Transformational Leadership Workshops, Masterclasses & Retreats for Jamaica, the Caribbean & the Global Diaspora
Sterling Business Management curates high‑impact workshops, masterclasses, retreats, and leadership circles that blend emotional intelligence, identity‑level leadership, and strategic communication. These experiences help leaders reconnect with their purpose, strengthen their presence, and lead with confidence.
Whether virtual or in‑person, each experience is crafted with intention, depth, and cultural resonance — honouring the unique leadership landscape of Jamaica, the Caribbean, and the global diaspora.
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🟦Transform to Lead: The Sterling Edge
Transform to Lead: The Sterling Edge is a powerful online leadership experience designed for professionals who are ready to rise with clarity, confidence, and authentic influence. Whether you’re leading a team, mentoring others, or preparing for your next bold move, this virtual forum meets you where you are — and helps you step into who you are becoming
Hosted by Paulette Sterling, this experience blends strategic leadership frameworks with emotional resonance, spiritual grounding, and practical tools that activate real transformation.
January | May | September
🟦Chasing Authenticity: Online Conversations That Happen When They’re Meant To
Every voice has a story. Every story has a truth. And every truth has the power to shape how we live, love, and lead. Chasing Authenticity — (real conversations with friends, family, and the familiar faces you thought you knew).
These sessions aren’t pre‑scheduled — they unfold when the right guest, the right story, and the right moment align. Each conversation is a divine appointment, crafted to meet you exactly where you are. Join the list to be the first to know when the next live session drops.
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✨ Upcoming Guests: A curated lineup of leaders, creators, and truth‑tellers who embody soulful authenticity. New sessions are added once a guest is confirmed. Stay tuned.
Pastor Rodrick Robinson
Richard Ceballo
Yolan Williams
1️⃣Leadership Identity Reset Workshop
Reconnect with your purpose. Strengthen your leadership identity. Lead with clarity.
This transformational workshop helps leaders pause, reflect, and realign with who they are becoming. Through guided reflection, identity mapping, and values alignment, participants gain clarity, confidence, and renewed leadership energy.
Perfect for:
Emerging leaders • Managers • Entrepreneurs • Leadership cohorts • Retreats
What’s Included:
Leadership identity mapping
Values & purpose alignment
Emotional intelligence practices
Reflection exercises
Leadership presence activation
Outcome:
A grounded, confident leader with renewed clarity and direction.
→ Book This Workshop
3️⃣Leadership Reflection & Renewal Retreat
A soulful, immersive leadership experience for clarity, grounding, and renewal.
This in‑person retreat blends leadership identity work, emotional intelligence, reflection practices, and strategic clarity. It is designed for leaders who need space to breathe, reset, and reconnect with their purpose.
Perfect for:
Mid‑career professionals • Executives • Entrepreneurs • Leadership teams
What’s Included:
Guided reflection sessions
Leadership identity deep‑dive
Emotional intelligence practices
Visioning & alignment exercises
Group dialogue & connection
Optional 1:1 coaching add‑on
Outcome:
A renewed leader with clarity, emotional grounding, and strategic direction.
→ Request Retreat Details
2️⃣High-Stakes Conversations Masterclass
Communicate with clarity. Navigate conflict with confidence. Lead with emotional intelligence.
This masterclass equips leaders with the tools and frameworks needed to navigate difficult conversations, regulate emotions, and communicate with influence. It is one of your most in‑demand experiences.
Perfect for:
Executives • Managers • HR teams • Nonprofits • Entrepreneurs
What’s Included:
High‑stakes conversation framework
Emotional regulation tools
Communication clarity exercises
Conflict navigation strategies
Role‑play and scenario practice
Outcome:
Leaders who communicate with confidence, clarity, and emotional intelligence.
→ Host This Masterclass
4️⃣Executive Roundtables & Leadership Circles
These small‑group experiences bring together leaders for high‑value dialogue, reflection, and shared learning. Each session is facilitated with intention, emotional intelligence, and strategic depth.
Perfect for:
Executives • Managers • Thought leaders • Entrepreneurs
What’s Included:
Curated leadership topics
Guided reflection
Peer dialogue
Strategic insight
Identity‑level leadership prompts
Outcome:
A connected community of leaders who learn, reflect, and grow together.
→ Quarterly LIVE Q&A with Paulette & Guest Experts
March | June | September | December
Why Our Experiences Are Different
We blend identity, emotional intelligence, and strategy.
Our events are not lectures. They are not generic workshops. They are transformational leadership experiences.
We bring together:
✅ Identity‑level leadership
✅ Emotional intelligence
✅ Strategic communication
✅ Cultural resonance
✅ Reflective practice
✅ Practical frameworks
✅ Safe, grounded facilitation
Every experience is designed to shift how leaders think, feel, and show up.
Custom topics include:
Leadership identity
Emotional intelligence
Communication & influence
Difficult conversations
Team alignment
Governance & culture
Strategic clarity
→ Request a Custom Experience
Let’s create a transformational leadership experience for your team or community.
Whether you’re hosting a retreat, planning a leadership summit, or developing your internal leadership pipeline, we can design an experience that inspires clarity, confidence, and alignment.
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