Leadership Insights 2026: What Real Leaders Are Learning (and Unlearning)
What started as a light-hearted Sidney Breakfast Club After Hours broadcast—complete with jokes about “32 billion viewers”—quickly turned into one of the most thoughtful leadership conversations we’ve had to date.
Building on the momentum of a record-breaking Breakfast Club session, this follow-up discussion brought together three local business leaders to explore a simple but powerful question:
What does leadership actually look like in 2026?
The answers were anything but simple—and that’s what made the conversation so compelling.
From Networking Club to Business Incubator
For those unfamiliar, the Sidney Breakfast Club has quietly evolved into something more than a weekly networking meetup. It’s becoming a Lower Vancouver Island / Peninsula business incubator—a place where leadership, strategy, and real business challenges are openly discussed.
This session focused on leadership not as a title, but as a lived experience—shaped by team size, industry, generational shifts, and a rapidly changing global environment.
Three Leaders, Three Perspectives
Leadership as Getting Out of the Way
Lacy Sheardown, GM of Meet Edgar, leads a small, fully remote team spread across the globe. Her definition of leadership was refreshingly simple:
“I’m the biggest cheerleader on the team. I give people the fuel they need—and then I get out of their way.”
That last part—getting out of the way—sparked immediate recognition. Too many leaders, as the group agreed, struggle to step back and let others do their best work.
From “Doing” to “Leading”
Trisha Sterloff, a career and leadership coach, picked up that thread by highlighting a common leadership trap:
High performers are often promoted because they’re great doers—but leadership requires a different skill set entirely.
“The challenge is helping people transition from being the fantastic doer to the person who creates space for others to shine.”
She also raised an important question that doesn’t get asked often enough:
Why do you want to be a leader?
The answer—title, money, or genuine desire to serve—shapes everything that follows.
Leadership Through Humility
For Jesse, leadership wasn’t a career goal—it was a survival skill. Burnout forced her to stop doing everything herself and start building a team.
Her leadership philosophy centers on humility:
“I love being wrong. Leadership is about admitting you don’t have all the answers and hiring people who are smarter than you.”
That openness, she argued, creates trust—and trust creates strong teams.
Command-and-Control vs. Collaborative Leadership
The conversation widened to a global scale. With political and economic uncertainty increasing worldwide, leadership styles are diverging:
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Command-and-control: fast, directive, top-down
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Collaborative leadership: adaptive, inclusive, relationship-driven
The consensus? Command-and-control has a place—but only in rare moments like crisis or emergency management.
Most organizations are living systems, not emergencies. They require curiosity, coaching, and clear non-negotiables—without crushing culture.
One Size Does Not Fit All
A recurring theme was individualization:
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Some people want public praise; others find it mortifying
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Some thrive in group brainstorming; others shut down
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Feedback, structure, and motivation differ wildly person to person
Great leaders learn these differences—and respect them.
As one participant noted, misunderstanding this early on can unintentionally alienate strong contributors.
Gender, Leadership, and a Necessary Conversation
The “elephant in the room” wasn’t avoided:
Are there meaningful differences in how men and women lead?
The answer was nuanced—and honest.
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Great leaders exist across genders
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Poor leaders exist across genders
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Emotional intelligence, vulnerability, and empathy are increasingly essential
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Leadership is less about gender and more about how masculine and feminine energies are used
There was also acknowledgment of past scarcity mindsets—especially among women competing for limited leadership roles—and how collaboration and mutual support are reshaping that dynamic.
The Future of Leadership: What Matters Most
As the session wrapped, each leader was asked to look ahead.
The themes converged clearly:
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You don’t need all the answers
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Admit mistakes early
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Let your team teach you
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Stay curious
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Build community
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Be transparently human
Perhaps the most powerful takeaway was this:
If you think you’re done learning—especially as a leader—you’re already behind.
Final Thought
Leadership in 2026 won’t be about certainty, control, or polish.
It will be about trust, humility, adaptability, and connection.
Conversations like this—open, imperfect, and honest—are exactly what communities and organizations need right now.
And if that’s the future of leadership?
We’re in better shape than we think.