Upwork Proposal Mistakes: What to Do About Them

Upwork Proposal Mistakes: What to Do About Them [+Samples]

Today, my conversion rate in Upwork falls around 20% to 40%. Meaning, for every five proposals I send, three will reply and one or two of them will proceed into creating a contract with me.

It looks amazing, especially if you’re someone who’s struggling to land a contract in Upwork.

But truth be told, things weren’t that smooth when I started. In fact, I checked my proposal archive and found out that it took 28 proposals before I bagged my first contract.

That’s a 3.45% conversion rate — too low compared to what I have now.

Over the years, I learned a lot from sending almost a thousand proposals. I gained an insight into what works and what doesn’t — mistakes to avoid when you submit a proposal to a job in Upwork.

That’s what I want to share with you today. Let’s start!

Table Of Contents

Mistake #1: Making it sound like it’s all about you

Seems basic, huh. But humor me for a second here…

Bring up the most recent proposal you sent and examine it. Come on, don’t be shy. I’m not asking you to upload a screenshot of your proposal in the comment section.

Now, count the times you used the words “I” [and “my”] and “you” [and “your”]. Basically, compare the number of times you referred yourself and the client.

Done? Okay, my turn…

Here’s a screenshot of the proposal I sent for the first job I got on Upwork (where I referred myself ten times and the client four times):

The cover letter I sent that got me my first contract in Upwork

You see now? I was lucky that I was chosen despite sending an obviously copy-pasted proposal like this.

The first mistake you need to avoid is to make the proposal sound like it’s all about you unless that’s what the client is asking for. Instead, make it about “them” — their business, problems, and challenges.

I understand though why you want to use so much “I” in the proposal. You feel the need to sell yourself and persuade the client that you’re the right fit — the best choice for the job. It’s tempting, I know.

Every time you feel the need to “prove your worth”, remember that the best way to do that is to show the client how you can help, not by rattling how great you are.

Mistake #2: Charging higher than what the client can afford

I don’t want to sound too pessimistic here…

But charging higher than what the client can afford doesn’t work most of the time (contrary to what “freelance gurus” preach out there).

As a client myself, I have a set budget for every work I outsource. Yes, I want the best possible freelancer to work for me, but I can’t pay him or her outside of my budget. If I do that, I will not be in business for too long.

Take note, however, that you can always try and charge a bit higher to test the water. But make sure not to charge too high.

I do it every time I see a job post that has potential but the budget is below my rate. If the client likes your approach, he or she will make contact. But it doesn’t always end up with a contract.

One time, I submitted a proposal to a job post even though the indicated budget was way below my rate. I tried because I saw in the client’s job history that he paid someone big to do something.

Here’s the result:

My conversation with a client who had a low budget for his project

As you can see, there’s nothing wrong with trying to bid a little high than the client’s budget. But most of the time, it will not work. Check the client history and see if the client paid big to a freelancer with similar services as you.

By the way, if you upgraded your freelancer account in Upwork into “Freelancer Plus”, you can see the bid range of all jobs. This enables you to compare your bid with that of the others who submitted a proposal.

Further reading: Upwork’s “Freelancer Plus” premium account costs $14.99 per month. There are many perks that come with it including 70 free connects per month. But is it worth it? I’ve talked more about it in my Upwork review article. Check it out!

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    Mistake #3: Copy-pasting proposals

    Looking back, one of the reasons why my proposals didn’t work was that they are 100% similar. I thought it will save me time if I copy and paste the proposals I send to different job posts.

    Here’s one embarrassing example of a canned proposal I used:

    An embarrassing cover letter I sent before where I tried to sell every skill I have in one go

    It’s true, though. Using the same proposals (or canned proposals) does save time. But you can’t expect a high conversion rate with this method.

    As James Clear said in his book, Atomic Habits:

    You can’t repeat the same things blindly and expect to become exceptional.

    If you want to save time while keeping your proposals effective, use a proposal template instead.

    With a template, you’re not simply copy-pasting your proposal, you’re changing things here and there to make it personal to the client.

    Changeable sections of your template include:

    • The client’s name
    • The client’s problem/challenge
    • Your proposed solution
    • Your questions
    • Link to your specific samples

    The outline and the basic format of your proposal can stay the same. But using a template will allow you to work faster while keeping the proposal as personalized as possible.

    Further reading: For some, it’s still hard to create a proposal cover letter if you don’t have one that’s working. That’s why I included a cover letter template in my Upwork cover letter guide. Feel free to use it.

    Mistake #4: Not making any research

    When you don’t mention something in the proposal that’s about the client, his company, or his job post, your proposal will sound canned and impersonal. Once again, your proposal will sound like it’s all about you.

    The opening line alone, whether or not you used the client’s name, is a sign already if you’ve done some research or not.

    Remember what Dale Carnegie said in How to Win Friends and Influence People:

    A person’s name is to him or her the sweetest and most important sound in any language.

    But of course, you shouldn’t stop with the name alone. Show some interest in the client’s problem and what value you can add to the table.

    Some suggestions:

    • Did you encounter a similar problem in the past with another client?
    • Do you know of any easy or fast solution you can implement to solve the problem?
    • Is there something you would like to ask or clarify about what the client needs?

    In addition, you will often find information about the client and his company on the client’s job post itself or in recent history. This is exactly what I did which led me to land a contract with a tech startup.

    Here’s a portion of the proposal I sent which shows that I researched the client’s company and their product:

    Gave a hint to my client that I've read their about me page

    If you really can’t find any clue at all, then try to settle by asking a specific question about the proposal or suggest a good approach to the problem.

    The goal here is to get the client’s attention and reply to your inquiry.

    Mistake #5: Spending all your energy on the cover letter

    Did you know that every time you submit a proposal to a job post in Upwork that has additional questions, it’s the questions the client sees first (and not the cover letter)?

    I discovered this when I created a job post myself…

    An example of a job post in Upwork that has additional questions

    Someone then replied to it and here’s what I saw:

    The answer of the freelancer to the first question is only a word

    That’s why it’s a big mistake to spend all your energy on the cover letter when there are additional questions in that job post. If the client doesn’t like your answer, he will never get to see your cover letter.

    What you can do here is to inject some parts of your cover letter into the answers. Make the answers meaty and assume that the client will only read the first or second answer before he replies to your proposal.

    Here’s an example of an answer I gave to an additional question:

    A meaty answer I gave to the first "additional question"

    My cover letter for this proposal was only 60 words, but I still got the contract. Naturally, I didn’t ignore the cover letter — I still indicated in the cover letter how I read the client’s brief that he included in the job post. But that’s it.

    In some way, your answers to the additional questions are more important than the cover letter itself.

    Mistake #6: Not giving the client any reason to partner with you

    I know, this might seem a bit contradictory to “not making it sound like it’s all about you”…

    However, what I mean here is when your proposal comes off as more of a resume and a biography of your life, you’re not presenting any solution to the client.

    If you tried applying for a job in a company in your area, the hiring manager must have asked you this question:

    Why should I hire you?

    It’s the same in Upwork. You must answer this question in your proposal in a low-key manner and not rattle everything about all the skills and certifications that you got.

    Here are a few suggestions that seem to work with the proposals I sent:

    • Present a solution to the client’s problem
    • Use case studies or past projects when applicable
    • Only send samples that are relevant to the client

    It also works to mention big brands you have worked with to give a hint to the client that big brands trust your expertise.

    Here’s an example of how I did it:

    Dropping a big brand name on the cover letter

    As you can see, I was implying to the client the many known brands and companies have trusted me and my services. Whether or not this is what convinced the client to hire me, I didn’t ask.

    But I’m sure that this increased my credibility in the eyes of the client.

    Mistake #7: Slapping a big wall of text

    This mistake is more of a technical nature and has something to do with how you format your proposals…

    But the bottom line is, you shouldn’t submit proposals with a big wall of text. No one wants to read a big slab of text.

    In case you don’t know what I’m talking about, here’s an example:

    A cover letter without any whitespace looks really ugly

    Note that I didn’t submit this proposal looking like this. I used DevTools to make it look like a slab of text, which you should always avoid.

    This happens when your proposal doesn’t have enough white space. Translation — you’re not using the “Enter” key that much.

    Aside from making your proposal look better, research from Wichita State University revealed that whitespace improves reading comprehension:

    Properly using whitespace between paragraphs and in the left and right margins can increase comprehension up to 20%.

    The bottom line here is you should always make your proposal more readable by using fewer sentences in a paragraph. Give your words space to breathe.

    Mistake #8: Submitting a proposal on stale job posts

    There may be times when you sat down for an hour or two and submitted a proposal to every job that fits the bill — even though the job post is a day old. I’ve done this a few times when I was still starting out.

    However, there’s little sense in submitting a proposal to a job post that’s more than 12 hours old — unless there are only a few people who submitted a proposal to it.

    But more often, the client may already be considering someone else for the job already. So you’re just wasting your precious connects with a job that’s already taken.

    While browsing for a job post, you can check how many hours the job was posted and how many proposals were sent already.

    Here’s an example:

    You can always check how many hours the job was posted and how many proposals were submitted

    In addition, clients will usually read only the first and last proposals sent. Those sent in between have smaller chances of being seen especially when there are more than 20 proposals.

    Personally, it’s a good habit to check Upwork one to two times a day. This enables you to stay on top of the jobs posted without spending too much time on it.

    Mistake #9: Selling everything all at once

    A common mistake that newbies commit is selling to the client almost every skill that he has that may be totally unrelated to what the client needs.

    Again, this happens if you’re using a canned proposal.

    Here’s the screenshot again of a canned proposal I sent that perfectly illustrates what you shouldn’t do:

    An embarrassing cover letter I sent before where I tried to sell every skill I have in one go

    Do you see it?

    I was practically throwing every I got out. Obviously, I didn’t get the job.

    A good approach is to sell your solution to the client — how will you be able to help him solve his business problem?

    Whatever your approach is, don’t sell everything at once. Focus on a single goal. That could be as direct as inviting the client to hire you or it could also be as simple as inviting the client for a chat.

    Oh, you should also avoid acting like a superman.

    Avoid making false promises to the client and making it appear like you can do everything. Sell your solution, but don’t go overboard and commit to giving the sun and the moon.

    I encountered a few people on Facebook who try their luck by submitting a proposal to a particular job that they don’t know how to do yet.

    It works in some cases. But it’s rare. It’s more possible that you end up disappointing the client or you end up getting bored doing something you don’t like to do.

    In any case, don’t claim to someone you’re not.

    Mistake #10: Not making a conversation

    This is a short one. If you tried receiving a reply to your proposal, you must’ve noticed that your proposal cover letter is the first message you sent to the client and it’s like the client is merely replying to your message.

    Take a look at this:

    The cover letter you sent will always serve as the first message you sent in the chat

    As you can see, the client actually replied to the question I threw in my cover letter.

    That’s why it’s a mistake to not make a conversation in your proposal (by asking or suggesting something).

    Don’t write the proposal like you’re submitting an essay to your English teacher. Don’t write in third-person either. Write it like it’s a chat.

    Mistake #11: Being cheap

    The reason why “freelance gurus” hate Upwork is because of its race to the bottom nature. It’s not entirely false. But it’s up to you if you go with the flow.

    Now, being cheap doesn’t exactly mean you will not get any jobs. On the contrary, you may more deals that you can handle. However, you may not be receiving compensation for what you’re worth.

    For example, I saw this job post one time that got me curious…

    An example of a job post in Upwork with a low rate

    I didn’t submit a proposal since I know I won’t be paid my worth. In the client’s recent history, I saw that he paid someone to write an educational blog for only $25, which is way below my rate.

    The client's history included a project where he paid someone a measly $25 for an educational blog

    My advice?

    Don’t compete by bidding the lowest price. You will come off as a newbie instead of a professional. Plus, you will not enjoy working for that client.

    Further reading: There are also clients who will try to fool you by entering a large budget for the project. But in reality, they will only pay you peanuts. That’s one of the tips I gave for new Upworkers. Check out the article.

    Mistake #12: Submitting a proposal for every possible job

    Lastly, one of the mistakes that may cost you your time and connects is submitting a proposal for every possible job post that you see. I foolishly did this in the past and used canned proposals to make the process faster.

    Before you submit a proposal, check first and see if it fits the bill.

    At the very least, ask these questions first before you submit a proposal:

    • Is there something you can do that could help the client achieve his goals?
    • Is the price right for you?
    • Does the client have a good relationship with his past hires?

    In addition, don’t submit a proposal to a job that has tasks you don’t like to do.

    One time, I submitted a proposal to a job that wants me to undergo a lot of verification tasks like creating a video — all for the sake of “proving my interest” on the job.

    I thought that if I submit a well-written proposal, the client would give me a pass. Unfortunately, he didn’t do that and instead forced the “verification process” on me.

    Here’s a part of our conversation:

    How I declined a client who wants me to submit a YouTube video as proof that I'm interested in the job

    So before you submit a proposal, examine the job post first and whether or not it passes your criteria. Never ever submit a proposal to a job that you don’t like to do in the first place.

    The Twelve Lessons in Creating a Proposal in Upwork

    After submitting close to a thousand proposals in Upwork, I gained insights on how to create a proposal that has a high conversion rate. I came face to face with embarrassments and wasted lots of connects to get where I am today.

    But you don’t need to experience the same things…

    All you need to do is to remember these twelve lessons I learned from the mistakes I committed when creating a proposal in Upwork:

    1. Don’t make it sound like it’s all about you.
    2. Don’t charge higher than what the client can afford.
    3. Don’t copy and paste proposals or use any canned proposals.
    4. Don’t submit a proposal without doing any research.
    5. Don’t spend all your energy on the cover letter when there are additional questions included in the job post.
    6. Don’t make it hard for the client to hire you.
    7. Don’t submit a proposal with a big slab of text.
    8. Don’t submit a proposal to job posts that are older than twelve hours.
    9. Don’t sell all your services to the client in one go.
    10. Don’t forget that your proposal cover letter is like the first message you send in a chat.
    11. Don’t be cheap.
    12. Don’t submit a proposal to every job post in Upwork.

    Now it’s your turn.

    • Which of the mistakes mentioned in this article do you find yourself committing the most?
    • The next time you submit a proposal in Upwork, take note of all the things you learned here.

    Share your thoughts and learnings below so others may benefit from your knowledge as well.

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      About Alan

      Alan is the founder of Work Pajama. When he's not writing here, he's busy helping clients generate more qualified leads and increase sales by educating readers with strategic content and writing blogs.

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