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What’s your close rate on proposals? Do you win one out of every 10 gigs you quote? Two of 10? Five of 10? More?

Even if you don’t know your close rate exactly, you probably have an idea of where you fall on the scale:

  • I win far fewer gigs than I want to--I need to close more!
  • I win a modest amount of proposals--but could still use more work.
  • I win tons of proposals and have more work than I can handle.

Me? I’m in the latter camp, and pretty much have been since I started freelancing 15 years ago. If you want to improve your proposals and win more gigs, read on. I’m going to teach you the secret to my proposal success--what I do to win lots of proposals.

By the way, I share this advice not only as a freelancer, but also as a consumer of freelance services. I’ve been on the buying side of freelance services for the last 15 years, too, both for my own businesses and for my clients’ businesses, so I know what turns clients on--and off.

Let’s dive in.

Step 1: Read the entire job description carefully, noting special requirements.

Seems obvious, I know. But I’m shocked at how few freelancers actually read proposals. I posted a few gigs recently asking prospective freelancers to respond to a specific set of questions, and immediately nixed those who ignored that request.

Some special requests may be unusual, like this one, spotted on an Upwork gig:

What do you think this cat is thinking?

If you missed answering that specific question, it wouldn’t matter how good your proposal was because the client would probably decline it without reading.

Step 2: Learn about the client.

This step is important because it tells you how serious the client is, the nature of her business, and whether you may have opportunities for future work.

I learned from the proposal page of the client who asked the cat question that she’s posted more than 6,000 jobs on Upwork (Elance / Odesk), and has spent more than $50,000. Other recent gigs she posted include:

  • Android developer, long-term, full-time position
  • Animator to illustrate process flows
  • Copy editor
  • Logo designer
  • Online researcher for sales team
  • Customer support associate
  • Economic consultant

You can tell from these details that the client is running or responsible for one or more serious businesses. She’s likely not a solopreneur or half of a mom-and-pop endeavor, although that could be the case. The takeaway? Step up your professionalism to win this gig.

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Step 3. Put yourself in the client’s shoes to analyze the project.

Talk is cheap, so let’s analyze a real-life proposal from Upwork together. I chose a job for a virtual assistant, and one for which the client is willing to pay for expert-level support. (I assume those are the kinds of jobs you want, right?)

Here’s the post:

I need to hire a virtual assistant to review some spreadsheets. You will need to perform some data entry. I've got several hundred job applications spread across a hundred open positions. I need some help evaluating these applications. Your job, if you choose to accept it, would be to read every job description, read some details from every application, and then write a short note and assign a numeric score assessing the fit of each applicant for the job in question.

This gig received 147 proposals. The client interviewed two freelancers, and hired three.

Would you have responded even if you lacked experience evaluating applications? What would your proposal have looked like?

Even though I’m not a virtual assistant, I’ll show you how I’d evaluate this request:

I need to hire a virtual assistant to review some spreadsheets. You will need to perform some data entry.

First, note that the client wants someone to review spreadsheets and do data entry. If you have that experience, great. If you’ve taken a data entry test and can speak to your KPH, better.

I've got several hundred job applications spread across a hundred open positions. I need some help evaluating these applications.

Next, note that the client needs to fill 100+ positions, and has hundreds of job applications for those positions. What’s that tell you?

It tells me that the client is probably extremely busy, and may be feeling overwhelmed faced with this monumental--and crucial--task. Making the right hires is super important to any company.

I’m betting that this client is looking for something far beyond data entry and spreadsheet experience, so if that’s all your proposal talks about, your chances of getting hired are likely low.

Your job, if you choose to accept it, would be to read every job description, read some details from every application, and then write a short note and assign a numeric score assessing the fit of each applicant for the job in question.

Wow. That’s a hefty responsibility. You will be, in effect, judging whether or not a candidate is suitable for a particular role as outlined in the description. Which means that the client is either directly or indirectly responsible for doing the same thing.

Let’s think about this work.

First, what abilities might you need? How about the ability to:

  • Read between the lines, so that if the job description says “marketing experience” and the resume says “grew a firm’s revenue from $120K to $360K using outbound techniques,” you can make the connection and score resumes appropriately
  • Identify candidates’ unique differentiators
  • Clearly and concisely communicate back to the client what those differentiators are

Second, what will the result be if you do a bang-up job and perform with excellence? The client is going to look good. She’s not going to miss great applicants, which means competitors won’t be able to snap them up.

Third, what will be the result if the client hires the wrong freelancer--someone who does a poor job? Well, the client is probably going to miss some really great people. Or hire the wrong people. Either way, that’s going to make her — or someone she’s reporting to — look really bad.

Granted, we might be overanalyzing, but most freelancers won’t bother with any analysis, which means that this work is going to help you set yourself and your proposal apart.

Step 4. Armed with your insights, write the proposal.

How would you start a proposal for a job like this? So many freelancers start this way:

Hello. I’m interested in this job, having worked for 10 years as a virtual assistant. I have a degree in journalism, and many satisfied and repeat clients. My Upwork success rate is 100% and I am a top rated provider. I am free to begin this work immediately. I … I … I ….

The problem with a proposal like that is that it’s all about you, the freelancer. I count five “I”s and “my”s over four sentences. That’s way too much. I also count zero “you”s. That’s way too little.

While it’s good to introduce yourself, you also want to stand out from the crowd by showing the client that you’ve thought about the work, have an idea of what’s needed, and will help her achieve the results she’s looking for. Make the proposal all about HER, and speak to what you’ve gathered from your evaluation.

“Hello. I’m Renae Gregoire, a virtual assistant here on Upwork. I’d be happy to pre-evaluate applicants for you by comparing the details of their applications to job descriptions and the scoring method you provide. I recognize the importance of this task because just as the right hires can put your company on the fast-track to success, the wrong hires can bring it down.

I’m not entirely sure what you’re looking for, but imagine that you’d want me to:

  • Read between the lines, so that, for example, if the job description says “marketing experience” and the resume says “grew a firm’s revenue from $120K to $360K using outbound techniques,” I could make the connection and score the resume appropriately
  • Identify candidates’ unique differentiators
  • Clearly and concisely communicate back to you what those differentiators are

If you have any questions, or if you’d like to speak further, please message me. I’m available to start immediately.

Do you see what I did? That’s what you need to do, too.

In summary:

1. Read the request thoroughly. Note any unusual requirements (like being asked to describe what’s happening in a cat gif) so you don’t forget to respond to those elements.

2. Check out the client. Is it a corporate thing? Is the work for an agency, or another freelancer? Different clients deal with different stressors, and you can address the right stressors in your proposal.

3. Put yourself in the client’s shoes to analyze the request. Write down your answers to the following questions:

  • Is the client in pain? What kind of pain? What might they be feeling?
  • What negative things will happen if the job is not completed successfully?
  • What good things will happen if the job is completed successfully?
  • What might YOU expect a freelancer to do if you were hiring for this job?

4. Write your proposal using the points you jotted down. Use the word “you” at least as much or more than you use the words “me, I, or my.” Focus on them, not on you.

If you follow these steps and start winning more proposals, please let me know. I love to know when I’ve helped other freelancers experience success!

Renae Gregoire is a freelance marketing writer who’s crazy-passionate about freelancing. Find her at www.facebook.com/realfreelancing, where she helps newbies to become freelancers, and established freelancers to win more freelance gigs.


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