Top 10 Upwork proposal tips: How to win Upwork jobs in 2018

It’s 2018, and writing great Upwork proposals has never been more important than it is today. If you’re new, or just haven’t noticed, Upwork and online freelancing have become much more mainstream over the past couple of years. Upwork’s CEO Stephane Kasriel has said that as many as 10,000 new freelancers come onto the scene every day, and there are millions of new clients as well.

All of this spells huge opportunity for anyone wanting to succeed as an online freelancer. And that starts with learning how to write an Upwork proposal that grabs attention, stands out from the crowd, and gets clients excited to hire you (yes, even if you think you don’t have enough experience).

With that, I’m proud to present to you my best tips for writing winning Upwork proposals in 2018.

My top 10 Upwork proposal tips for winning jobs in 2018:

1. Start your proposal with a “Decompression Zone”
2. Avoid the “Hybrid Proposal”
3. Offer a helpful suggestion right in your cover letter
4. Show an example of similar work (even if you’re brand-new)
5. Don’t bury the lead
6. Find common ground
7. Become a screening question “smuggler”
8. End your cover letter with a Call To Action
9. Don’t sell yourself short
10. Use the client’s name

Tip #1: Start your proposal with a “Decompression Zone”

To write great Upwork proposals in 2018, learn from businesses that have stood the test of time — I’m talking about big, successful retail stores like The Gap, the Apple Store, or Bed Bath & Beyond.

Watch the video below to learn about one of their most powerful persuasive strategies (which I’ve been successfully applying to Upwork proposals for years).

Tip #2: Avoid the “Hybrid Proposal”

I’ve always warned against reusing the same (copy-and-pasted) proposal over and over again for different jobs. Many of you have gotten the message loud and clear.

But there’s a new, equally poisonous shortcut in full force this year. I call it the “Hybrid Proposal”. This is when someone uses a canned (pre-written) proposal, but they try to make it appear original by adding in one or two “customized” lines.  

They may fool themselves into thinking it’s a good strategy, but it doesn’t fool clients nearly as well. You can spot these Hybrid Proposals a mile away because 98% of it sounds completely generic — usually a boring list of facts about the freelancer’s experience, with little-to-nothing in the way of specifics about how they can help the client (which is 98% of what the client really cares about).

Writing awesome, original Upwork proposals doesn’t have to take long, and ensures you’ll always be able to find new clients whenever you need them. If that isn’t a good reason to invest a few extra minutes of effort, what is?

Tip #3: Offer a helpful suggestion right in your cover letter

The past few years have burned us all out on advertisements, clickbait links, and self-aggrandizement by consultants and gurus who will do anything to get into our pockets.

Now, in 2018, your best shot is to turn the tables and be generous instead. (I call this the Generosity Economy. You’re experiencing it right now, even as you read this post.)

Once you decide that creating a “Decompression Zone” to start a conversation with clients is smarter than coming in hard with a full blown sales pitch, you can use your proposal to deliver value — which helps you stand out and become a client-magnet.

One of my favorite ways to do that is to offer a helpful suggestion, right in your cover letter (or even in a screening question).

Mind you I am not talking about doing any free work here. Just a friendly suggestion, pointer, or tip or two that shows the client you know what you’re doing, you’re a good person to work with, and you care about helping them win.

Tip #4: Show an example of similar work (even if you’re brand-new)

Clients today have more choices than ever. Before you get all worried about the excessive competition, realize that this presents a new problem for clients — too many options! You can help them solve that problem and become their hero by helping them narrow down those options…to JUST YOU.

How? By showing them examples of previous work you’ve done that are similar to what they need. Since few or none of your competitors will do this, clients will love it and — if done right — will usually shortlist or even hire you fairly quickly because they now know you can get the job done.

Anyone can take advantage of this strategy. It doesn’t matter what category you’re working in, or how little experience you might have. Here are some ideas to get you started:

• A client needs an excel spreadsheet; you create a similar spreadsheet and show it to them as proof that you can complete their job.
• A client needs a business plan for their company; you write a marketing plan for a similar company (doesn’t even have to be an existing company) and show it to them as proof that you can complete their job.
• A client needs some visual effects added to a video; you add those same visual effects to a different video and send it to them as proof that you can complete their job.

(Btw, I wrote an entire post about how you can create a portfolio in one afternoon here.)

Tip #5: Don’t bury the lead

It’s 2018, and everyone’s patience has left the room. Case in point: A journalist can ruin an otherwise amazing piece simply by burying a lead.

But it’s not just journalists that do this. You can easily bury the lead in your proposal if you’re not careful. For example, I once reviewed an unsuccessful proposal where the freelancer had included a highly relevant sample of his work … way down at the bottom, beneath nine paragraphs of mostly irrelevant fluff. Lead buried.

Think about how strapped for time we all are these days. How do you feel when someone sends you a long email to communicate something that could have been said in the first sentence?

Tip #6: Find common ground

People may technically be more connected than ever, but ironically we’ve also never been so longing for personal connections.

Yes, the client reading your proposal on the other end is a human. Which means they respond to traditional human connection, just like anyone else.

One of the best ways to make that connection is by finding common ground whenever you can.

For example, I sometimes point out that the client and I are both located in the midwest — even if we’re 300 miles apart! A guy reached out to me on Twitter once to let me know he took this advice and got hired for a job because he was from Boston, a city the client loved.

Of course, this isn’t limited to your geographic location. You can use your background, education, personal interests, passions, or anything else.

Tip 7#: Become a screening question “smuggler”

Back in 2016 I showed you how your answers to Upwork’s “Additional Questions” are actually the first thing clients see, even before your Cover Letter, making them a critical component of writing winning proposals.

But how can you take maximum advantage of this knowledge and make sure clients love your answers?

The way I do it is to take all of the great information I’d normally put into my Cover Letter, and “smuggle” it into my answers to the “Additional Questions”.

For example, let’s say I have a highly-relevant sample of work I know the client will love. Instead of hoarding it for my Cover Letter, I work it into one (or even more) of my  “Additional Question” answers.

Of course, you can do the same thing with any key piece of information the client will love — useful tips and suggestions, ideas, and helpful insights can all be “smuggled” into your answers, too.

Tip #8: End your cover letter with a Call To Action

2018 isn’t only the year that Upwork proposals became one of the most valuable skills on earth — it’s also the year of “I’m so distracted — please just tell me exactly what to do next!”

Persuasion scientists have long since discovered that they could persuade more people to get vaccines by giving them specific next steps (i.e. “Go to this local drug store at this exact address now to get vaccinated”) vs just telling them about the benefits of the vaccine. You can do the same thing with your Upwork proposals.

For example, I often end proposals by asking clients if they are up for a 5-minute voice call on Skype so they can tell me more about their project. It works much better than something like, “Hope to hear from you soon.”

Tip #9: Don’t sell yourself short

While negotiation used to be something we associated with hardcore businesspeople, in 2018 it’s practically a national hobby (thanks largely to popular TV shows like Shark Tank and The Profit).

This means that clients often understate the true amount they’re willing to pay when they post a job on Upwork because they’re “leaving themselves room” to negotiate.

This creates enormous potential for earning more on Upwork because it means you can charge above the client’s budget and still get hired.

You need to write a great proposal to make this strategy work, but it’s more than worth it. I’d never have been able to earn over $100,000+ on Upwork in a single year if I’d let clients decide on my prices for me.

Tip #10: Use the client’s name

In How to Win Friends and Influence People, Dale Carnegie offered a piece of timeless advice that might be more relevant in 2018 than it was when the book was written: People love, love, love the sound of their own name.

Whenever I post a job on Upwork as a client, I sign my name at the bottom of it. Then, I virtually ignore any proposal that doesn’t start out with the words “Hi Danny”.

This isn’t narcissism, it’s just a practical way to narrow down the field. In my experience, freelancers who use my name are more likely to be the helpful type clients like me want to hire.

Even if a client doesn’t sign their name in their job post, you can sometimes find it by clicking on the job post and scrolling down the page to see if other freelancers have left them reviews that include their name.

If that doesn’t work, look for other clues in their job post. For example, their company name or a website link can lead you to an About Us page or blog that reveals the name of the person who wrote the post. (Don’t worry about looking like a stalker, clients like it when you take an interest in them. Just don’t be weird or creepy about it.)

Alternatively, if you can’t find their name, or just don’t want to dig too much for it, just make sure you use the word “you” as much as possible. It has a similar effect and gives your proposal a “client-centric” feel that will stand apart from the “Me, myself and I” proposals your competitors will bury them in.

Take a look at these real, winning proposal examples

No matter how many tips I give you, there’s nothing quite like seeing what real winning Upwork proposals actually look like.

That’s why I want to show you some, free of charge — my gift to you. You can get them here.

I’ve shared these with thousands of my readers, and the responses have been incredible. Like this:

“LOVE THIS! Thanks for creating this resource Danny! It was so eye opening! I’ve read so many articles on writing great Upwork proposals and most of them advise boring, cookie cutter proposals like some boring cover letter you would staple to the front of your CV for doing the job searching rounds around the town.

But this approach is so casual and personal that it really captures the reader. I mean I don’t know why I should be surprised this is the winning formula because it’s the exact tone I’m trying to tell people all the time to use in their marketing copy! I really need to follow my own advice!

It’s so funny to think even though we may tell our clients one thing, when it comes to marketing ourselves as freelancers we default to a boring, corporate clone…the very thing so many of us became freelancers to escape from!”

See the real, winning proposal examples (for free) here.