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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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Finding the Right Words in a Crisis

Illustration by Simoul Alva

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When New York Governor Andrew Cuomo announced that all nonessential workers should stay home to slow the spread of the novel coronavirus, a reporter asked why he had decided to issue a “shelter-in-place” order. Cuomo corrected him:

“It is not shelter in place. Words matter, because people are scared, and people panic. Shelter in place is used currently for an active shooter or a school shooting. We are fighting a war on two fronts. We are fighting the virus, and we are fighting fear. When we act on fears, then we’re in a dangerous place.”

Throughout much of human history, leaders have relied on their words to spark action. And many economists and CEOs today swear that words are the most important tool in a world where “command and control” leadership has given way to power by persuasion.

Cuomo has mastered the skill. His press briefings demonstrate how in times of crisis, words are essential to capturing the attention and trust of your audience. Business leaders who want to serve as beacons of clarity and hope for their teams during this uncertain time can follow his lead by applying a few best practices to their speech.

Replace long words with short ones. In his groundbreaking book Thinking, Fast and Slow, Nobel economist Daniel Kahneman writes, “If you care about being thought credible and intelligent, do not use complex language where simpler language will do.” Effective leaders speak in simple language — and simple means short.

Further Reading

This is especially true during a crisis, when attention spans are flagging and noise levels are high. People are being bombarded by information, some of which is misleading or false. The clearer and more concise you are, the better your chances of getting your message across and persuading people to act on it.

In mid-March, when Cuomo issued the order that would upend life for millions of New Yorkers and shut down the world’s financial center, he had to make the news instantly clear and understandable. So he tweeted this message: “Stay Home. Stop the Spread. Save Lives.” The post spoke volumes — in just 39 characters amounting to seven one-syllable words.

If Cuomo had tried to come off as what many consider “professional,” his message might have sounded like this: “For the preservation of public health and safety, I hereby order all residents not engaged in essential activities that impact critical infrastructure to remain in their residences in order to mitigate the propagation of the coronavirus and to minimize morbidity and mortality.”

Consider the two messages side-by-side. The “professional” version is confusing and convoluted, full of the bureaucratic jargon effective communicators avoid. The Twitter message uses simple Anglo-Saxon words such as “stay,” “home,” and “lives.”  Compared with words derived from Latin, Anglo-Saxon words are more likely to be monosyllabic, concrete, and easy to understand.

As you think about how to share your next message, remember that language influenced by the Anglo-Saxon period has been used by many great leaders. Winston Churchill once said, “The shorter words of a language are usually the more ancient. Their meaning is more ingrained in the national character and they appeal to greater force.” In a memo titled “Brevity,” he urged government administrators to replace long “woolly phrases” with single conversational words, pointing out that brevity equals clarity and that directness makes things easier to understand.

Find analogies. Neuroscientists have found that our brains process the world by associating the new or unknown with something familiar. When presented with a novel idea, our brains don’t ask, “What is it?” They ask, “What is it like?”

Analogies answer that question. They serve as mental shortcuts that help us understand complex events. Leaders who are great communicators in a crisis are skilled at finding analogies, because they have to persuade people to act quickly.

Cuomo used that strategy on April 4, resurrecting President Franklin D. Roosevelt’s “fire hose” analogy to explain why it was in Oregon’s best interests to send 140 ventilators to New York. “We’re all in the same battle,” he said. “You want to contain the enemy. Oregon could have a significant problem towards May. Our problem is now. It’s smart from Oregon’s self-interest. They see the fire spreading. Stop the fire where it is before it gets to my home.”

Let’s look at the original context. In 1940, with Nazi Germany having set its sights on England after conquering France, Churchill appealed to Roosevelt for arms and supplies. In response, Roosevelt proposed the Lend-Lease program, under which America would loan war supplies to allies while remaining neutral itself. Here’s how he sold it to the public: “Suppose my neighbor’s home catches fire, and I have a length of garden hose four or five hundred feet away,” he said. “If he can take my garden hose and connect it up with his hydrant, I may help him to put out his fire.”

Roosevelt emphasized that he wouldn’t ask his neighbor to pay for the hose ahead of time. If it was intact after the war, the neighbor would return it. If it was damaged, the neighbor would replace it. The message, in short: Although both sides are acting out of self-interest, they can work together to stop chaos from spreading.

After drawing on Roosevelt’s analogy from 80 years before, Cuomo observed that “FDR had such a beautiful way of taking complicated issues and communicating [them] in common-sense language.”

Personalize the crisis. The human brain is also wired for storytelling. In his best-selling book Sapiens, historian Yuval Noah Harari argues that it was only through stories that our species was able to conquer the world. Our advanced language skills — specifically, our ability to connect with one another through narrative — allowed us to cooperate in ways other species could not.

Cooperation is essential in a crisis, so effective leaders need to be strong storytellers.

Dr. Deborah Birx, the White House’s Coronavirus Response Coordinator, is a case in point. She has built a reputation for using personal stories to connect with her audiences. On March 25 she told a heart-wrenching story to underscore the importance of social distancing.

Birx’s grandmother, Leah, was just 11 years old during the 1918 flu pandemic, which killed some 50 million people. Leah caught the flu and infected her mother, who had a comprised immune system and died from the disease. “[Leah] never forgot that she was the child who was in school who innocently brought that flu home,”Birx said. “My grandmother lived with that for 88 years. This is not a theoretical. This is a reality.”

Birx told the story to reinforce her key message: All Americans play a role in protecting one another. The message appears to be working. On April 8, she announced that expected deaths from Covid-19 had dropped from earlier forecasts because “Americans are…following through on these behavioral changes.”

Observe the rule of three. Scholars of rhetoric and persuasion argue that people like things grouped in threes, because we can hold only a few items in short-term memory. If you give people three instructions, they’re likely to remember them all. Give them five, six, or more, and they’ll probably forget most of them. And people can’t act on what they can’t remember.

In a crisis, leaders who give fewer instructions — but more-concrete ones — are more likely to see people act on their words.

Dr. Anthony Fauci, the director of the National Institute of Allergy and Infectious Disease at the National Institutes of Health, is widely admired for his straight talk and steady demeanor. CNN has called him “a public force” who translates complex medical information into everyday language. His strategy? “You don’t want to impress people and razzle-dazzle them with your knowledge,” Fauci says. “You just want them to understand what you’re talking about.”

To that end, Fauci often limits himself to three key points. For example, in an April 5 appearance on Face the Nation, he said the country would be able to relax social-distancing guidelines only when three things were in place: “the ability to test, isolate, and do contact tracing.”

Fauci also stressed that Americans must continue to “physically separate” from one another by doing three things: staying six feet apart, limiting gatherings to 10 or fewer people, and avoiding mass interactions, such as in restaurants, bars, and theaters.

Like a virus, words are infectious. They can instill fear and panic or facilitate understanding and calm. Above all, they can spark action. So choose them carefully.

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3 Ways to Make Your Writing Clearer

Executive Summary
Next time you finish a document with a few minutes to spare, don’t squander your time editing with minor sentence-level revisions — changing a word here, cutting a word there (and then putting it back). You should certainly spell-check and proofread every document before you click submit. But if your message isn’t as clear as it needs to be, changing the word “purchase” to “buy” isn’t going to help. Instead, focus on the big picture with these three strategies: 1) Cut the “since the dawn of time” opening and get right to the point. 2) Turn those descriptive topic sentences into topic sentences that make claims. 3) Make sure people are doing things in your sentences — unless you don’t want them to be doing things. If you get in the habit of using these three strategies, you should find you won’t need to do as much last-minute editing in the future.

Illustration by Jason Schneider

Writing is hard, and writing under deadline pressure is even harder. If you’re like many of the writers I work with, you may be squandering precious minutes before your deadline making relatively minor sentence-level edits — changing a word here, cutting a …

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How to Transition Between Work Time and Personal Time

Executive Summary
Physical presence doesn’t always equate to mental presence. You could be sitting at your desk but more preoccupied about a home repair than the assignment at hand, or you could be at the kitchen table thinking more about the proposal you have to finish than the people eating dinner with you. That’s why transitions from work mode to personal mode are so essential.
Whether you’re heading into the office or working from home, here are some tips for making the shift between work and personal time. First, have a starting work routine. Set up habits that tell yourself it’s time to start work. Then, make a plan for meetings, the projects you work work on, and when. Prioritize your communication to limit distractions whether you’re on work or personal time. Finally, set a wrap-up routine, so you end your workday and can be fully off-the-clock later.

PM Images/Getty Images

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Physical presence doesn’t always equate to mental presence. You could be sitting at your …

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How to Elevate Your Presence in a Virtual Meeting

Executive Summary
Communication tactics that work well among colleagues in a conference room may not translate seamlessly to a virtual meeting. Elevating both your point and your presence in a Zoom, Skype, or similar virtual meeting requires engaging in video conference-friendly tactics. Every presentation coach will tell you that direct eye contact is a vital way to reinforce your point. In a video conference, this means looking into the video camera. Use a louder-than-usual voice because, in addition to being audible, strong voices convey authority, credibility, and confidence. In a video conference, your head and the top of your shoulders should dominate the screen. Be mindful of your background. Cluttered rooms make communicators seem disorganized. Distracting elements will pull attention away from you. Find an environment where the background is simple, reflecting your professionalism. Even if you don’t need to be fully engaged in the meeting, your professional reputation can suffer if it even looks like you’re not paying attention. So close those other windows, turn your phone upside down, and remember that you’re always “on camera.”

Illustration by Michał Bednarski

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Stay safe and in touch

This is a critical and unprecedented time for communities, businesses, and the wider economy of the world. The world has faced similar tough times in the past and conquered over it with the power of generosity and collaboration. As the COVID-19 pandemic accelerates worldwide, millions of people, including us and …

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How Dual-Career Couples Can Work Through the Coronavirus Crisis

Executive Summary
Faced with a crisis, our focus often narrows to the immediate tasks at hand. For dual-career couples now facing working from home — especially those with children at home — this means getting bogged down in questions of how each hour will be scheduled and how chores are divided. Instead, …

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10 Digital Miscommunications — and How to Avoid Them

Executive Summary
In light of COVID-19 (and all of our heightened stress levels), it’s crucial to take steps to avoid miscommunication when working as part of a virtual team. How do you avoid sending a passive aggressive Slack (“let’s chat.”) or email (“just bumping this up in your …

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People who mostly get news from social networks have some COVID-19 misconceptions

A new survey conducted by the Pew Research Center shows a COVID-19 information divide between people who mostly get their news from social networks and those who rely on more traditional news sources.
Pew surveyed 8,914 adults in the U.S. during the week of March 10, dividing survey respondents by the …

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Real Leaders: Rachel Carson Seeds the Environmental Movement

In 1958, writer Rachel Carson began her exhaustive research on the effects of widespread pesticide use for her next book, Silent Spring. Over the next four years, she built up an airtight case showing how the world’s most powerful chemical companies were harming animals, plants, and people. Her effort was …

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