And “Dear Hiring Manager, I am excited to apply” just wasted both of them.
I've made over $300K on Upwork.
And after writing God knows how many proposals, testing different approaches, getting hired, getting ignored, and figuring out what actually gets clients to respond, I've learned something important:
There is no magical Upwork proposal.
There isn't one template that gets everybody hired.
There isn't one opening sentence that works on every client.
And anybody selling you the idea that you can copy and paste your way into a booked-out business is leaving out the most important part.
You have to understand the person reading it.
Before I Write Anything, I Go Snooping
Not creepy snooping.
Professional snooping.
Before I spend Connects applying for a job, I want to know what I'm walking into.
I'm reading the entire job post.
I'm looking at the client's reviews.
I'm checking their hiring history.
If they've included their company name, I'm looking them up.
Website.
LinkedIn.
Whatever information is available.
Because I'm trying to answer a much better question than:
What does this client want me to do?
I want to know:
Why do they need somebody to do it?
That's where the proposal starts getting interesting.
Stop Introducing Yourself Like You're at a Networking Event
Clients already know you're applying.
You don't need to open with:
“Hi, my name is Monica and I'm excited to apply for your Virtual Assistant position.”
You have limited real estate at the beginning of that proposal.
Use it.
If the client says they're drowning in onboarding tasks, I'm probably going to start there.
Something like:
“I saw you're trying to clean up your client onboarding before bringing on more customers. Smart move. Fixing the process now can save your team a lot of unnecessary work later.”
Now we're having a conversation about their business.
Not my résumé.
They can learn about me in a minute.
First, I want them to know I actually read the damn job post.
Skills Are Nice. Tell Me What They Do.
One of the biggest mistakes I see VAs make is giving clients a grocery list of skills.
Inbox management.
Calendar management.
Project management.
Canva.
Notion.
ClickUp.
Google Workspace.
Wonderful.
What does any of that do for me?
Translate the skill.
Instead of:
“I manage inboxes.”
Try:
“I can organize your inbox and create a communication system so important messages aren't getting buried.”
Same skill.
Very different conversation.
One tells me what you do.
The other helps me picture what changes after I hire you.
That's what I care about.
Then Give Me a Reason to Believe You
You don't need six paragraphs explaining why you're amazing.
Give me proof.
Maybe you helped another client solve something similar.
Maybe you reduced response times.
Maybe you organized a messy process.
Maybe you've supported the same type of business.
Maybe your previous experience makes you particularly good at the problem they're trying to solve.
One useful proof point can do more work than an entire paragraph full of adjectives.
And please don't make shit up.
If you're newer and don't have the perfect testimonial yet, that's okay.
Use relevant experience.
Use a sample.
Use a portfolio piece.
Use your understanding of the problem.
Everybody starts somewhere.
Keep the Damn Thing Moving
I generally want a proposal to feel easy to read.
Hook.
Re-hook.
Relevant approach.
Proof.
Invitation to talk.
That's why I sometimes tell people to think about proposals the same way they think about social content.
You have seconds to earn the next sentence.
Then that sentence needs to earn the next one.
You're not writing your autobiography.
You're creating enough interest for the client to think:
Okay. I want to talk to this person.
That's the job of the proposal.
You Don't Need to Sound “Professional”
You need to sound like a professional.
There's a difference.
One sounds like:
“I am confident that my extensive skill set and proven expertise make me an ideal candidate for this opportunity.”
The other sounds like an actual person who understands the work.
I know which one I'd rather interview.
Your proposal should sound like something you'd reasonably say to the client on a call.
Warm.
Capable.
Specific.
Human.
If you've edited every ounce of personality out of it because you're trying to sound impressive, put some of yourself back in.
They're hiring a person.
And Please Stop Writing Novels
I don't need 700 words to decide whether I want to talk to you.
Around 250 words is plenty for many proposals.
Sometimes you'll need less.
Sometimes the project warrants more.
Again, there isn't one sacred formula.
But every sentence should have a reason for being there.
If you've already proven you understand the problem, shown me how you'd approach it, given me some proof, and invited me to talk...
You can stop typing.
Seriously.
Step away from the keyboard.
My Favorite Proposal Test
Before submitting, I read it and ask myself:
Could I send this exact proposal to five other clients?
If the answer is yes, I'm probably not finished.
Because a strong proposal should contain enough specific information that it clearly belongs to that job.
That's why templates can get dangerous.
A structure?
Absolutely.
A framework?
Love one.
Copying the same 200 words into every application and changing the client's name?
Baby, they know.
There Are a Lot of Ways to Get Hired on Upwork
I want to make that part very clear.
This is one approach I've used and taught.
It's not Upwork gospel.
I've seen short proposals work.
I've seen longer proposals work.
I've seen people lead with questions.
I've seen people lead with proof.
I've seen people get hired because their portfolio did most of the talking.
The point isn't memorizing my proposal.
It's understanding why each piece is there.
Research the client.
Understand the problem.
Open with something relevant to them.
Connect your skills to what they need.
Give them a reason to believe you.
Then get the hell out of the way.
Because your proposal doesn't need to close the entire deal.
It needs to get the conversation started.
And sometimes?
Two really good opening lines are what get you there.
CURRENT MOOD
“Espresso” by Sabrina Carpenter.
Because a good proposal should have a little of that same energy.
Short.
Confident.
Memorable.
And just interesting enough that somebody wants another sip.
You're not trying to tell the client everything you've ever done.
You're trying to make them curious enough to click your profile and reply.
That's the assignment.
Listen to “Espresso” by Sabrina Carpenter on YouTube
PEAK OF THE WEEK
Remembering just how many versions of my own Upwork proposals I've written over the years.
Some worked.
Some absolutely did not.
And that's probably why I don't believe in pretending there's one perfect formula.
You test.
You pay attention.
You get better.
And eventually that blinking cursor stops being quite so intimidating.
#EarnTheReply
XXX,
M💋
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