The Sterling Executive Peer Group

OUR PROGRAMS

Elevate Leadership, Transform Operations: Lead More, Manage Less

How Our Structured Meetings and Workshops Work

We organize regular meetings where members engage in group meetings, workshops or seminars. These sessions can cover various aspects of leadership, like decision-making, communication, strategic thinking, empathy, and team management. In these meetings group members will:

Executives and ceo meeting virtual and in person
Executives discussing and talking

Experiential Learning: High Retention and Deep Impact

Our goal is simple: improve leadership abilities. We take a unique and collaborative approach by tapping into the collective wisdom of our group members. 

Through experiential learning, we deepen understanding and ensure practical application of skills and knowledge. This method has a lasting impact, providing members with the insights and competencies necessary for effective leadership in today’s dynamic world.

Collaborative Problem-Solving

Article Discussions

Discussion and Dialogue

Action Learning Projects

Experience Sharing

Reflective Practices

Workshops and Seminars

Feedback and Peer Review

Peer Mentoring and Coaching

Networking Opportunities

Asian woman manager meeting talking

Sterling Membership: Ideal for a Diverse Range of Leaders

Sterling membership is designed to cater to a broad spectrum of leadership roles and stages, making it an ideal platform for individuals committed to growth and excellence. 

We cater specifically to people that are permanently employed within companies that do a minimum of $3 mil with 15 FT employees.

Our membership is particularly well-suited for:

The Membership - How it Works

THE MEMBERSHIP

  • Invitation only sponsorship
  • Current members sponsor new members
  • Groups will be limited to a productive size
  • Competitive businesses are never placed in the same group
  • One person from the same company permitted in each group

MONTHLY ENGAGEMENT

  • 12 one-on-one meetings per year
  • 12 half-day executive group sessions per year
  • 8 half-day virtual workshop sessions, featuring industry speakers

 

Our Programs

Every leader’s journey is unique. Our peer groups offer personalized development experiences tailored to your goals and challenges.

Sterling Emerging

Businesses doing from $3 to $9 million in annual revenues, and employing over 15 people.

Sterling Core

Businesses doing between $10 to $49 million in annual revenues.                  

Sterling Enterprise

Businesses doing more than $50 million in annual revenues.                                            

Sterling Emerging

Businesses doing from $3 to $9 million in annual revenues, and employing over 15 people.

Sterling Core

Businesses doing between $10 to $49 million in annual revenues.

Sterling Enterprise

Businesses doing more than $50 million in annual revenues.

Charter

Be Consistently Present and Focused:

Attend all meetings, stay for the entire session, and actively contribute. Notify the Chair in advance if unable to attend. Missing two or more meetings may result in membership termination.

Support Challenge and Adversity:

Provide support during personal or business challenges, not only at meetings but also one-on-one. Connect and lift each other’s success beyond the meeting room.

Keep Your Commitments:

Honor commitments to build trust. Keep your word, expect the same from others, and be accountable. Failure to honor commitments may lead to group accountability.

Be Yourself:

Bring creativity and uniqueness to meetings. Express personal views boldly without judgment. Build strong personal bonds with each member and have fun while learning and growing together

Own the Group:

Take responsibility for the success of the Sterling CEO Peer Group. Challenge and suggest improvements, present your own issues, actively assess others’ challenges, and engage in group activities.

Be Comfortable being Uncomfortable:

Embrace discomfort for faster growth. Allow members to ask tough questions and make non-judgmental suggestions. Be open, vulnerable, and receptive to critical feedback without defensiveness.

Celebrate Success:

Recognize and celebrate members’ achievements, reinforcing motivation and gratitude. Acknowledge the effort that leads to success.

Show Tough Love with Care:

Ask necessary questions, share ideas, and raise issues with humility and care. Push each other without being aggressive, recognizing the privilege of being invited into someone else’s innermost thoughts.

Be Transparent and Real:

Disclose challenges and struggles to enhance value. Discuss issues openly to facilitate mutual support. Share openly about your unique challenges to enable collective assistance.

Maintain Undoubted Confidentiality:

Uphold confidentiality to build and maintain trust within the group. Treat disclosed information as a privilege and refrain from sharing member details outside the group

Grow as Leaders:

Embrace a growth mindset by being curious, challenging each other, receiving feedback, trying new things, and continually improving. Cultivate emotional intelligence for high-performance leadership.

Stories from Sailors of Success in Sterling Waters

“You receive an external perspective on what’s going on. You have people who aren’t involved in the day-to-day operations of your business, and they can identify blind spots that you may have.”

WILLIAM GORTEMAKER – PRESIDENT

Premier Printing Ltd – Winnipeg

Benefits of Becoming a Member

ENHANCED LEADERSHIP SKILLS

Get exposed to various leadership concepts, strategies, and styles

ACCESS TO DIVERSE PERSPECTIVES

Interact with peers from different industries and backgrounds

PERSONAL GROWTH

Become more self-aware and emotionally intelligent

NETWORKING OPPORTUNITIES

Build professional relationships with other leaders

ACCESS TO RESOURCES AND EXPERTISE

Access exclusive materials and learn from industry experts

SUPPORT AND ENCOURAGEMENT

Discuss challenges and setbacks openly

REAL-WORLD PROBLEM SOLVING

Apply theoretical concepts to practical situations

MENTORSHIP AND COACHING

Get the opportunity to mentor other members

IMPROVED ORGANIZATIONAL IMPACT

Enhance team management and boost employee engagement

ACCOUNTABILITY

Be encouraged to progress in your leadership journey

Are you poised to take your career to new heights with the power of peer collaboration?

Become a part of Sterling Executive Peer Groups and open the door to unparalleled professional development and collaborative opportunities. Embark on your journey towards a remarkable success story today.

FAQ

Whether you’re considering joining our programs or have already embarked on this exciting journey, we understand that you may have questions. This FAQ page is designed to provide clarity and insights into the core aspects of our approach.

Peer groups are collaborative networks of professionals with similar job roles or industry backgrounds who share knowledge, experiences, and support. These groups offer a valuable platform for members to engage in shared learning, problem-solving, and networking. 

They foster an environment of trust and confidentiality, allowing for open and honest discussions of challenges and strategies. By bringing together diverse perspectives, peer groups provide a unique opportunity for personal and professional growth, idea generation, and mutual motivation. 

They are a resourceful tool for individuals seeking to enhance their skills and expand their professional connections.

A Sterling peer group operates on a dual approach that combines the collaborative dynamic of group meetings with the tailored focus of one-on-one executive sessions. Here’s how each component works:

1. Regular Sessions: The group typically meets two half-days each month, allowing members to discuss various topics relevant to their roles and industries.

2. Structured Yet Flexible Agenda: Meetings are structured to cover specific themes or issues but remain flexible enough to address the emerging needs of group members.

3. Collaborative Learning: Members share experiences, challenges, successes, and strategies, fostering a rich learning environment. This collaboration encourages peer-to-peer mentoring and diverse perspectives.

4. Facilitated Discussions: A Chair, who will have extensive careers of executive success, guides the discussions to ensure they are productive, focused, and valuable for all members.  The Chair will also take the group through a guided discussion in one of the Leadership Development Discussion Series booklets.

5. Confidential Environment: The group operates under strict confidentiality rules, creating a safe space for open and honest dialogue.

1. Personalized Attention: These sessions provide individual attention to address the members’ specific challenges or development goals.

2. Coaching and Mentoring: The Chair can provide mentorship and observations tailored to their unique situation.  Where it might help, the Chair will also work with each member to package their issue or opportunity, so the group can review it at a future meeting.

3. Actionable Strategies: The focus is on developing actionable strategies that the member can implement.

4. Accountability: These meetings also serve as a check-in point for members to review their progress on goals set during peer group meetings or previous one-on-ones.

5. Flexible Scheduling: These sessions are scheduled at the convenience of the executive to ensure they fit into their busy schedules.

In summary, the Sterling peer group model effectively combines the collective wisdom of group interaction with the personalized focus of one-on-one meetings, providing a comprehensive approach to leadership development.

Joining a Sterling peer group offers several significant benefits for executives and leaders designed to enhance their professional and personal growth:

1. Diverse Perspectives: Members gain insights from various industries and backgrounds, broadening their understanding and approach to business challenges.

2. Collaborative Problem Solving: The group setting allows members to collectively brainstorm and tackle complex issues, often leading to more innovative and effective solutions.

3. Enhanced Decision-Making Skills: Exposure to different viewpoints and experiences helps refine members’ decision-making abilities, making them more effective leaders.

4. Accountability and Support: The group provides a supportive environment where members hold each other accountable for achieving their goals, which can significantly impact their success.

5. Networking Opportunities: Members build valuable professional relationships that can lead to new business opportunities, partnerships, and collaborations.

6. Leadership Skill Development: Regular interactions and discussions focus on enhancing leadership skills, which are crucial for career advancement and organizational growth.

7. Confidentiality and Trust: A safe and confidential space allows members to openly share and discuss sensitive issues without fear of external judgment or repercussions.

8. Personalized Coaching and Feedback: The one-on-one sessions offer tailored review and direct feedback, helping members address specific personal and professional growth areas.

9. Professional and Personal Growth: Members are exposed to growth opportunities that enhance their professional capabilities and contribute to their personal development.

10. Staying Current: Regular meetings and discussions on current trends and best practices keep members updated with the latest in leadership and management.

Overall, a Sterling peer group provides a unique combination of communal wisdom, personal development, networking, and skill enhancement, which are invaluable for today’s leaders.

Sterling carefully places members into specific peer groups by evaluating several vital factors. This includes assessing industry and professional background, leadership level, and experience to ensure compatibility with peers of similar stature. The size and complexity of members’ organizations and their personal and professional development goals are also considered.

Additionally, the existing group dynamics, member preferences, geographical location, competitive conflict, and the need for a diverse range of skills and experiences within the group play a crucial role in this decision-making process. This thoughtful approach ensures that each member is placed in a group that best supports their growth and aligns with their objectives.

Sterling Chairs are selected based on their extensive leadership experience and proven business acumen, typically having served as CEOs, business owners, or top executives. They have a strong track record in managing and growing successful businesses and have expertise in strategy, operations, finances, and team building.

In addition to their business credentials, these chairs are skilled in coaching and mentoring and equipped with excellent communication skills to facilitate group discussions and encourage open dialogue effectively. Many hold degrees in business or related fields, along with certifications in leadership, reflecting their commitment to continuous professional development.

Integral to their role is a vast professional network and a wealth of resources, which they leverage to benefit group members. Above all, Sterling chairs uphold high ethical standards and integrity, essential in maintaining the confidentiality and trust that is the foundation of the peer group experience. This blend of experience, skill, and ethical commitment ensures that Sterling chairs can guide executives through complex challenges and foster personal and professional growth.

In Sterling peer groups, the main focus areas for developing leadership capacity and competence include:

  • Strategic Planning and Execution: Formulating and implementing business strategies.
  • Leadership Development: Enhancing personal leadership skills and team management.
  • Financial Management: Making informed decisions on budgeting and investments.
  • Marketing and Sales: Developing effective growth and customer acquisition strategies.
  • Human Resources: Talent management and fostering a positive organizational culture.
  • Technology Integration: Leveraging technology in business processes.
  • Risk Management and Compliance: Understanding and mitigating business risks.
  • Work-Life Balance: Managing professional demands with personal well-being.
  • Networking: Building and utilizing professional relationships for success.

These points collectively contribute to the overall goal of elevating leadership abilities within the Sterling peer group environment.

Sterling memberships are crafted with a strong emphasis on the power of ‘Intellectual Diversity.’ While memberships are not confined to specific industries, this approach is intentional and strategic. By bringing together executives from various sectors, Sterling harnesses the strengths of diverse thought, experiences, and perspectives. This intellectual diversity is fundamental to the group’s philosophy, as it enriches discussions, broadens viewpoints, and fosters innovative problem-solving. 

Members are exposed to a variety of business models, strategies, and challenges, encouraging them to think outside their industry silos. Sterling believes this cross-pollination of ideas is crucial for developing well-rounded, adaptable leaders who navigate various business environments and challenges. While ensuring relevance to members’ professional development needs, the focus remains steadfast on the unique benefits only intellectual diversity can provide.

Sterling maintains strict confidentiality through rigorous practices and a strong culture of trust. Members must sign a confidentiality agreement in the membership application form, binding them to discretion. Clear guidelines on confidentiality are outlined in the group’s charter and regularly reinforced, ensuring members understand the importance of keeping shared information private. 

The selection process for new members includes evaluating their commitment to ethical standards, including respect for confidentiality. Group chairs monitor discussions to maintain these standards, and secure communication channels are used for all group interactions. This comprehensive approach ensures a safe environment where members can openly share sensitive information, confident that their privacy is protected.

Sterling builds groups around the concept of virtual meetings for several vital reasons, even though some members may prefer in-person interactions:

1. Broader Access to Diverse Perspectives: Virtual meetings allow for the inclusion of members from a wide geographic range, bringing together diverse insights and experiences that might not be possible in a strictly local or in-person setting.

2. Flexibility and Convenience: Virtual meetings offer greater flexibility, making it easier for busy members to participate without traveling, saving time and resources.

3. Increased Frequency and Consistency: The convenience of virtual meetings can lead to more frequent and regular interactions, ensuring consistent support and engagement within the group.

4. Leveraging Technology for Enhanced Interaction: Modern communication tools used in virtual meetings can enhance the experience through features like screen sharing, document collaboration, and breakout rooms for smaller discussions.

5. Safety and Accessibility: Particularly in times of health crises or travel limitations, virtual meetings provide a safe and accessible option for members to continue their collaboration and learning without interruption.

6. Eco-Friendly Option: Virtual meetings reduce the carbon footprint associated with travel to in-person meetings, aligning with sustainability goals.

Sterling recognizes the value of in-person interaction and will incorporate face-to-face meetings or events when feasible. However, virtual meetings are primarily aimed at maximizing participation, having a national diversity of membership, and convenience for all members.

Yes, membership in the Sterling Executive Group involves a cost that supports its lean, virtual operational model, devoid of traditional bricks-and-mortar expenses. This fee structure covers various aspects essential to the group’s functioning and value offerings. Here’s what the costs typically include:

1. Facilitation and Expert Guidance: Membership fees help compensate the chairs who bring expert leadership and guide the group’s discussions.

2. Resource Materials: Members gain access to exclusive content, including research materials and educational resources, along with the Leadership Development Discussion Series booklets.

3. Meeting and Technology Costs: Since Sterling operates without physical locations, fees are used to maintain high-quality technology platforms for virtual meetings and communications.

4. Events and Workshops: The cost also covers special events, guest speakers, workshops, and seminars organized for the members.

5. Personalized Mentoring: Personalized mentoring by the Chair is part of the membership benefits.

6. Lean Administrative Expenses: Reflecting Sterling’s operating philosophy, the fees contribute to the essential administrative support needed for the smooth running of the group without incurring traditional office space costs.

This fee structure reflects Sterling’s commitment to providing high-value experiences and resources while maintaining a lean and efficient operational approach, ensuring members benefit most from their investment.

Joining the Sterling group involves a comprehensive process that ensures each new member is a good fit for the group’s dynamic and objectives:

1. Initial Inquiry: Your journey begins with contacting Sterling through their website, email, or phone to express interest and request detailed membership information.

2. Interview or Assessment: Next, you’ll have an exploratory discussion with a Sterling representative, typically our CRO, and then with Wayne Cole our Executive Chair, to determine fit with the program. These conversations focus on mutual expectations, commitment to the group’s values, and willingness to contribute to a collaborative environment.

3. Review Process and Engagement: After your interview, you’ll enter the review process, which includes opportunities to engage more deeply with the group. This involves attending a meet-and-greet with current members, the Chair of the group you’re the best fit for, and participating in a speaker workshop, giving you a firsthand experience of the group’s dynamics.

 4. Securing a Sponsor: During this process you will also be introduced to a specific member that shares similarities with your industry/background, who will evaluate your fit with the program, and allow you to ask questions. This existing member must be willing to endorse your invitation to join, signifying their support and belief in your potential contribution to the group.

5. Approval: If you have not secured approval within your organization to participate, this step must be completed.

5. Membership Invitation: If the review process goes well, you will receive an invitation to join the Sterling group. This invitation will finalize details about membership fees, meeting schedules, and other relevant information.

 6. Application Form: After completing the review process, including endorsement from a current member, you may be formally invited to join. Then you’ll complete the formal application form, binding your confidentiality and commitment to the group.

 7. Acceptance and Onboarding: Finally, you’ll go through the onboarding process upon accepting the invitation, you’ll schedule your one-to-one’s with the Chair, who will lead you through an orientation session to familiarize you with the group’s norms, processes, and existing members.

 This structured approach, including the critical step of securing a sponsor, ensures a thorough vetting and integration process, fostering a strong, cohesive, and mutually beneficial environment within the Sterling group.