Sharks in Suits: Negotiating With Difficult People

Sharks in Suits: Negotiating With Difficult People

Negotiation is rarely easy—but it becomes especially challenging when the other person discloses difficult personality traits or behaviors – is defensive, aggressive, manipulative, or uncooperative. The key to success isn’t winning the argument—it’s managing the interaction.

This is what make you can do to manage difficult personalities better:

1. Understand What Makes Someone “Difficult”

Difficult behavior usually comes from one (or more) of these sources:

  • Fear of loss, failure, or change
  • Ego and a need to feel powerful or right
  • Lack of trust or past negative experiences
  • Stress or pressure unrelated to the negotiation

Instead of labeling the person as the problem, focus on the behavior and underlying motivation. This mindset shift alone can reduce tension and open the door to solutions.

2. Control Your Emotions First

When someone is confrontational or unreasonable, it’s easy to react emotionally. Unfortunately, emotional reactions weaken your position.

What to do instead:

  • Pause before responding
  • Keep your tone calm and steady
  • Use neutral language, even when provoked

Remember: the calmer party has the advantage in any negotiation.

3. Listen More Than You Speak

Difficult people often want one thing above all else: to feel heard.

Active listening helps disarm hostility and builds leverage.

Try:

  • Letting them finish without interruption
  • Paraphrasing their concerns (“What I’m hearing is…”)
  • Asking clarifying questions instead of pushing back immediately

Listening does not mean agreeing—it means gathering information and lowering resistance.

4. Set Clear Boundaries

Being calm does not mean being passive. Difficult negotiators often test limits.

Be clear and firm about:

  • What you can and cannot agree to
  • Consequences of non-agreement
  • Timeframes and expectations

Boundaries protect you and signal confidence.

5. Know When to Walk Away

Not every negotiation is worth winning.

If the other party:

  • Refuses to negotiate in good faith
  • Becomes abusive or unethical
  • Pushes terms that harm your core interests

Walking away is not failure—it’s strategic self-respect.

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