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How to Write Proposals That Actually Win

Most proposal advice is garbage. "Be professional." "Know your client." Thanks, very helpful. Here's what actually works—the strategies that took my win rate from 20% to over 65%.

15 min read
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The Hard TruthDiscovery CallStructurePricingFollow-upTemplates

The Hard Truth About Proposals

80% of proposals lose before the client even reads the pricing section.

Here's what I learned after sending 400+ proposals over 8 years: most freelancers and agencies treat proposals like a formality. They slap together some bullet points, throw in a price, and hope for the best.

That's exactly why they lose.

A proposal isn't a quote. It's not a contract. It's a sales document. Its only job is to make the client say "yes, let's do this."

Everything else—the fancy design, the detailed scope, the terms and conditions—is secondary. If your proposal doesn't make them want to work with you, none of that matters.

The One Thing That Changed Everything

I stopped sending proposals to people who weren't ready to buy. Sounds obvious, but I used to spend hours on proposals for anyone who asked. Now I qualify hard before writing a single word. My win rate tripled.

The Three Types of Proposal Requests

When someone asks for a proposal, they fall into one of three categories:

Ready to Buy

They have budget, timeline, and authority. They're comparing you to 1-2 others. Win rate: 60-80%

Gathering Info

They're interested but not committed. Need more nurturing before a proposal. Win rate: 20-30%

Price Shopping

They need a number for comparison or internal approval. Don't waste your time. Win rate: 5%

The goal isn't to write more proposals. It's to write fewer proposals to better-qualified prospects. That starts with a proper discovery call.

The Discovery Call That Wins Before You Write

A great proposal starts 30 minutes before you open your laptop.

Most people use discovery calls to gather requirements. That's a mistake. The real purpose of a discovery call is to:

  1. Qualify the opportunity (should you even send a proposal?)
  2. Understand their pain (not just what they want, but why)
  3. Establish yourself as the expert (so price becomes secondary)
  4. Get them to sell themselves (the most powerful technique)

These questions help you understand the real problem—not just the surface request.

"What's driving this project right now?"
Reveals urgency and budget priority. If they can't answer this clearly, they're not ready.
"What happens if you don't do this project?"
Forces them to articulate the cost of inaction. Use their answer in your proposal.
"What would a successful outcome look like in 6 months?"
Gets specific success metrics you can promise to deliver.
"Have you tried to solve this before? What happened?"
Reveals past failures, objections, and what NOT to do.

The Structure That Converts

Forget everything you've read about proposal structure. Here's what actually works.

Most proposal templates have this structure: About Us → Services → Pricing → Terms. That's backwards. You're leading with what you care about, not what they care about.

Here's the structure I use for every proposal. It's based on a simple principle: they need to feel understood before they'll trust your solution.

01

The Hook (Their Problem)

~100 words

Start with THEIR situation, not your introduction. Restate their problem using the exact language they used on the discovery call.

Example:
"You mentioned that your current website converts at 1.2% - well below the 3-4% industry average. That's costing you roughly $15,000/month in lost revenue."
This proves you listened and understand their specific situation.
02

The Stakes (Cost of Inaction)

~75 words

Paint a picture of what happens if they do nothing. Use numbers if possible.

Example:
"At current rates, you'll leave $180,000 on the table over the next 12 months. Meanwhile, your competitors are investing in conversion optimization and pulling ahead."
Creates urgency without being pushy. They sell themselves on needing to act.
03

The Transformation (Their Future)

~100 words

Describe what success looks like. Be specific and tie it to their goals.

Example:
"Imagine: 90 days from now, your site converts at 3.5%. That's an extra $8,000/month in revenue without spending more on ads. Your sales team has more qualified leads than they can handle."
Helps them visualize the outcome and builds desire before you present the solution.
04

The Solution (Your Approach)

~300 words

NOW you can talk about what you'll do. Focus on methodology and deliverables, not features.

Example:
Break it into 3-4 clear phases with outcomes for each. "Phase 1: Research & Audit - You'll know exactly why visitors aren't converting"
They understand the logic of your approach, not just a list of tasks.
05

The Proof (Why You)

~150 words

One or two relevant case studies. Not your whole portfolio - just proof you've solved THIS problem before.

Example:
"We did this exact work for [Similar Company]. They went from 1.8% to 4.2% conversion in 60 days, generating an additional $240,000 in their first year."
Reduces perceived risk. They're not the guinea pig.
06

The Investment (Pricing)

~200 words

Present options if possible. Always anchor against the value, not the cost.

Example:
See pricing section below for detailed strategy.
By now they want the solution. Price is a detail, not a barrier.
07

The Next Step (Make It Easy)

~50 words

One clear action. Not "let me know if you have questions" - that's weak.

Example:
"To move forward, click Accept below or reply to this email. I'll send a welcome packet and we'll schedule our kickoff call for next week."
Removes friction. They know exactly what to do.

Pricing That Doesn't Scare Them Off

The difference between a $5,000 project and a $15,000 project is usually presentation.

Here's the uncomfortable truth: most clients can afford more than you're charging. The reason they say no isn't the number—it's that you haven't made the value obvious enough.

❌ How Most People Present Pricing

Website Redesign: $8,000
SEO Setup: $2,000
Content Writing: $1,500
Total: $11,500

This invites line-item negotiation and comparison shopping.

✅ How to Present Pricing

Your investment to increase conversions from 1.2% to 3.5%:
$11,500
Projected first-year return: $96,000+ (8x ROI)

This anchors price to value, not to line items.

The 3-Option Strategy

Offering options does two things: it shifts the conversation from "should I buy?" to "which one should I buy?", and it anchors your preferred option against something more expensive.

Essential
$8,000
  • • Core deliverables only
  • • Standard timeline
  • • Email support
~15% choose this
RECOMMENDED
Professional
$12,000
  • • Everything in Essential
  • • Strategy session
  • • Priority support
  • • 30-day optimization
~60% choose this
Premium
$18,000
  • • Everything in Pro
  • • VIP onboarding
  • • 90-day optimization
  • • Quarterly reviews
~25% choose this

Quick Pricing Psychology Wins

  • Use "Investment" not "Cost" or "Price"
  • Show monthly payment options for large projects ($12,000 = $4,000/month for 3 months)
  • Add a "What's Not Included" section—it builds trust and prevents scope creep
  • If they ask for a discount, remove scope instead of lowering price

The Follow-Up Sequence

Most deals are won or lost in the follow-up, not the proposal.

44% of salespeople give up after one follow-up. 80% of sales require 5+ follow-ups.

Here's the follow-up sequence I use. It's not pushy—it's helpful. Each touchpoint adds value instead of just asking "did you get a chance to look at my proposal?"

Day 0

Send the proposal

Send during business hours (Tue-Thu 10am works best). Include a personal note, not just "please find attached."

Copy this template:
Hi [Name], Great talking yesterday. As promised, here's the proposal for [project]. I've outlined three options based on what we discussed. My recommendation is [Option B] because [specific reason tied to their goals]. I'm blocking time Friday at 2pm for us to walk through this together. If that doesn't work, let me know what does. Talk soon, [You]
Day 2

The value-add check-in

Don't ask if they read it. Share something useful.

Copy this template:
Hi [Name], I was thinking about your [specific challenge] and found this [article/case study/resource] that might be helpful regardless of whether we work together. [Link] Let me know if you have any questions about the proposal - happy to hop on a quick call. [You]
Day 5

The direct check-in

Now you can be more direct. Reference the scheduled call if you set one.

Copy this template:
Hi [Name], Just checking in on the proposal. I know things get busy - want to make sure you have everything you need to make a decision. Any questions I can answer? [You]
Day 10

The timeline nudge

Create gentle urgency without being pushy.

Copy this template:
Hi [Name], Wanted to give you a heads up - I'm finalizing my schedule for [month] and have [one/two] spots left for new projects. If you're still interested in moving forward, let me know and I'll hold a spot for you. No pressure if the timing isn't right. [You]
Day 21

The breakup email

Works surprisingly well. Give them an easy out.

Copy this template:
Hi [Name], I haven't heard back, so I'm guessing the timing isn't right or you've decided to go another direction - totally understand. I'll close out this proposal on my end, but feel free to reach out if anything changes. I'd love to work together when the time is right. Best, [You]

Ready-to-Use Templates

Stop starting from scratch. Here's what actually works.

Opening Lines That Hook

Your website is leaving money on the table. Right now, you're converting 1.2% of visitors—which means for every 100 people who land on your site, 99 leave without taking action. At your current traffic levels, that's approximately $15,000/month in missed opportunities. Here's how we fix that.

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