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Short Summary
Main recommendation: Use "How am I supposed to do that?" as a deliberate phase of no, a calibrated question that makes the other party reconsider their demand and solve the problem themselves. Hold it for when it is most appropriate in the conversation or relationship, and prime the other party beforehand so the phrase does not shock them. The speakers also stress building the skill in your own voice and combining tactical empathy with assertive, firm statements.
Key Points
- Priming matters: saying something like "That's going to be really difficult, and we're going to have to try to think of a creative solution" before implying "How am I supposed to do that?" lowers the other party's expectation so the phrase does not come as a shock.
- The question works by shaping thinking: it engages the other party's problem-solving brain so they bargain with themselves, meaning you do not have to state a no or offer alternatives.
- Keep the other party disarmed for as long as possible, using tactical empathy, and only switch to a serious tone when a firm line must be drawn.
- Firm limits still have to be stated at some point: "That is something that will have to remain," said in a serious voice the speaker says he's only used twice out of 50 other times.
- Adapt the method to your own style. The speakers say everyone has their own spin on the Black Swan method, and the goal is to make these skills part of your repertoire.
Details Worth Noting
- Concrete instructions:
- Priming step: before using the question, say something like "That's going to be really difficult, and we're going to have to try to think of a creative solution," then imply "How am I supposed to do that?"
- Reserve the direct phrase "How am I supposed to do that?" for later in the conversation or relationship, when it is appropriate, rather than early on.
- Keep the tone warm and curious for most of the conversation, and only drop into a serious voice when you must draw your line.
- Firm-line script for a serious moment: "I'm sorry, I ran up the flagpole and nobody saluted. This is going to catch you off guard. This is going to be disappointing to hear. It's going to feel like I punched you in the stomach. We just can't do that."
- After asking the question, let the other party stew rather than immediately offering solutions or explaining a no. In the example given, silence for two days led the customer to return with a signed proposal.
- A negotiation example: after three or four months of back-and-forth on prices, a customer began picking apart the proposal à la carte. The caller asked "How am I supposed to let you pick apart my proposal like that?", the customer went silent for two days, and then signed.
- Caveat from the speakers: a skilled-sounding approach can still backfire. The other party can arm up quickly, so getting things right 90 percent of the time can be undone by the remaining 10 percent.
Bottom Line
A calibrated question like "How am I supposed to do that?" is most effective when it is prepared, timed, and followed by silence, letting the other party solve the problem themselves rather than receiving a flat refusal.
