This article was submitted by Danny Margulies and does not constitute the views or opinions of Upwork.


Imagine being able to confidently go after any project that catches your eye, knowing you’ll have an excellent chance of landing a new client. Knowing the tactics that work for other freelancers can be the confidence boost you need to quickly and consistently crank out amazing, winning proposals.

Through my experience as a six-figure freelancer, as well as a client on Upwork and the founder of Freelance To Win, I’ve seen and written the good, the bad, and the really ugly when it comes to proposals. Based on my own experience and that of other successful freelancers, here’s a look at the “invisible questions” your proposal should address, tips to give your pitch and your presence a more polished look, and common mistakes that even experienced freelancers can make.

Your next project may be closer to your reach than you think!

Before you start: 3 “Invisible Questions” your proposal must answer

To write a winning proposal you need to first understand what’s going on inside the client’s head.

Through years of carefully reviewing and analyzing tens of thousands of Upwork proposals (not to mention writing a few thousand myself), I’ve discovered three key questions virtually all clients want answered in your proposals.

But here’s the strange part: even though clients are intensely interested in these answers, they virtually never ask for them!

At least, not directly.

This is why I call them the “Invisible Questions”.

Invisible Question 1: “Are you capable of doing my project?”

Clients want to know without a shred of doubt that you can complete not just any similar project, but their specific one.

Most “web design” or “article writing” projects might appear similar to us as freelancers—but from the client’s perspective, their project is unique!

It’s a bit like the way parents think of their kids: They may act and play like other kids, but to the parents they are totally unique and require their own special care and attention.

Understanding, respecting, and acknowledging this aspect of the client’s psychology goes a long way in winning them over.

Upwork proposal — example

Invisible Question 2: “Will you make my life easier?”

Clients are busy people with a lot on their plate.

They’re looking for clues that working with you won’t be yet another item on their to-do list—that you’ll be easy to work with and proactive.

A good way to look at this is to view your proposal as not just another “pitch,” but a preview of what it’s like to work with you.

For example, a logo designer might curate a few relevant samples of their work to show directly in their proposal instead of dumping a link to their entire portfolio (which can be overwhelming and time-consuming for the client to sift through—more on this later). This kind of extra attention is easy to do. And it’s not lost on clients, who appreciate your going out of your way to save them time and energy.

Invisible Question 3: “Do you care about helping me succeed?”

This is often a difficult one for freelancers to adjust to, because on the surface it can seem as though your skills and price are all that matters.

But all of the best clients I know make hiring decisions based at least as much on how they feel about you as anything else.

Clients on Upwork want to know you’re going to be in their corner. They want to know you’re not just technically skilled, but that you’ve got their back and are ready to go the extra mile in order to help them succeed, and even help them look good and impress the other people in their world (e.g., their customers, associates, etc.).
In a conversation on the Freelance to Win website, one reader shared how a repeat client chose her more for her attitude than her technical skills:

“I’m a graphic designer on Upwork… I recently had a “failed job” experience – my client had hired 2 designers on Upwork for the project. They liked her designs better (they really were better) but because I cared more about the project and was willing to go back and figure out what was different, his team went with me and he’s now a repeat client.”

5 proposal tips to instantly improve your success rate

Tip 1: Avoid “hybrid” proposals

In a previous post on how to write winning proposals, I highlighted the risks of copy-and-pasting the same canned or pre-written proposals for every project you’re interested in.

Since then, many people have asked:

“But Danny, what if I come up with a solid proposal template, then modify it a bit for each individual project?”

In theory it might seem that such a “hybrid” proposal strategy could save you time and energy while avoiding the traps of a canned proposal.

But when you examine the risk/reward ratio, I don’t believe the justification is there. At best, you may save a few minutes here and there — at worst, you can cost yourself tens of thousands of dollars a year in income (or more). Better to take a couple of extra minutes and do it right. If you follow the advice in this post, you’ll see it isn’t even that hard to do.

Tip 2: Show off a relevant example of your work

There may be no better way to prove to clients that you can succeed at their project than showing them an example of something similar you’ve already done.

Before all the “non-creatives” out there sigh and say, “Oh, that only works for writers and designers!” I assure you absolutely anyone — in any Upwork work category — can include an example of their work in a proposal.

All it takes is a little imagination and out of the box thinking.

If you’re new to freelancing, you can even create a relevant sample of work from scratch — a strategy I refer to as my Crystal Ball Technique. The way it works is simple: You create a sample piece of work that’s similar — though not identical — to what a client needs. This shows clients you’re capable of succeeding at their project, without crossing the line into inadvertently doing “free work” for them (which is never a good idea).

(For ideas, see my post titled How to build a freelance portfolio from scratch — in 1 afternoon.)

Tip 3: Start your proposal off strong

Think of a new TV show: If they fail to hook you with that opening episode, it won’t matter what comes after because there’s a good chance you’ll be tuned out by then.

The same principle applies to your proposals. You do not need to be a talented TV writer to get clients interested in you, you just need to get to the point — quickly.

From the client’s perspective, the point of your proposal is the stuff that helps them.

That’s all of the good stuff where you say, “Hey, I worked on a project that I think has some relevance to this. Here’s some more information about that…” Or, “Hey, you mentioned you’re concerned about X, Y, and Z, and here are some ways I think we could address that.” Or, “Hey Ms. Client, here are a few common pitfalls I’d like to help you avoid on this project…”

When you get to the points the client really cares about, and you do it quickly, they start to think, “Wow, this person totally gets it. She’s super helpful!” or “He really seems to know what he’s doing.”

It’s okay to start with a friendly warm-up sentence to break the ice. But if you meander on, you’ll lose their attention fast.

Tip 4: Don’t limit yourself to the client’s specified budget

When a client’s project posting specifies a budget, it can be a good guideline or starting point, but it doesn’t have to be set in stone.

Maybe a client chose an amount you think is too low given what they’re asking for. That’s okay — freelancers often have a better sense than the client about what their services should cost. Maybe you’re confident you can add enough value to their project to justify a higher fee.

The important thing to understand is that it is certainly possible to charge more than the client’s budget — and still get hired.

Common Upwork proposal mistakes (that even experienced freelancers make

Mistake #1: Taking “Preferred Qualifications” too literally

Before you skip over a new opportunity because you feel you don’t fit a client’s preferred qualifications, remember there is only one question you should be asking yourself:

“Can I add value to this project?”

If the answer is yes, then you should consider submitting a proposal regardless of the client’s Preferred Qualifications.

If you aren’t sure, simply go back to the three “invisible questions”:

  1. Can you do the project well?
  2. Can you make the client’s life easier?
  3. Do you care enough to help them win?

If the answer to all three is yes, do you really think the client wouldn’t want to hear from you? As an active client myself I know I would love to receive a proposal from anyone who can honestly answer yes to all of these. (And no, your proposal won’t be hidden from clients if you don’t meet the preferred qualifications. Go for it!)

Mistake #2: Writing your proposal “upside down”

Perhaps you’ve noticed that a significant number of Upwork project postings require you to answer one or more “Additional Questions” after you write your cover letter.

What you may not know is that your answers to these “Additional Questions” are actually the first thing clients see when your proposal pops up on their screen.

This is what clients see when they review your proposal.

This is what clients see when they review your proposal.

This is key intel, not only because it means you should focus at least as much of your energy on “Additional Questions” as you should on your cover letter but also because the reason the questions are there in the first place is that the client chose to add them as “Screening Questions”. Meaning that, if you don’t do a great job answering them, the client may not move on to your cover letter (let alone check out your profile, portfolio, etc).

Now that you know this, you can tackle your cover letter accordingly. Instead of treating it as the “main course” — while thinking of the additional questions as an afterthought — flip it around!

Fill out the additional questions first, using some of the tactics from this post. For example, you can use a question about your experience level as an opportunity to show off a relevant piece of work; a question about which part of the project you think will be most challenging can be turned into an opportunity to offer a strategic idea or suggestion.

Mistake #3: Selling too hard

No one likes being sold to.

The approach I prefer is more natural, more fun, and more effective. Instead of asking myself, “How can I sell this client?” I ask, “How can I help this client?”

This leads to better proposals and a higher response rate from clients. And it’s easier because I can simply be myself instead of putting on a facade in the name of “selling.”

The first project Chris hired me for.

I want to share something special with you. It’s a two-minute segment of an audio interview I did with Chris Davis, a premium Upwork client. In it, you’ll hear him explain, in his own words, why he decided to hire me for $135/hr…

(Note: Video is audio only.)

Pay close attention to the types of words Chris uses:

  • “Trust”
  • “Being a human being”
  • “Getting to know you”
  • “You weren’t trying to sell me”
  • “You respected me”
  • “You talked to me like a person”
  • “People crave connection”

See examples of real winning proposals: Feast your eyes on three proposals that won $3,000+ in projects through Upwork

I hope you’ve enjoyed the strategies and tactics I’ve shared with you in this post. It took me a long time to figure them out, and I always promised myself that I’d eventually show others (like you) how to do it much faster.

That’s why I’ve carefully selected three real winning proposals to share with you now, so you can see exactly what a successful proposal can look like. You can pick them up here.


This article was submitted by Danny Margulies and does not constitute the views or opinions of Upwork. Find out how you can publish your content on Upwork.