Paul Estes Wants You To Be Curious

Bringing the gig mindset to the corporate space

If you want Microsoft’s Paul Estes to attend a meeting, you’re really going to have to convince him why he should take the time for it. In line with other tech titans and leaders like Elon Musk, he’s found it valuable to think about where his time is best used. In his article “#DeathToMeetings” he notes that “the incoming workforce wasn’t raised with meetings. They were raised with instant gratification. They expect this with work. Not because they feel entitled, but because they’re passionate about making real change.”

Meetings are one of the traditional aspects of a business Estes thinks that people do because they feel they’re supposed to, but often don’t add any value. By disrupting this traditional corporate structure and not hosting or participating in meetings, Estes avoids the “busy trap” and instead makes time to try out new ideas in the workplace. “Now more than ever people need to really think about how they are spending time, so they can invest in their learning and re-skilling,” Estes says. “This requires pushing against norms. Leaders have a responsibility to help their teams reclaim time and need to be thoughtful and intentional when asking for time. I have worked to create a culture where we are focused on the work and give as much time as possible back to individuals to innovate, recharge, and reskill.”

At Microsoft, Paul works on the product team and leads the Gig Economy strategy. “Gig economy” might not seem like it should be synonymous with an established Fortune 500 company that’s defined and transformed the tech industry long before the term “gig economy” was a thing—and for Estes, that’s the point. He thinks traditional companies need to start thinking like a startup in order to stay relevant and be more efficient; employers shouldn’t just think of the gig economy as something that’s associated with entrepreneurs and small businesses. Technology has made the gig economy an on-demand possibility, and employers should start tapping into the global freelance market to find expertise and experience they can use on a project-to-project basis, and to give them the freedom and flexibility to experiment with new ideas.

“The future of work is hybrid and agile,” Estes says. “Freelancers represent another set of experts along with full-time employees that can be brought in to help drive innovation and better serve customers. This trend will start pushing the traditional employee role to evolve.”

In order to help large corporations make disruptive transitions, Estes has developed the Gig Mindset, a combination of Tim Ferriss’ “four-hour work week,” Carol Duet’s “the growth mindset,” and the concept of the gig economy: it’s the inclination for people and organizations to engage on-demand expert intelligence to re-claim time, drive innovation, and re-think what’s possible.

Gig strategies don’t just have to be about hiring freelancers: Estes points to the examples of Ikea partnering with TaskRabbit to assist customers with furniture assembly, Shutterfly adding designers to their team to help customers assemble photo books, Amazon has drivers to complete last-mile delivery of packages, and TurboxTax Live allows customers to have CPAs complete their Tax Return.


When Estes was growing up, he figured that his career path would involve going to college and getting a job—a familiar, linear, safe trajectory. Up until now it’s served him well, but he’s realized that it’s not the same path that his young daughters will eventually take, or even one that he should be continuing on.

“I’m fighting to stay relevant,” Estes says. “I’m getting mid-career, and I want to make sure that I can continue to provide value to [Microsoft]. “By leaning into the gig economy and learning what it had to teach me, I started to reinvent myself and radically change the way I valued time and got work done. It was clear to me that things I thought were impossible were within reach.

“I think [my daughters] will enter a job market that’s not going to be as stable as the one I started out in. They’re going to have to learn to operate with a lot more fluidity than with which I had to operate. I feel a sense of responsibility to them just as my parents felt for me.” Estes brought disruption and the gig mindset to Microsoft by embracing the freelance market. One of his full-time team members, Ken, wanted to make a series of engaging training videos based on Buzzfeed—another disruptor—videos. He produced a few short videos that were highly engaging and successful, and the marketing team wanted to see more. But Ken only had the capacity to produce one or two every week. Estes suggested he partner with freelancers, and Ken started finding talent who, in some ways, were faster and better than him. Ken was worried about being replaced, but in Estes’ view Ken was doing the closest thing possible to cloning himself.

“He went from producing four or five videos in a month to 46 or 47 videos in a month,” Estes says. “When you’re in a constrained environment, you have to reinvent how things are done. Our teams are getting excited because they’ll say, ‘I couldn’t do this the old way, but now I can do this and I can experiment.’”

This trial on Paul’s team led to Microsoft starting a pilot project with Upwork Enterprise—the corporate stream of the popular freelancing platform, which allows business to find professional, talented freelancers to complete projects.

“When we started working that way, I saw the innovation from my team go through the roof,” Estes says. “They were now empowered to go experiment whenever they had an idea. Before this, experimenting could be expensive and time-consuming. Now employees can go ahead and do what’s right for the customer or the company or strategy, and it’s really exciting to watch the company embrace this mindset. We realized that our technology was driving our ability to work in this way.

The pilot project was a success for Microsoft, who continues to work with freelancers through the Upwork Enterprise platform extensively. Estes and his team wanted to help others integrate freelancers into their workshop, including the Microsoft 365 Freelance Toolkit: a series of resources to help large companies make the transition to working with freelancers. Estes wants companies to feel supported when making a big change, and to see the payoff of taking a risk he’s certain has immense value.

“I can have freelancers, agencies, and full-time employees interacting together [in an Upwork team] doing a massive amount of skilled work using Microsoft Team within the Microsoft 365 Toolkit. We’ve created a system. It’s been a real evolution for people to get their heads around what scaling themselves means. Initially it’s an affront to their core, to the thing that’s kept them safe. You have to work through it and think about how do I bring other people, or other technology, in? Where do I use technology? Where are your skills most valuable? If you think you’re going to do the same thing the same way for the next ten years, you’re wrong. I think it’s important for people to think about reinvention. There’s not a single job I can think of where you don’t have to at least give some thought to what the next couple of years are going to look like, and what you can do to re-skill.

“I think sometimes people reach out to freelancers, have a bad experience, and then write the whole thing off and say it didn’t work,” Estes says. “It does work. Lots of people do it successfully.”

“Engaging with freelancers used to be something that small businesses and entrepreneurs did out of necessity,” Estes says. “Big companies are now needing to compete with these small businesses and startups that are causing massive disruption to a lot of different sectors. YouTube, WhatsApp, and Instagram all started as startups with 65, 55, and 13 employees, respectively, when they were purchased. Companies are going to need to be more nimble and more reactive, and to do so you need to have access to on-demand experts at the time that you need them. I think freelancers are a tool more companies will use—along with traditional employees, and agencies, and technology—as things evolve. Now I get to work with amazing traditional corporate employees, and with people around the world. These are talented, amazing people who have a ton to give and have chosen a path [freelance] that is on trend for the future. Pushing against the norms of how we were working has benefited me and the company, and it helps the amazing people who have chosen or found themselves in this non-traditional work environment as a freelancer. I’m surrounded by these amazing people I wouldn’t have access to if it wasn’t for the work that Upwork, and many other companies around the world, do.”


The gig mindset and working with freelancers is something that Estes is passionate about, but he acknowledges that it wasn’t something he himself could instantly change at Microsoft. He partnered with HR, legal, procurement, strategy, and research departments to develop a responsible, trusted method.

“It took a village, it wasn’t just me. We spent a year before the pilot program as a team talking about ideas. I needed the input. We couldn’t have launched the program without everyone’s voices because each of them brought something to the table. It is disruption, but we’re moving at a pace that’s responsible and trustworthy. It’s interesting when I find other people like me in large companies, how disruptive they feel, yet many feel like misfits for thinking that way. I was very fortunate to have an internal group of people willing to participate and come on the journey. Disruption isn’t just an instantaneous change, it can be any of those things you put practice or training into as well.”


Introducing freelancers into your workforce may certainly be a big change that takes a lot of time to plan for, pilot, then implement, but that doesn’t mean it’s not worth the effort. In fact, Estes found it much less expensive and arduous to implement than other projects he’s taken a risk on. “You can’t change or evolve if you don’t have the time to do so. I say to people ‘you should hire a freelancer and try this out,’ and they say they’re too busy. That’s the busy trap. They’re too busy to change, but they’re not happy, and they’re not moving forward. Yet they’re not re-skilling, they’re too busy to learn. It is now no longer an option to constantly be learning as part of your career, it’s a requirement.”

Estes’ solution to the busy trap is to learn how to delegate, give up control, and learn to trust others—which itself is a long process. No one should expect changes to happen instantaneously. Estes admits it was hard for him, as it is for many, to learn how to delegate, and to accept that there are others who are just as capable as him, if not better, at certain tasks.

“I’m still learning how to find experts, how to build my network of people who are a fit for what I do, and to help me with my work,” Estes says. “I think it’s hard for people to give someone else your work to do, because there’s nothing more personal than people’s jobs. We think if we give up work, we’re saying we’re not capable. But what you’re saying is that you’re wanting to be more efficient and more valuable.

“The gig mindset is a shift, it’s about your relationship with time and about learning from a diverse network of experts. I needed to find that intersection of purpose and passion. It’s a hard process, but this mindset is one that helps you stay relevant, helps you reclaim time, and gives you options about where to spend your time–whether that’s side projects, volunteering, hobbies. When you learn to delegate and let others help you with their skills, it gives you a lot of options to find projects that give you purpose, and not feel so stuck.”


In a world where we can watch movies on demand with Netflix and order a car on demand with Uber, Estes thinks that eventually companies will see the value in having experts in a variety of fields on demand, too. B2C companies are creating new consumer expectations for companies and this will change how companies operate, as well as how employees expect to work.

“I just think that consumer expectations of on-demand experts will be a big thing. The consumerization of IT is a new model that needs to be considered along with other models. I think it’s going to be transformative, it’s been very transformative to me personally. I didn’t want to choose: should I have a career or hang out with my daughters? Now I can have both.”


Estes thinks that companies should not be intimidated by the imagined difficulty of implementing change; he’s confident that curiosity can pay off not just in terms of innovation and efficiency, but in corporate culture. “At Microsoft, we practice the growth mindset: be a learn it all, not a know it all. I used to be obsessed with being right, and my mentor told me that it’s about being relentlessly curious. The only thing that’s going to keep you safe is being curious, being curious makes you empathetic. If everything is an opportunity to learn, you’re going to be genuinely interested.”

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