Best Way to Win Projects on Upwork

winning projects is never about luck. Every era brings its own challenges, and unless you understand the science behind proposals, you'll keep wasting connects and wondering why clients don't respond. In this article, I'll break down the common mistakes almost every freelancer makes, why AI-generated cover letters don't work, and how I consistently win high-paying projects.

I've seen a lot of freelancers complain about not getting enough projects on Upwork. And I get it. But let me tell you this - it was not easy for us who started more than a decade ago either. In every era, there's a different challenge, and the only way forward is to understand the rules of the game.

Before I tell you what works now, let's first look at the methods that don't work anymore.

What Upwork Itself Suggests (and Why It Fails)

If you go to Upwork's own resources, you'll see they suggest using Uma, their AI tool, to write proposals.

Once you actually generate a cover letter with it, here's what comes out:

"Hi, my name is …" - why does that matter? Your profile already shows your name.

"I have X years of experience …" - again, your profile already tells that.

Pasting a bunch of links to samples - looks spammy, and that's what the portfolio section is for.

Claiming you're the most expert person for the job - come on, no client is convinced by that line anymore.

I've seen so many freelancers making the same mistakes because they rely blindly on AI. And trust me, clients can tell instantly. It doesn't sound human, it sounds like a template.

If you don't want to waste your connects, don't write cover letters like this.

The Mistakes Everyone Makes

The biggest mistake I see is freelancers filling their proposals with things the client doesn't even care about. You're telling them your name, your years of experience, dropping links all over the place, saying you're the best person for the job - none of that makes a client trust you.

They don't know you yet, so those words don't mean anything. And when your proposal looks the same as the other hundred people applying, why would they bother replying?

That's why blindly using AI or those automated proposal tools never works. They all produce the same generic lines, and clients can spot it instantly. You might get a small job here or there, but you won't win serious, high-paying clients like this.

The Only Thing That Works is.. "Providing Value"

You're not the only one applying for a project - there are hundreds of others sending almost the same kind of proposals. Everyone is saying they're experienced, they can do the job, they've built similar sites before. None of that really makes you stand out.

What actually works is when you throw something different on the table - when you give value to the client even before they hire you. That's the moment trust starts to build. The client sees you're serious about their project, that you've already put effort in without asking for anything in return. And believe me, people always appreciate that.

How I Do It (Real Example)

Let me show you exactly how I bid on projects.

One of my clients posted a job on Upwork. Instead of writing a long generic proposal, I simply copied his job description.

Then I put it into Devta and clicked generate.

Within a minute, Devta created a complete document for me - timeline, cost, tech stack, and a clear breakdown of how the system would be built.

I shared that detailed plan with the client and wrote a short, simple note in my own words as the cover letter. Nothing fancy, just human.

Now see what happened. The client responded instantly.

And in our very first meeting, he openly said my proposal stood out from all the others. He had already made the hiring decision before the call even ended.

You can also view that same plan here: AI-Powered RAG System MVP

But that's not all. Here are more examples of how I've used this approach to win different types of projects:

More Project Plans That Won Clients

Each of these plans helped me stand out from other freelancers and win the project. The key is showing clients you understand their needs before they even hire you.

Nobody does that! Take benefit of it.

The Role of Devta

What makes this whole process easy for me is Devta. With just one click, it creates a detailed and professional plan that I can attach to my proposal. It even has a Devta AI chat widget that can help draft a cover letter if you need it, and also help you in understanding the project before you jump on a call with the client and much more.

But here's the important part - never depend completely on AI to write your cover letter. Clients are smart. They want to feel a human on the other side, someone who actually read their job post, understood their problem, and cared enough to respond in their own words.

So let Devta handle the heavy work - the timelines, cost breakdown, system plan - and then add your personal touch when writing the note. That combination is what really works.

Final Thoughts

Upwork is crowded. Clients receive dozens, sometimes even hundreds of proposals for a single job. And most of those proposals look and sound exactly the same - generic lines, copy-paste experience, and links no one clicks. They disappear in the pile.

What actually makes a freelancer stand out is trust. Clients don't want to be convinced with empty words, they want to see clarity. When a proposal shows a real plan - how the project will be built, what it will cost, and how long it will take - it proves seriousness from the very first message.

That's why providing value upfront changes everything. Instead of being just another freelancer asking for work, you become the one who already started solving the problem. And in a marketplace this crowded, that's what wins projects, builds client confidence, and opens the door to high-paying opportunities.

Remember: This approach isn't limited to software development projects. You can apply it to any niche on Upwork - writing, design, marketing, virtual assistance, or accounting. The key is focusing on solving the client's specific problem upfront, regardless of your field. When you demonstrate problem-solving before they even hire you, you'll stand out in any category.