The Guide to Acing Remote Talent Management: Dos & Don’ts of Working with Freelancers on Upwork

Why freelancing is the next big thing, the attitude shift that will give companies an edge & 10 (little known) tips to cultivate the best Upwork talent

As someone who had a start on the platform, I have seen a distinct shift in the attitudes of clients who frequent Upwork.

Questions like “How do I get the best talent to bid on my projects?” “How do I hold on to my freelancers?” are now common.

5 Years Ago, the Dance was to a Different Tune

Independent contractors had it tough.

Jobs were few and far between and only those who were committed to the lifestyle of flexibility braved the feast or famine work mode to gradually reach a steady income.

In short, clients had the upper hand.

They could post 10-dollar gigs and have a plethora of talented individuals fight for the right to take it on.

A dream come true for any business.

But Times Have Changed

Millennials around the world are rejecting the restrictions of a cubicle and a 9 to 5 job to embrace the freedom that comes with freelancing.

By 2027 more than half the workers in the US will be freelancers. The 1.4 trillion dollars they add to the economy will only grow in proportion.

Freelancing in America

From rapidly scaling start-ups to established Fortune 500 companies – businesses hailing from myriad industries and with vastly different backgrounds concur when it comes to the benefits of collaborating with freelancers on Upwork.

This has tipped the balance in favour of talented professionals willing to consistently upgrade skills and disregard the allure of “health & benefits” which traditional employment models offer.

The mind-set of “There’s plenty more where that came from” is phasing

They have the privilege of being courted by market leaders and boast stunning profiles with glowing references that are more “proof of competence” than any standard performance appraisal.

With this spike in demand and broadening of scope for contractors, clients have woken up to a new reality.

The reality in which their global talent pool is their competitive advantage and requires careful management to inspire loyalty and thus retention.

The mind-set of “There’s plenty more where that came from” is phasing.

Freelancers worth the investment have heavily packed schedules and unique work ethics.

And they are negotiating contracts not as underpaid workers but as empowered expert consultants who can take their pick of assignments.

Where to Start If You Want to Build a Global Talent Pool

Freelancer, Upwork, Remote, Fiverr – the list keeps growing by the second.

But a quick Google search reveals that Upwork is a superior choice.

  • It stands on the shoulders of two veteran providers, Elance and oDesk. Top rated contractors from both platforms now call Upwork their home. The line-up is enviable.
  • It prunes what doesn’t work. The move Upwork made of shutting down inactive freelancer accounts is actually a blessing for clients. The pairing algorithm is that much more accurate thanks to the professionals who are not only interested in projects but also capable of delivering quality results.

10 Little Known Tips That Help You Work Long-Term with the Best Contractors & Make the Most of Upwork

Upwork offers a comprehensive guide to help clients master the marketplace.

A Client’s Guide to Upwork
DOWNLOAD: A Client’s Guide to Upwork

And this document covers a lot of the accepted best practices.

But the businesses that consistently get the pick of premium talent and manage to hold on to star performers without blowing their budget or violating the terms of service do things differently.

Here are 10 strategies that only the insiders know and use.

#1: Extra Questions are Not Torture

Visit any freelancing forum and you get the idea that contractors want nothing more than to write short cover letters for their Upwork proposals.

And the extra questions that clients add to their job posts? They are despised by one and all.

What can I say – not true!

It is the same logic that settles the debate of long form questions vs. MCQs.

A well-prepared student will gravitate towards the multiple-choice format.

Someone who has just mugged the class notes will love the long form questions.

Anything that is not specific leaves room for obfuscation.

Freelancers who have toiled hard at their craft prefer laser focused queries that demand equally to the point responses.

upwork freelancers

They know two things:

  1. Follow-ups to these questions are displayed to the clients before the cover letter and are the actual first impression.
  2. The queries are a way to separate the grain from the chaff. Contractors who haven’t worked on similar projects may not have the best answer to curve-balls like “What about this assignment is the most difficult to accomplish?”

So feel free to quiz those who will eventually bid on your jobs.

If what you ask is relevant to the project, top freelancers will be happy to oblige. And both parties will learn more about each other through the exercise.

#2: Don’t Evoke the “Seriously?” Reaction

The easiest way to puncture your credibility as a client is to solicit “the most experienced” contractors with a shoestring budget.


Upwork wants you to set the right expectations from the get go.

The details you supply with your job posts allow the platform’s algorithm to suggest best fit candidates.

This is why choosing to optimize your project for bids by “Expert” freelancers but quoting pay that doesn’t match up leads to dissonance.

Prized contractors may decline such invites with the exclamation, “Seriously?”

And it also deters those who are comfortable with the budget but don’t feel they can qualify for the tag of one of the best performers in their field.

#3: Project Type is Not Set in Stone

Upwork offers two payment modes – fixed price and hourly rates. While both come with protection for freelancers and clients, there are pros and cons to the options. Try a fixed price project broken into individual milestones if you have a fairly limited budget. This allows you to control your spend and is the preferred way to initiate “test” assignments.

Jobs where there are lots of ad hoc tasks coming your contractor’s way fare better with an hourly setting. You can restrict the addition of manual time – that is time not tracked by the Upwork team application. A limit on the number of hours your freelancer can bill per week is another way to cap the expenses.

Rate and Availability

In short – if you are bringing onboard a Virtual Assistant who will be your “jack of all trades”, go with hourly billing for the flexibility. If you are getting your sales page re-done, fixed price is your best bet.

Having said that, you can actually change a project from fixed to hourly. A handy hack to know!

#4: Reviews Everything

Reviews are important. But they aren’t everything.

odesk review

Clients often choose freelancers based on the most effusive reviews. But there is a truth that can’t be denied.

Testimonials are subjective.

Numbers don’t lie.

Many businesses do not leave feedback even if they are thrilled with a freelancer’s performance.

Others may not re-hire the contractor but prefer to be gracious in the reviews.

Humans are unpredictable.


  • Let the candidate’s Job Success Score lead the way. The JSS is cumulative and a fairly accurate gauge of talent consistency since it takes into account both public and private feedback.
  • Next look at the freelancer’s response time. Going back to the principle of setting the right expectations, a candidate who takes 48 hours to respond to most messages is perhaps not the best person for a rush job – even if their availability says otherwise.


  • Last but not the least, map skills to tests and certifications. If the contractor professes to be adept at Inbound Marketing, look for evidence of proficiency in completed projects, in the Upwork tests and independent certifications.

#5: Interviews aren’t About What You Think…

They’re not about skills.

When you interview shortlisted candidates, the conversation should focus on:

a) their temperament

Is the freelancer a quiet, competent workhorse? Are you looking for someone who can take initiative or follow orders?

b) their technical assets & resource accessibility

Does the freelancer have access to co-working? What is the state of their internet connectivity and will the bandwidth suffice for your requirements?

Can the freelancer access all the websites that are critical to the completion of the assignment? If they hail from a different (and more conservative) nation, this might be a big problem.

Drilling down even further, software solutions matter too. If you want a logo that can be enlarged without undermining the integrity of the design, you are better off hiring someone who possesses an original copy of Adobe Illustrator instead of a pixel based tool.

c) their fluency in your native language

Even if the job involves Ruby on Rails and not a single line of copy!

Projects can quickly turn into frustrating nightmares if your brief isn’t understood by the contractor. Communication is key to building a talent pool. It sets the stage for future associations. And it is the last thing you should compromise when looking for suitable candidates.

d) their work hours

Getting a sense of the time zone they operate out of is also important. Communication gaps resulting from this restriction are often unnavigable.

upwork interview

For example, a client in Australia may not be able to work synchronously with a contractor from Los Angeles, even if both parties are ready to stay up past bedtime.

#6: Handling the “Bad Apples”

What do you do if you come across a provider who isn’t all fair and square?

While most well-placed freelancers never default delivery dates or short-change clients, some may indulge in practices like having multiple accounts with different hourly rates. This is against the platform’s policies and could earn the provider a permanent ban – thus affecting your projects.

Conducting a quick search using your chosen contractor’s full name (not the display name) will reveal any such anomalies. If you do come across an issue, it is better to start afresh than proceed with someone who has breached your trust right out of the gate.

upwork's bad apples

Even though we’ve discussed that reviews shouldn’t be the only factor guiding your vetting process, multiple tasks without feedback are a sign that all isn’t right with the contractor.

#7: Kick Out NDA Jargon

The freelancer signs your NDA.

And you think you’re done.

Well…. you’re just getting started.

Non-disclosure covers a lot more than working with competitors or sharing proprietary knowledge.

DOC]Sample Non-Disclosure Agreement
[DOC] Sample Non-Disclosure Agreement
Ensure that your chosen candidate:
  • Understands what you mean by proprietary knowledge and Intellectual Property (IP).
  • Understands that sensitive information will be appropriately marked and classified when shared with them.
  • Understands that signing an NDA may restrict them from adding the work they do with you to their portfolio. This in particular is something that top-rated freelancers avoid committing to. It is best to make the implicit known before embarking on a collaborative journey.

#8: Divide Communication into “Tactical” & “Governance”

Tactical has everything to do with the actual execution of the project.

Governance refers to the terms of the engagement, payment and timelines.

Upwork recommends restricting all conversations to the platform. This helps them settle disputes when the need arises.

Account flagged for Policy Violation

But if you work with a group of professionals and wish to continue your contract with the freelancer you’ve just onboarded, communicating in isolation is not a great idea.

upwork odesk

Shift the tactical dialogues to where your team congregates. This is a sure-fire way to make talent feel welcome and it also expedites familiarization.

Remuneration details may live on Upwork.

This compromise allows you to document progress on the platform but at the same time lets the relationship expand beyond the limited definition of freelancing.

#9: Keep the 4 Week Rule in Mind

Projects rarely go as planned.

Funds may exhaust. Delays abound.

Most freelancers are better at adjusting to contingencies than full time employees.

But Upwork frowns on hourly contracts that sit idle for more than 4 weeks.

Such engagements are paused and this action directly impacts freelancer Job Success Scores (JSS).

upwork schedule

So when you find yourself looking at a stretch of inactivity that might span a month, close out the existing project on Upwork and discuss future availability with your contractor.

Not doing this gives off an impression of lack of consideration.

And busy contractors always end such project themselves, instead of risking their JSS.

#10: Your Record Matters Too

Freelancers also get to score you and leave feedback – both public as well as private, when a job wraps up.


And this score is prominently displayed with your posts.

Top freelancers not only take this rating into account, they even read up past reviews left by other contractors.

If they see something that raises a red flag, they do what you would.

They bail.

Leverage this opportunity to establish a solid reputation and share testimonial templates with freelancers to frame reviews that sell your business as a desirable client.


Guide them to talk about:

  • Your responsiveness
  • Your ability to set the right expectations
  • Your preparedness and domain knowledge

Because positive testimonials do go a very long way in assuring contractors of your track record!

#11: You May Surprise Yourself

So you have your heart set on a freelancer who is not in your budget?

If a gaping difference doesn’t exist between what you can offer and their asking rate, you may still go ahead and send them a personal invite.

Make sure you add something “special” to the post to make it worth their while – perhaps the right to feature the work in their portfolio.

money isnt everything

Money isn’t the only thing that sets the ball rolling here. You might just surprise yourself.

#12: Bonus Tip

Make sure you add something “special” to the post to make it worth their while – perhaps the right to feature the work in their portfolio. Another way to ensure you get and keep top talent, especially if you are a small business, is to have quality branding on your communications.

Freelancers are more likely to favour a company that appears successful and presents well, as they can then use that branding in their portfolio and increase their credibility. For small to mid-sized companies, getting a quality logo is affordable and reliable through online logo makers. It also doesn’t hurt to have a catchy business name attached to the job request.

* * *

All ten tips in this article have a common theme. They help clients and freelancers communicate transparently and trust the process of remote work.

A marketplace like Upwork offers distinct advantages to both contractors and businesses.

Faith in the idea that the relationship can be mutually beneficial is a proven way to find and retain premium talent.


Written By

Norberts Erts

HR Degen and Product Marketing Manager at Sage. Former Co-founder of HR software company CakeHR (acquired by The Sage Group plc in 2019). Keep a sharp eye on HR, marketing, business, finance, science, technology, and the connections between them.