6 Techniques To Write Winning Proposals On Upwork

I’ve landed 138 Upwork jobs and counting. Let’s dive into how you can get more yourself.

It’s true what they say, that words are the true weapons. Those who fight with steel are limited to the strength of their arm, the reach of their blade, and the timing of their strike; but those who fight with persuasion know no limits.

— A.J. Darkholme

Landing Jobs as an Upwork Freelancer

Ah, the art of persuasion — I guess you want to stand out from the crowd and convince someone you’re the right person for the job?

Good, then you’re in the right place.

When you apply to any job on Upwork, you’re competing against a large pool of talent.

Some jobs you apply to on Upwork have under five proposals — others have over 50. However, many of these proposals are cut and pasted. Others are rife with errors. Others don’t even address the job.

In short, many of these proposals will be binned before the client gets beyond the first sentence.

You may think you’re competing against a large number of people. In reality, you’re only competing against 5 or fewer people for any job.

Of course, part of the game of landing jobs is the number of proposals you send out. Sending out 100 proposals will more likely land you quality jobs than sending out one.

But, I hear you saying, sending lots of proposals takes a lot of time. And yes, it does. If you don’t think you should spend time writing a great proposal, why should the potential client take time to read it?

Although quantity is important, quality is essential. Writing winning proposals is a skill. If you feel you’re not good at that skill, fear not! You can get better at a skill.

How, you ask?

Internalize and embody the word your parents annoyed you with as an adolescent: Practice.

Without further ado, let’s dive in!

6 Winning Proposal Techniques

1) Actually read job posts

You’ll be surprised how few people read job posts in their entirety.

That’s why some clients will write something along the lines of, If you read this whole job post, write “purple” at the top of your proposal.

But you can go one better.

I advise you to copy and paste the job post into the text box to write your proposal. As you go through it, make sure you address every question the client has.

Also, make sure you answer the client’s key question: Why do I trust you’re the best person for this job?

Tip: The more you individualize your cover letter and answer any client concerns, the more likely you’ll land the interview.

2) Send proposals every day

If you check your Upwork Job Feed Daily, you’ll stay on top of new jobs that are posted.

Some clients look for an urgent turnaround, and some quickly hire.

If you get in first, your chances of being hired increase — because your client is far less likely to have proposal fatigue.

Dedicate yourself. Make a schedule. One proposal every morning Monday to Friday. Five a day. Whatever suits your schedule.

If you want to make it in this Upwork world, you’ve got to be proactive.

3) Only send proposals to jobs you want to do

This may sound obvious, but when you write a proposal for a job you don’t even want to do — that you’re only looking at the money aspect — you’ll likely find it a lot hard to convince someone else you want to do it.

Why?

Think of it like this: If you’re struggling to convince yourself that you want to do a job, why on earth would the client believe you?

They wouldn’t.

A winning proposal is authentic, and it reflects who you are and what you will do. Being hired means the client trusts you. They trust you’ll care about the work, and they trust you’ll do the job.

Be authentic. Gain their trust.

Ask yourself the following: Would you tell your friend you love watching a Netflix series even though you hated it? When they ask you what you love about it, do you think you’d give a convincing answer?

Tip: Know that the perfect jobs will show up. There’s no need to apply for application’s sake, but if you dig deep enough, you’ll find jobs that sound great every day.

4) Post a job yourself

I can hear you now: Wait, what?! I’m looking for a job — why would I post one?

Because you can learn first-hand what works and what doesn’t.

You can post a really small job. You have no obligation to hire either way, so there’s no risk to you.

Post a job related to your field of interest, then read the proposals that flood in. Determine what other people’s proposals grip you and what you find less interesting.

Then, make two lists. In one list, write what you liked about the proposals — what convinced you. On the other, write the things that didn’t convince you. Use these lists as a framework.

In the list I made, I realized that often really long proposals get boring. Keep your sentences and paragraphs short. Get to the point. Learn the art of cutting out unnecessary words.

Tip: See how much you care about people telling you their experience versus telling you how they’re going to complete your job.

5) Ask your client relevant questions

Asking questions shows your engagement with what your client is looking for in an applicant.

Keep these questions relevant. There’s no need to ask them how they’re doing. Ask them how many words their book is. Ask them what style of graphic design they’re looking for.

If you’re asking questions, you’re showing your willingness to understand not only the job but the client as well.

6) Put a call to action in your proposal

Okay, the client has read your proposal, but you should ask them what you want them to do next.

Think about how many times you hear YouTuber’s say “like and subscribe.”

Why?

It’s a call to action. When you hear them say that, you’re far more likely to click like and subscribe, and you take the YouTuber’s desired action — meaning they’ll get more viewers and a better reach.

So ask your potential client to invite you to an interview!

Tip: What I like to say as a call to action is, “I’d love to hear your questions. Invite me to an interview, and I’ll answer them!”

Conclusion

So there you have it, you now know have six winning proposal techniques in your Upwork arsenal. You should now have a deeper understanding of how to land more jobs.

If you want to learn more about becoming successful on Upwork, follow me here on Medium. I’ll be writing regularly about how you can be more successful, the pros and cons of the freelance lifestyle, and a host of other topics. If you have any questions, feel free to write a comment. I read every comment, and I’ll always do my best to answer.

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