How to Win Interviews on Upwork


It is hard finding work from home. I spoke to nearly 40 freelancers from all over the western world in the first half of 2020 about their processes for winning work. Every one of them expressed a tough road to building a work-from-home freelancing business. They shared stories of months working for far less than they made previously until they won consistent clients, earned references on their profiles, and learned how to sell themselves. This article aims to help shortcut that months-long process by sharing what I’ve learned about writing cover letters that win interviews.

I received the cover letter below after posting a job on Upwork, looking for an expert to help me prepare for an interview. Please take a moment to read it:

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How to not write a freelancer cover letter

Have you read the proposal above? If not, go back and try to read it before moving on. I’ll wait.

Did you skip over the proposal the first time? Me too. I’ll admit, I didn’t read it in full until this morning. Unfortunately for the freelancer, that meant he did not get the job.

Why did you skip the proposal the first time? Take a moment to think about that before moving on. Maybe share what you come up within the comments below — I’d love to hear your thoughts.

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Stop writing about yourself; the client won’t read it.

I skipped the first paragraph because it’s about the freelancer and not about me or the job I am trying to get done: three sentences, three I’s. Imagine chatting with a new match on Tinder and first thing, right after saying “hello,” the other person says, “As a proven partner in relationships, I excel when on dates to the theatre, after traumatizing life events, and when meeting parents.” Most people would never respond. Upwork works the same way.

If you start a proposal talking about yourself, most clients won’t continue reading.

Talking about yourself is not necessarily bad; if done correctly, it can be very engaging. The problem is this freelancer wrote about themselves without relating it to the job or to me. If they had talked about themselves in relation to me or the job, I would have answered.

Back to the Tinder example: if the person on Tinder said, “I noticed from your photos that you’re a Batman fan, me too! I loved the Broadway show — Batman was even more badass in person.” That is interesting (Batman has a broadway show?!), assuming you’re really into Batman. (If you’re not and what you actually like is football, maybe take Batman off your profile. You’re attracting the wrong kinds of people, and that might be why you’re still using dating apps.)

Write about yourself in relation to the client or the job.

Look for ways to relate your strengths to the job posting. In this case, I was looking for someone to help me understand an interviewing technique called Top Grading. This was the job posting:

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Here are some examples of more engaging ways to start the proposal.

  • I applaud your effort to understand Top Grading. I have spent years evaluating executives using the process with outstanding results.
  • I have designed Top Grading interview programs for several organizations and found it one of the best processes for identifying talent. I’d love to teach you how the process works.
  • I have held 30+ mock top grading interviews over my career with executives. I have not worked with software companies, but have the experience needed to teach you the process.

Writing like this shows you read the job description and understand what the client is looking for. With this information, the client can make a quick judgment on whether or not this proposal is worth reviewing.

Don’t provide too much information.

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This is too much information for an Upwork cover letter.

This proposal has too much text in it:

  1. People don’t like to read long things.
  2. , and most freelancers over-share.

The first reason is simple. The longer something is, the less likely someone is to read it. This proposal cover letter is 344 words; about 200 too many. In my experience, the most effective proposal cover letters are 150 words. They are concise and persuasive. Successful proposals pair tailored content with brevity.

The second reason is less intuitive.  that when someone is trying to sell something, most people communicate all the reasons why it could be valuable, thinking they all add up. But when evaluating a purchase, people naturally average what they know about the product or service. That means that when a freelancer includes many reasons they are a good fit for a job in a proposal cover letter each additional reason after the first bring down the client’s assessment of them.

Instead, .

If you leave the best paragraph for last, the client won’t read it.

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The best paragraph of the whole proposal is the last thing this person wrote. It demonstrates he read what I was looking for and represents himself as a qualified candidate. He could have sent only these two sentences and would have probably landed an interview.

Start your proposals with your most persuasive message. You should communicate that you understand the job description and are qualified to help. Choose the top reason you’re a good fit, add nothing more. With that, you’re onto the last step.

Don’t submit a proposal without asking for the interview.

This proposal cover letter ends with Please let me know if you would like to arrange a call. This does not communicate confidence, nor does it call me to action. Instead, ask for a call directly and provide a reason for the meeting. For example:

  • Are you available on Friday or Monday for a conversation? I’d like to understand how you plan to use Top Grading. I’d also like to understand your timeline for this work.
  • Are you available on Friday or Monday to speak? I’d like to understand a bit more about the company you’re using Top Grading for.
  • Are you available on Monday afternoon for a quick meeting? I would appreciate learning more about the roles you’ll be evaluating for with Top Grading.

Writing like these examples does three things. Your question demonstrates your experience, it shows you want to work collaboratively, and if they accept, it lands you the interview!

Effective proposals will help you get a work-from-home freelancing business off the ground faster.

Instead of hitting next on Medium, go to Upwork or now and try writing a cover letter using these tips. Once you get the hang of it, you will become faster, choose jobs that are a better fit, and win more work.

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