In the high-stakes world of hostage negotiation, words can mean the difference between life and death. During my years as the FBI's lead international kidnapping negotiator, I discovered that some of the most powerful phrases are also the simplest.
Today, I want you to explore four seemingly innocent words that can completely transform your negotiation power: "How am I supposed to do that?"
This calibrated question™, delivered with genuine curiosity and the right tone of voice, is one of the most effective tools in a negotiator's arsenal. It's not confrontational, yet it stops aggressive demands in their tracks. It's not defensive, yet it protects your position. Most importantly, it forces the other party to engage with reality and collaborate on solutions.
Let me paint a picture from my experience. Imagine you're negotiating with someone who demands, "I need this done by tomorrow morning, no exceptions." Instead of saying "no" or scrambling to comply, you respond with "How am I supposed to do that?" The magic happens in what follows.
This question accomplishes several critical objectives simultaneously. First, it makes the other party stop and consider the practical implications of their demand. They must now mentally walk through the actual steps required, often realizing the unreasonable nature of their timeline or request.
Second, it shifts the problem-solving burden back to them. When someone makes an impossible demand, they often haven't thought through the execution. By asking them to explain the "how," you're not being difficult – you're inviting them to engage with the operational reality of their request.
Third, and perhaps most powerfully, it does all this while minimizing defensive reactions. You're displaying genuine curiosity about their perspective while subtly exposing the flaws in their position.
The effectiveness of this phrase lies in its delivery. The tone should be calm, measured, and genuinely inquisitive. Think of yourself as a doctor asking a patient about their symptoms – professional, interested, and focused on understanding. This is not about being passive-aggressive or sarcastic. The moment your tone suggests mockery or frustration, you've lost the tactical advantage.
What makes this question particularly valuable is its versatility. It works in personal negotiations ("How am I supposed to pay that much?"), business settings ("How are we supposed to meet that deadline?"), and even internal dialogues when managing expectations ("How am I supposed to balance all these priorities?").
But here's the crucial point: this isn't just about buying time or deflecting demands. It's about initiating a collaborative problem-solving process. When used effectively, "How am I supposed to do that?" eight out of ten times leads to one of three outcomes:
The other party realizes their demand is unreasonable and modifies it voluntarily.
They begin brainstorming alternatives with you, transforming a confrontation into collaboration.
They reveal additional information or resources that actually make the request feasible.
What about the other two out of ten? The hidden point here is that this phrase is so instantly effective at such a high rate (80% success is a fantastic win rate) that the two times you get a different result will catch you unprepared if you don’t know what they are and how to respond.
#1: They tell you quite calmly exactly how to do it. This lets you know clearly they don’t intend to modify this point in any way.
Example: “How am I supposed to pay that price?” Answer: “You get out your credit card and pay it.”
You’ve just successfully learned you’re done the best you can on this point, without inflaming the situation - which is your job. Your choices are either: accept - or if you can’t, “I’m sorry that just doesn’t work for me.” And mean it. This is not a ploy and only works with complete integrity.
#2: Anger. “I don't care what happens to you! Just do it!” Reality here is they are under tremendous pressure. 1st: Mirror - “Just do it?” (Gently, calmly, soothingly.) This will buy you a few precious moments. Then (after a pause) “It sounds like you are under a lot of pressure.”
The beauty of this approach is that it maintains relationships while addressing impossible demands. You're not saying "no" – you're inviting the other party to help you understand and potentially find a way forward.
Remember, great negotiation isn't about winning or losing. It's about finding solutions that work for both parties. "How am I supposed to do that?" isn't a roadblock; it's a bridge to better understanding and more realistic agreements.
In your next difficult conversation, when faced with an unrealistic demand, try using these words. But remember – your success depends not just on the words themselves, but on your genuine curiosity and willingness to listen to the answer. The question might seem simple, but its impact on negotiations can be profound.