Why Mastering Delegation is Crucial in the Gig Economy


In my own life, I’ve seen massive shifts in delegation since I began to engage regularly with freelancers. I get more done, and the projects benefit from the contributions of experts. I also get to spend more time with my family, doing things we all enjoy.

I also spend a lot of my time writing and teaching on the Gig Mindset. Both writing and teaching require a great deal of communication. In addition to speaking at conferences, I deliver a weekly newsletter to more than 60,000 people and record regular podcasts.

I call this approach the Gig Mindset.

The Gig Mindset involves making my network of freelancers my first port of call when I have something to accomplish. Every element of the Gig Mindset takes practice. By far, the hardest, in my experience, is delegation.

Delegation requires you to let others run with your ideas.

It’s difficult because, to delegate successfully, you need to be willing to give up control. It takes courage to change your mindset, trust in people with diverse backgrounds, and radically reinvent how you work and live.

To truly engage with what is possible in the Gig Economy, however, delegation essential. Let’s break down what I mean by delegation in a Gig Mindset context — and why it’s such an important skill.

Giving up Control

What is delegation? When I use the term, I’m not simply saying that you tell a freelancer what you want to be done. Imagine you’ve ordered an Uber. The app allows you to plot your journey and dial in the exact spot to be dropped off. When you get in the car, you could ride the entire way in silence. Maybe, as you approach your destination, you offer a few bits of clarity to guide in those last few blocks. Think about the trust you just placed in your driver.

Could you have sat down in the passenger seat, app out, playing navigator the entire time? Sure. You could also just drive yourself if you need to have that much control. Delegation means stepping back from the driver’s seat and trusting your freelancer to follow directions and ask questions if they get stuck.

Right now, I have people that do web research and data to support my arguments and narratives around a variety of topics. I have an expert who does motion graphics. I have another editor for videos. Sometimes I need graphs and charts based on the data I’ve sourced to support articles and newsletters.

All of these tasks represent someone I’ve delegated to. Someone I’ve trusted to run with my instructions. This is the type of delegation that will allow you to thrive in the Gig Economy.

Conferring Authority on Your Team

The reason delegation is difficult is that it requires you to assign both responsibility and authority to the freelancers with whom you work.

Responsibility is easy. When you hire someone full time, you are giving them responsibility. It’s part of their job description. When you delegate to someone, you are assigning them authority. They can make decisions based on your instructions and your intent. You are trusting them to make the right choices in pursuit of a shared goal, for which you are ultimately accountable. For so many people I’ve met, that is the scariest thing imaginable.

I can’t emphasize enough how hard that idea was for me and still is for people who are beginning to work without a shared context. Human beings have difficulty seeing how delegation can be a blessing.

If we’re honest with ourselves, it looks like a threat. We all have that expectation that we are “the only ones who can do this task.” We tell ourselves that we’re the only person who can do it. If we don’t do it personally, it just won’t get done. Or it won’t get done right.

For anyone who has managed a team of people, you know delegating won’t lead to the same end result as doing something yourself. But I’ll bet that you have experience of getting things done through delegation.

No matter the task, you and your team pulled through. And that diversity of thought made the project better. Different doesn’t equal worse. Working with a wide group of people adds new voices and perspectives and helps find new solutions to a variety of challenges.

When I engage with freelancers and bring together a wider team, I gain knowledge. My life experience is limited to my gender, my race, the neighborhood I grew up in, and the schools I attended, as well as the companies and industries where I worked.

What looks “right” to me is fixed and rigid. Adding in the perspectives of people from around the world teaches me how to connect on a whole new level. It makes the market research better, designs products better, and forces me to improve my management skills and communication.

The Gig Mindset is not a shallow pond. You can’t just dip in your toes, play around, and then go back to your old lifestyle. In fact, you have to come to this with a little faith, the belief that this will work. You have to lean into it, dive into the deep end with the expectation that—for just a moment—you will be completely underwater.

How to Communicate Effectively

The number one challenge, the number one place where people struggle, is communication. I’ve seen it from thousands of people. They struggle with how to communicate their expectations to someone who may not have a shared context; to give up control and trust.

The “control” problem isn’t exclusive to business relationships. Control affects millions of intimate relationships too. Couples counseling is a huge industry in the United States — becasue of the “control” issue.

Now they have to articulate those tasks. They have to provide specific instructions and then just walk away. For a lot of people, this is new. It’s easy to sit in a meeting and just talk, but far more difficult when you have to write a descriptive project brief to delegate.

It’s understandable. Your tasks are so innate to you. If you closed your eyes, you could picture every detail. Now you have to work with someone who doesn’t share that context, and you have to place all your hopes and expectations into them. It’s a real learning process.

Delegation isn’t just saying, “Go do this.” It’s building expectations, setting timelines, and really engaging with these experts. To delegate is to get your vision on paper with examples of things that inspire you.

Effective delegation is inviting the other individual to provide guidance –to you– on how they work and feedback on your thinking. It’s trusting that they are professionals and want to deliver the very best. Most of all, it’s about having an open and curious mind throughout the process.

Delegation in Action

Let’s use an example to illustrate how delegation works—and how it doesn’t work. You need to cater to a working lunch for a group of ten. Now, if you were to ask a virtual assistant to find a place to eat, you’d get back a pretty bland response. Maybe something on their list would fit your needs, but it would be a roll of the dice. What about dietary restrictions or allergies? In this case — you’ve provided too little information and context to expect a good result.

So, you go back to the freelancer, but you ask a more detailed question: “I’d like somewhere to order lunch. It needs to be within fifteen miles of my office, my boss prefers Italian, and it needs to be vegan-friendly. Also, we are capped at $30 a person.”

You’ve provided the same request but with context. You want something specific, but not so specific that the request is redundant. If I engaged a virtual assistant and said, “I’d like to eat at McDonald’s tonight,” I’ve wasted our time and my money.

The sweet spot lies in providing enough information to your freelancer for them to come back with specific recommendations that meet your needs, but not so much that their input is redundant. To delegate effectively, you need to know what you want, create a brief, then trust an expert to fulfill that brief.

A Delegation Revolution

To excel at delegation, you need to be clear about what you gain. It is all about your relationship with time. You have to go back and look at all the tasks for this project. What are the trade-offs? What has to go? No matter what you do in life, your time is finite.

Whether you work in the mailroom or the top-floor corner office, you have the same number of hours in a day. You can’t do everything you want. You can’t even do all the tasks you need to do, at least not alone. So, you need to start looking at your life and selecting those items you can delegate out. What can you give up, relinquish all control of, so you can have more time and space?

Radical delegation is about practice. Start delegating with small tasks, which leads you to more complex tasks. Do a couple of projects in the virtual system. Engage with a virtual assistant on one of the platforms and practice giving detailed instructions. You’re not writing pages and pages of notes, just a few bulleted guidelines.

Giving up control is hard. It takes time. But it gets easier as you build your trusted network of freelancers. The goal is to find your tribe. After a while, you will see that your value isn’t the control. Your value comes with the exponential opportunities you create by engaging with these experts.

When you empower your employees to use the Gig Mindset, you add a force multiplier to your team. Each person becomes an engine of activity, bringing in expertise that you couldn’t have expected before.

Do you have a special project you want to do at work? Or a family activity that keeps being pushed back? Or a trip to visit family and friends? Find a freelancer, brief them thoroughly, then stand back and allow them to do their job.

For more advice on mastering delegation, you can find Gig Mindset on Amazon.

Paul Estes

Paul Estes is an unstoppable advocate for the gig economy who is dedicated to creating opportunity for everyone, reskilling by doing, and bringing diversity to our work. After twenty years of driving innovation in Big Tech (Dell, Microsoft, Amazon), Paul transitioned into working as an independent, remote freelancer. He shares his insights from main stages as a keynote speaker and offers his thoughts and advice through articles on LinkedIn. By engaging with freelancers, Paul gets exponentially more done at work and has more time for his wife and two daughters. He’s the author of the best-selling book, Gig Mindset: Reclaim Your Time, Reinvent Your Career, and Ride the Next Wave of Disruption.



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