I've always been an entrepreneur who’s worked at the edge of innovation by launching start-ups. But I rarely see the same innovative thinking that happens at a start-up applied and integrated into larger corporate systems. Until I met Paul Estes. Paul, host of the Gig Mindset podcast and other great writing is a hero in that arena, championing gig-economy thinking within Microsoft. Paul has a curious entrepreneurial spirit with a unique capacity to learn, experiment and grow. He also deeply understands what it takes to inspire cultural change. I recently sat down with Paul to talk about how he creates momentum balancing the entrepreneurial spirit of innovation with a pragmatic approach to culture shift.
John Winsor: How did you start working with the gig economy?
Paul Estes: It started in my personal life. I was a chief of staff and very busy. One Saturday I was working on a presentation for a big executive meeting. My wife and I had just had our second child. I was stressed and felt that my life was out of whack. A friend of mine, a startup founder, had a virtual assistant. He kept bugging me to try one, and so I reached out to a virtual assistant. An hour later they came back with solutions for me. In that moment I realized that I could reach out and get expert help and that things would be different.
Winsor: What gig platforms did you start with when you first tried this?
Estes: Although I knew about the gig economy I didn’t tap it until it became very personal to me—until I hit a constraint on my time and needed help. I was able to reclaim time and spend time on things important to me like my family. I tried Fancy Hands and Stitch Fix and Uber and UpWork. I used Fiverr, Clarity.fm, Ask Wonder, TaskRabbit, Instacart and Thumbtack. Then when I came into work I started to see: Wow, the way I work is broken too. I started working with virtual assistants at work. I found amazing people to do market research and design and PowerPoint and all sorts of projects. And the way I had started to live my personal life became how I worked. I began thinking about how to bring this new mindset into our organization. I realized that there was a world of people out there who were learning and retraining every day and that I would need to reskill and contribute in a different way to stay relevant and find purpose. It’s important for everyone to be thinking about how to work differently.
Winsor: I hear you guys at Microsoft have launched a new tool to facilitate working with freelancers to make it easier for people and companies to work this way.
Estes: Yes. We’ve just introduced Microsoft’s 365 Freelance Toolkit to help companies launch and scale their freelance workforces. The program fits into the existing Microsoft 365 software and adapts that for freelance participation in areas like internal communication, team-wide collaboration, data analytics and workflow automation. We created this after looking at our own needs when trying to work this way. Then our customers started asking us for support managing their freelance workforce, so we created this solution. The number of companies reaching out has far surpassed our original expectations. It’s a game changer.
Winsor: What are you seeing, in terms of timing on this transformation for business?
Estes: I believe the time is now. We’re seeing IPOs for Upwork, Lyft and Uber. Other companies like Fiverr and WeWork are going through the IPO process. Companies like Slack and Zoom represent new ways of working remotely and collaborating digitally. Amazon is now down to one-day shipping for prime customers and has also started Amazon flex, which is a gig-economy last-mile delivery service. IKEA purchased TaskRabbit because everybody doesn't want to put together their own furniture. Turbotax includes accountants through their software. TeleDoc is one of many platforms in the growing tele-medicine space transforming healthcare. We're starting to see companies focus on outcomes. What is the outcome that the customer wants and how can I apply technology and gig economy strategies to that? One of the things that I tell leadership teams is that consumer behavior will change the way we work.
Winsor: How’s the change going, both for you, and for the people you work with?
Estes: Look, change is hard. When you start working this way you move from being a pilot to an air traffic controller. To scale what you can do, you have to trust someone else to deliver when you're ultimately responsible. You have to trust someone who doesn’t have shared context. You may have never met them in person. We've been trained to hold information tight. If I have information, I have power and that power gives me safety. This new way of working says: I'm getting ideas from a wide and diverse group of people. I work with freelancers all over the United States and the world. The diversity of thought and experience makes every project better. When you have access to a world full of experts, the possibilities are unlimited.
Winsor: What happens once people commit?
Estes: When you begin to work this way—when you start trusting others to support you with your work—your purpose, value and sense of job security actually increase. This is because the diverse group of people you’ve reached out to will eventually help you perform better, both in your job and in your life. And ultimately you will become more productive and effective in the areas that are meaningful to you, which will increase your sense of belonging and security.
Winsor: Tell me what you're discovering about how mindsets shift—or need to shift—with the gig economy.
Estes: When we transformed my content team at Microsoft the first thing I told everyone is, ‘Hey, you're safe. This is not a strategy to replace you. We're being asked to do more for our customers than we’re funded to do or have the capability to do under the current structure. In that constraint we have to innovate.’ The team started to understand that engaging with experts from around the world represented opportunity, that we couldn't just work more hours. They saw that interacting with freelance experts could help accomplish goals. They dramatically changed the way they worked and their productivity by embracing the Gig Economy.
Winsor: So what advice would you give to others hoping to shift people’s mindset?
Estes: There’s a false notion that you’ll get less quality because you’re working with someone who didn't come through a traditional staffing agency or who is not sitting in a cubicle down the hall. When you reach out, you start to find amazingly talented people who do top-quality work. I spend a lot of time educating people through free lectures because it’s hard to envision this change, so it gets them curious and opens them up to new ideas that can change their future and how they work.
Winsor: I’ve heard that you offer funding to anyone at Microsoft who's willing to try this as a new way of working. How is that going?
Estes: I do. I try to take down every barrier that I can. I offer them budget to try a project, and it’s surprising how many people don't take me up on the offer. But everybody approaches change and innovation differently. The gig economy is both an innovative way of working and it is a complete change in the way of working. I encourage people, especially leaders, to think about how it can help your team. How can this way of working—this way of thinking—help your customers and your company? If you start tapping into the gig economy with those things in mind, you'll be on the path to a world that looks and feels radically different. Every successful business has an internet strategy and a mobile strategy. Those companies that can lean in will do well, replacing the many that don’t. The Gig Economy wave is coming, and to survive, you’ll need a gig strategy. You will need to rethink what’s possible. To quote Simon Sinek, “Dream big. Start small. But most of all … start.”
