How Jesse nailed an Upwork interview and won a $6,000 freelancing job

I’d been combing through the latest Upwork jobs for two hours, with zero luck.

I was ready to throw in the towel and call it a day.

Just before signing off, I noticed one last job listing. It stood out to me because it sounded like it’d be an interesting project to work on.

But when I saw that the client wanted monthly work done for an entire year, I told myself it was probably out of my league – there was no way I could get an interview. Since I was still pretty new to Upwork, I’d been sticking mainly to the small jobs, just trying to “get my feet wet.”

Still, I couldn’t help but read the full job description, if only to torture myself.

My suspicion was confirmed the moment I clicked to read more… The client wanted a freelancer with credentials and experience in Electrical Engineering. I sighed, realizing this was one of many Upwork jobs I simply wasn’t qualified for, at least technically.

Then I had a crazy thought.

What if I sent in a proposal anyway? It’d be good practice, and, more importantly, I didn’t want to quit for the day without at least applying to at least ONE job.

Then, an even crazier thought…

Since I wasn’t even expecting to hear back from the client — let alone win the job — why not be the highest bidder, too?

I had nothing to lose, so I decided to go for it.

Without a second thought, I fired off the following proposal to the client:

Hello <first name of client>,

I see you are looking for an author who can ghostwrite 2,000 word articles twice a month in the portable power field.

You want your content to generate interest, leads and opt-ins by writing actionable business oriented copy.

I write long form content. If we were to work together I could create multiple mock-ups of articles before writing them so your article will have the content you want in the voice you desire.

Content and voice are key to generating leads. If your content is geared towards electrical engineers you will generate leads by writing content that helps them solve their problems.

Here is just a few ideas I have for ‘problems’ portable power solves.

*Easy to move quickly in rough terrain. (which is great for both mining and entertainment.)
*The power source is reliable in any condition.
*Your power source is long lasting and effective no matter the energy demands.

If you are interested in creating content that solves these problems and generates leads, I am available to talk.

Regards,

Jesse G.

I figured it was such a long-shot that I promptly forgot about the whole thing after clicking “submit.”

You can imagine my surprise when, two hours later, I received a message back from the client. He wanted to schedule a phone interview with me!

My fleeting pleasure was quickly replaced with self doubt. Was this for real? Didn’t the client see that I was the least experienced, most expensive choice?

I hadn’t exactly mastered the Upwork interview process yet…and to be honest, I felt a bit out of place. Rather than wasting my time (and the client’s), I decided right then and there to decline the interview.

Unfortunately, my fingers seemed to take on a mind of their own, and I found myself typing out a response to the client, confirming the interview for 2 hours later.

I hit the “send” button quickly, before I could change my mind.

Though it was nice to finally have SOMETHING to show for the two hours I’d spent sifting through the Upwork jobs that day, I was in over my head.

I’d jumped out of the frying pan…and into the fire.

The accidental Upworker

Like many people, I initially stumbled across Upwork pretty randomly.

It all started back when I was performing stage hypnosis shows.

Yeah you read that right. I am a comedy stage hypnotist.

As far back as I can remember, I’ve always wanted the freedom and income potential of being my own boss. Unfortunately, the rewards of stage hypnosis were pretty limited. I had to stick to a strict travel schedule, and there were only so many shows I could perform each year.

In other words, my progress had struck a plateau.

Eventually I traded in my hypnotist watch, and opened up a coin, jewelry and gold shop.

I opened up the doors right at the start of the precious metals boom. But even though business was rolling in, cash often left just as quickly as it came. Worse yet, after about a year of doing the books, I finally realized that unless I aggressively expanded my territory and opened new shops, my income couldn’t grow. I had hit another hurdle.

Nothing seemed to be working. It felt like the economy was rigged against me. I went through some pretty negative self-talk, which didn’t help.

Then I came across Ramit Sethi’s Zero To Launch course, which promised to teach me how to launch a successful online business. I’d been reading Ramit’s blog for years, and I liked the idea that I could grow an online business as big as I wanted to, without worrying about the physical limitations I’d run into in my previous ventures.

There was just one “problem”…it takes months or years to see results from an online business.

Don’t get me wrong, I wasn’t in a rush. But I was looking for a way to support myself (and have control over my schedule) WHILE I built my online business.

And freelancing on Upwork seemed like a great way to do that.

Thanks to Danny’s Freelance To Win blog, I’d already learned quite a bit about how to make money on Upwork. And I’d landed a couple of small gigs, which was great.

But now I was in danger of wrecking my Upwork career before it even got off the ground.

I needed to figure out a way to ace this interview, and I needed to do it fast.

Of all the Upwork jobs I could have applied to…

Even right after agreeing to the interview, I thought about calling the whole thing off.

It seemed a little intimidating to jump on the phone with the client when I obviously lacked the credentials he was asking for. Especially since there were several competitors who DID appear qualified. And they were charging less than I was, too!

Then I remembered something Danny had said about the competition on Upwork not being as stiff as it often seemed. AND the fact that lots of clients were willing to pay for VALUE.

I went back and took a second glance at the client’s Upwork history:

And you know what? He seemed like a REALLY GOOD client.

Out of the 18 Upwork jobs he’d posted, he ended up hiring someone 78% of the time. And he’d spent almost $10,000 on Upwork this year alone.

This gave me a hunch that he might be exactly the type of client who IS willing to pay for value, rather than just going for the cheapest freelancer.

And while my competitors may TECHNICALLY have been more qualified, I figured I could offer more value by outworking them, outsmarting them, and…upworking them! (Bad joke, couldn’t resist.)

I started to go from feeling unsure, to bouncing up and down like Rocky right before the big fight. Okay so Eye of the Tiger wasn’t playing anywhere, but it was there in spirit.

I was determined. If the client wanted the cheapest freelancer, or the one with the most technical experience, then that was fine by me.

But either way, I was committed to doing everything I could to get the gig.

My interview with the project leader was in two hours.

Time to start training hard.

I brought the entire artillery to the gunfight

Without a moment to spare before the interview, it hit me: I could WOW the client by over-preparing to the point where I knew more about his needs needs than even HE did.

That would give me a big leg up compared to my competitors, who would probably be talking all about themselves during the interview (“Here’s MY experience…here’s why I’M qualified…here’s why you should hire ME…”)

So I went into Private Detective mode and started doing some serious homework. This is the “deep dive” research process I went through:

1. I looked for clues about the client’s business. You may have noticed that the job posting didn’t contain any specific information about the client. But their Upwork username did (it was their business name). If I didn’t have my detective hat on, this key piece of intel would probably have gone right over my head. But being under pressure forced me to be on the lookout for any helpful info I could find. Just as importantly, this was information my competitors would likely miss, not care about, etc.

2. I figured out who the END-CLIENT was. If you look back at the job post, you’ll see that the client who posted the job was looking for someone to ghostwrite for one of THEIR clients. This is a subtle but very important point. It meant that the person interviewing me (the “client”) would be very concerned with making HIS client (the end-client) happy. That would be his #1 goal. My competitors probably didn’t realize this. If you asked them, they would likely say that the client’s goal would be to “hire the best writer” or “hire the most experienced freelancer.” WRONG. The client would want to hire someone who makes him look like a genius to HIS client! Everything else would be secondary. So the more I knew about the client’s client, the better I’d look in the interview.

3. I read through the end-client’s entire website. Not just their home page, but every page, top to bottom. I checked out their team, their customers, their products and services, their company’s history, etc. I wanted to make sure I went into the conversation knowing EXACTLY who they were, what they do, and who they do it for. Remember that the interviewer’s top priority would be to take care of this client. “Writing” was just a small piece of the overall puzzle. If I wanted to win this job (especially as the most expensive freelancer applying) I needed to become an expert on the end-client, quickly.

4. For good measure, I went through their COMPETITORS’ websites, too. Business doesn’t happen in a vacuum. Every company has competitors who threaten to eat their lunch. If you really want to help a client, you need to understand who they are competing against, and how they measure up to what those competitors are doing. Keep in mind that clients want to work with freelancers who have their back. Knowing this extra bit of info would give the client confidence that I am the type of freelancer who offers lots of value and is willing to go the extra mile to help them succeed.

5. I researched their products and services. I wanted to get a thorough understanding of the client’s business. Not just their industry, but the real reasons WHY their customers buy their products and services. I even went to Amazon and read dozens of customer reviews on many of the products they sold. I focused mainly on the 5 star reviews, since those customers were the most satisfied (though I also looked for negative reviews, since those represented potential opportunities for improvement — remember, being an awesome freelancer is all about helping the client as much as possible.)

6. I called their actual customers on the phone. Yes. I am crazy. But if you want extraordinary results then you have to be willing to step out on a limb. So I called real companies that have purchased the products being sold by the end-client, and I asked them questions about their experiences. Some of the reps I reached weren’t so friendly. A few even hung up on me. But there were a handful who were happy to give me a few minutes of their time. The information they gave me was pure GOLD, and I got some amazing insights about their purchasing behavior that even the client would likely not be aware of.

Do you think this would affect how much the client valued me as a collaborator? Damn right it would.

HOW MANY OF MY COMPETITORS WOULD EVEN DO 1/10TH OF THE AMOUNT OF PREPARATION I DID FOR THIS INTERVIEW?

The answer is almost certainly…none of them.

I was choosing to put myself into a Category Of One.

By the way, you if doubt whether or not it was worth the extra time and effort, I want you to keep 3 things in mind:

• This client needed two articles every month for at least a year. In other words, this was a LONG TERM job, so it was undoubtedly worth going the extra mile to snap it up.

• Remember that the client had paid out almost $10,000 for various Upwork jobs so far. So there is every reason to believe that this initial research would pay off at least 100x, especially since it was likely to make a lasting impression on the client (one thing I learned from Danny is that clients like to find a freelancer and stick with them).

• All of my preparation for the interview took me just two hours TOTAL. So at the end of the day it’s a small price to pay in order to win the job.

By the time the interview rolled around, I had some huge advantages over my competitors.

I knew exactly what the end-client did, who their competition was, how their customers made their purchasing decisions, and even the exact type of words their customers used to communicate their wants and needs. And I’d used that info to create a list of ideas for different pieces of content that I thought would benefit their company.

I was 110% prepared.

The only thing left to do was nail the interview itself.

The interview

The client called me at 4pm sharp. I looked at the number on my screen, brushed away all lingering feelings of doubt, and swiped to answer the phone.

The moment the client started talking I knew exactly what I needed to do.

Instead of letting him ask the questions while I played the “good interviewee,” I decided to LEAD the conversation. A bold move, but remember, my goal was to stand out, not fit in.

I told him I’d like to start by asking him some questions. There was a moment of uncomfortable silence that made me wonder if I went too far.

When he finally answered, he sounded very surprised, but agreeable: “Oh, uh…okay.

(YES!)

Without wasting a second, I immediately asked him for more details about his goals for the project, what he was trying to accomplish, and what would have to happen in order for him to consider the project a success. Like the information I’d gathered previously, this was extremely important intel, but more importantly it would show the client that I CARED about helping him (and his client) produce RESULTS.

Next, I gave him a rundown of what I’d learned while researching his client’s company, their competitors, the products they sell, the reviews they have gotten, and even the insights I was able to dig up on their customers’ psychology and preferences.

Then I threw out a few suggestions for the type of articles I thought would work best for what they were trying to accomplish.

I even capped the whole thing off by telling him I talked with his client’s customers! I told him about what they said and how the language they used would be great to include in their copy for maximum effectiveness.

There was another dead silence as the client appeared to be in utter shock.

When he finally spoke, he told me, “I was only calling you because it was a matter of company policy. I had no interest in hiring you.”

Then, after another pause, he continued: “But you are the ONLY person we’ve talked to that did this kind of research. I’ll have to clear it with my boss, but…I think we are going to hire you.”

They did.

As you can see, I’ve earned $250 writing for them so far. But remember that this is an ongoing MONTHLY contract. By my calculation, it’ll be worth $6,000 to me over time. (And that doesn’t even include potential work the client may hire me for after this contract is up.)

YOU can make money on Upwork, too

Let’s go over some of the key takeaways from this story.

When I first looked at some of the bigger Upwork jobs that get posted everyday, I was worried I wasn’t ready.

My mind was telling me a story that I didn’t have the credentials, the portfolio, or the experience I thought I needed.

But the reality was that I was keeping myself from getting some of the bigger, better Upwork jobs that were available.

Yes, I was technically less qualified than some of the bigger guys. And they charged less than me. But I was able to overcome that by focusing on what the client wanted.

Qualifications, credentials, and experience may be hurdles, but they aren’t roadblocks.

Just because you don’t have “X years of experience” or specific industry knowledge, doesn’t mean you can’t make up for that in other ways.

The only question is, will you?

Jesse Gernigin is a freelancer, entrepreneur and expert on a mission. He trains freelancers and writers so they can get more gigs, higher rates and the best clients.