Leaders face increasingly complex challenges that perpetuate stress, frustration, and costly missteps—yet the root causes are often overlooked. Instead of addressing these foundational issues, many leaders default to quick fixes that provide only short-term relief, leaving the underlying problems intact. This reactive cycle fuels burnout, unresolved conflicts, unconscious biases, and poor decision-making, which ultimately limit the potential of their people, purpose, and profits.
For companies, this cycle erodes stakeholder confidence, wastes valuable resources, and can lead to significant financial losses. If left unaddressed, it threatens market competitiveness and long-term stability, undermining the organization's capacity to thrive in a rapidly evolving landscape.
Princess Castleberry invites leaders to Go Deeper to Grow Faster™. Leveraging her proprietary framework and transformative tools, she guides them to uncover hidden triggers that drive burnout, reinforce toxic behaviors, and stall progress. By moving beyond surface-level solutions, leaders can redefine their narratives, unlock new avenues for growth, and invest in people strategies that deliver sustained impact and resilience in today’s dynamic environment.
The Truth is in the Trigger! Get to the root!
20+ Years of Solving Complex People and Operational Challenges
Princess Castleberry’s approach to speaking and facilitation goes beyond delivering practical tools—it equips leaders and individuals with actionable insights to anticipate and mitigate challenges that undermine organizational resilience, engagement, and well-being. By addressing core factors that drive leadership success and adaptability, she challenges organizations to ‘Go Deeper to Grow Faster’ in a landscape where the future of work demands a profound commitment to both people and performance."
Her signature blend of bold strategy and narrative-driven engagement reflects over two decades of global expertise in enterprise risk management, wellness, and learning design. She has advised Fortune 500 firms across industries, including insurance, construction, staffing, and tech.
A proud Detroit native, Princess brings unmatched authenticity, depth, and practical wisdom to every engagement, equipping organizations and individuals to uncover root challenges, reimagine their paths, and build lasting growth solutions.
"I was moved by [Princess'] vulnerability, but also walked away with a practical framework for identifying the triggers than can lead to burnout. She illustrated how individuals in positions of power can often fall into the trap of trying to excel in every aspect of their lives...leading to unsustainable lifestyles. It was such a good reminder to assess my various roles and relationships, and make conscious decisions about where I want to be the top performer."
Elena Hassan | Global Head of Integrated Marketing
Visa Direct
"You were amazing, and the presentation 'Burnout-Proof Your Team' was exactly what our team needed. The buzz continued throughout the rest of our meeting, and comments continue to flow today. Thank you so much for the targeted and thoughtful approach you took with our team.
Barbara Rossman | Former CEO
Henry Ford Hospital Macomb
"Princess, we are incredibly grateful for you and your amazing presentation. Many leaders and team members remarked you as being not only their favorite element of the day, but as the best speaker of the past 3 years since we have come back in person. We appreciate you!"
Cheryl H. C. Duncan, SHRM-CP | AVP of Human Resources/Training
Community Choice Credit Union
Burnout-Proof Your Team
An insightful, story-filled keynote helping leaders in high-stress/high-risk roles identify their triggers and use innovative techniques to prevent and recover from chronic stress
How to Have Conflict and Still Win Together
A mind-shifting, actionable keynote to help leaders and their teams reframe the use of conflict to spur innovation, collaboration, and reconciliation
Unstuck, Unbothered and Uninterrupted
Unstuck, Unbothered, and Uninterrupted is more than a keynote - it's a strategic playbook that allows leaders to examine four ways high-performing individuals get stuck and learn practical strategies to adapt their perspectives, manage stress, navigate conflict, and build healthy momentum.
The Future of AI is Now
A hands-on learning series equipping leaders and teams to leverage AI's productivity, generative, and advisory capabilities
Building Belonging
A deep dive experience into how leadership and authenticity directly influence an organization's well-being and culture of belonging
AIM - Align. Ignite. Manage.
An immersive boot camp experience that helps cross-functional leaders and teams align to manage projects more effectively and develop solutions to real-time project challenges
Keynotes and Workshops
Align Internally
Recognize & Manage Triggers
Reduce Chronic Stress & Decision Fatigue
Build Belongers & Believers
Reconcile Conflicts
Leverage Well-being
The Every Leader is a Risk Manager™ methodology empowers you to think like a risk manager, proactively addressing generational gaps and diverse opinions. By fostering inclusive communication and creative alignment, you’ll unify your team and drive your organization forward in today’s ever-changing environment.
Using the Every Leader is a Risk Manager™ methodology means approaching conflict with a proactive, creative mindset. By fostering inclusive, healthy debates, you turn potential conflicts into opportunities for innovation and collaboration, strengthening your team’s trust and unity.
The Every Leader is a Risk Manager™ methodology encourages proactive inclusion, recognizing that when people feel they belong, they become believers in your vision. This approach nurtures a creative, motivated team committed to driving success together.
Thinking like a risk manager through the Every Leader is a Risk Manager™ methodology helps you proactively identify and manage stress triggers. This approach encourages creative problem-solving and inclusive decision-making, ensuring that your actions protect and uplift your entire team.
The Every Leader is a Risk Manager™ methodology inspires proactive strategies to reduce chronic stress and decision fatigue. Creatively streamlining processes fosters an inclusive, balanced environment where everyone can contribute their best, driving organizational growth and well-being.
Integrate Technology
The Every Leader is a Risk Manager™ methodology guides you to proactively and responsibly integrate AI and technology with creativity and inclusion in mind. Enhancing human capabilities and fostering collaboration ensures your team thrives while driving sustainable growth.
How Risk Management Thinking Helps You Go Deeper and Grow Faster
I've seen hundreds of speakers at TEDxDetroit. Literally, one of the very best - Princess Castleberry! You lit up the stage there...you had me taking notes and rethinking things.
Charlie Wollborg | Producer
TEDxDetroit
"If you are very fortunate, you might have a once-per-lifetime opportunity to work with someone such as Princess. Whether it be her ability to apply her unmatched creativity to practical issues or her deep command of a remarkable spectrum of subject matters, she leaves you amazed."
Gary Pearce | Former Chief Risk Architect
Aclaimant
"Princess, you were the best! I would recommend you to anybody needing coaching!!"
Bob Fish | Co-Founder & Co-Visionary
Biggby Coffee