For more than 40 years, executive peer groups have offered what many CEOs quietly crave: a confidential setting, a trusted cohort, and the opportunity to pressure-test decisions with individuals who understand the weight of the role. The concept has endured. The operating model behind it, which is local, in-person, and travel-dependent, remains expensive and time-consuming, even as the business environment has shifted toward distributed teams, faster decision-making cycles, and increased organizational complexity.
Wayne Cole, CEO of The Sterling Executive Group Inc., argues that the moment calls for a practical upgrade that modernizes experiential peer learning without losing what made it valuable in the first place: candour, trust and disciplined challenge. The breadth of experience shapes Cole’s view after three start-ups, years in mergers and acquisitions, deep financial management and business reporting work, and 25 years with large multinational corporations. Across those settings, he says, one pattern kept repeating: the leaders who win don’t simply have better plans; they build better leadership systems.
“The peer group concept works,” Cole says. “But the operating model needed an upgrade. And the real constraint most executives run into isn’t a lack of strategy, it’s the leadership team’s ability to execute it.”
Why leadership development matters more than ever
In today’s environment, CEOs are expected to deliver performance while also shaping culture, retaining talent, managing change and building resilience. Teams are more distributed. Feedback comes faster. Tolerance for ambiguity is lower. A leader’s influence is more visible and more frequently tested.
That reality changes what “leadership development” must mean. It cannot be occasional inspiration, a once-a-year retreat, a training program, or a keynote-driven event. It must be repeatable tradecraft: practical skills that consistently demonstrate themselves in decision quality, team alignment, operating cadence, accountability, delegation, and conflict resolution - week after week, under pressure.
Cole’s organizing belief is simple: clarity creates momentum. But clarity does not happen by accident. “Most executives don’t need more ideas,” he says.“ They need a sharper thinking environment and accountability that turns complexity into decisions and decisions into action.”
Sterling’s design: pan-Canadian peers, built for applied growth
Sterling positions itself as a pan-Canadian, virtual-first executive peer model designed to replace geography-bound “local clubs” with carefully curated cohorts focused on experiential learning and actionable takeaways. The point is not convenience. The fact is that reach and diversity through leaders with comparable responsibilities, but different markets, industries, and realities, are all in the virtual room at the same time.
That intellectual diversity matters because leadership blind spots are often invisible from inside a single local context. “Local groups can become echo chambers,” Cole says. “When peers aren’t embedded in your market, they’re more likely to ask the questions you’ve stopped asking.”
It also addresses a practical Canadian constraint: many municipalities lack sufficient C-level leaders to form high-quality cohorts—especially common-interest groups, such as CFO-only or COO-only tables. Virtual, pan-Canadian groups remove those barriers, enabling membership to be curated around role, complexity and learning objectives rather than postal code.
Not another video call: cognitive design that protects executive attention
If there is one phrase executives have grown tired of, it’s “another Zoom call.” Sterling’s response is to treat virtual sessions as performance environments, not calendar placeholders. Meetings are designed to manage cognitive load and protect attention, featuring structured segments, purposeful breaks, alternating modes (listening, dialogue, reflection, and decision capture), and a disciplined close that produces tangible outputs.
The goal is explicit: reduce fatigue, increase retention and make “takeaways” a design outcome rather than an accident.
The real differentiator: a leadership-team operating system
Where Sterling leans most heavily with C-level leaders is leadership team development. Many executives can articulate a strategic plan. Few have engineered the leadership team system needed to execute it with consistent accountability.
Cole describes common patterns he sees at the top:
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Activity masquerading as progress: “busy” leadership teams that aren’t moving the enterprise past its actual constraints.
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Under-built team systems: unclear decision rights, weak operating rhythm and inconsistent performance accountability.
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Delayed hard conversations: role clarity, misalignment, succession and performance issues pushed down the road.
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Local-market tunnel vision: assumptions shaped by one geography and one competitive reality.
Sterling’s methodology is designed to surface these issues quickly and convert insight into action through a repeatable loop:
1. Cohort session: a member brings a live issue; peers pressure-test assumptions and options; the chair keeps it decision-centric.
2. Commitments captured: the member leaves with follow up specific actions.
3. Chair 1:1 coaching: the member and chair translate peer insight into a concrete leadership plan—often focused on the leadership team system: decision rights, role clarity, cadence, accountability, bench strength and succession priorities.
4. Leadership team moves: the member applies changes inside the business.
5. Report back and refine: progress is reviewed; learning compounds.
A typical scenario, Cole says, is the CEO whose growth plan looks sound on paper, but execution keeps stalling. “Often the constraint isn’t strategy,” he explains. “It’s leadership team capacity, role clarity and decision rights.” In practice, peer discussion identifies the root cause, while the chair’s one-on-one conversation converts it into team actions that restore momentum: clarified ownership, a tighter operating rhythm, and stronger accountability.
Trust by design: curation, sponsorship and chair discipline
Sterling is deliberate about culture. The cohorts are curated and non-competing, with confidentiality standards that protect candour. That matters, Cole notes, because leaders won’t talk honestly if they believe the information will travel.
Accountability is operationalized through structure: commitments are made, captured and revisited. Chairs are trained to prevent sessions from becoming just “good talk,” and to keep discussions anchored to decisions and follow-through.
Membership sponsorship adds another layer: cohorts help shape the growth and culture of their cohort over time, protecting fit and reinforcing shared ownership of the learning environment.
Curriculum without the conference model
Sterling also begins each year with a slate of 12 to 15 virtual speaker workshops available to all members. They are intentionally not large, travel-based conferences. They are limited-participation, interactive workshops designed for application. Members ask context-specific questions, work through scenarios, and bring insights back into their cohort commitments.
Technology supports delivery, while structured assessment tools such as Sterling’s LEADSET© (www.https://sterlingexecutive.org/leadership-self-evaluation-tool/) help members clarify their development priorities and make one-on-one coaching more precise. But the emphasis remains human and applied: tools support clarity; chairs and cohorts drive execution.
Who this is for
Sterling’s proposition will resonate most with CEOs and C-level executives who feel a familiar tension: strategy is clear, but execution and accountability is uneven; the organization’s next phase depends on the leadership team system; and the leader wants a confidential, high-rigour environment to sharpen decisions and build capability over time.
Inquiries about Sterling membership typically begin with a simple question: Is this the right peer cohort for my level of complexity and my leadership agenda? For many executives - especially those outside major centre - the answer can be transformational: the right peers, the proper structure, and a leadership development loop that strengthens not just the individual leader, but the leadership team that ultimately determines performance results.
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