June 2016
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TD Magazine

The Remote Boss

The Remote Boss

Your entire team works from home. You do, too. What's the best way to manage a virtual team?


It's 9 a.m. on a Tuesday morning and Sarah Parker is leading her team. She's not dressed in a suit, and she's not getting in her car or hopping on a train. She has no office to go to and no specific arrival time to meet. Parker works for a major software company, and she manages a group of developers who work out of their houses all around the globe.

Using Skype, Parker starts her day by seeing who's online, and chatting with her team. She also logs into a project management system to see what's on the docket for today. Her calendar is shared and reflects time blocks for calls with clients, a check-in with her team, and a block of time to build out a resource proposal to add additional contractors to a project. She takes a sip of her coffee, made fresh in her own kitchen, and gets down to business.

As broadband Internet access spread around the globe, businesses began to question why they were spending money on physical office space. With collaboration tools and resources, low-cost videoconferencing technology, and e-commerce, virtual companies went from concept to reality.

What is a virtual company?

The term "virtual" has come to mean a variety of things. Before it was co-opted to mean something that exists in cyberspace, but not in the real world, virtual meant "almost" or "very nearly identical." But the rise of the Internet has spawned a whole new lexicon, and many words that meant one thing before the Internet now mean something quite different.

When we talk about a virtual company, we're not discussing something that is almost, but not quite, a real business. A virtual company is an organization that typically exists without an office, without a warehouse full of goods or a store full of merchandise. It's a business that runs primarily online. And in addition to not having a headquarters or a bunch of stock on the shelves, virtual companies typically have employees who work from anywhere.

Enrique Levin, co-founder of Zintro, has been operating his company virtually since its inception. Zintro is a platform that helps connect companies with highly specialized experts for projects, phone consults, and jobs. The company has employees all around the world, doing everything from software development of their platform, to account management for clients, to sales and marketing. Levin sees tremendous benefits in operating as a virtual organization, and wouldn't work any other way.

"By not being bound to a specific location, the pool of talent is expanded globally, allowing us to hire the best talent available in the world," he says. "Due to the reduced 'control' over employees, it forces us to manage by goals and measurable results. It makes us more cohesive, and more responsible of our work. We communicate more transparently and it allows for better accountability."

You wouldn't be alone if you assume that virtual companies often are startups or very small businesses, but you might be surprised at how many larger organizations operate this way. In fact, there doesn't seem to be a limit on how big a virtual organization can get. Companies such as Mozilla, Automattic (the business behind the hugely successful blogging platform Wordpress), Basecamp, and Wikipedia all operate as virtual organizations.

Management practices of virtual organizations

The defining feature of a virtual business is that it doesn't have an office. No headquarters with a big neon logo on the outside, no physical space where employees can gather around the water cooler, no cubicles filled with fake plants and family photos. Virtual companies exist primarily in cyberspace. In addition to being office-free, virtual companies also practice the following management strategies that set them apart from more traditional businesses.

  • Free-agent workforce. While some virtual organizations take a traditional approach to employment, and use mostly full-time employees to get their work done, it's the exception, not the rule. Most use a mix of employees, freelancers, and online services and tools to keep their businesses lean, and minimize the need for office space.
  • Flexible schedules. Along with not sitting side-by-side in cubicles and offices, virtual co-workers often don't share the same schedules. As a result, they measure success more often by results and deliverables than by time in the office. It also means that vacation and time off tend to be handled loosely or not tracked at all.
  • Flat organizational structure. Although larger firms may adopt a hierarchy, it's typical of smaller organizations and startups to work as colleagues rather than having a pyramid of management roles. This is often true in virtual organizations, although it's important to provide support and communication—particularly for more junior resources who may need mentoring and support to develop their skills.

    Managing virtual teams

    Working virtually seems like a great plan—lower costs for office space, happier employees working from wherever they feel most productive, and a global talent pool. But it's not all smooth sailing, particularly when it comes to managing people you can't see.

    "Remote work is not for everyone," says Levin. "A culture focused on results requires commitment, focus, organization, and very hard work. In a remote environment, the yield per employee is much higher than in a physical environment. For a lot of people this means working harder than if they were in an office. There is no chance for faking it; you either make it or you don't. This can be very hard for some people and especially for those that are used to the traditional model, where getting dressed, showing up and smiling is 50 percent or more of the work. Remote work requires you to be self-driven and organized. If you require a lot of hand-holding or are not very organized, you will struggle to get things done."

    The nature of virtual work is such that sometimes team members don't interact for long periods of time. There's no casual social interaction such as what you find in offices where people share physical space. That turns out to be both a positive and a negative. On the one hand, without forced social interaction, people are able to focus solely on the work without getting enmeshed in office politics. On the other hand, without day-to-day interaction, it can be tough to build a cohesive and supportive culture.

    Levin recommends hiring methodically and focusing on fit over skills. "Hire people slowly and progressively and hire those who are a good fit culturally, instead of those that have the strongest skills or experience," he says. "Look for people that get you and that are likely to get each other."

    Jason Fried is founder of Basecamp and a passionate advocate for this model of business management. He says when in doubt, hire clear thinkers and communicators. "If you are trying to decide among a few people to fill a position, hire the best writer," he suggests. "It doesn't matter if the person is marketer, salesperson, designer, programmer, or whatever; their writing skills will pay off. That's because being a good writer is about more than clear writing. Clear writing is a sign of clear thinking. Great writers know how to communicate. They make things easy to understand. They can put themselves in someone else's shoes. They know what to omit. And those are qualities you want in any candidate."


    Finding the right tools to communicate

    In the 1987 movie The Secret of My Success, Brantley Foster (played by Michael J. Fox) made his way up the corporate ladder by setting up shop in an empty office in a large corporation and posing as part of the organization's management. He succeeded by a clever use of interoffice mail—a system of passing memos through a physical internal mail system, which (thanks to email) almost no one working today even remembers. Before email, people sent memos, wrote briefs on typewriters or by hand, and used the telephone to communicate critical information. Today's technology landscape has brought us an immense variety of tools and resources for team communication, such as:

  • email
  • instant messaging
  • videoconferencing
  • virtual collaboration space
  • project management workspaces
  • document collaboration and management systems
  • customer relationship management systems.

    All these tools can make it easier to communicate, set goals, see what's happening, and operate your business without seeing the people who work within it. But with so many options to choose from, it's important to set some ground rules for communication.

    First, focusing on a central repository for information is a good place to start. When people are working remotely, and especially if some of them are contractors, you're going to want to have a single, secure space for people to store the work they do so you can access it if they are unavailable. Document management solutions such as Google Drive, DropBox, SharePoint, or Box are a good starting point.

    Another important tool for communication is instant messaging. Some solutions such as Skype or Lync are integrated into other tools, while others (for example, Slack) are more stand-alone team messaging tools. In addition to enabling team members to communicate in real time, these tools keep track of conversations and allow you to search and revisit conversations later.

    Project management and task management systems are a great way to give the whole organization visibility into their work streams, and help manage dependencies. There is a huge range of tools in this category, from single-user options such as Microsoft Project to team collaboration tools like Asana, all the way up to full-service tools such as Basecamp. The benefit to collaboration tools is that it brings visibility to the workflow within individual teams, as well as to the organization as a whole.

    Zintro employees use a suite of tools for various purposes. "For day-to-day communications we use a chat window for every functional team. We also have cross-functional chat for handoff procedures and meeting chats for weekly or daily calls," explains Levin. "We mainly use Skype for everyday communications. We frequently have videoconferences and very frequently share screens."

    Looking into the future

    Work is changing. Technology is enabling individuals and organizations to collaborate in ways that were unimaginable just a few decades ago. In particular, more companies are embracing remote work. According to new data released by Global Workplace Analytics, telecommuting has grown 103 percent during the past decade in the United States.

    Leading a virtual team involves understanding not only the skills required to be a great manager, but also how to apply those skills across time and space to engage a team you don't see in the office every day. With the continued growth and interest in flexible and virtual work arrangements, leadership skills, especially virtual leadership skills, are more important than ever.

About the Author

Katy Tynan is the bestselling author of practical guides to career transitions, and an internationally recognized expert on how work is evolving. In a world where 70 percent of employees are disengaged, Katy helps organizations ditch out of date management practices and create an inspiring, engaging culture.

Over her 20 year career in IT and operations consulting, Katy has advised hundreds of organizations on how to find innovative solutions leveraging technology and human capital for competitive advantage. Katy has been part of multiple successful startup exits including Winphoria Networks (acquired by Motorola in 2003) and Thrive Networks (acquired by Staples in 2007).

Katy is currently Managing Director of CoreAxis Consulting, a leading talent strategy and elearning and training firm based in Boston, Massachusetts. Katy is the author of Survive Your Promotion! The 90 Day Success Plan for New Managers, and her most recent book Free Agent: The Independent Professional's Roadmap to Self-Employment Success.

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