Proposal Writing: Making a Real Connection

Connecting with the client is one piece of the proposal writing puzzle.

Proposal Writing: Making a Real Connection

Freelancers are amazing at what they do. Business development, though? That’s a different skill set.

There’s a lot of discussion on social media about how to write an effective proposal—especially on Upwork. This is the first blog in a four part series to help you write proposals that resonate with clients and land more work:

1. Connection Statement

2. Your Services

3. Your Impact

4. Closing and Call to Action (CTA)

This blog on the Connection Statement.

Proposals Require Strategy—and a Spark

Proposing on Upwork involves strategy, tactics, and, truthfully, a little bit of luck.  This post leans into the tactical side—specifically, how to make a quick and meaningful connection with a client you know almost nothing about.

What Is a Connection Statement?

It’s the line in your proposal that makes a client say: “They hear me and understand what I need.”

Connection statements reflect the emotional tone, goals, or frustrations in the client’s job post without simply mirroring it back. You’re not just regurgitating the words they used; you’re tuning in to what they care about and showing them you get it.

Why This Matters (Even More Than You Think)

I took inspiration for this blog from the process authors use to write query letters. When authors query literary agents, they have just 300–350 words to convince someone to keep reading. One of the top complaints from agents? Very few people make a connection. Queries often feel cold, generic, or transactional.

It’s a little easier in the query world: agents have bios, social media, interviews—context clues to help you tailor your message. On Upwork, though, you’re flying almost blind. All you have is the job description.

Here’s how to connect when that’s all you’ve got:

Step 1: Read the Job Description Thoroughly

It’s tempting to skim and rush. You may think you already know what the client wants. But slow down. Read the job description carefully. You’re looking for clues—not just about the work, but about the person behind it.

Step 2: Assess the Tone

Ask yourself:

• Is this person frustrated? Excited?

• Are they overwhelmed, decisive, hesitant?

• Do they drop hints about what’s driving this project?

Let’s look at two examples pulled directly from Upwork.

Example 1: Executive Assistant Job Post

"We are seeking a proactive Executive Assistant to support our operations by managing communications and providing organizational assistance. The ideal candidate will excel in multitasking and possess strong communication skills. Responsibilities include handling additional postings, coordinating schedules, and assisting with various management tasks. If you are highly organized and have a knack for effective communication, we would love to hear from you!”

What does this client value?

• Efficiency

• Organization

• Communication

What’s the tone?

• Direct, crisp, efficient—but also warm. That final line ("we would love to hear from you!") includes an exclamation mark, which adds a friendly, upbeat vibe.

Example 2: Shopify Web Designer Job Post

“We are seeking a Shopify expert to design and launch an online store for [Company]. The ideal candidate should have a strong background in Shopify development and a knack for creating visually appealing, user-friendly e-commerce sites. Responsibilities include setting up the store, customizing templates, integrating payment gateways, and optimizing for SEO and performance. If you have a proven track record of successful Shopify projects and can deliver a high-quality store efficiently, we want to hear from you!”

What does this client value?

• Experience

• Technical skill

• Results

What’s the tone?

• Professional, knowledgeable, clear—and again, warm. The last line opens the door with a friendly invitation.

Step 3: Look at the Client Reviews

If the client has worked with freelancers before, check their reviews. How do they speak about past collaborations? That can give you even more insight into their personality, preferences, and values.

In the Shopify example, this client consistently leaves thoughtful, encouraging feedback reinforcing key skills. That tells you they likely appreciate strong communication and mutual respect.

Step 4: Craft Your Connection Statement

Your connection statement should be 1–2 sentences max. The structure is simple:

Acknowledge their situation → Pivot to what you offer.

Examples:

“You’re ready to level up—and you need someone who can keep pace and bring clarity. That’s where I come in.”

“You have a lot on your plate. I specialize in jumping in with minimal ramp-up and creating calm.”

Based on the samples above:

Admin Role:

“It sounds like you manage a busy office where organization is critical. I thrive in fast-paced environments.”

Web Designer:

“Congratulations on deciding to launch your store! That’s a big step. As a Shopify expert, I’ve helped clients launch clean, high-converting sites efficiently.”

You’re not trying to become the client’s best friend. You’re demonstrating that you hear them—and you’re already tuned into their priorities.

Bottom Line

A strong connection statement is one of the simplest ways to differentiate your proposal. It shows empathy, insight, and professionalism in just a few words. And that can be the difference between getting ignored and getting hired.

Want to Learn More?

✨ Ready to see real examples in action? Click here to grab the freebie with two pages of connection statement examples you can adapt to your voice.