Change and the Stockdale Paradox

stockdale paradox

I’ve drawn one of the most powerful lessons on change from a philosophy Jim Collins refers to as the Stockdale Paradox in his book “Good to Great”.

The Stockdale Paradox refers to the inspiring perspectives that not only kept Vice-Admiral James Bond Stockdale alive but turned his 7-year stint as a POW at the Hanoi Hilton into one of the “defining moments” of his life.

Stockdale was the highest-ranking US soldier captured during the Vietnam War. The Vietcong’s strategy to discourage American participation in the war was to use propaganda, getting American prisoners to voice, after torture and under duress, their disapproval of the US government’s policies. Refusing to cooperate with his captors, Stockdale cut his face, bashed himself with a chair and even slit his own wrists.

In his book, Collins writes about a conversation he had with Stockdale regarding his coping strategy during his period in the Vietnamese POW camp.

“I never lost faith in the end of the story, I never doubted not only that I would get out, but also that I would prevail in the end and turn the experience into the defining event of my life, which, in retrospect, I would not trade.”

When Collins asked who didn’t make it out of Vietnam, Stockdale replied:

“Oh, that’s easy, the optimists. Oh, they were the ones who said, ‘We’re going to be out by Christmas.’ And Christmas would come, and Christmas would go. Then they’d say, ‘We’re going to be out by Easter.’ And Easter would come, and Easter would go. And then Thanksgiving, and then it would be Christmas again. And they died of a broken heart.”

And Stockdale added:

“This is a very important lesson. You must never confuse faith that you will prevail in the end—which you can never afford to lose—with the discipline to confront the most brutal facts of your current reality, whatever they might be.”

Witnessing this philosophy of duality, Collins went on to describe it as the Stockdale Paradox.

When facilitating change in organisations, I find it incredibly useful and important to engage staff in frank conversations about the brutal reality surrounding the change.

My experience informs me that managers often fail to bring up these fundamental realities. Some underestimate their staff’s ability to handle the “truth”, seeing it as their role to “protect” them. For others, this is revealing of their personal pessimism about the future. And thus, they fail to utilise an invaluable tool for engaging the hearts and minds of their staff, so powerful in helping them get out of their comfort zone.

Take the example of a manufacturing concern in Singapore looking to restructure its organization to eke out greater efficiencies. The brutal reality here is that they are in an industry and environment where staff want growing returns year on year, customers are conditioned to expect annual price reductions and their main competitors are from countries with significantly lower labor costs. By communicating this reality and then asking the “consequences of the status quo” question, staff typically draw the same conclusions that the change in not only desirable but necessary.

This applies equally to the publicly listed organisation in Malaysia seeking to outsource part of its I.T. operations in order to reduce operational costs and enhance competitiveness. And the government department in Australia seeking to transform its “top down”, “do as you’re told” culture to one that fosters greater collaboration and innovation in order to retain and attract top talent and in the process, enhance its credibility with its clients.

Just as it’s important to have the “brutal reality” discussion with the team, it is equally important to instill hope through a clear and compelling vision of the change. It is through leveraging this paradox that you create what Kotter calls a “true sense of urgency” for change that comes from within

“Leadership is the art of getting someone else to do something you want done because he wants to do it.” – Dwight Eisenhower

In summary, to strengthen emotional buy-in for change, draw from the lessons given to us by James Stockdale to help staff confront the brutal reality whilst always keeping the faith that the team can and will prevail by moving with courage towards a compelling vision.

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Andrew Davey

Andrew is a Master Trainer and Executive Coach known for helping organisations shift from transactional leadership to emotionally intelligent cultures. A Tony Robbins Mastery graduate, Certified Life Coach, and MBA holder, he empowers leaders to unlock clarity, resilience, and purpose.

Dominic Siow

Co-founder and EQ Alchemist at EQ Strategist, Dom has inspired leaders and transformed cultures across 260+ organisations in 10 countries. He is the author of the Amazon best-seller *What’s GREAT About This?* and host of the *Inspiring Leadership* podcast.

Sue Siow

Co-founder and Director of EQ Strategist, Sue is known for her calm presence, strategic clarity, and deep empathy. With a background in information systems and advanced leadership training, she has supported leadership journeys for global clients across Asia-Pacific.

Caroline Crosbie

Caroline is a sought-after trainer and psychologist based in Perth, delivering experiential leadership and wellbeing programs. With expertise in resilience, work-life integration, and communication, she helps leaders sustain performance while leading with care, clarity, and balance.

Vivien Ong

Vivien is a seasoned facilitator and coach with 20+ years of corporate leadership experience. She specialises in mindful leadership, communication, and team dynamics, creating vibrant, high-trust learning environments where individuals step into leadership with clarity and voice.

Dale White

Dale is a high-impact leadership and performance coach with 19+ years of experience across government, corporate, and education. Known for his energy and practical insight, he helps leaders align strengths with strategy to drive sustainable, high-performance outcomes.

Vivien Ong

Vivien Ong is a seasoned leadership facilitator, coach, and trainer known for helping professionals grow into self-aware, courageous and impactful leaders. With over 20 years of corporate experience in sectors such as banking, telecommunications, BPO, and media,

Vivien brings a strategic yet deeply human lens to leadership development. At EQ Strategist, she facilitates programmes in mindful leadership, communication, psychological safety and team dynamics. Celebrated for her vibrant facilitation style, she combines energy, empathy, and practical insight to spark meaningful dialogue where learning and growth happen. She also mentors youth through a social enterprise and serves in the leadership team at the

Contact Centre Association of Singapore, where she advocates for better leadership and service standards. Her work is rooted in the belief that better leadership builds a better world. Through storytelling, behavioural tools, and reflective practice, she helps individuals step into leadership with presence, clarity, and voice. Vivien’s clients value her ability to create high-trust environments where people feel seen, heard, and empowered to lead from within.

Caroline Crosbie

Caroline is a sought-after trainer and psychologist who brings warmth, depth, and structure to leadership and wellbeing programmes. At EQ Strategist, she delivers experiential learning focused on resilience, work-life integration, and effective communication. Her academic background includes a Master of Clinical Psychology and certifications in Extended DISC, NLP, and EFT. Caroline’s clients appreciate her thoughtful approach to coaching and her ability to simplify complex psychological principles into actionable steps. With professional experience in five countries, she brings a culturally attuned perspective to her facilitation. Her goal is to help individuals and teams sustain performance without burning out—leading with insight, care, and clarity.

Dale White

“Real transformation doesn’t come from more information—it comes from aligned action.”

Dale White is a high-impact, outcome-focused leadership and performance coach, known for his energy, strategy and ability to drive real change. With 19+ years of experience helping professionals perform at their highest potential & a background in business, behavioural psychology, and high-performance coaching, Dale supports leaders to build clarity, confidence, and resilience in both work and life. At EQ Strategist, Dale facilitates training & coaching that blend behavioural insight, personal mastery, and practical implementation. His sessions are known for being dynamic, personalised, and results-focused – ensuring participants take real-world action that sticks. Dale holds degrees in Business and Exercise Science, and certifications in NLP, PCM, and Robbins Leadership Mastery. Whether supporting government departments, corporate leaders, guiding frontline teams or values-driven founders, Dale’s mission is to help people cut through theory and lead with purpose.

Jack Rankin

Jack Rankin is a high-impact trainer, executive coach, and culture catalyst with over 1,500 workshops delivered globally. His client portfolio includes leading names across government, finance, insurance, construction, and retail. At EQ Strategist, Jack helps organisations strengthen leadership capability, stakeholder alignment, and communication excellence. He is known for making learning engaging and actionable—tailoring each session to drive meaningful outcomes. His past clients include Singapore Airlines, Rio Tinto, Visa Westfield, Nike, Schneider Electric, and City of Parramatta Council. Jack is a Tony Robbins Leadership Mastery graduate and serves on the Synergistic Results Leadership team. Through each programme, he inspires individuals to elevate how they speak, lead, and influence.

Sue Siow

With a heart for people and a sharp strategic lens, Sue Siow co-founded EQ Strategist to help individuals and organisations flourish from the inside out. As Operations Director, she ensures the seamless delivery of high-impact programs while supporting clients with insight, empathy, and practical wisdom.

In addition to leading operations and client experience, Sue is also a skilled Facilitator and Participant Coach—contributing to larger workshops through 1-on-1 coaching, small group facilitation, and experiential team-building segments. Her calm, grounding presence invites reflection, trust, and personal growth.

With a background in Information Systems and advanced training from Tony Robbins’ Mastery University, Sue has supported programs across Singapore, Australia, Malaysia, China, and Indonesia for clients including Sembcorp, Esker, DBS Bank, Changi Airport Group, FedEx, Yokogawa, and AirAsia.

Dominic Siow

“Be the light or the mirror that reflects it.”

These words define Dominic Siow’s approach to life and leadership. As a globally recognised leadership facilitator, keynote speaker, coach, and co-founder of EQ Strategist, Dom is known for helping people reconnect with their purpose, lead with heart, and create cultures where everyone can thrive.

Drawing on senior leadership experience from IBM and Grapevine Technologies, he has spent the past two decades empowering over 260 organisations across 10 countries—from multinational corporations to public sector agencies and values-driven startups.

Dom’s facilitation style is equal parts insight, empathy, and inspiration. Whether leading a leadership retreat, designing a culture transformation program, or coaching executives through complexity, he helps people become not just better leaders, but better human beings.

He is the author of the Amazon bestselling book What’s GREAT About This?—a guide to building resilience through disruption—and the host of the Inspiring Leadership Podcast, where he shares real stories of growth and grit.

For Dom, leadership is not about titles. It’s about helping others find their light—and reflecting it back so they can shine.

Andrew Davey

At EQ Strategist, Andrew Davey is known for helping organisations move from transactional leadership to purposeful, emotionally intelligent cultures. As a master trainer and trusted coach, he brings a rare blend of business insight, coaching expertise, and facilitation mastery. Andrew’s clients span industries from logistics and software to government and education. He is a Tony Robbins Mastery University graduate, a Certified Life Coach, NLP Master Practitioner, and MBA holder. His mission is to empower leaders to unlock clarity, strengthen resilience, and lead inspired teams that drive results. Andrew delivers programs that are practical, energising, and deeply human—enabling sustained transformation at both the individual and organisational level.