Deanna Singh
Inclusive Leadership Expert (JD, MBA)
WI, USTransform your leadership with actionable strategies that drive measurable results. Learn powerful techniques to elevate team performance, navigate complexity with clarity, and build cultures where everyone contributes their best work. Leave energized, equipped, and ready to lead with impact.
Deanna Singh is a powerhouse leadership strategist and acclaimed executive consultant whose electrifying keynotes transform organizational culture and accelerate business performance. Her signature approach breaks through conventional barriers, delivering innovative frameworks that drive exceptional results, boost employee engagement, and create workplaces where everyone thrives. As Founder and Chief Change Agent of Flying Elephant, she operates five successful social enterprises spanning education, healthcare, and entrepreneurship—exemplifying her ability to turn strategic vision into measurable impact. She also owns and operates the Uplifting Mansion, a historic Milwaukee landmark that serves as an entrepreneurship hub fostering innovation and professional development.
Deanna's commanding stage presence captivates global audiences at Fortune 500 companies, international associations, and premier leadership conferences, leaving executives energized and equipped with actionable strategies for team transformation, change management, and sustainable growth. With a Georgetown Law degree and an MBA from the University of Wisconsin-Madison, this award-winning author has written seven books, including her latest, The Bridging Leader: Transforming Teams Through Connection, as well as Actions Speak Louder and Purposeful Hustle. She has designed many leadership certification programs independently and on behalf of the University of Wisconsin Business School Center for Professional Development.
Annually reaching over 50,000 leaders through keynotes, summits, and leadership development programs, her company's mission of Building Bridges resonates across industries seeking to strengthen collaboration, foster innovation, and develop high-performing teams. A LinkedIn Top Voice, TEDx speaker, and named among Forbes' "African American Women Everyone Should Know," Deanna brings 25+ years of executive leadership experience to every engagement, empowering leaders to transform bold vision into lasting impact.
Deanna Singh is a powerhouse leadership strategist and acclaimed executive consultant whose electrifying keynotes transform organizational culture and accelerate business performance. Her signature approach breaks through conventional barriers, delivering innovative frameworks that drive exceptional results, boost employee engagement, and create workplaces where everyone thrives. As Founder and Chief Change Agent of Flying Elephant, she operates five successful social enterprises spanning education, healthcare, and entrepreneurship—exemplifying her ability to turn strategic vision into measurable impact. She also owns and operates the Uplifting Mansion, a historic Milwaukee landmark that serves as an entrepreneurship hub fostering innovation and professional development.
Deanna's commanding stage presence captivates global audiences at Fortune 500 companies, international associations, and premier leadership conferences, leaving executives energized and equipped with actionable strategies for team transformation, change management, and sustainable growth. With a Georgetown Law degree and an MBA from the University of Wisconsin-Madison, this award-winning author has written seven books, including her latest, The Bridging Leader: Transforming Teams Through Connection, as well as Actions Speak Louder and Purposeful Hustle. She has designed many leadership certification programs independently and on behalf of the University of Wisconsin Business School Center for Professional Development.
Annually reaching over 50,000 leaders through keynotes, summits, and leadership development programs, her company's mission of Building Bridges resonates across industries seeking to strengthen collaboration, foster innovation, and develop high-performing teams. A LinkedIn Top Voice, TEDx speaker, and named among Forbes' "African American Women Everyone Should Know," Deanna brings 25+ years of executive leadership experience to every engagement, empowering leaders to transform bold vision into lasting impact.
Purposeful Hustle
Format: Keynote
Description: Imagine a world where everyone lived and led from their unique purpose. The challenges we face today would become opportunities for transformation. While many aspire to purpose-driven leadership, fear and uncertainty often hold them back. If you're tired of watching your leadership dreams drift further away, this keynote is your catalyst for change. Through powerful storytelling and actionable strategies,...
The Bridging Leader: Connecting Across Differences for Extraordinary Results
Description: In today's increasingly complex business landscape, the ability to build bridges across different perspectives, backgrounds, and thinking styles is the hallmark of exceptional leadership. This keynote explores how forward-thinking leaders create environments where diverse talents and viewpoints become catalysts for innovation rather than sources of friction. Through research-backed insights and practical strategies, Deanna Singh demonstrates how intentional...
Groundbreakers: Strategic Career Acceleration Program
Groundbreakers is a comprehensive 30-day leadership development program that transforms your high-potential employees into strategic, self-directed leaders who drive greater organizational impact while strengthening retention. Over the course of one month, participants gain the unspoken career strategies that accelerate advancement—including building strategic networks, positioning their value for recognition, advocating effectively within complex organizational dynamics, developing...
Bridging Intensive: Strategic Leadership Development for Your Culture Builders
Bridging Intensive is a comprehensive month-long executive development program that transforms your senior leaders into culture architects who build high-performing, cohesive teams where differences drive innovation, and every team member contributes at their highest capacity. Based on the research-backed framework from The Bridging Leader by Deanna Singh and Justin Ponder, this investment addresses the critical leadership capabilities required in today's rapidly changing...
Purposeful Hustle Intensive for Executive Directors
The Purposeful Hustle Intensive is a transformative 5-week program designed specifically for nonprofit executive directors who are ready to move from constant motion to strategic momentum and for boards committed to supporting their leaders' long-term effectiveness and organizational sustainability.
Meeting weekly for three focused hours, this cohort-based experience tackles the unique pressures facing nonprofit leaders: leading with strategic clarity when...
Building a Thought Leader
When employees establish themselves as thought leaders in their field, it can significantly benefit their professional growth and career advancement. When they consistently share unique ideas, insights, and best practices, they build a reputation as experts. This helps them gain credibility and influence. As more people look to them for guidance on trends, challenges, and innovations in their expertise, they expand their opportunities, professional network, and ability to effect change and...
Winning at Failure: The Surprising Power of Strategic Failure
Description: What if the greatest leaders aren't those who avoid failure, but those who've mastered the art of failing strategically? In this candid and transformative keynote, Deanna Singh shares personal stories from her own "Failsume" to demonstrate how high-performing leaders leverage setbacks as catalysts for extraordinary growth and innovation. Through engaging storytelling and practical frameworks, you'll discover why developing comfort with failure is the hidden...
Actions Speak Louder
Drawing upon her two leadership books, Actions Speak Louder and Purposeful Hustle, Deanna Singh will lead audience members through a process to move past the status quo and help lead the charge. Through the power of storytelling, sharing practical tips, and individual reflection, audience members will be able to identify the unique way to view their leadership, positively impact the future of their organizations, and elevate their unique skills.
Key...
Talking Across Differences
Before striving for greater belonging, people must first be able to talk about identity differences. In this session, participants learn strategies for discussing this topic constructively. For people to flourish in their organizations, they need to feel included. Unfortunately, too often, leaders believe that to foster inclusion, they must avoid conversations about things like race, gender, and sexual orientation. However, ignoring these difficult discussions can breed distrust,...
Indentify Your Purpose
General Overview: Knowing your purpose is critical if you want to make a difference in the world. If you know your purpose, you can be more focused on your day-to-day life. You will know what you should be pursuing and what you should be walking away from. But maybe you are not sure how to go about finding your purpose just yet. If you need help discovering your purpose and turning it into a concrete statement that will empower you to unleash your full potential, then this...
9 recommend Deanna
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Quad
On-Site
C.W., Community Relations and Inclusion Manager, Quad
Working with Deanna is an empowering and refreshing experience. Her enthusiasm, her wisdom and her presence is a motivating force that will not only make you want to go out and conquer the world, but it would make you want to better the world of others. Her presentations are incredibly engaging and will create a positive ripple effect among individuals in your organization
United Way
On-Site
R.R., Vice President, Marketing & Brand Management, United Way
Deanna Singh's talk during the United Way of Summit County's Annual Knight Breakfast was dynamic and inspiring. She was a lot of fun to be around and we hated to see her go.
CUNA Mutual
On-Site
J.H., Diversity & Inclusion Manager, CUNA Mutual
Deanna is a true storyteller who brings her energy and passion to her work and shares it with others. She helped many folks in the audience not only feel compelled to make our organization more diverse and inclusive but also gave great actionable steps for all of us.
Ascension
On-Site
S.R., Director of Ministry Formation, Ascension
Deanna's ability to engage a group around their sense of purpose shines a bright light on where people can more clearly see and express where they are or could be having an impact.
Center for Urban Teaching
On-Site
H.H., Teacher Coach, Center for Urban Teaching
Just what the room and the team needed to hear. Your energy is contagious. I love how animated you are when she shares stories and lessons learned. I think that the statistics you shared about diversity in the literature (or lack thereof) was alarming and your work to not just talk about it but do something about it is what makes you so inspiring. Thank you for what you brought to the room and our team!
The Ridge Community Church
On-Site
J.T., Director of Weekend Experience, The Ridge Community Church
Verified @theridgecc.comDeanna was able to inspire and challenge a wide range of people and guests within our community. It's been amazing to see how many people her story has touched and we look forward to hearing how the ripple effects will have an impact on not just those people but on our city and the world!
LIFT
On-Site
J.R., Senior Executive Office Coordinator, LIFT
Verified @whywelift.orgI feel so motivated after hearing Deanna's presentation. She keeps it real and is so passionate about ensuring that everyone is working in a career that they love.
Lumin Schools
On-Site
T.H., Principal, Lumin Schools
Verified @cuslight.orgIf you want your students to be driven then they need to hear Purposeful Hustle by Deanna Singh
College Possible
On-Site
K.S., Program Director, College Possible
Verified @collegepossible.orgDeanna was such a great speaker for our team. She brought energy, thoughtfulness, opportunities to reflect and tools for helping every person be their very best!



















