Chapter 10

Chapter 6: The Art of the Ask

6 min read

Jennifer sat in her car for twenty minutes, rehearsing.

"I deserve this raise. No, that sounds entitled. I've earned this raise. Too aggressive? I'd like to discuss compensation. Too weak!"

Sound familiar?

Here's the truth: How you ask determines what you get. The good news? Asking effectively is a skill anyone can master.

Framing Your Request for Success

The same request can sound reasonable or ridiculous depending on how you frame it.

Watch this:

Poor Frame: "I need a raise because my rent went up." Strong Frame: "I'd like to discuss adjusting my compensation to reflect my expanded role and contributions."

Poor Frame: "Can I have Friday off?" Strong Frame: "I'd like to propose a schedule adjustment that maintains my productivity while addressing a personal commitment."

The first versions focus on your needs. The second versions focus on mutual benefit.

The Psychology of Persuasion

People naturally respond to certain psychological triggers. Use them ethically:

Reciprocity: People want to return favors "I've taken on extra projects these past six months. I'd like to discuss how we can align my compensation with these contributions."

Social Proof: People follow others' lead "Based on my research of similar roles in our market..."

Authority: People respect expertise "In my ten years of experience, I've found that..."

Consistency: People align with their stated values "You mentioned valuing innovation. My proposal supports that by..."

Liking: People say yes to those they like Build rapport before making your ask

Scarcity: People value rare things "This opportunity won't be available long..."

Kevin used these principles when asking for a promotion. He mentioned his unique certifications (scarcity), quoted industry standards (authority), and reminded his boss of past praise (consistency). He got the promotion and a 20% raise.

Timing Is Everything

When you ask matters as much as what you ask for.

Good Timing: - After a success or win - During planning periods - When they're in a good mood - Before busy seasons - When you have leverage

Bad Timing: - During crisis or stress - Right before deadlines - Monday mornings or Friday afternoons - After bad news - When they're rushed

Maria wanted to negotiate work-from-home privileges. She waited until after successfully completing a major project, during the company's annual planning cycle. Her boss was receptive and approved two days per week.

The Perfect Ask Formula

Use this structure for any request:

1. Context: Brief background 2. Value: What you've contributed 3. Request: Specific and clear 4. Benefit: How it helps them 5. Next Step: Clear action item

Example: "Over the past year, I've expanded our social media presence by 200% and generated fifty qualified leads. Based on this performance and market research, I'd like to discuss a salary adjustment to $75,000. This ensures you retain top talent as we enter our growth phase. Could we schedule time this week to discuss?"

Power Phrases That Work

Keep these in your back pocket:

To Open: - "I'd like to propose something that benefits us both..." - "I've been thinking about how we can..." - "I have an idea that could help us achieve..."

To Build Agreement: - "As you know..." - "You've mentioned before that..." - "Building on our conversation about..."

To Handle Resistance: - "I understand your concern. What if we..." - "That's a fair point. How about..." - "I hear you. Another approach might be..."

To Close: - "What questions do you have?" - "What would make this work for you?" - "What's our next step?"

The Anchor Effect

The first number sets the tone. Start higher than your target.

If you want $70,000, ask for $78,000. If you want two weeks vacation, ask for three.

This isn't greed—it's psychology. The anchor gives you room to negotiate while making your real target seem reasonable.

Tom wanted to sell his consulting services for $5,000. He quoted $7,500. The client countered at $6,000. Tom "reluctantly" accepted—$1,000 more than his target.

Making the Intangible Tangible

Abstract requests get abstract responses. Concrete requests get concrete results.

Weak: "I want more responsibility." Strong: "I'd like to lead the product launch team and manage the $50,000 marketing budget."

Weak: "I need work-life balance." Strong: "I'd like to leave at 3 PM on Tuesdays and Thursdays to coach my daughter's team, making up the hours by starting at 7 AM those days."

Specificity shows you've thought it through and makes it easier to say yes.

The Confidence Connection

Your delivery matters as much as your words.

Body Language: - Stand or sit tall - Make appropriate eye contact - Keep hands visible and still - Smile when appropriate - Breathe normally

Voice: - Speak slowly and clearly - Lower your pitch slightly - Pause after important points - Avoid uptalk (ending statements like questions?) - Project calm confidence

Practice in a mirror or record yourself. You'll be surprised what you notice.

Handling Common Responses

Be ready for these standard pushbacks:

"We don't have budget" "I understand budgets are tight. What would need to happen for this to become possible?"

"That's not our policy" "I appreciate policies exist for good reasons. Have there been situations where exceptions made sense?"

"I need to think about it" "Of course. What specific information would help you evaluate this?"

"The timing isn't right" "I understand. When would be better? What would need to be in place?"

Never accept the first no as final. It's often just the beginning of the conversation.

The Email Ask

Sometimes you need to ask in writing. Follow these rules:

1. Subject line that summarizes: "Proposal: Part-Time Remote Work Arrangement"

2. Brief and scannable: Use bullet points and short paragraphs

3. Clear call to action: "Could we discuss this Tuesday at 2 PM?"

4. Professional but warm: Write like you talk, but polished

5. Proofread twice: Errors undermine credibility

The Ask Recovery

Messed up your ask? It happens. Here's how to recover:

"I realize I didn't explain that well. Let me try again..."

"Actually, let me back up and share the full context..."

"What I meant to say was..."

Don't panic. Pause, breathe, and reframe.

Building Your Ask Muscle

Like any skill, asking gets easier with practice:

Week 1: Ask for small things (extra sauce, different table, early appointment)

Week 2: Make medium asks (return without receipt, deadline extension, small favor)

Week 3: Practice work asks (feedback meeting, resource request, schedule change)

Week 4: Go for something big (raise, promotion, major purchase negotiation)

Track your success rate. You'll be amazed how often people say yes.

Your Ask Action Plan

1. Write your next ask using the Perfect Ask Formula

2. Practice in the mirror until it feels natural

3. Identify your anchor - what's higher than your real target?

4. List three power phrases you'll use

5. Schedule it - pick the optimal time

Remember: You miss 100% of the shots you don't take. But when you master the art of the ask, your success rate skyrockets.

The worst they can say is no. But when you ask skillfully, they usually don't.

In the next chapter, we'll prepare you for those times when you do hear no—and show you how to turn objections into opportunities.

Get ready to become unstoppable.