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Remote Work: Michelle Labbe Of Toptal On How To Successfully Navigate The Opportunities & Challenges Of Working Remotely Or From Home

An Interview With David Liu

The mindset that presence equals productivity. Strong and frequent communication can be even more meaningful than simply physically sitting next to someone. At Toptal, trust is the foundational element that allows for this to happen effectively. We’ve found that focusing on clear goals, aligning on ownership, and holding colleagues accountable for outcomes are ultimately much more successful approaches than simply an in-person presence.

Career development is the ongoing process of choosing, improving, developing, and advancing your career. This involves learning, making decisions, collaboration with others and knowing yourself well enough to be able to continually assess your strengths and weaknesses. This can be challenging enough when you work in an office, but what if you work remotely? How does remote work affect your career development? How do you nurture and advance your career when you are working from home and away from other colleagues? How can you help your employees do this? To address these questions, we started an interview series called “How To Advance and Enhance Your Career When You Are Working Remotely”. As a part of this interview series, I had the pleasure of interviewing Michelle Labbe.

Michelle is the Chief People Officer at Toptal, which operates a curated network of freelance talent with business, design, and technology expertise that allows companies to scale their teams on demand. She leads the organization’s People, Recruiting, and Learning and Development teams, creating and maintaining a world-class experience for Toptal’s more than 1,000 fully remote team members through hiring, developing, and retaining top talent. Her more than 20-year career includes senior talent leadership roles across both the startup and agency worlds, spanning multiple industries.

Thank you so much for doing this with us! Before we dig in, our readers would love to get to know you a bit better. What is your “backstory”?

I majored in political science at the University of Arizona, where I am not embarrassed to admit I went for the weather. After taking a year off following graduation and deciding not to go to law school, I ended up in marketing for a well-known book retailer. When the company relocated to another state, I found a temp job at Deloitte’s headquarters and ended up working for the female partner in charge of HR executive matters (compensation, partnership, diversity, etc.). I had found my calling! In hindsight, growing up with a father who worked at IBM and moved us to various states every few years taught me to be flexible, be at ease with meeting new people, and adapt easily to change. I was always the person who my friends came to for advice and was the mediator in many an argument. I didn’t realize until a few years ago how my upbringing was the perfect fit for my role in HR. I went from Deloitte to Accenture to smaller, fast-growing startups where I could really create change and structure teams, corporate cultures, and functions for success, which has become my sweet spot.

Can you share the most interesting story that happened to you since you started your career?

I have worked for some companies that sponsored events with celebrity guest speakers. As the senior-most People person, I was usually the one to act as their “handlers” since others knew I could maintain confidentiality. My favorite guest was Ben Stein (the teacher from Ferris Bueller’s Day Off:Bueller? Bueller? Bueller?”). After spending a few hours with him one-on-one, I came to truly adore him. When I was flying back from the event, he left me a voicemail to thank me for my help and kindness.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

I can think of a few, but there is one that sticks with me the most because it taught me a valuable lesson about how to relate to — and get the best outcome from — people. When I started at Deloitte HQ, one of my responsibilities was collecting expense reports from senior partners. These were partners who were close to retirement and would go out to long “three martini lunches” every day. In the beginning, whenever I approached them to request their paperwork, I faced lot of resistance. I quickly realized that if I wanted to get what I needed to do my job, I had to adapt to the culture of this group. Once I shifted to a more casual style, joking and acting like “one of the guys,” I found they were much more receptive to me and my requests.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

“Let it go” or “Pick your battles” are the two life lessons that go hand in hand for me. I think we all have to choose what we are going to engage in, know when we have to move on, and realize we can’t always win or control an outcome.

What advice would you give to other business leaders to help their employees thrive and avoid burnout?

Every employee has different needs and different priorities. Managers need to identify what is important to their team members and support them. Research has shown that people tend to stay in their roles if they have great managers. So, managers need to make sure their employees are taking time off to recharge. One of the best and most effective ways to do this is to lead by example.

Ok, let’s jump to the core of our interview. Working remotely can be very different than working with a team that is in front of you. This provides great opportunities but it can also create unique challenges. To begin, can you articulate for our readers a few of the main benefits and opportunities of working remotely?

Flexibility and the opportunity for better work-life balance are probably the most familiar benefits of remote work. I can share two others that may not be as widely known.

First, remote work enables a true meritocracy. As digital borders open up, remote work creates new pathways for talented individuals to succeed, no matter where they are located. For example, the world’s best developers no longer have to relocate to expensive areas like Silicon Valley to work for leading tech companies, as that work can be done anywhere. A top finance expert doesn’t have to live in New York City to land a role with a leading bank. With remote work, location matters less. The greater emphasis is on who you are — your skills, your expertise — and what you can do.

Another benefit of remote work is that it prioritizes results over and above time spent at a desk (regardless of whether that desk is in an office or in someone’s home). Numerous studies have shown that individuals who work remotely are more productive than their in-office counterparts. They tend to work a full day without the distractions of an office or the pressures of a commute — arriving late due to traffic or having to leave early for a parent-teacher conference. Simply put, they’re able to work when they’re at their most productive and get more done in less time.

Can you articulate for our readers what the five main challenges are regarding working remotely?

In my experience, the top five challenges are:

  • The mindset that presence equals productivity. Many companies transitioning to a fully remote workplace often seek to maintain the “presence” element of an in-office environment, equating greater face-to-face time with an increase in accountability or productivity.
  • Creating and upholding a corporate culture. A well-defined and meticulously cultivated culture is core to the long-term success of any company. It’s even more critical for those with remote workforces that lack the shared experiences and physical spaces that are common to in-office culture.
  • Balancing work and personal commitments. When your office and your house are the same place, it’s easy for the line between work and personal to blur. This is often a pain point for employees who feel that their managers don’t trust them to work from home.
  • Clients struggling to see fully remote employees (and companies) as world-class. The most common reasons clients might be uncomfortable with remote work could be the preconceived notion that remote workers lack productivity or, in extreme cases, won’t be working at all. Additionally, clients in some industries might not have experience with the latest tools, technology, and/or processes to support a remote environment.
  • Lacking the right technology. In the absence of physical proximity, remote companies need to think strategically about the tools they use. Those decisions can make or break their ability to communicate effectively — internally and externally — and their ability to maximize productivity. Equally as important are the policies and processes that are established to ensure consistent and appropriate usage of those tools.

Based on your experience, what can one do to address or redress each of those challenges? Can you give a story or example for each?

  • The mindset that presence equals productivity. Strong and frequent communication can be even more meaningful than simply physically sitting next to someone. At Toptal, trust is the foundational element that allows for this to happen effectively. We’ve found that focusing on clear goals, aligning on ownership, and holding colleagues accountable for outcomes are ultimately much more successful approaches than simply an in-person presence.
  • Creating and upholding a corporate culture. For remote companies such as Toptal, culture is often built on intangibles, such as values, trust, and a commitment from everyone to understand and uphold them.
  • Balancing work and personal commitments. Employers must presume trust and continually communicate the value of flexibility. This contributes to exceptional levels of retention and satisfaction while promoting a high level of productivity. For example, we encourage Toptal employees to be vocal about their workload, and we remind them that our discretionary time-off policy exists to be used at their discretion. Flexibility is woven throughout our policy to the point that making a time-off request is as easy as sending a Slack message.
  • Clients struggling to see fully remote employees (and companies) as world-class. The quickest way we’ve found to alleviate clients’ concerns about remote work is to teach them how it’s done. For example, offer to use every service and expert you have to show them how effective remote collaboration can be. In our experience, clients tend to find that remote team members are even sharper than many on-premise peers because of fast and transparent communication, expertise with well-organized tools to facilitate interaction and flag issues, and a strong online presence that showcases authority.
  • Lacking the right technology. The right technology tools and processes are some of the strongest ways remote teams can perform in a seamless, productive, and rapid manner. For example, given Toptal’s heavy reliance on Slack (versus email) for our regular communication, we have adopted detailed internal policies around channel structure and etiquette to enhance clarity and set a professional tone that’s appropriate for our culture. When off-the-shelf solutions don’t meet our needs, we develop customized in-house tools. We built TopTeam to help people visualize the company’s org structure and maneuver through its virtual environment. It also acts as a centralized repository for the company’s Objectives and Key Results (OKRs), which help assign ownership and accountability throughout the company.

Let’s talk about Career Development. Can you share a few ideas about how you can nurture and advance your career when you are working from home and away from other colleagues?

Be curious. Take advantage of all that your company has to offer. Toptal provides licenses to training platforms such as LinkedIn Learning and Udemy. We have a vast library of homegrown training programs on remote work, management courses, AMA (Ask Me Anything) sessions, roundtables, and much more. Additionally, we offer a mentor program, and we have a book club to foster discussions about various business topics and trends.

It’s also important to remember that managers don’t have full visibility into or are not aware of all the things their employees do on a daily basis. You need to control the narrative of your career. At Toptal, we encourage all team members to document their activities throughout the year: goals, actions, and opportunities. This documentation forms the backbone of annual self-evaluations and can be very helpful in balancing accomplishments and opportunities.

That brings up another point: Don’t hesitate to advocate for yourself. That can often feel like bragging, which is uncomfortable, but it’s integral to advancement. Similarly, there’s nothing wrong with saying, “I didn’t make as much progress on X as I wanted to this year.” That is valuable perspective and highlights an area of growth that both you and your manager can make progress against before the next review cycle.

Can you share a few ideas about how employers or managers can help their team with career development?

Most importantly, employers must create a smooth transition to remote work. This requires much more than simply granting employees permission to work from home. It starts with building a culture of trust, accountability, and transparency that empowers workers and encourages them to develop the habits necessary to be productive and successful in this new environment.

Employers must also create strong alignment of goals across the entire company and proper accountability for those goals. This is true of any organization but it’s particularly critical when some or all employees work from home because it ensures that everyone, regardless of where they are located, is focused on the same objectives.

Knowing that productivity and accountability work hand in hand, Toptal has adopted a formal process for establishing OKRs at the company, function, and individual levels. We track them regularly and make them visible to everyone in the company. This way, we can be confident that all team members are connected by shared, clear goals and are then rewarded when they meet or exceed those goals.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. :-)

This is a difficult question because I could answer in many ways. I have causes (women leaders, climate change, animal rescue) that I am dedicated to but, since starting at Toptal, I’ve become a champion of remote work, which has grown because of the pandemic. To me, the idea that people can work for companies in roles that don’t require them to be in a physical office is a novel and inspiring one. We have team members around the world, including those in countries challenged by civil and economic disruption, but they are still able to put their exceptional skills to work, grow their careers, and support themselves and their families without having to relocate. I firmly believe that remote work is the future of work, but it represents much more than just flexibility. Remote work has the potential to be a movement that opens a new world and new opportunities for so many people.

How can our readers further follow your work online?

Please visit or follow us:

Thank you for these great insights! We wish you continued success.



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David Liu

David Liu


David is the founder and CEO of Deltapath, a unified communications company that liberates organizations from the barriers of effective communication