Lindsay Groves, Lookout Newspaper.

  • Outgoing Base Commander Capt(N) Kevin Whiteside reflects on three years leading CFB Esquimalt and the leadership lessons that shaped his career.
  • He shares insights on courage, character, morale, culture, and why investing in people remains his greatest priority.
  • As he departs, Capt(N) Whiteside leaves the Defence Team with a message of gratitude, optimism, and confidence in the future.

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Before Canadian Forces Base (CFB) Esquimalt bid fair winds and following seas to Captain(N) (Capt(N)) Kevin Whiteside on July 21, we sat down with Capt(N) Whiteside in the run up to his Change of Command ceremony.

Earlier this year, the Lookout launched a series exploring leadership through themes of courage, character, and morale. Though these concepts define so much of military service, definitions and details can often change from leader to leader. We’re interested in understanding these definitions and details. As such, it seems fitting that our conversation continued with the outgoing Base Commander, whose three years leading CFB Esquimalt have been defined as much by people as by projects and missions.

The Canadian Armed Forces (CAF) are experiencing a level of investment not seen since the Second World War. New ships, submarines, housing, training facilities, infrastructure, and equipment are defining the future of the institution. Yet, as Capt(N) Whiteside reminds us, investment alone does not solve every challenge. It creates opportunity — and opportunity requires leadership.

“It sounds cliché: it’s a great time to be in the Navy and the CAF,” he said. “If there is something frustrating for a member of the team right now, they need to talk to somebody about it. Three years ago, I couldn’t use the word ‘guarantee,’ but now I can almost guarantee whatever is frustrating is being talked about and a plan is being developed to improve it. I wish I was getting in now.”

For Capt(N) Whiteside, leadership has never been about waiting for the perfect conditions. It is about having the courage to move forward despite uncertainty.

“Courage is what we need to harness and dig deep sometimes to pull forward when we are in situations of adversity and in unknown situations,” he said. “You have to be courageous to face the unknowns.”

That mindset was formed long before command appointments or executive positions. He traces his leadership style back to his childhood.

“My leadership style was informed by my childhood – the way I was raised, the environment I was raised in,” he said. “I’m the same Kevin now as I was on the ice rink as a hockey player, as I was as a football player, and in groups of friends growing up in Scarborough [Ontario]. If you grow up paying attention to what’s going on around you, you will learn the key tenets of leadership naturally.” He added that his leadership continues to be refined by the influences of the team and his mentors, including current MARPAC leadership.

Having joined the CAF at 18 years old, he has now spent most of his adult life in uniform. Some of his most influential lessons came aboard his first warship, where the two Operations Officers responsible for mentoring him were both women serving in what was then a predominantly male environment.

“They were incredible humans and incredible leaders,” he shared. “They led with absolute confidence in everything we did. We crushed every mission set that we were faced with.”

When both leaders later left the CAF, Capt(N) Whiteside questioned his own future.

“It made me question whether or not I should stay. If the best leaders I had seen so far in the CAF decided to leave, then I wondered what was wrong that I wasn’t seeing.”

Over time, he came to better understand potential reasons why they had left.

“Through some of the studies that you’ve seen over the past couple decades, it became more clear to me why they may have left, which helped me focus on culture. Both of them leaving the CAF was my drive. Seeing the CAF and Department of National Defence (DND) put more emphasis on culture evolution, I was proud of this institution. That drove me to stay and continue pushing in the right direction.”

That commitment to culture has remained central throughout his career thus far. When asked what advice had stayed with him the longest, his answer was straightforward: “I was told to know your job, know your people, and everything else will work out.”

Simple advice, perhaps, but one he believes many organizations could benefit from embracing.

Outgoing Base Commander Capt(N) Kevin Whiteside converses with a guest during the July 21 Change of Command ceremony. Photo: MCpl William Gosse, MARPAC Imaging

“A lot of people think constantly about what’s next for them and they’re not in the moment. If you’re getting to know the people around you and understanding your purpose every day while contributing to the team effort, then it’s true: everything will work out.”

One of Capt(N) Whiteside’s many meaningful responsibilities as Base Commander has been managing Indigenous Relations on behalf of MARPAC.

“You read about it, you hear about it, you understand the Government of Canada has a priority for reconciliation. You want to be a part of it, but you don’t really understand how.”

Rather than arriving with all the answers, he thought carefully about his approach. “I decided I was going to be the best human that I could be and see how that worked out.”

Throughout our conversation, one idea surfaced often: leadership begins with what you bring to others every day.

“Character, in my words, is what you present every day,” he said. “How do I define my character? My character is defined by my team and those around me.”

One saying has followed him through multiple command appointments: “Never pass a water fountain without taking a sip.” He adapted the saying into his leadership philosophy. “Never pass someone without smiling, looking them in the eye to see how they are doing, or giving them a high five.”

Those seemingly small moments, he believes, are directly connected to morale. “I switched about 10 years ago to say happiness is a key component of morale.”

Happiness, however, cannot be assigned by leadership.

“It’s not a leader’s responsibility to make you happy. You, as a member of the team, have to understand what makes you happy and try to build that into your every day.”

He continues to say that the strongest teams are inspired not from the top down, but by one another.

“I think the greatest teams are the teams that are inspired. Elements of happiness, inspiration and focus on mission – those are the three elements I think are most important. When you have those, you will have that thing called morale.”

He also spoke warmly of Chief Petty Officer 1st Class (CPO1) Sue Frisby, the Base Chief, and Danielle Smith, the Base Chief of Staff, as well as labour leadership, branch leadership, and the Defence Team writ large.

“[We] have faced a lot together over the last few years. There was not one challenge that we did not know we could figure out because of the incredible team we have here. The Defence Team has never failed us.”

Capt(Navy) Kevin Whiteside, CFB Esquimalt Base Commander (left) and Jackie Carlé, EMFRC Executive Director during the May 22 community barbeque. Photo: Geoff Howe

As our interview ended, Capt(N) Whiteside smiled before saying: “You didn’t ask me about my regrets.”

His answer came quickly.

“It was a tough decision to take the Lookout out of print. I wish I could have progressed security improvements in a more timely fashion. I wish I could have brought more housing and accommodations up to current standards in a more timely fashion, but it’s coming! I wish I could have had more time to interact with the Defence Team.”

Then, before departing for his next appointment, he offered this message to the Defence Team.

“First, I want to say thank you. I would love to sit down with every member of the Defence Team because I would learn a lot more from them than they ever would from me.”

He added, “Keep going. Canada needs us and they need more of us.”

Capt(N) Kevin Whiteside’s legacy at CFB Esquimalt will not be measured solely by infrastructure projects or operational milestones. It will be found in the people he invested in, the culture he helped shape, and the reminder that leadership often begins with something as simple as a high five and the courage to step forward into the unknowns rather than away.

Thank you, Capt(N) Whiteside. Onwards into the awesome future.

Fair winds and following seas.