How to write Upwork proposals that get replies

Sending Upwork (opens in a new tab) proposals and hearing nothing back? A proposal that gets a reply breaks the pattern of the fifty others the client is skimming: it is short, opens with something that proves you read the job, asks one real question, shows a small piece of the work in a two to three minute video where possible, and arrives early.

What the client sees

Imagine the job from the client's side. On one job I looked at with a freelancer I coach, the client had 142 proposals. People who hire freelancers are busy, which is why they are hiring in the first place. They are usually founders or agency owners, and sometimes their assistants, and they have no time to read 142 cover letters.

So they skim, and this is roughly what their list looks like:

• "Hello William, over the last nine years I have worked on…"
• "Hi there, I am very interested in your job…"
• "Hello team, I have carefully gone through your requirements…"
• "Hi William, I am a certified expert with…"

Every proposal has the same shape: a greeting, years of experience, a list of skills and a promise to deliver. Many are written with AI tools, so they sound even more alike. The client reads the first line of each, and most of the time that is all they read.

Why the same message never works: pattern interruption

When a busy person sees the same thing again and again, they stop reading and start skimming. Anything that breaks that pattern makes them stop and look. In sales this is called a pattern interrupt, and it is the first job of your proposal. Sending one more well-written version of what everyone else sends does not work, no matter how good your experience is, because the client has stopped reading by the time they reach it.

A proposal can break the pattern in two ways.

It can look different. In a list of long paragraphs, a proposal that is one short question with no greeting stands out on the screen before the client reads a word of it. One of mine was just: "I want to know what's not working for you."

It can say something different. Instead of agreeing with the job post, it questions it. One of my proposals asked the client why they needed a person to set this up at all, and whether they could do it on their own. It sounds like a strange thing to send to someone who is hiring, but she replied, and we booked a call.

Neither of these tries to sell anything. The proposal's only job is to get you out of the noise and start a conversation. Once the client replies, you can explain everything else on a call.

Read the job first, looking for what won't work

Before I write anything, I read the whole post, and I spend five to ten minutes on it. That is also why I look at five jobs a day at most. I read for the one thing in the job that will not work as described.

It is usually one of these:

• A number that is not realistic, such as a client who wants to send 100,000 cold emails a month. It is technically possible, but it will not get them results.
• Too many jobs for one person, such as a post asking for cold email, ads, LinkedIn (opens in a new tab) and a CRM setup (the CRM is the software that keeps track of their customers), all from one freelancer.
• A post written by AI that lists everything and never says what the real problem is.

Open with something that proves you read it

Put it in the first line, politely, with no greeting in front of it. There are three ways to open, and I use all three:

1. Push back on one point. Say what will not work and why, in one or two sentences. This suits an unrealistic number or a job that needs several people.
2. Ask a real question about their work, one that only someone who read the post would ask. For a post that reads as if AI wrote it, I often open with: "Hey, it looks like this is generated from AI. Are you really looking for…" and then name the one thing they seem to need.
3. Show the exact thing they asked for, if you have built it before, with a link or a video.

You do not have to be rude about it. In one job, the client wanted inbound and outbound marketing (people finding them, and them reaching out to people), ads and LinkedIn, all from one person.

Keep it short, and end with one question

Clients do not have time to read PDFs or long cover letters, so leave them out. Mine are often one or two lines on where I would start, a question, and a video.

Ask one question, and only one. It should be about their situation, for example:

• "Is your email list built from your own customer records, or bought?"
• "What's not working for you right now?"
• "Which of these three is costing you the most?"

Show a small piece of the work

Record a two to three minute video. Start the recording on their job post, talk about their situation, and then show something real.

When I started, I had zero reviews, so the video was my proof. I built what the client asked for and showed it working. If it would take longer than 15 or 20 minutes to build, I showed something similar I had already made, or built just one part of it, the step that looked like their biggest problem. A screen recorder such as Loom (opens in a new tab) is enough, and you paste the video link into the proposal.

Send it within minutes

Clients often post a job and go back to their own work. A proposal that arrives in the first five or ten minutes has a much better chance of being read than one that arrives that evening.

You cannot read a job properly and build a custom demo in ten minutes, so keep a few short recordings of your past work ready. For a job you catch early, send a short proposal with the closest recording, and build something new only when the job is worth the time. How to get your first client as a freelancer explains how saved searches that alert you to new jobs, and weekends when clients are free to reply, help you get there first.

A proposal, start to finish

For a job asking for 100,000 cold emails a month, a full proposal could look like this.

The rest happens on the call, and How to talk to US clients on your first call covers that.

For each of the five, note the first line you used and whether the client replied, and keep the first lines that got answers.