5 Secrets to Building Your Super Team of Remote Freelancers — and How to Retain Them


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Recent labor market trends show that 78% of companies use remote freelancers, and 59% plan to use more remote freelancers within the next six months.

Uncertainty in the economy, shifts in workforce models, culture and perception and employees reprioritizing work-life arrangements all contribute to the reliance on (and the continued rise of) the “high-skills gig economy,” as Harvard calls it.

While hiring a remote freelancer may seem like just one job post away, there’s a science and skill to attracting and retaining the right freelance talent for your business. Engaging a freelancer is far from just a one-off transaction.

Here are five secrets to hiring a remote freelancer as a long-term win-win for your business and your future super team of remote talent.

Related: How Businesses Can Adapt to a Growing Freelance Movement

1. Know where to look

Companies of all sizes are increasing their reliance on freelancers to boost productivity, increase innovation and improve speed to market — just a few of the advantages reported by nearly 700 senior business leaders in the U.S.

In the same study, almost 90% of business leaders reported that digital talent platforms and freelance marketplaces are essential to building their blended workforce — a combination of full-time employees and freelancers to create an “on-demand” workforce.

Gone are the days when freelance marketplaces were just the go-to for a $5 logo.

The ecosystem of digital talent platforms has quadrupled within the past decade, and freelance marketplaces have evolved to meet the demands of Fortune 500 customers, like Amazon and Unilever, and small businesses alike, who now use digital talent platforms as viable scouting tools for their short-term and long-term business needs.

More remarkably, you don’t need to be a publicly traded company to access a global talent pool. Regardless of the size of your business, you can look for freelancers across specialized marketplaces for premium talent, digital freelancing marketplaces or crowdsourcing platforms.

While digital talent platforms create ease and expansion of search for freelance talent, referrals, word of mouth and actively scouting online professional networks are also effective and relevant means to building your super team.

2. Ask the right questions

At our agency, we hire freelancers to augment our teams for select creative projects. We’ve found that internal and external alignment is the root of any fruitful freelance engagement.

Get clear on your needs and expectations when hiring remote freelancers. You can build your freelance team around your needs when you know exactly what you need.

Internal questions to consider:

  • What specific skills would add more value to our client or project?
  • How long will we actively need this freelancer?
  • Which freelancers on our roster can we re-engage, and what have they more recently worked on?

External questions to consider (what to ask prospective freelance candidates):

  • Do you have the capacity to take on new projects? Any conflicts of interest?
  • Do you have relevant case studies that reflect our specific skill requirements?
  • Are you available during our projected duration of the assignment?
  • What time zone(s) are you available to work in?

Related: 5 Data-Backed Benefits of Working With Freelancers to Grow Your Business

3. Have an onboarding plan or process

Once you’ve recruited the right freelancers for your business, maintain a good rapport and continue to build trust.

Onboarding goes beyond the formality of signed contracts. Remember, the start of a short-term project is the beginning of a long-term relationship that can serve your business needs as much as the freelancers’.

Some freelancers share that your business reputation, transparency and trust are among the priceless non-negotiables that freelance talent may consider when choosing to work (and keep working) for you.

Further, demonstrating process, planning and structure within your organization ensures your freelance talent receives clear direction, understands their assignment and operates seamlessly within your existing operational flow — all of which can make your life (and theirs) easier.

Some ideas to consider for seamless onboarding include:

  • Set up a kick-off or onboarding call
  • Share brand guidelines with creative freelancers
  • Discuss internal language, file structure or other day-to-day logistics
  • Establish preferred methods of communication and key points of contact
  • Set expectations around progress, key milestones or check-ins

4. Maintain an ongoing relationship

One enterprise-level digital talent platform shared that “it takes five times the resources and effort to find a new freelancer every time you have a new project, compared with establishing strong ongoing working relationships.”

While you don’t have to commit to a future time frame or project, keeping the line of communication open with freelance talent can save you five times the time and effort the next time your business has a need.

Make your freelancers feel valued and leave the door open for future opportunities.

Related: Employee or Freelancer: Which One Do I Need?

5. Expect limited availability and high demand

Reports show that 56% of freelancers are working 30 hours or less per week, with 80% of the freelancers surveyed either satisfied or very satisfied with their freelancing lifestyle — which is generally location-agnostic, flexible and allows for a regionally diverse client base, as 32% of freelancers have expanded their client base to new countries.

These factors mean your star freelancer might only sometimes be available when you need them, but the best dream teams have more than one key player, plus a solid bench.

Build your super team (with backups).

Long-term impacts of short-term hires

Hiring freelancers is vital to staying competitive and surviving in a hyper-competitive market.

Businesses have come to appreciate the value of the agility of the freelance market, and, as expedited by the pandemic, companies now have greater tolerance and experience with trust and legal and compliance procedures that make hiring highly skilled remote freelancers more the norm.

But to maximize the benefits of engaging freelancers, be ready to build relationships, integrate freelancers into the DNA of your company and workflow and empower your current employees to be part of the process and see that a freelancer is an extension of your shared mission.

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