6 things to remember when managing Millennial freelancers

Elena Prokopets
Written by Elena Prokopets
on April 08, 2022 6 minute read

The “avocado toast overspenders,” “narcissists,” “immature dreamers,” — Millennials got a lot of bad rap from the media. And even more so when it comes to their work habits. "Entitlement," "laziness," and "inability to follow instructions," are some of the commonly-cited Millennial antics managers should be prepared to deal with. 

In reality, however, the work habits of Millennials are not much different from other generations. Yes, we are ambitious and opinionated (sometimes), but we are also hard-working and committed to making an impact with everything we do.

So once and for all, let’s bust some myths about the Millennial generation in the workplace and on the freelance talent market. 

In this post, we’ll examine exactly how to manage Millennial freelancers to make them the driving force behind your business.


Who are Millennial freelancers?

To better manage Millennial freelancers, you need to understand our background (as it has a lot to do with how we think and communicate). 

Millennials were born between 1981 and 1996 (aged 26 to 41 in 2022). We are no longer the “youths” who are obsessed with TikTok and Billie Eilish (ask our Gen Z cousins about those things). 

According to the latest US census data, Millennials represent 35% of the US workforce and around an equal percentage globally. The older folks, entering their fourth decade, are also sitting in managerial positions and make up the bulk of the highly-experienced workforce available for hire today. 

Millennial culture is hard to synthesize in several paragraphs, but our backgrounds were shaped a lot by:

  • Major economic events like the 2008 financial crisis and subsequent recession 
  • Rapid digitization — iPhones, social media, cloud connectivity 
  • Rising levels of diversity and tolerance towards being “different” 

Growing up in an ambiguous world of change and possibilities, we became resilient, creative and purpose-driven. Millennials cultivate and prioritize the following skills among themselves (and others they work for) as per the 2021 Deloitte survey:

  • Flexibility/adaptability
  • Creativity 
  • Technological savvy 
  • Empathy
  • Critical thinking 
  • Curiosity and growth mindset 

Compared to other generations, we’ve experienced less job security, so we remain adaptable — 60% of Millennials are open to new job opportunities. But Millennials are not job-hopping more than other generations. We just like to know what our options are. 

When it comes to Millennials expectations in the workplace, we also seek flexibility in our working arrangements

  • 68% of Millennials like working remotely
  • 90% would prefer a 4-day workweek 

At the same time, 60% of us find great meaning and purpose at work. In fact, Millennials are the most fulfilled and happy generation at work. But that’s because we are being selective with whom we want to work with. We want to be part of organizations that care about employees' well-being, ethical leadership, inclusivity, transparency, and diversity. 

Sometimes we find employers that match these criteria and stay with them for the long term. In other cases, we choose to freelance or start a business instead. 

That’s good news for you because you can partner up with swaths of talented independent creatives, available on the freelance talent market. 


How to work with Millennial freelancers: 6 facts to remember

Millennial freelancers represent the core of the self-employed workforce. In the US, for example, 40% of Millennials do part-time or full-time freelance work. In Europe, over 13 million digital freelancers are available for hire. 

But the big question remains: how do you engage Millennial freelancers? 

In short, you have to respect our work styles and view us as a partner to your business — and remember the following 6 things about us:

1. Freelancing is a choice, not a necessity

For many Millennials, freelancing is a career power move, not a temporary plan until a full-time opportunity comes along. 

We work for ourselves not because no one is hiring us, but because we enjoy self-employment. According to a Freelancer Map 2021 study, 79% of freelancers say that “being their own boss” is the reason why they left traditional careers. 

The same study suggests that EU freelancers are seasoned pros, averaging 12 years of work experience before going freelance. Meaning they got to sample both the corporate world and self-employment. 

Management tip: Treat millennial freelancers as equals. They may lack a fancy title, but have heaps of knowledge, accumulated from other projects. Give them room to speak up and suggest different ways of doing things, instead of forcing them to “do what they're told.” 

2. Freelancing offers the flexibility Millennials want

The Global Freelancing Survey done by the University of Toronto found that 78% of freelancers choose this career because it provides the flexibility and independence they crave. 

Data from Freelancer Map mirrors this sentiment. In fact, the different flavors of flexibility offered by freelancing often trump the “money factor.” The ability to work on things they are interested in and with clients they enjoy is more important to Millennial freelancers than making more money.

Management tip: If working with you is a nuisance because you demand unreasonable involvement, impose rigid policies or love to micromanage, many Millennial freelancers will switch to the next best project. It’s not just you with the power to pick.

3. Millennials are committed, but not always perfect with project management

Self-employment comes with the added responsibility of managing your schedule. Juggling multiple projects can be tough even for Millennial multitaskers. 

So when you work with freelancers, remember that you should be making an effort with project management too. 

While 70% of freelancers agree that they can meet commitments and accept accountability/responsibility for the work entrusted to them, less than half (48%) say they are effective time managers and planners. 

That’s not to suggest that you can’t rely on freelancers. But if you want to get the best results, take the lead on the admin side of things. 

Management tip: Good collaboration comes from well-defined expectations. To set the scene, do the following steps during the freelancer onboarding stage: 

  • Provide all the information your hire needs to get the job done
  • Discuss a timeline and milestones for main deliverables 
  • Agree on preferred reporting format and communication schedule


Remember: every freelancer has a lead time for new projects — a timeline they need to set everything up at their end for delivery. This includes having an approved scope of work, contracts signed, and payments sorted out. If there are delays on your end, the freelancer will scramble to readjust their schedule and tuck you in among other projects. 

A platform like Xolo Teams can help you streamline a good chunk of admin work. We handle the mundane, but important things like compliance, payroll, and contract paperwork. So that both you and your new hire could focus on the project work.


4. Millennials seek a project + purpose fit when freelancing

Millennials are often dubbed the “purpose-seeking” generation. Indeed, we don’t just want to change our time for money — we also want to feel connected to the work we do. 

“Doing meaningful work” is not just a stilted sentiment  — we back it with action. Nine out of ten Millennials would consider taking a pay cut if offered work by a company whose values better align with their own, according to LinkedIn’s Workplace Culture Trend Report

Management tip: Freelancers may be “guns for hire” that you call in on-demand. But if you want to build long-lasting partnerships, show us the value and meaning behind the work we do. Give your freelance teams feedback and show how their contribution helps shape your business if you want to retain Millennial talent.

5. Millennial freelancers prefer "collaborators" over bosses

As Gallup said back in the day:

“Millennials don’t want bosses — they want coaches.” 

We want to be trained and instructed on how we can do our work better, rather than see our ideas dismissed with a “this isn’t how we do things around here” mantra. People are the creative power behind your business. But you can’t expect innovative thinking and improvements in performance if you aren’t open to “collaboration” — as in bottom-up, cross-function idea exchanges, circulating across your organization. 

When it comes to managing Millennial freelancers, the command-and-control line of management works even worse because:

Millennial freelancers expect you to seek out their services when you trust their judgment and feel confident in their ability to deliver. But we do appreciate proactive advice on how we can course-correct when needed to build up our strengths even further. 

Management tip: Freelancers don’t want to be preached at and told how to do their work. Instead, most of them want feedback on how they can improve their services. This doesn’t have to be a formal performance review, but rather quick, ongoing suggestions on how they can hit the mark every time. 

6. Network to find your best Millennial freelance hires

Millennials are hyper-connected and started their careers when social media was rising to the fore. That’s why you are most likely to see us musing on Twitter, chatting on LinkedIn, or being active in niche communities

Our connectivity pays off. Successful freelancers get most of the new business via referrals and online networking, rather than freelance platforms or in-person events. So when you approach us with a request to “submit a proposal for ongoing collaboration” or complete a 5-page intake form, we might pass on that in favor of a quick “I’m hiring, send me your portfolio” request, published by an Internet friend of a friend. 

Management tip: Finding the best freelance talent takes more effort than publishing a job post on a freelance marketplace. At most, freelancers are members of only 1-2 platforms, so there’s strong competition for top talent.  More experienced folks prefer to work with clients directly. So the best way to connect with experienced freelancers is to follow their online  “breadcrumb” trail of bylines, podcast appearances, online project spotlights, etc. 

More Millennials are joining the freelancing ranks soon

As Fortune points out: “The greatest number of conversions from independent work to full-time hires came after the Great Recession ended in 2009.”

And we are now seeing a similar scenario happening once again. Last year, almost 65% of new businesses registered in France were micro-enterprises (solo-owned businesses). Estonia welcomes over 12,000 new e-residents in 2021, many of whom went on to incorporate new companies.  

In the US, new business registration applications are booming too. And as you may have guessed, much of this change is driven by relentless Millennial entrepreneurs. 

So there’s no way around it — you’ll have to learn how to manage Millennial freelancers if you’d want to partner with the best talent on the market.

Freelancer Management System

About Elena

Elena Prokopets writes content for tech-led companies & software development businesses, marketing to them. Her empathy for the customer, expertise in SEO, and knack for storytelling help create content that ranks well and drives industry conversations.

Elena uses Xolo so she can focus on her solo B2B content writing business without stressing over the compliance and admin overhead.