Years ago, I participated in an exceptional training program at Harvard Law School. One of the most valuable lessons I’ve applied in my negotiation advising and training is how to handle “Their Hardest Question.”
These are the questions you’d rather avoid but are bound to encounter, such as “Will you accept the margins we’ve proposed?”, “What’s your best price?”, or “Why should I choose your company over a cheaper competitor?”.
If you’re not ready for these questions, you risk leaving money on the table or losing the deal entirely. To ensure you’re prepared, consider these best practices for handling Their Hardest Question:
- Anticipate and imagine what their hardest question might be.
- Write out your full response in advance.
- Practice your delivery until it feels natural—whether that means reading it out loud, talking in front of a mirror, or role-playing with a colleague. Keep your response concise and to the point.
- A trusted friend can serve as your best devil’s advocate, offering valuable feedback.
- Record yourself delivering the answer using your phone.
- Review the video. Your first attempt might not be perfect but keep refining until you’re confident.
This approach works. I recently helped a client prepare for a negotiation meeting. Thanks to a structured preparation process, he felt more confident and was even looking forward to the toughest questions because he was ready. The result? He secured a significant margin increase.
In just a couple of hours, you too can be better equipped to succeed in your next negotiation. If you and your team need help crafting a compelling response (without compromising on honesty) and want to practice in a confidential and safe environment, reach out to us.