Virtual Leadership: Real or Oxymoron?

Clark Waterfall
5 min readApr 19, 2020


Can you tackle the challenge of leading without all your senses?

So think about this… You & your team are given a task: Go through a door in front of you that leads into a room on the other side, navigate a maze that’s laid out inside, and find the door on the other end of the room. It’s like one of those “escape room” games we’ve all either heard about or in which we’ve participated at a corporate team building event, or child’s birthday party, or college reunion event. In fact, a fellow entrepreneur and friend of mine Nicole Chan started and runs one of these physical brainteasers in Boston called Trapology (

But wait — let’s say that instead, you can’t actually be in the room with your team. You have to remain outside. And they all have to report in to you the challenges and problems they see and find. You can’t see it with your own eyes. Or test it yourself with your own hands. Oh, and while that sounds challenging, we’re going to turn the lights off in the room in which your team is working. Oh, and none of them can help each other inside the room… oh, and there’s a clock ticking. If it runs out before you get your team safely out the other side of the maze and through that 2nd door, you lose. Oh, and if you lose, your company disappears. Poof. No second chances. No do-overs. You’re forced to move all your poker chips to one color and one number and spin the roulette wheel.

If this sounds eerily familiar to the challenges of leading a company in today’s business context of “blink-and-new-rules-appear”, no surprise. Where one sense after another is taken away — you can’t meet with your employees in person one-on-one or as a team, you can’t meet with your clients in person, you can’t meet with your advisors in person. They can’t meet with each other either. Oh, and the “maze” that’s being navigated is actually the business landscape — an ever-shifting topography that seems to morph every night from when you went to bed to when you wake up the next morning. Each day a different “next normal. ” Week after week. And if you screw it up as a leader?

For larger businesses, perhaps a bad quarter. Maybe a bad year. You might be deemed “too big to fail” and get propped up by government bailouts or an equity investment. But for small and medium-sized business? Most of these businesses are one quarter away from extinction. Some that were more fragile as the Corona virus hit wouldn’t likely be able to last even a quarter, having only a month or perhaps a mere few weeks — either because they were younger businesses in their infancy or adolescence, or because they’d made a big bet from which they couldn’t reverse, or they just happened to be “wrong place, wrong time” and were in an industry that got completely shut down (hospitality, restaurants, entertainment, travel).

So, why all the melodrama? Because we’ve just taken what is already incredibly hard to do well — Leadership — and made it exponentially harder. In the 21st century, we’d begun to grapple increasingly effectively with “virtual management.” We had tools like video conferencing, email, chat, Slack, Asana etc. These were most often referred to as “collaboration tools,” great for smaller team project management. But if you Google “virtual leadership tools” there’s a deafening silence. You get things that point you back to management, like “9 awesome tools for managing virtual teams.” Why? Because most leadership has been done face-to-face, from annual sales kick-off meetings, customer user group conferences, annual company off-sites, symposiums, senior leadership team gatherings, and “retreats.” These were the picks and shovels of leadership. There was even a room for businesses that had a name — the boardroom. That’s where the leadership magic happened. That was the “heart” from which leadership arteries emanated, where strategies were formulated, and visions were born, bred and burnished.

So, if you strip the ability to physically gather — boardroom, dorm room, war room or other — can we lead effectively? Or are we relegated to “management only,” trying to tape-and-band-aid our companies together until and if we can all gather again to truly move the needle?

While some might argue differently, the tip of the leadership spear is culture. We can throw in values and mission and vision, but what’s the gasoline fueling all of this? Culture. Can we actually manifest a virtual culture? Can we identify “who” we are, and how we behave in our virtual work environment when others aren’t looking, including bosses, peers & subordinates?

10 steps to finding and fostering a vibrant company culture in the next normal of a virtual company structure:

· Test what you’ve got: First principles for fostering culture is determining what culture you currently have. And taking for granted that your culture in a virtual workplace is the same as it was in a predominantly physical workplace is probably a risky gambit.

· Determine if & what you need to “start, stop, or continue.”

· If your culture is healthy, don’t assume you can focus on other priorities. The cliché of “if you’re not moving forward, you’re moving backward” applies here.

· Establish trust. Trust is the cornerstone of a healthy culture. Coaching teams around trust, especially with new team members/new hires, is critical.

· MORE communication is required than was in the physical cultural norms pre-2020.

· More expression of caring is critical. If a company doesn’t have caring as one of its cultural ingredients, it is likely very short-lived. And caring isn’t just a written value, it’s a “kinesthetic action.” There’s no “do as I say, not as I do” on this one.

· More transparency is essential. Team members when now stranded on their own physical island, can quickly feel isolated and alienated. And when there isn’t trust, transparency, and communication, effective leadership is neutered.

· Self-reliance is critical. Working virtually, and generating or accepting virtual leadership is predicated on employees having a strong sense of self-reliance. This can be tested for, and coached up.

· Reward cultural table stakes. Create a reward system that is visible to all, that reinforces each key plank in your cultural platform.

· Enforce consequences of cultural transgressions. As the saying goes, “if action & elimination of a given behavior isn’t taken at each cultural transgression, then you’ve established a new culture.”



Clark Waterfall

Co-founder and Managing Director of BSG, a boutique retained executive search firm focused on privately-held, investor-backed clients both PE and VC-backed.