#423: Herding Digital Cats? How to Lead in the Gig Economy
Mastering Connection, Growth, and "Micro-Management with a Twist" for Distributed Teams.
I've often delved into the intricacies of leadership within traditional corporate structures, now it’s time to navigate the ever-changing work landscape. We've talked about the art of delivering feedback (remember that deep dive in #360?), the power of goal setting (channeling Ziglar's wisdom from #347), and the general pursuit of excellence within established teams. We’ve written about developing a culture that all the teammates adhere to, but here's the kicker: the world of work is rapidly reshaping itself. An often overlooked frontier of leadership challenges is emerging, I'm talking, of course, about the gig economy.
By 2027, 40% of the U.S. workforce is projected to be freelancers. That's a massive shift, and it presents a unique leadership vacuum. How do you lead, motivate, and foster excellence among a transient workforce that, by its very nature, lacks the traditional long-term loyalty of full-time employees? This isn't just about managing projects; it's about coaching individuals who might be simultaneously juggling three other clients, working from a coffee shop in a different time zone, and whose primary concern might not be the same as yours. It's a leadership puzzle wrapped in a riddle, sprinkled with the delightful chaos of coordinating Zoom calls across multiple continents. This task often feels like trying to herd digital cats.
Boom to Bust
Now you’re asking yourself, what can a Boomer like Kole tell me about herding digital cats? Well, in the past, I managed a global group of independent contractors, engineering teams, and distributors. Sales Managers like myself can relate today’s freelancers to independent sales agents (manufacturers’ representatives). What were the challenges then that still exist today?
Keeping top of mind status
What do I mean by this? Managing a group of freelancers requires you to ensure that they think about your offering every day. In the past, I used the telephone to check in with each of them weekly. What were their priorities for the coming week? What did they accomplish? What roadblocks did they come across that I could help remove? And when I could figure out the correct sequence on the touch-tone phone, we would plan a group conference call to discuss common problems and challenges.
Today it’s even easier. Set up a coffee Zoom for the global team to dial into. It’s just like management by walking around (like I wrote about in #420). Use today’s technologies to find out what they plan for the day. Implement a team Slack Channel or Group Text, where they can post about new ideas or problems, and encourage them to reach out to each other to help. This can create a team atmosphere that makes career employees feel good.
Support personal growth
As a global director, I had a budget for team development. That could include teaching them how to use Excel or Presentation Techniques. Part of the budget was completely discretionary, and we could invest in those independent reps so they became more well-rounded and fulfilled personal goals. I recall one rep who wanted to take a cooking class, and we offered to pay half upon completion.
Even though these freelancers are independent businesses, they are still people. Investing in them for skills development or personal growth shows that you care and adds value to them. Sure, they can invest in themselves, but you want to keep them around, and this is how you can also add value and develop a loyal team. You need their loyalty just as you do your full-time employees.
Micromanagement, with a twist
Engaging with a team on a long-term project makes it easy for time to get away from you, and then suddenly, you're up against a deadline. How can you stay on top of these freelancers and keep the project on track? It might sound scary, but micromanaging is an option, but one that the team will gladly allow.
Much of my experience was in multi-year developments where the payoffs would be significant, sometimes three to five years away. Keeping reps and contractors engaged for that long was demanding, and to keep them invested, we set up progress payments and micro-goals with compensation tied to achieving them. For example, get an appointment with a prospect, earn a bonus of X, redline the terms and conditions of the contract, and get paid. This approach created immediate incentives and kept everyone focused on incremental wins.
You can do the same with your graphic artist working out of Mumbai or your software developer who moves from beach to beach. A significant overall goal must be completed, but to stay ahead of the game, stay invested in their progress. The project might be massive, but these micro-goals are precisely what I've said in the past: "eat an elephant one bite at a time."
This isn't about stifling creativity or trust but providing clarity and consistent reinforcement. Breaking down significant deliverables into smaller, manageable chunks reduces ambiguity and allows freelancers to see their tangible contributions more frequently. This fosters accountability through clear expectations and builds trust as they consistently hit milestones and receive timely recognition or compensation. Is it risky? Yes, but it's no less or more risky than managing a traditional team of employees trudging along the same project path. This method can increase engagement and commitment for a transient workforce, turning potential chaos into productive momentum.
Conclusion
Leading in the gig economy presents unique challenges, but as my experiences with independent reps taught me, the core principles of engagement and motivation remain. The keys lie in consistent, intentional connection to stay top of mind, genuine investment in personal growth, and the strategic application of micro-goals – eating that elephant one bite at a time. This isn't just about getting the job done; it's about building meaningful, albeit temporary, relationships that drive excellence. So, which of these strategies will you implement first to cultivate a more engaged and successful freelance team? The future of work is here, and it's time for our leadership to evolve with it.
Please comment on what makes sense in your group of freelancers?