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Chapter 14: Writing Proposals That Win

Beyond structure, specific tactics improve conversion rates. The first 48 hours after discovery are critical.

What You'll Learn

  • The 48-hour rule for follow-up
  • Payment structures that close deals
  • Building social proof systematically
  • Loom videos for proposal delivery

The 48-Hour Rule

Critical Window

Proposals sent within 48 hours are significantly more likely to close than those sent after a week.

The Follow-Up Timeline

Time Action
Same day Thank you email with next steps
24 hours Send something valuable (article, resource)
48 hours Deliver proposal before review call

Why Speed Matters

  • Momentum is high immediately after discovery
  • They haven't talked to competitors yet
  • Your conversation is still fresh
  • Urgency you created is still active
  • They haven't gotten distracted by other priorities

Same-Day Follow-Up Email

Send within 2 hours of the discovery call:

Subject: Great conversation about [specific outcome discussed]

Hi [Name],

Thank you for taking the time to discuss [specific challenge] today. 
I'm particularly excited about your vision to [specific goal they mentioned].

As promised, I'll have a comprehensive proposal ready by [specific date]. 
I've blocked time on [date/time] for us to review it together—
I'll send a calendar invite shortly.

In the meantime, I'm going to research [specific area discussed] 
to ensure our approach aligns with your [specific constraint mentioned].

Looking forward to our next conversation.

Best,
[Your name]

24-Hour Value Add

Send within 24 hours with relevant value:

Subject: Resource for [specific challenge discussed]

Hi [Name],

I was thinking about your [specific challenge] after our call. 
Here's a [case study/article/framework] that might be relevant: [link]

The particularly relevant part is [specific section] which addresses 
your concern about [specific concern].

This reinforces my thinking about the approach we discussed. 
Looking forward to sharing the full proposal on [date].

Best,
[Your name]

This email: - Shows you're thinking about them - Provides immediate value - Reinforces your expertise - Builds anticipation for the proposal

Proposal Delivery Email

Send with the proposal:

Subject: Your [Company] AI Strategy Proposal

Hi [Name],

Attached is the proposal we discussed for achieving [specific outcome].

I've structured it around the three key objectives you mentioned:
1. [Objective from call]
2. [Objective from call]
3. [Objective from call]

I'm looking forward to walking through this together on [day] at [time]. 
Please review beforehand if you have time, but we'll cover everything 
in detail during our call.

Best,
[Your name]

Using Loom Videos

Record a video walking through the proposal:

Benefits

Benefit Why It Matters
Personal touch Is different from text-only proposals
Handles objections Address concerns proactively
Easy to share Client can forward to stakeholders
Shows expertise You're presenting, not just documenting

The Script

  1. Open (30 sec): "Hi [Name], I'm excited to walk you through this proposal..."
  2. Situation (1-2 min): Summarize what you heard and understood
  3. Approach (2-3 min): Walk through your methodology
  4. Options (2-3 min): Explain each tier and who it's best for
  5. Close (30 sec): "I'm looking forward to discussing on [date]..."

The Power Move

"They sent me a Loom video going over the proposal in case I had to share with somebody else. They wouldn't even let me pitch their proposal to somebody else—they pitched it for themselves."

Your video does your selling even when you're not in the room.

Payment Structures That Close

The right payment structure can turn a "maybe" into a "yes."

Structure 1: The 50/50 Split

  • 50% upfront
  • 50% at 45 days

Why it works. Gives clients confidence while securing your commitment.

Structure 2: The Upfront Discount

  • Standard: $50K in two payments
  • Prepaid: $45K if paid in full now (10% off)

Why it works. CFOs love saving money. Most clients choose this.

Structure 3: The Success-Based Option

  • Lower base fee
  • Bonus tied to specific outcomes

Why it works. Aligns incentives perfectly.

How to Present

Investment: $50,000

Payment Options:
- Standard: $25,000 upon agreement, $25,000 at 30 days
- Prepayment: $45,000 if paid in full (10% discount)

Building Social Proof

Nothing sells your services better than proven results.

When to Ask for Testimonials

Timing. After delivering a clear win (30-60 days in)

How to Ask

Make it easy—draft the testimonial for them:

Subject: Quick favor - sharing our success

Hi [Name],

I'm thrilled with the progress we've made on [specific achievement]. 
Your team's execution has been outstanding.

Would you be comfortable providing a brief testimonial about our work together? 
I'm particularly proud of [specific result] and would love to share this.

I've drafted something below based on our results—feel free to edit or provide your own:

"[Draft testimonial focusing on specific results and value]"

Also, may I include [Company] logo on my website's client list?

Thanks!
[Your name]

What to Request

Type Usage
Written testimonial Website, proposals
LinkedIn recommendation Profile credibility
Logo rights "Clients include..." section
Case study permission Detailed marketing content
Referral commitment New client introductions

Follow-Up Sequences

If you don't hear back after the proposal:

Day 5

"Hi [Name], wanted to check if you're still committed to [specific outcome by specific date]. Happy to adjust our approach if priorities have shifted."

Day 10

"Hi [Name], I know you mentioned [specific consequence of not solving problem]. Is this still a priority? If timing has changed, I can adjust our proposal accordingly."

Day 15

"Hi [Name], I'll close out your proposal for now. If [specific pain point] becomes urgent again, I'm happy to revisit. Wishing you success with [their goal]."

Key Principles

  • Reference their stakes, not your proposal
  • Give them an easy out (preserves relationship)
  • Set clear expectations about follow-up
  • Know when to stop (3 follow-ups maximum)

Schedule the Next Meeting Immediately

At the end of every discovery call:

"It sounds like what you really need is to [summarize need]. I'm going to send you a proposal sometime next week. Are you available this time next week to review it together?"

Then send the calendar invite before you hang up:

"Great, I'm sending the calendar invite now so we have it locked in. Let me know if you need to reschedule."

This single habit increases close rates.

Common Proposal Mistakes

Mistake 1: Waiting Too Long

Every day you wait, conversion probability drops.

Mistake 2: Generic Content

The proposal should feel like it was written for this specific client.

Mistake 3: Missing the Review Call

Without a scheduled review, proposals go into a black hole.

Mistake 4: No Video

You're missing an opportunity to stand out and handle objections.

Mistake 5: Weak Follow-Up

Generic "checking in" emails don't create urgency.

Action Items

  1. Create your email sequence. Write templates for same-day, 24-hour, and proposal delivery emails.

  2. Record a sample Loom. Practice your proposal walkthrough on a recent proposal.

  3. Define your payment options. Create 2-3 payment structures you can offer.

  4. Write your testimonial template. Draft the request email with placeholder testimonial.

  5. Build your follow-up sequence. Write the Day 5, 10, and 15 follow-up emails.

Key Takeaways

  • The 48-hour rule: proposals sent within 48 hours close at significantly higher rates
  • Use a three-email sequence: same-day thanks, 24-hour value, proposal delivery
  • Loom videos let your proposal pitch itself even when you're not there
  • Payment structure matters: 50/50, upfront discount, or success-based
  • Ask for testimonials 30-60 days in, after delivering a clear win
  • Follow up references their stakes, not your proposal
  • Always schedule the review call before the discovery call ends

Next: Chapter 15: Handling Objections →