Writing Proposals That Win

The Proposal Black Hole

In the previous lesson, we explored building your brand and portfolio. Now let’s build on that foundation. You find a perfect project. Great client. Right scope. Good budget. You spend two hours crafting a thoughtful proposal, hit send, and… silence. Two days later: “We’ve decided to go with another freelancer.”

What happened? Usually one of three things:

1. Your proposal sounded like everyone else’s
2. You listed your capabilities but didn’t address their specific problem
3. Your price was the only differentiator, and someone was cheaper

The fix isn’t writing more proposals. It’s writing better ones. A strong proposal does three things: demonstrates understanding, presents a clear approach, and makes the decision easy. Let’s build one.

What You’ll Learn

By the end of this lesson, you’ll write proposals that stand out from the competition, address the client’s specific needs (not just your capabilities), and win projects at rates that reflect your value.

From Portfolio to Proposals

In Lesson 2, you built a portfolio that attracts interest. Interest becomes an inquiry. An inquiry becomes a proposal. This is the conversion point – where a potential client becomes a paying client. Your portfolio gets them to your door; your proposal gets them to walk through it.

The Anatomy of a Winning Proposal

Here’s the structure that works:

1. The Problem Restatement (Shows you listened)

Start by describing the client’s problem in your own words. Not by listing your credentials. Not by saying “Thank you for the opportunity.” By proving you understand what they need.

Weak:

“Thank you for considering me for this project. I am a web designer with 8 years of experience and have worked with over 50 clients…”

Strong:

“Your current website isn’t converting. You’re getting 2,000 visitors a month but only 1.2% are buying – which means 98.8% of your traffic is leaving without spending a dollar. Based on your product quality and price point, your conversion rate should be closer to 3%. That gap represents roughly $15,000 in monthly revenue you’re leaving on the table.”

Which proposal would you read past the first paragraph?

2. Your Approach (Shows you’ve thought it through)

Don’t just say “I’ll redesign your website.” Describe how. What will you look at? What will you change? Why?

Help me outline my approach for a client project.

Client problem: [specific problem from their brief]
My specialty: [what I do]
Relevant experience: [similar projects I've done]

Write a 3-4 paragraph approach section that:
- Explains my process in plain language
- Mentions 2-3 specific techniques or strategies
- References similar work I've done (without name-dropping
  if confidential)
- Makes the client feel confident I know what I'm doing

3. The Scope and Deliverables (Shows what they get)

Be specific about what’s included. Ambiguous scope is the #1 cause of freelance project disputes.

Weak:

“Website redesign including design and development.”

Strong:

What’s included:

• Homepage redesign (desktop + mobile)
• 5 product page templates
• Checkout flow optimization (current 5 steps → 2 steps)
• Speed optimization (target: under 2 seconds load time)
• 2 rounds of revisions
• 30-day post-launch support for bug fixes

What’s not included:

• Product photography
• Copywriting (I’ll work with your existing copy or your copywriter)
• SEO strategy (available as a separate engagement)

Explicitly stating what’s NOT included prevents scope creep and shows professionalism.

4. Timeline and Milestones (Shows how it unfolds)

Clients love timelines. They remove anxiety about “how long will this take?” and create natural check-in points.

5. Investment and Terms (Shows what it costs)

Frame pricing as an investment, not a cost. Link it to value.

Weak:

“My rate is $75/hour. I estimate this will take 80 hours.” $6,000 total.

Strong:

Project investment: $6,000

Based on your current traffic (2,000 visits/month) and the conversion improvement we’re targeting (1.2% → 3%), this project should generate an additional $15,000/month in revenue. The investment pays for itself in the first 2 weeks of the improvement.

Payment structure:

• 50% ($3,000) at project start
• 25% ($1,500) at design approval
• 25% ($1,500) at launch

Quick Check

Pull up the last proposal you sent. Does it start with your credentials or the client’s problem? If it leads with you instead of them, you’ve got an easy win: rewrite the opening to focus on their challenge.

Using AI to Draft Proposals

Here’s a comprehensive prompt:

Write a freelance proposal for this project:

Client: [name/type of business]
Their problem: [what they told you they need]
Their goal: [what outcome they want]
Budget: [if mentioned]

About me:
- Specialty: [your positioning]
- Relevant experience: [similar projects]
- Key differentiator: [what I do differently]

Project details:
- Scope: [what I plan to deliver]
- Timeline: [estimated duration]
- Price: [my proposed price]

Write the proposal with these sections:
1. Problem restatement (1 paragraph, shows I understand)
2. Approach (2-3 paragraphs, my specific plan)
3. Scope and deliverables (bullet list of inclusions
   and exclusions)
4. Timeline (table format with milestones)
5. Investment (price with value framing)
6. Next steps (what happens if they say yes)

Tone: Confident, clear, conversational. Not salesy.
Length: Under 800 words total.

Important: AI generates the structure and draft. You add the specific details that only you know – the insight from your discovery call, the nuance from your experience, the personal touch that separates your proposal from a template.

Handling Common Objections

“Your price is too high.”

Don’t immediately lower your price. First, ensure your proposal clearly communicates value. If it does, ask: “Compared to what?” Often clients are comparing you to a different scope or quality level. Clarify what they’d get at a lower price point (less scope, not less quality).

“Can you do it faster?”

Be honest about tradeoffs. “I can accelerate the timeline from 7 weeks to 5, but we’d need to reduce revision rounds from 2 to 1 and have all content ready by the start of development.”

“We’re talking to other freelancers.”

Good. That’s normal. Don’t panic. Focus on making your proposal the strongest, not the cheapest. Ask if there’s anything specific they’d like you to address.

“Can you do some work first so we can see your style?”

This is a spec work request. Generally, decline politely. Instead, point to relevant portfolio pieces that demonstrate your style. “I’d be happy to share my approach in a brief project plan – that way you can see my thinking process without either of us investing in production work before we’ve agreed on scope.”

The Follow-Up

Proposals don’t end at send. Follow up:

• Day 2-3: Brief check-in. “Just wanted to make sure the proposal came through and see if you have any questions.”
• Day 7: Value-add follow-up. Share something relevant – an article, a quick insight about their industry, an observation about their site.
• Day 14: Decision check. “I’d love to help with this project. Is there anything else you need to make a decision?”

AI prompt for follow-ups:

Write a follow-up email for a proposal I sent [X days ago].

Client: [name]
Project: [brief description]
Any recent interaction: [notes]

Tone: Helpful, not pushy. Add value, don't just ask
"did you decide yet?"
Length: 3-4 sentences max.

Exercise: Write a Complete Proposal

Choose a real project you’re bidding on (or a hypothetical one in your niche). Write a complete proposal using the structure above:

1. Problem restatement (1 paragraph)
2. Your approach (2-3 paragraphs)
3. Scope with inclusions and exclusions
4. Timeline table with milestones
5. Investment with value framing
6. Next steps

Use the AI prompt to generate a first draft, then customize it with your specific knowledge and voice.

Key Takeaways

• Lead with the client’s problem, not your credentials – show you understand before you sell
• Be specific about scope, including what’s NOT included, to prevent future disputes
• Include a timeline with milestones – it builds confidence and sets expectations
• Frame pricing as an investment with a value connection, not just a cost
• Follow up with value, not just “did you decide?”
• AI drafts the structure; you add the insight, personality, and specific expertise

Next lesson: you’ve written a proposal. But how did you decide on the price? Let’s fix that.