3 CEOs, 4 Takeaways, 1 question - What do you wish you knew before you got the job?

What if true leadership development—guiding people to be great leaders inside organizations, on the field of play, and in the community—isn't about traditional training or passive networking alone? What if it's about recognizing the unseen gaps and creating something meaningful for those stuck between their first leadership roles and the executive suite? Great leaders don't wait for solutions—they create them, tailored specifically for those who need them most.

This vision sparked the Champions Summit, a fantastic event I was fortunate enough to help lead that took place in my home city of Calgary last week. Part of my current life phase of “do big things with people I like” found me collaborating with two of the city’s most powerful philanthropists, one of the city’s most prolific connectors and marketers, and the owner of the city’s best leadership development firm, Level 52.

Building Events That Matter: Start by Listening

The Champions Summit was intentionally created for an often-overlooked group: leaders moving toward senior executive roles, alongside top-tier athletes and musicians. Corporate leaders in this transition frequently experience a lonely gap, missing structured training and valuable networking. Similarly, athletes and musicians are typically excluded from traditional leadership development opportunities. We believed there was a better way.

To shape the Summit effectively, we started by closely listening through breakfast focus groups. Experienced CEOs openly shared their expectations and concerns for upcoming leaders, while rising leaders revealed their own anxieties, fears, and skill gaps. By bringing these perspectives together, we crafted an event designed specifically to support and empower this crucial group.

At the heart of the event were insightful panels featuring current and former CEOs. These leaders candidly discussed what they wish they'd known before stepping into their roles, providing relatable and powerful lessons for those aspiring to follow in their footsteps.

I had the privilege of moderating our opening panel, "What I Wish I Knew Before the C-Suite," featuring CEOs who collectively lead companies valued at over $10 billion: Brendan McCracken (Ovintiv), Iggy Domagalski (Wajax), and Dr. Radhika Dirks (Icons AI).

Our conversation dove deep into the vulnerabilities, misunderstandings, and constantly shifting expectations faced by leaders at the top of organizations—individuals who are often mistakenly perceived as having all the answers.

Here are four powerful insights from the discussion that stayed with me:

Navigating Contradictions

One important lesson these leaders wish they had known earlier is that great leadership doesn't mean having all the answers. They reflected on initially believing that becoming a CEO meant having complete control and clarity, only to discover it actually involves thoughtfully balancing multiple, often conflicting, priorities. Exceptional leaders learn how to understand and harmonize the diverse needs of stakeholders such as investors, boards, employees, and customers.

As always, I love to hear from the experience of others and then dive down the research rabbit hole to understand more about why these practices work!

So here’s what the research says - leaders who master paradox management—balancing seemingly contradictory demands—are better positioned to drive sustainable organizational success (Smith & Lewis, 2011). That’s a mouthful. 

Simply put: Leaders who can adjust their thinking and approach problems from multiple angles can turn contradictions into valuable opportunities for innovation and growth. We heard this in various ways from everyone on stage at the summit.

Risk and Confidence

Another powerful realization the panelists shared was that stepping into leadership often requires moving beyond analyzing data to trusting instincts. Initially, they underestimated how crucial confidence in one's judgment, especially in uncertain situations, would be. They learned through experience that relying solely on data could sometimes hinder decisive action.

Considering all three come from engineering and analytical backgrounds, their shared perspectives really hit home for everyone in the audience.

The research agrees. Psychologist Albert Bandura found that "self-efficacy"—or believing in your abilities—is key to performing well in tough situations. Leaders who trust themselves are more likely to take necessary risks that push their organizations forward. Building this kind of confidence involves gradually taking bigger risks and learning from each experience. Explore Bandura’s work here.

Scaling Influence Effectively

Panelists also wished they'd better understood how leadership fundamentally changes as an organization grows past about 150 people. Initially, many assumed leadership strategies that worked well with smaller teams would naturally scale up. However, they quickly discovered the need to shift from direct personal management to influencing through strong systems, clear communication, and shared values.

Anthropologist Robin Dunbar showed that humans naturally manage about 150 relationships effectively. Beyond this number, leaders must use clear communication, foster trust, and empower teams to maintain alignment and effectiveness throughout the organization.

Innovation Meets Practicality

Last and certainly not least, the panelists emphasized wishing they'd known earlier the critical balance between visionary thinking and practical actions. Initially captivated by big ideas, they learned through experience that sustainable success depends on grounding ambitious visions in practical, achievable steps. They emphasized that successful leaders don't just dream boldly—they rigorously prepare and execute methodically.

Clayton Christensen’s theory of disruptive innovation emphasizes the importance of balancing new ideas with practical implementation. Leaders who master this balance ensure their organizations can innovate boldly while staying stable and effective in daily operations.

What I really loved about the Champions Summit was that it was so much more than just an event—it was a call to action to reimagine leadership development. By facilitating authentic dialogue and embracing diverse perspectives, we enabled rising leaders to learn deeply, engage meaningfully, and inspire transformation. Ultimately, leadership is about serving and uplifting others. When we intentionally address overlooked needs, we do more than lead—we ignite meaningful change.

- Steve

steve.mesler

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steve.mesler

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