reached, concluding on an amicable note will help with future negotiations. Expressing genuine appreciation or even a little humor can go a long way. As Chris Voss advises, “Never be mean to someone who can hurt you by doing nothing. If you’re good, they’ll be delighted to do for you whatever they can. A playful, enjoyable attitude gives you latitude.”


Negotiation can be a challenging process, especially when faced with difficult counterparts. However, with the right strategies in place, individuals can achieve positive outcomes and maintain important relationships. By being prepared, generous, and focused on the other party’s needs, individuals can move towards a mutually satisfying outcome for both parties.

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