How Am I Supposed to Do That? Tactical Phrases to Push Back Without Losing the Client

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(7–8 minute read)

Somewhere between the client saying, “That’s more than we expected,” and your urge to slash your rates to save the booking… is the real work of negotiation.

It’s where strategy lives.
It’s where your confidence matters.
And it’s where a single, well-placed sentence can shift the whole energy of the conversation.

That sentence?

“How am I supposed to do that?”

It’s one of the most powerful tools in a vendor’s communication toolkit—and it doesn’t just come from gut instinct. It comes from hostage negotiation strategy.

Let’s break down how to use this and other calibrated questions to maintain control, gain clarity, and guide potential clients without giving up your value.


Why This Phrase Works

This isn’t a flippant retort or passive-aggressive jab. It’s a tactical calibrated question—a technique that:

  • Keeps the conversation open

  • Places the problem in the client’s hands (without creating defensiveness)

  • Signals to the client that you're listening and engaged

  • Gives them a sense of control, while you stay in charge of the direction

When delivered in a calm, confident tone, “How am I supposed to do that?” doesn’t read as resistance—it reads as realism.

And the best part? It invites collaboration. Instead of defending your price or justifying your expertise, you’re allowing the client to walk themselves toward understanding your limits.


The Psychology Behind It

Chris Voss calls this technique “creating the illusion of control.”

In wedding vendor terms? It means your client feels like they’re leading the conversation, when in fact, you’re the one holding the reins.

Here’s why it works:

  • It’s disarming. The question sounds humble and open-ended—not combative.

  • It’s personal. The word “I” forces the client to see you as a real person with limits, not just a service provider with a price tag.

  • It’s solution-focused. It doesn’t shut the conversation down—it opens a path to problem-solve together.


When to Use It

Use this phrase any time a client asks for something outside of scope, budget, or boundaries. Some examples:

When they ask for a lower price:

“How am I supposed to offer the same experience at a lower rate?”

When they want extra hours or services added without cost:

“How am I supposed to provide all of that without changing the agreement?”

When they ask for last-minute flexibility or add-ons:

“How am I supposed to accommodate that with the timeline we have?”

Every version communicates this: I want to help you, but we have to solve this together.


Other Calibrated Questions to Keep in Your Pocket

If you’re trying to move the conversation forward without folding, rotate in these powerful follow-ups:

  • “What about this is most important to you?”
    Helps shift the conversation away from price and toward priority.

  • “How would you like me to proceed if we can’t change the price?”
    Gives them ownership of the next move—without you backing down.

  • “What’s the biggest concern you’re trying to avoid?”
    Brings their fear or hesitation into the open, which gives you leverage.

  • “What would make this feel like a win for you?”
    Creates a collaborative frame. You're not enemies. You’re partners trying to build a great outcome.


Tone Matters More Than Words

Your tone is everything here. Voss calls it the “late-night FM DJ voice”—calm, slow, low, and relaxed.

Here’s what that does:

  • Prevents defensiveness

  • Creates an environment of trust

  • Sends the signal that you’re composed, not desperate

Tip: Practice delivering these phrases out loud until you can say them with zero edge or apology in your voice.


Real-World Example: The Over-Eager Add-On

Let’s say a bride asks for you to add an extra hour of setup the morning of her wedding—at no extra charge.

Here’s the wrong approach:

“That’s not included in the package. I’d have to charge extra.”

Here’s the better approach:

“I want to make sure your morning goes smoothly. How am I supposed to shift my schedule and staffing without changing the agreement?”

She now sees it’s not a flat-out no. It’s a practical limitation—and it gives her a chance to adjust or prioritize. She might offer to pay, scale something back, or drop the request altogether.


My Advice

When clients make big asks or push your boundaries, don’t jump into defense mode.
And definitely don’t jump to discounts.

Use these questions to keep the door open and the tone respectful—while still protecting your time, expertise, and bottom line.

Negotiation isn’t about having the right answers.
It’s about asking the right questions—and letting those do the heavy lifting for you.

Want to take it further? Start tracking the kinds of pushback you hear most, and build a script library using the questions in this post.

Because when you learn to lead the conversation with strategy, not emotion?

You don’t just book more clients.
You book better ones.


—Bailey J.