Agile Talent6 minute read

Managing Remote Freelancers? These Principles Will Help

As remote freelance work grows more prevalent, managers need new skills. Jon Younger, Founder of the Agile Talent Collaborative, introduces five principles to help managers lead distributed teams of agile talent.

Jon Younger

Jon Younger

Jon is the founder of the Agile Talent Collaborative, a non-profit cooperative that leads research to define best practice for agile talent.


There’s little doubt that remote work is on the rise. A new Toptal survey of over 1000 global leaders and managers, advised by the author, found that over half of participating executives anticipated an increase in remotely performed work. By contrast, only five percent of the surveyed audience expected the amount of remote work to decrease.

This is no topsy-turvy change. Most executives continue to prefer co-location where possible, and express a reasonable level of concern about work and workers that are physically distant from their management and teammates. But it is evident that remote work performed by agile talent is now well entrenched across functions and industries, as well as generally on the upswing. The chart below illustrates that the proportion of remote workers is large and growing in professions as varied as engineering/IT, marketing, project management and HR:

Why Remote Freelance Work Is Growing

Beyond the empirical data surfaced in this survey, there are clear reasons why the volume of remote agile work will continue to grow. First, new communication technology makes it far easier for organizations to support real time collaboration on a global scale. Applications like Slack are explicitly designed to support and reinforce cooperation across regions and time zones.

Second, the rise of online talent platforms has enabled the “discovery” of non-local talent and provides an efficient mechanism for engaging them on a temporary basis. These networks permit customers to precisely define and hire for the set of skills they need, and do so without the cost or administrative hassle of relocation, settlement, spousal benefits and visa issues. The Pew Research Center reports that over 10% of U.S. based individuals between the ages of 18-29 have used online platforms to obtain work.

Taken together, these trends proffer a redistribution of knowledge and power within the talent economy. The combination of advances in collaboration techology and platforms that efficiently match talent with business needs has shifted agency from organizations to the individual, creating a more even playing field and providing agile talents with increased access to opportunity and greater choice.

How Managers Can Do A Better Job Managing Remote Agile Talent

While the benefits of remote work for both workers and organizations are real and significant, change of this kind is always challenging. A report in Moneywatch, for example, warns us about the “four pitfalls” of remote teamwork. In identifying some of the risks that may arise from working remotely, the author summarizes a concern that many executives share.

In fact, executives in our study express a range of concerns about the effective utilization of remote teams, starting with how well managers are able to manage remote work and workers. As the data below illustrates, when asked about the barriers preventing teams from better leveraging remote agile talent, the number one worry expressed in our survey was the need for better management training in supervising remote work.

We found the data particularly interesting, and they fit with one of the central arguments of our book Agile Talent: the effective use of a blended workforce, a resourcing strategy that brings together traditional and agile talent, depends significantly on a set of key skills required of team leaders.

We spoke to a wide range of business and HR leaders, along with agile talents themselves, to understand the building blocks for success in managing remote agile talent. We learned that organizations which depend on a blended workforce and want to engage and retain top agile talent should attend to five rules for the effective management of agile talent:

1. Collaborate, Don’t Subordinate

Agile talents are employed but not employees. Understanding this distinction has broad implications for team leaders: in order to succeed, they must strike a more collaborative, collegial relationship, rather than attempting to manage agile talents as they would a traditional full-time employee.

Agile talents choose independence because they want to have a high degree of freedom over their lives and work. They remain agile talents because they demonstrate the expertise and experience to establish a successful career as an independent professional. They are, in a real sense, volunteers, and in many cases have a track record of expertise and accomplishment established over a significant career. To view and manage them with a hierarchical mindset misses the point of who they are, and is likely to be unproductive.

2. Be Inclusive: Establish Regular Engagement Discipline

Any smart leader understands that his or her principal objective is to ensure the full productivity of the team. But when this approach is applied naively to agile talent, the result is often a transactional attitude instead of a relationship-first mindset. When agile talents are working remotely this is more likely and more problematic.

Amy Gallo in HBR notes the importance of treating freelancers as real members of the team, rather than as marginal replacement players. In practical terms, what does inclusivity look like in this context? If you are currently working with agile talents who are contributing remotely, ask yourself how often you do the following:

How regularly and consistently do I:

  • Include remote agile talents in regular communication with the team?
  • Invite their active participation in team meetings?
  • Invest time in getting to know them beyond the work?
  • Encourage their suggestions and recommendations?
  • Actively support them in dealing with organizational policies and with the bureaucracy; for example, ensuring regular payment.

3. Set Performance Expectations From A Visionary Perspective

Good managers know how to set performance objectives and milestones. But relationships with agile talent in general, and remotely performed agile work in particular, add a factor of uncertainty and may invite a degree of suspicion. Is she really giving me her best work? Is he working the full number of hours he’s billing? The alternative is for the manager to change his or her mindset to one that builds commitment instead of compliance and contractual obligation.

The first step is an approach to goal setting that begins, and ends, with a broader focus on the vision of the project, and its larger impact on the client organization’s growth and prosperity. This has several benefits: it appeals to an emotional as well as occupational obligation to do one’s best work. It reinforces the shift in relationship away from the transactional. It implicitly encourages agile talents to identify with the project and its importance, rather than a meal ticket by the hour. And it enables a different performance review conversation, one that is properly contextualized in the importance of the work, the necessity of productive collegial relationships, and the encouragement of honest and straightforward dialogue about how the work is proceeding and what changes may be needed.

4. Encourage Mentorship

In a recent HBR paper, we made the case that agile talents are an attractive and underutilized resource in mentoring and developing more junior team members and other professionals. Without question, mentorship is simpler to arrange when external experts are co-located with internal full-time staff.

But executives should not be dissuaged by let logistical difficulties from inviting agile talents to share their broad and distinctive expertise. Technologies like JOLT, a peer to peer educational platform, makes it possible for team leaders to offer real time workshops led by agile talents on topics where they bring a unique expertise or experience. And the more they are invited to contribute what they know, the more likely they are to feel a deeper sense of commitment to the team and its purpose.

5. Make Change Fast When Things Aren’t Working

It’s challenging for new members of an organization to quickly establish good relationships, which is what agile talents must do to be effective. It’s harder still when individuals work remotely and lack informal opportunities to get to know one another and bond as team members. Despite the best efforts of both agile talents and team leaders, sometimes an effective working relationship doesn’t gel.

Whatever the reason, we encourage team leaders to consider that relationships that start badly—especially when remote work is a further complicating factor—are more likely to continue to deteriorate than improve. Therefore, make change fast, as soon as it is clear that work styles or other factors will impede success on both sides.

As Remote Work Grows, Managers Need New Skills

There is so much new opportunity being created by the agile talent revolution. Technology makes it possible for an organization to scale fast, accessing the best technical and professional talent from around the world, and deploying their expertise with less cost and administrative hassle by enabling these agile talents to perform their work remotely, where they live.

But as we learned from our recent survey, executives recognize that managers need new skills, and new ways of working with external experts, in order to benefit fully from this opportunity. The five tools and principles offered above are part of the solution.

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