Timing Your Calibrated Question: How to Use “How Am I Supposed to Do That?” Effectively

"How am I supposed to do that?"—it's one of the most powerful phrases in negotiation, but most people fumble the timing. This Calibrated Question, an important part  of The Black Swan Method™, is not just about what you say but when and how you say it. Let’s unpack the art and science behind this pivotal question  and explore why using it too soon can backfire.

Negotiation, like any complex dance, unfolds in phases. First, there’s the rapport-building phase, where you establish connection and trust.  This happens when you explore the other side’s vision and circumstances through Tactical Empathy™—acknowledging their feelings and demonstrating you understand their perspective.  The Black Swan skills allow you to gather information that will prove valuable when collaborating with your counterpart.  If needed, the Calibrated Question “How am I supposed to do that?” can then effectively allow the other side to solve your problem.  

The Power Behind “How am I supposed to do that?”

At its core, the question  isn’t a refusal; it’s an invitation. You’re flipping the dynamic, prompting your counterpart to want to solve a problem for you. They feel like they’re still in charge, even though the work is now on them.

Here’s why it works:

• It’s not a yes-or-no question. You’re not shutting the door but asking them to reframe the terms of the discussion.
• It does not induce an obligation to give something back when your counterpart gives you the answer.
• It is a Phase of No, without saying “no.” Rather than rejecting an offer outright, you’re nudging them to re-examine it.
• It shifts responsibility. Your counterpart now must justify or tweak their position without you coming off as combative.  They begin to negotiate with themselves

When Not to Use “How am I supposed to do that?”

I’ve seen negotiators deploy this phrase like a sledgehammer, hoping it will instantly flip the script. 

1. Too Early in the Negotiation. Jumping to this question too soon is like trying to drop the punchline before you’ve told the joke. Asking this before understanding the other side’s needs or expressing Tactical Empathy™ will feel like stonewalling. You must first recognize and articulate their perspective, a key component of Tactical Empathy™. If you place this query on your counterpart too early, you risk offending the other side due to its assertive nature.  Without first demonstrating Tactical Empathy™, “How am I supposed to do that?” will might feel like an attack on the other side.
   
   The mistake of using “How am I supposed to do that?” too early comes from anxiety. People get nervous about confrontation and want to push back before they’ve absorbed the other side’s point. It’s a knee-jerk reaction to feeling uncomfortable with the conversation's direction.
   
   To avoid this, lean into the discomfort. Slow down the negotiation. Use asking Labels and other Calibrated Questions first.  It sounds like you have given some thought to how that might look?  Or, “What is the biggest obstacle you face?” This allows you to draw out your counterpart’s thinking without putting them on the defensive.   
   
   
2. Without Adequate Setup. Tactical Empathy™ followed by an Accusation Audit or two should precede your, “How am I      supposed to do that?”   It could sound something like, “Your offer is very generous (Dynamic Silence).  This is going to sound horrible (Dynamic Silence).  “How am I supposed to do that?” 
   
   
3. In Response to a Genuine Offer. If someone presents a reasonable offer, throwing this question out can derail the progress. You need to feel the flow of conversation. Use it when the other side is pushing for an unreasonable concession, not when they’re extending a hand.

How to Use “How am I supposed to do that?” Like a Pro

1.  Delivery is everything. Chris Voss often refers to the “late-night FM DJ voice”—calm, slow, and deliberate. Tone determines how your counterpart receives your message. A rushed or aggressive delivery can be interpreted as frustration, while a low and slow tone invites reflection and problem-solving.
   
   
2. Let it Breathe. Once you ask, stop talking. Dynamic Silence is your ally here. It forces the other person to think, filling the space with psychological weight. They will often negotiate with themselves as they search for a solution to your problem.  Fear is a strong driver of human decision-making and behavior.  When the other side starts negotiating with themselves, they fear they might lose something if they do not solve your posed problem.  They want to give you the “how.”   
    
3. May have to use it more than once. The first use may garner some movement in your direction but you should not stop there.  Hit it at least one more time.  You will either get additional movement or you will get, “If you want this, you’d better figure something out”, which is actually where you want to be as this is an indication you have pushed as far as you can. 

Once you’ve gathered enough information, framed the conversation through Tactical Empathy™, and given the other side room to explain their position, you ask, “How am I supposed to do that?” By this point, they’re emotionally invested, and their instinct will be to work with you rather than against you.

Final Thought: Mastering the Phases

Negotiation is a strategic game.  It’s not the moves you make but when you make them. “How am I supposed to do that?” is a game-changing move, but only if you play it correctly.. First, demonstrate Tactical Empathy™, establish trust, build rapport, and show that you’re listening. Then, when the moment is ripe, drop the question like a velvet hammer and watch your counterpart scramble to make things work for you.  '