The Talent Economy Podcast


How Building Remote Leadership Skills Supports Business Resiliency

Season 1, Ep. 29

When did you first realize the benefits of remote work? Were you hearing requests from your employees for more flexibility around their work?

Was it talent-driven? Did you realize that requiring employees to be on-site was limiting your ability to attract top talent?

For those of you who are still on the fence about remote work, what’s still giving you pause?

Iwo Szapar is a remote work advocate and the CEO of Remote-how. Remote-how is a platform powered by and for the community of leaders of distributed teams from 128 countries. Described as an online campus where you get to meet and grow with top remote managers from all around the world, Remote-how is at the forefront of the remote work revolution as the ultimate solution for remote education, recruitment, and international employment. Iwo is also a sought-after speaker and the founder of The Remote Future Summit, the largest virtual event focused on remote work featured in Forbes and BBC.

Iwo and Paul discuss his journey into remote work and how he’s worked with C-suite executives and HR leaders to broach the topic, turning their “I don’t know about this…” into a “Maybe it could work, how can it be done?” While getting top-level buy-in is key, the real challenges with remote work tend to occur with front-line management, ensuring that these leaders are properly equipped to manage and support a team they cannot see.

Once US states begin to reopen, organizations will be faced with how to properly re-integrate their teams back into a fully on-site or hybrid work structure. Iwo speaks to the importance of educating the market and providing leaders with examples and resources. He also offers his expertise on how managers and HR leaders can prepare for team inquiries about fully or partially maintaining their remote work status.

Questions I ask:

  • You just launched a training program for managers. What is the training designed to do and how do you prepare managers to support this new way of work?
  • Give me an example of a coworker who was on location with a traditional setup and is managing a blended team.
  • What would you advise newly remote people on how to create a work-life balance?
  • For managers who lean in and work to build their (remote work) muscle, does the process eventually become easier, or do they still struggle?

In this episode, you will learn about:

  • Iwo’s journey into getting excited about remote work and launching Remote-how.
  • How to structure your operation for remote work, no matter how big or small your remote team is.
  • How to manage the angst around the “need” to be visible when working remotely.
  • Best practices that managers can implement to provide a remote framework for their teams.
  • The Remote Future Summit 2020 and what attendees can expect this year.

Connect with Iwo:

More Episodes


Chegg: Taking On Employees’ Education Debt

Season 2, Ep. 38
Chegg is a connected platform enabling students to learn more in less time—and at reduced costs. The company offers discounted textbooks, online tutoring, and other student services, while providing diverse employee upskilling and development opportunities. Debra Thompson is Chegg’s Chief People Officer, infusing the brand’s culture of innovation, transparency, wellness, and work/life balance throughout the company. Previously, she served as Director of Compensation, Benefits, and HR Operations at Amyris and held directorial and managerial roles at RMS, CNET Networks, and Lucent Technologies. She holds a bachelor’s degree in business administration and personnel administration/industrial relations from California State University, East Bay.Some Questions Asked:What is Chegg’s approach to the upskilling, learning, and development of internal teams? 5:17What is the culture like at Chegg, and how do you maintain it? 11:53Can you tell us about Chegg’s partnership with the Tides Foundation? 21:54 In This Episode, You Will Learn:How Chegg offers learning opportunities for all employees, such as its Level Up initiative that includes seven different flagship management trainings, like giving and receiving feedback and behavioral interviewing, as well as its EDU for You program that gives staff money to pursue education in their personal fields of interest.That the culture at Chegg is built on openness, assumptions of positive intent from everyone, and optimal work/life balance—and that the company holds an annual culture, belonging, and diversity summit.How the brand’s philanthropic arm,, partners with groups to combat hunger, promote good health and well-being, deliver access to quality education and decent work opportunities, and reduce inequalities throughout the world. Links:Debra Thompson - LinkedInMichelle Labbe - LinkedInToptal - LinkedInThe Talent Economy podcast