IT leaders share learnings on challenges of leading virtual teams

How do you manage a team of people when you never see them? Learning how to run a remote workforce was a major challenge last year, say IT executives from across Canada.

While video conferencing no longer offers the same kind of personal leadership as in the past, participants are finding value in new platforms and new leadership and collaboration strategies.

At a recent virtual Canadian CIO luncheon, IT executives shared stories, articles, and resources they thought were valuable to developing the kind of leadership that an increasingly virtual workforce needs.

Jim Love, IT World Canada CIO, outlined the challenges of maintaining a human-centred workplace in a work-from-home WFH world. “Things have to work,” he said. “How do we promote collaboration and innovation while keeping everyone on track?”

Advice on leadership and organization

Love pointed out that one of the keys to the new style of leadership we need is to be found in the YouTube video Why we are wrong when we think we are right. Today, the “command and control structure” we grew up with in IT simply won’t work. “We need a cooperative style, but we still need to be able to act decisively.” Building on Love’s theme another participant spoke of the difficulty of making decisions in the videoconferencing pipeline. “How do we reach consensus and hear as many voices as possible,” he asked. “How can we address some of the prejudices that come to the table?”

The vice president of a software development company encouraged the group to listen to one of the podcasts produced by Brene Brown, a research professor at the University of Houston, where she holds the Huffington Foundation’s endowed chair. Brown, author of five New York Times best-sellers, including a comprehensive study of the future of leadership, says the bottom line is that one has to go through vulnerability to take heart. Leaders, Brown says, need to embrace their imperfections to cope in these disruptive times.

A new approach to large-scale projects is needed, said a VP of a portfolio management firm. Even before agile and implemented DevOps are discussed, the focus should be on leadership. “The first thing we did was to break through the pyramids of command and control and take on what we call holacracy,” he described as a method of decentralized management.

The director of Enterprise Services at a leading charity suggested that the group watch a video about service leadership, a style of leadership that sees service as the primary responsibility of leaders and focuses on improving both people and organizations.

Failure is an option

Paradoxically, said one technology CIO, we often hear the phrase “failure is not an option.” “Well, it should be,” he said. “Then we would be able to improve and move forward. In my company, we often say fail often, fail fast, fail cheaply.”

“The key to failing fast is applying agile to the process,” the transport manager added. “Don’t spend six months working on all the outcomes. Make iterative changes as you go, and when things are good, you can move on. In today’s world, even non-IT organizations need to do this to keep up with the Amazons.”

What makes great leaders

Participants were asked how they balance the dynamic tension between short-termism (agile, fail fast, sooner results) and the long-term commitment needed for transformation. For a health-care chief technology and innovation officer, it’s about shedding traditional hierarchies and figuring out how to connect and empower people. “The mindset of leadership growth is more about influencing change than demanding it,” she said.

Jim Love recalled people saying they could do their job more effectively if they only had more authority. “I learned a long time ago that all the authority in the world does not make people follow you,” he said. “Great leaders emerge almost everywhere, not because they have authority, but because they have the ability to make people listen to them.”

Learn to recognize the employees who are struggling

After a brief discussion about how important it is to be able to inspire, the Chief Knowledge Officer CKO of a marketing solutions group pointed to an article about a lawyer who had a breakdown after a year at the helm of WFH. “When people aren’t coming into the office each day, it’s much harder to see that they are struggling,” said the CKO. “High performers might not recognize they need help and even if they do, they might hesitate to ask for it. We need to be alert for signals during digital meetings. Listen and watch for clues.”

Some participants, including the chief technology officer of a large chain of theme parks, expressed their agreement. He stressed the importance of staying at the level of emotional intelligence before the pandemic and of paying attention to signals that cause difficulties for team members. Referring to a major Fast Company article on improving emotional intelligence, he said, “Forms of communication are different today, so we have to pay attention to them differently.”

Resources shared by the group:


Mindfulness at Work – 5 Ways to Improve this Key Component of Emotional Intelligence

Agile Compendium

Growth Mindset

How to Better Support a High Performing Workforce and Yourself During the Pandemic

How to Lead When Your Team is Exhausted and You Are Too

The Johari Window Model

You May Be Tired Of ‘Agile,’ But It’s The Only Way To Make Hybrid Work

Videos and Webinars

Building a High Performance Culture in a Digital World

Power of Vulnerability by Dr. Brené Brown

Servant Leadership


Leading Without Authority by Keith Ferrazzi and Noel Weyrich

Sense and Respond: How Successful Organizations Listen to Customers and Create New Products Continuously by Jeff Gothelf and Josh Seiden

Think Again: The Power of Knowing What You Don’t Know by Adam Grant

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Jim Love, Chief Content Officer, IT World Canada

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Suzanne Robicheau
Suzanne Robicheau
Suzanne Robicheau is a communications specialist based in Wolfville, Nova Scotia, where working remotely continues to fuel her passion for new mobile technologies -- especially on snowy days.

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