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Best Boss Ever Leadership™ Program
Elevate the Leaders Who Shape Your Dream Team
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LEARN MOREOverview of the Program
The best leaders don’t just manage; they inspire, support, and create an environment where people actually want to work.
The Best Boss Ever Leadership™ Program is designed to help managers and executives develop the self-awareness to recognize their blind spots, the communication skills to lead with confidence, and the leadership strategies to build trust and collaboration.
This isn’t about outdated management techniques or corporate buzzwords—it’s about real, practical leadership growth that helps you become the boss your team remembers for all the right reasons.
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What Type of Leader are You?
If you lead people, this program is for you. Whether you're new to leadership or a seasoned executive, becoming the Best Boss Ever isn’t about your title—it’s about your impact. This program is designed for leaders who want to develop self-awareness, build trust, and lead with confidence.
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Executive
HR Leader
Director
Team Lead
New Manager
Founder
This Isn't Your Typical Leadership Training
Bad bosses create disengaged teams. Good bosses keep the machine running. Great bosses make people feel like they matter.Â
But let’s be honest —many leadership training feels like a corporate history lesson: outdated theories, little real-world application, one-size-fits-all approaches, and no real impact. That’s not this.
The Best Boss Ever Leadership™ program is a leadership experience that’s as practical as it is fun—something leaders actually look forward to being a part of. It’s designed to help them grow as a leader, strengthen their team’s collaboration, and shape a workplace where people want to stay and succeed.
Because when leaders lead well, their impact lasts far beyond the job—it shapes careers, teams, and company culture for years to come.
When leaders lead with purpose, teams follow with passion.
Let’s build leaders worth following.
Great Leaders Can Have Blind Spots Too
Common challenges companies face - even in senior leadership
The Alternative to Boring, One-Size-Fits-All Training
Five Key Components of Becoming The Best Boss Ever
 When people reflect on the leaders who made the biggest impact on them, they often say, “They were the best boss ever.”
Great bosses aren’t just remembered for what they did—they’re remembered for how they made their teams feel. The Best Boss Ever Leadership™ Program is designed to help your managers become the kind of leader that people talk about for all the right reasons—trusted, inspiring, and truly impactful.
Through this highly interactive, data-driven experience, your leaders will develop deeper self-awareness, refine their leadership approach, and build meaningful connections through five components:
- Personalized Leadership Coaching → 1:1 coaching focused on Enneagram-driven leadership growth.
- Team Interviews & Leadership Impact Report → Insights from team feedback to highlight leadership strengths & blind spots.
- Leadership Huddles → Live, interactive sessions that combine training with practical application & discussions.
- The 21-Day Best Boss Challenge → Daily leadership actions to build habits and reinforce learning.
- The Best Boss Capstone Experience → Final reflection, team integration strategies, and official Best Boss Ever certification.Â
 Self-awareness isn’t a luxury at the leadership level—
it’s a competitive advantage.
Benefits of Completing the Program
While 83% of organizations believe it’s important to develop leaders at every level of the company, only 5% of businesses have implemented leadership development at all levels. That's where we come in.
Deeper Self-Awareness
Understand your leadership style, strengths, and blind spots through personalized coaching based on the Enneagram so you can lead with intention.
Strong Team Relationships
Learn how to motivate, coach, and communicate in a way that builds trust, drives engagement, and creates a workplace where people want to stay.
Real-World Leadership Strategies
No boring trainings, no outdated theories— practical tools, and personalized leadership plans you can use immediately to navigate feedback, decision-making, and team dynamics more effectively.
Accountability & Long Term Growth
Through coaching, peer discussions, and a final capstone project, you’ll not only develop leadership skills—you’ll apply them in ways that create lasting impact.
A Collaborative and Trusted Culture
Great leadership creates a workplace where people want to stay and where like-minded, high-performing talent is drawn in.
Find the Right Program for Your Leaders.
Below are standard program outlines for various needs, but we'll work together to tailor to your specific people and goals.
Individual ExperienceÂ
Choose between a 6 or 12 month track.Â
- Individual Executive CoachingÂ
- Team Interviews + Analysis
- 21-Day Leadership Challenge
- Capstone Certification Project
Investment: Starting at $12,000 or $1,000 - $2,000/monthÂ
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Leadership Teams (5-12 People)
- Program Kick-Off
- Individual CoachingÂ
- Quarterly Group Leadership HuddlesÂ
- Enneagram Team Mapping
- Team Interviews + Analysis
- 21-Day Leadership Challenge
- Cross-Functional Leadership Collaboration Workshop
- Capstone Experience + Closing Retreat
Investment:Â Starting at $55,000 or $4600/monthÂ
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Executive Teams
- Program Roll-Out Session
- Executive Coaching
- Quarterly Group Leadership HuddlesÂ
- Enneagram Team & Department Mapping
- Team Interviews + Analysis
- 21-Day Culture Challenge
- Executive & Team Leaders Compatibility Workshop
- Closing Retreat
Investment:Â CustomizedÂ
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How the Enneagram is Used with this Program
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For the best results, the Best Boss Ever Leadership™ program is a powerful enhancement as your team moves through the Dream Team Certified Workplace Program. While your team explores the Enneagram’s 5-step journey, you’ll go deeper into how your leadership style impacts them—and how to lead more effectively.
Whether you’re adding it on or using Best Boss Ever on its own, coaching is tailored to each leader's unique strategy type and instinctual bias, helping maximize strengths, navigate blind spots, and customize how they support, challenge, and motivate their team.
*At Enneagram MBA we practice the Awareness to Action Enneagram model. Learn more about the model and why we use it here.
Ready to Elevate the Leaders that Shape Your Dream Team?
Getting Started is Simple.
Schedule a Call:
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Schedule a Team Strategy call to share about your organization and leadership team(s), the current dynamics, and goals for the program and learn about the right-fit options for your leaders.
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Input from Your Leaders
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Each leader will complete the Best Boss Scorecard and the feedback will be used to tailor the program to your team/organization.Â
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Launch Your Game Plan
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Implement tailored topics and a customized schedule that matches your team's needs and goals.Â
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