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How To Ace Upwork’s Interview Process (And Obliterate Your Competition)

Let's face it, nobody likes interviews.

Having to prove yourself to someone you likely don't even know is tough. And when it goes wrong, it's demoralizing.

But what few freelancers realize, is that Upwork's interview process is far from a typical job interview. And, once you fully understand how it works, you'll see that it's actually not all that scary.

In today's post, I'll reveal how interviews truly function on Upwork, and more specifically, some core principles that allow you to breeze through Upwork interviews every single time.

The Initial "Interview" Phase

There's a reason I put the word "interview" in quotes.

Not because I like quotes (who doesn't like quotes?). It's actually because the term is a little misrepresented on Upwork, specifically.

In the real world, an interview would be defined as:

"A somewhat formal discussion between a hirer and an applicant or candidate, typically in person, in which information is exchanged, with the intention of establishing the applicant's suitability for a position."

But on Upwork, that's not strictly the case.

In fact, the official moment an interview begins is when a client responds to a freelancers application (or proposal). You can even see this publicly.

A response doesn't necessarily mean they want to interview you per se, and in many cases, it means:

  • Scenario 1: The client wants to give you more information about the task
  • Scenario 2: They're already sold on you and want to ask some general questions (ideas, availability, etc.)
  • Scenario 3: They're looking to negotiate (price, deadline, scope of work, etc.)

All of that stuff just relies on basic communication and negotiation skills.

Of course, there will occasions where the client prefers to do a separate, slightly more literal interview to help narrow down their options.

Lewis's Note
It's even possible to skip the "interview" process entirely if the client sends a hire request in direct response to your proposal. It's quite rare, though.

2 Types Of Dedicated Interviews

So let's assume the client does want you to prove yourself, how does that actually translate?

In my experience, it can be broken down into two core types.

  • Type 1: The Call
  • Type 2: The Sample

In this post, I'll only be breaking down 'Type 1' since that's the area people tend to struggle with, and it's also what most people would associate with being
"an interview."

(Don't worry, I plan to a release a separate post on samples soon. I'll update this section when I eventually hit publish on that bad boy.)

The Call

In this case, the the client will reach out to request to have a call with you. Usually on a separate platform (although you can actually call directly through Upwork now.)

Here's how that might look:

A key thing to keep in mind here, is that most clients will assume this to be an unpaid offering of your time.

Now, there are very few cases where I recommend working for free, but given how well these calls convert, I'd say it's very low-risk on your end -- providing you execute properly, of course.

That said, there are a couple boundaries I'd recommend you communicate to the client from the offset.

Boundary #1: Date And Time

As you can see in the screenshot above, the client will often suggest a date and time for the call.

Since Upwork is an international marketplace, it's very likely that clients will suggest times that are super inconvenient for you. And, if that's the case, don't be afraid to offer alternatives that better suit you.

In fact, you can even use a tool like Calendly to give the client a visual overview of your availability, and they can book themselves in. (This is also great for positioning yourself a high-level, in-demand freelancer.)

Lewis's Note
If the client doesn't show up and fails to give you notice of cancellation, I recommend taking that as a pretty big red flag and considering passing on the opportunity entirely.

Boundary #2: Duration

This is a BIG one and something I was always reluctant to do when I first started out, but it's a necessary part of establishing yourself as a professional and learning to respect your own time.

Most invitations for a call are open-ended. They have no specified duration and could last anywhere from a few minutes to an hour (or longer).

That's why it's your responsibility, as the service provider, to communicate the allotted time-frame of the call. Especially if you're not being paid for you time.

Not only does this BEAM authority, but it forces both parties to get all their ducks in a row before the call and make it a highly-focused and productive 10...15...20 minutes.

How To Pass With Flying Colors

Ok so you've had a response to one of your proposals, and you've successfully scheduled a time to jump on a call.

What next? 

Well, one of the best ways to ensure a smooth interview (and to almost certainly bag the job) is to be irrationally prepared for every scenario.

Now, as I said before, these interviews are almost never like traditional job interviews. They tend to be a lot more informal and sometimes even require YOU to take the lead.

As long you're prepared, that will never be an issue. In fact, taking the lead is often something you want to strive for. Being able to direct the conversation in a way that hits all the right notes is exactly what you want.

Being Irrationally Prepared

I don't care how nervous or inexperienced you are for a call, being unreasonably and irrationally prepared is the only way to overcome the negative emotions and absolutely blow your prospective client away.

Look, 90% of the interview takes place before the interview even starts. The rest is just executing on what you've already laid out for yourself prior to jumping on the call.

Okay, I've got a lot to share so this will a bit of a quick-fire section:

#1: Just Ask

Once you've scheduled a call with the client, you should always ask if there's something they'd like you to prepare for the call.

Even though you'll already be preparing everything you could possibly need, their answer can often give insight into what kind of interview the client wants this to be.

(Whether it be a casual chat, a strategy call, or a more traditional, question-by-question grilling.)

This is more of a mindset thing more than anything else, and going in with the right mindset is another form of preparation that should never be underestimated.

#2: Reread The Job Description

Rereading the job description you applied for is a great way to get a quick refresher on what the opportunity is actually about.

It can sometimes be weeks until you hear back from a client, let alone end up on a call with them, which is why it's crucial to remind yourself of why you were interested in the first place.

This also ties in heavily with the new few points...

#3: Research The Company

The job description rarely offers enough information to get a complete understanding of the clients company and their goals.

A great place to get that information is from the company website. If the client didn't mention their website anywhere on Upwork, take a note from the first point and just ask.

You don't have to spend hours combing through each page of their website, but a quick read over the home page and about page will likely give you more insight than you know what to do with.

#4: Always Be Taking Notes

As you do your research prior to the call, you should always be taking notes. It sounds obvious, but you'd be amazed by how many people skip this part.

Relying on your brain to recall information at just the right time is a risky move, and the payoff for getting it right is significant enough to warrant going the extra mile to have it all written down.

Trust me, something as simple as reading back a clients mission statement in the midst of a conversation will earn you HUGE brownie points.

#5: Have Samples Ready

Often times, even though you've likely provided a sample prior to the call, you will mention something that ties in closely to something you've done previously.

For example, that might be a particular strategy you recommend the client take, which is likely something you've executed in the past. Wouldn't it be awesome to back up your advice with a proven case study?

It's all well and good saying "I'll send that to you after the call", but walking the client through it right there and then has significantly more impact than letting them figure it out solo. (And that's if they even remember to check it.)

#6: Watch Your Connection

I won't jabber on about this because it's fairly straightforward -- but it's so important to take the call on a stable internet connection.

There's nothing worse than having to repeat yourself countless times (or worse, asking the client to repeat themselves) because you couldn't be bothered to check your WiFi capabilities.

No matter how prepared you are in terms of what to say, none of it matters if you're not able to properly communicate.

#7: Don't Dodge Questions

Very occasionally, you'll get that one question you're not quite sure how to answer. It may be that you don't know how to phrase it, you're not confident in your ability to explain it, or you simply don't know the answer.

It happens. Don't sweat it. But the last thing you should do in that situation is try and dodge the question. Just be straight about your concern in answering that specific question.

Being upfront and honest is something that anyone (and especially clients) will appreciate, and maintaining authenticity is always a good substitute for when you don't simply don't have the answer.

Wrapping It Up

As I'm sure you've gathered by now, Upwork interviews aren't something to get your knickers in a twist over.

At it's core, the key is to understand the true definition of an Upwork interview and how it actually functions in comparison to a traditional interview.

From there, success simply comes down to your ability to be irrationally prepared for every possible scenario. And believe me, few freelancers are taking advantage of this crucial phase of client acquisition.

Upwork Proposals: A Deep And Thorough Analysis Of A Real Cover Letter

Ahh… Upwork proposals.

As a long-time Upwork client, I’ve personally read well over 1,000 proposals and hired my fair share of freelancers along the way.

If there’s one thing I can say without a doubt, it’s that the majority of proposals I’ve received over the years have been… well... awful.

The truth is, most freelancers are completely oblivious to what really makes a great Upwork proposals (even if they think they know).

So here’s the deal…

Today, I’m not just going to tell you what makes a winning Upwork proposal, I’m going to show you.

Making The Cut

I recently posted the below job ad on Upwork (twice), where I was looking to hire a content writer.

Within 24 hours, I’d already managed to attract a couple dozen applicants.

As usual, though, I ended up deleting 98% of the responses I received. (Out of 31 responses, I was left with 2 reasonably good candidates.)

Like I said…

...I’ve gone through this elimination process countless times already, and this kind of result isn’t too far from the norm.

If you’ve ever found yourself applying to endless jobs only to never hear back, it’s because you’re just not making the cut.

The good news?

It’s easily fixable once you learn and implement what I’m about to teach you. Today, I’ve picked out one cover letter I'd like to share with you.

Obviously, my goal isn’t to “out” anybody here, it’s to highlight common mistakes in the hope that I can help you better your proposals and land more clients.

Note: When I say “proposal”, in most cases, I’m actually talking about the cover letter in particular, which is the written part of an Upwork proposal.

The Cover Letter

Below is the cover letter we'll be analyzing, and this is one I received only a few days ago in response to my job ad.

I've blurred out some personal information for anonymity, but have a quick read over it. Please. 🙂

I chose this one for the case study because if you read it, you’ll probably struggle to find anything inherently “wrong” here.

(In fact, it's a lot better than most proposals I receive through Upwork.)

But, while I will admit this isn’t a terrible cover letter, there are still a few fundamental flaws I'd like to address.

Pay attention, because I bet your bottom teeth you're doing at least one of these yourself.

The Bad Stuff


Before we even get into the meat of this cover letter, there’s already a slip up on the very first line.

If you look at my job advert again, you’ll notice I actually included my name at the very end.

Obviously, this freelancer didn’t bother to address me by name, despite the fact I gave it to them on a silver platter.

Maybe they didn't read the entire job ad, or maybe they just didn't think it was important to include it. Either way, these are not traits I would personally be looking for in a freelancer.

Lewis's Pro Tip
Many clients - including myself - purposely include a name to quickly eliminate ~60% of applicants who miss it. It's just another filter, so don't get caught by it.


This is the one most freelancers get caught up in - and likely the one you missed after reading the cover letter.

It’s not what they said, it’s HOW they said it. The entire letter is focused on the freelancer, not the client.

In fact, just look at how many "me" statements there are (yellow) compared to statements that are focused on me (green):

Look, I get it. It makes complete sense to mention your achievements, your experience, and your talents. There’s nothing wrong with that.

But unless you can directly relate those things back to the client and explain exactly how they will benefit, none of it matters. It’s just waffle.

Lewis's Pro Tip
Try turning a "me” statement into a “you” statement wherever possible. And if you absolutely have to talk about yourself, be clear about why the client should even care.


I always get asked about the “correct” length for a cover letter, and honestly, it’s hard to say exactly what that is.

What I can say is, the goal should be to include only the essential elements in as few words as possible. (It's obvious, but you'd be surprised.)

From my experience, the sweet spot tends to be somewhere around 120-150 words. Considering this cover letter stands at 226 words, it’s already a bit too long in my opinion.

Remember, clients are busy people. The last thing they want to see is a wall of text. Keep it short, fluff-free and punchy.

Lewis's Pro Tip
Psst.. I share my exact cover letter structure with email subscribers. Just click this box if you're down.


This is another "hidden" filter I plant inside my job ads.

Some freelancers are very quick to just point you to their portfolio and have you wade through different samples until you find a relevant piece. (Please, please, pleeeeease don't do that.)

Others will do one slightly better and attach half a dozen relevant pieces to the cover letter itself. But again, that's hardly respecting the clients time.

That's why, in my job ads, I make sure to slot this little gem in somewhere:

Even with that so bluntly thrown in, roughly HALF of applicants fail to include a single sample piece.

The proposal (or cover letter) above was no exception. No links. No attachments. Not even a portfolio on Upwork. Nothing.

The Good Stuff


If there's one thing this cover letter is full to brim with, it's credibility.

This particular freelancer is involved at high-level with several recognized online publications. And that says a LOT in terms of writing ability.

Not only that, but I can actually verify whether these claims are true, just by going to each website and looking for the name. (Some form of verification is crucial whenever you're trying to establish credibility.)

Of course, the freelancer has gone a little overboard in this case, but the right ingredients are definitely buried in there. No doubt about that.

Lewis's Pro Tip
If you're looking for other ways to establish credibility, I wrote a killer post on something I call "The Mind Map Method".


What can I say... the spelling and grammar is flawless.

As someone who's hired more writers than anything else on Upwork, it's clearly important for me to see stellar writing ability within the cover letter itself.

Even if you're not a writer, it still doesn't hurt to run your cover letter through some free tools before you send it off. (Bad spelling and grammar is still a low quality indicator.)


Your proposal (and your cover letter in particular) is easily one of the biggest contributing factors when it comes to winning contracts.

Fortunately, as long as you follow the principles I've outlined in this case study, you'll be able to take your own cover letters to the next level.

In fact, get yourself over to Upwork right now. Fire off some proposals while this stuff is still fresh in your head. Never know, you might surprise yourself.

How To Beat Upwork’s Fees (And A Look Back At Last Years Infamous Fee Hike)

If there's one thing freelancers always complain about when it comes to Upwork, it's the fees.

And you know what? I get it. I really do.

Upwork is easily one of the highest commission freelance platform after last years fee hike. And that's not an easy pull to swallow when you're out there busting your gut, trying to make a living.

The good news is, Upwork is still one of the best places online to find high-quality, long-term clients... even with the increased costs.

Don't believe me? Keep reading.

The Price Hike

In case you just recently joined the party, let me get you up to speed.

Almost exactly 1 year ago, we, the freelancing community, woke up to the news that Upwork were about to change their fee structure.

Here's a snippet from the email:

The changes meant that, as of June 2016, freelancers would forfeit more of their earnings on future jobs with new clients. (At least until they hit the threshold.)

Essentially, Upwork wanted to implement a "sliding fee structure" that both rewarded high value-contracts AND punished low-value contracts.

Before the hike, it was a flat 10% fee across all contracts (and even then, some people argued this was too high.)

Fast forward today, here's what it looks like:

And while a sliding structure does make a lot of sense, it doesn't necessarily work out better for the little guy.

Lewis's Note
A fee was also introduced for clients, which previously didn't exist. It still stands at 2.75% on all payments.

Doing The Math

Now, I'll be real with you.

I'm a huge fan of Upwork. I used it to kickstart my freelance business. I've recommended it to countless people. And I've even built a complete video training course around it.

But that doesn't mean I agree with everything they do. I don't.

Just running the math on Upwork's "improved" fee structure shows why the move didn't benefit the majority of freelancers on the platform.

Here's what the sliding structure really meant:

  • You now pay 10% more on earnings for the first $500
  • You now pay the same on earnings after $500
  • You now pay 5% less on earnings after $10,000

Lewis's Note
This means for every new contract, you now pay an additional $50 upfront, and that will only balance out once you exceed $11,000 in earnings (for each client.)

And look, I always advocate charging premium prices and building long-term relationships with your clients. Regardless of price hikes.

But I'm sure I don't need to tell you, securing $11,000+ clients just isn't feasible for most freelancers. Far from it.

Of the 12 million freelancer accounts in Upwork's system, less than 1% have earned over $10,000. Much less with a single client.

What I'm saying is, the community had every reason to be upset. And believe me, they were upset...

The Backlash

The change was always going to ruffle some feathers, but I was still surprised at how seriously pissed some people were.

These are some snaps I took from Twitter when the news went out...

Some freelancers even vowed to leave the platform, using the hashtag #boycottupwork

And it wasn't just Twitter.

Shortly after the announcement, many headed to Upwork's own community forum to get some things off their chest.

This thread reached 576 replies in a single day - something I've never seen happen before in this particular forum.

Fighting Upwork's Corner

Like I said earlier, I get it. Having to pay a fee on your earnings is a bitch. I think we can all safely agree on that.

But let's take a step back for a moment. Let's look at what you're really getting for your 20%.

For starters, Upwork harbours more than 5 million client accounts, a good chunk of which are actively hiring through the platform.

How do I know?

Because there are around 3 million jobs posted every year, or 3 million opportunities to secure work. That's without taking into account the fact these jobs are worth a combined $1 billion (with a b).

And let's not forget that Upwork handles payments, provides time tracking software AND offers a payment guarantee.

As a freelancer, you don't even have to pay anything upfront. You only pay once you actually start earning through Upwork.

Weighing it all up, can you confidently say that Upwork's fees are unreasonable? Personally, I'm not so sure.

Beating The Fees

Most people's answer to last years fee hike was to either leave Upwork, or take clients off the platform.

I don't think either of those are smart.

By leaving the platform, you're also leaving behind a HUGE pool of potential clients that are only active on Upwork. It is the biggest freelance marketplace, after all.

(Not only that, but finding clients elsewhere will almost always cost you time or money anyway.)

As for taking clients off the platform? That's probably the worst thing you can do in Upwork's eyes. That s**t will get you banned for life if you get caught.

So what SHOULD you do if you're not happy with the fees?

Simple; Bake them into your prices.

Think about it. You're running a business. Every business has overheads, and those overheads should always be reflected in your pricing.

(When manufacturing costs rise, retail prices have to scale with it. It's no different.)

Lewis's Note
If you're worried that raising your rates by 10% will make it harder to win clients, then you're going after the wrong type of clients.


I've tried to be as objective as I can with this post, and I can absolutely see both sides of the argument.

At the end of the day, acquiring clients always comes at a cost. It's up to you to decide where those costs lie.

Upwork isn't the only place to find high-quality clients, but it's still a great resource to tap into and one that can be justified if you simply raise your rates accordingly.

New To Upwork? Quickly Boost Your Credibility With The ‘Rising Talent’ Status

When you’re new to Upwork, gaining credibility can sometimes feel like you’re in a catch-22 situation.

You need clients to build credibility, and you need credibility to win clients. Annoying, I know.

But Upwork can throw you lifeline.

You can use Upwork’s “Rising Talent Badge” as a fast-track ticket to credibility with little experience. And it’s easier to get than you might think.

In this post, I'll show you how to improve your chances of obtaining the “Rising Talent” badge and quickly boost your credibility on the platform.

(Even if you’ve never had a single job on Upwork.)

Rising Talent Status (And Why It Matters)

The rising talent program is run by Upwork, and it awards new freelancers who show early promise.

If you qualify, you’ll receive a number of benefits:

This matters because you’re marked with a “Rising Talent Badge” that clients will be able to see on your profile and proposals:

The badge instantly offers you credibility as clients have no way of gauging your reputation when you’re new to the platform.

This status is a good alternative until you receive your job success score, which can take several months to obtain.

Lewis's Pro Tip
90% of freelancers won’t get their job success score until they’ve completed 5 projects.

How To Earn It FAST

Personally, I earned the “Rising Talent” very quickly on Upwork; it only took me a few weeks and one completed project.

Let’s take a look at Upworks requirements:

You too can acquire it quickly, if you hit the right notes...

The Key Ingredient

Upwork states, "even new freelancers who have yet to complete any projects on Upwork can be admitted into the Rising Talent program."

Surprised? Yeah, so was I...

And it’s why I believe your profile strength is the key ingredient to earning your “Rising Talent Badge” quickly.

You can take these steps to ensure you’ve optimized your profile:

  • Make sure your profile is 100% complete
  • Upload a professional looking photo (not at your family BBQ)
  • Take 2-3 relevant Upwork tests
  • Don’t price yourself too low (read this)
  • Be thorough with ALL the sections (overview, experience, education, portfolio, etc.)

Aside from that, make sure your profile is focused.

Focusing your profile means you should only be offering ONE service. And I'm convinced this is crucial to earning your badge quickly.

It just makes sense.

High-level freelancers generally don’t offer a mixed service.

A professional video editor wouldn't be offering logo design at the same time. It would just dilute the impression of expertise.

How To Further Improve Your Odds

To improve your odds of being accepted into the program, start by getting a couple jobs under your belt.

If you're really struggling with this, check out my Mind Map Method to layer on some additional credibility.

When you’re applying for jobs, consider the statistics Upwork keeps on you:

Aim to keep these ratios as high as possible because low statistics will send low-quality signals to Upwork about you.

The logic behind this is simple...

  • 50 proposals yields 1 reply = low-quality signal
  • 10 replies results in 0 contracts = low-quality signal
  • 100 profile views results in 0 invitations = low-quality signal

To help keep these ratios high, don’t get trigger happy with your proposals. Be picky, and really concentrate on nailing your proposals for job adverts you’re confident you can do successfully.

And when you do win a job…

Give your client the experience of a lifetime. Blow them away by communicating well and efficiently, meeting or beating deadlines, and offering to do revisions when necessary.

It’s not hard, and I promise you, doing these three things will put you ahead of most other freelancers on Upwork.

Once you’ve completed a job, you’ll want to make sure your client leaves a nice review. What’s likely to happen, is that they’ll end the contract and Upwork will ask them to leave feedback.

So if you’ve given your client a world-class experience then you shouldn’t have any worries.

But, if you want to make doubly sure you’ll get an awesome review, you could send something like when you submit your work:

I’d recommend you say something along the lines of...

“Hi [clients name],

I’ve attached [completed work]. I’ve really enjoyed working with you, so let me know if you’re not 100% happy with anything and I’ll get to work on it right away.

If you’re happy with project, please could you end the contract and leave some nice feedback? My success on this platform depends on my feedback so I’d really appreciate a good rating.

[your name]"

They’d have to be a real sour grape to leave a bad review after that message.

Lewis's Pro Tip
Occasionally, a client will forget to end the contract. If that's the case, you can end the contract yourself, then be the first to leave an awesome review.

After that, simply copy and paste it it to them and politely ask for one in return. Doing it this way taps into the law of reciprocity, so they're much more likely to do it.

And On That Note

Building your credibility on Upwork doesn’t have to feel like an uphill slog.

Upworks “Rising Talent Badge” is a perfect for quickly gaining credibility when you’re new to the platform.

...all you need to do is follow the tips we’ve discussed to speed up your process.

And once you’ve earned the badge, clients will find it much easier to trust you. You’ll get more work which leads to more credibility.

So use it to your advantage, optimize your profile.

How To Choose The Perfect Upwork Hourly Rate (In Any Niche)

I think you’ll agree that choosing the perfect hourly rate on Upwork can seem like an impossible task at times.

(Especially if you’re new to the platform.)

But when you understand how to price yourself correctly, you’ll be able to win higher paying jobs with great clients, without ever having to grind on low-paying jobs.

And in this article, I'll explain exactly how to do it.

Upwork Scams: How to Protect Yourself on Upwork

As a kid, I always found myself watching a show called “BBC Rogue Traders”.

The host of the show, Matt Allwright, would track down and confront dishonest tradesman during the climax of their scams.