In a time when digital transformation is often reduced to speed, scale, and the latest technology, it’s easy to lose sight of what actually drives meaningful change. Real progress doesn’t start with platforms or roadmaps—it starts with leadership, clarity, and shared understanding. This book brings together practical lessons and hard-earned insights about leading digital work with intention, discipline, and accountability, especially amid complexity and constant disruption. Digital Inside Out is meant to serve as a steady guide for leaders at every stage: those shaping strategy, those leading teams through change, and those working to translate digital ambition into outcomes that truly matter.
Table of Contents
Chapter 1: The Digital Leadership Journey: Understanding Your Phases of Influence
Chapter 2: Shifting into High Gear: CIOs as Strategic Leaders.
Chapter 3: Designing Strategy with a Customer Lens
Chapter 4: Recalibrating Strategy from the Core
Chapter 5: Scaling Innovation for Enterprise Impact
Chapter 6: The CIO as Cultural Catalyst
Chapter 7: Navigating Internal and External Disruptions
Chapter 8: Future-Proofing the Organization
Chapter 9: Preparing for the Next Chapter
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Digital Inside Out
“With the AI era upon us, CIOs and ‘the business’ must finally collapse the silos and act as one. Digital Inside Out guides CIOs, who are stuck between legacy tech and new AI demands, to get out of the messy middle and lead. Colisto offers us practical guidance and honest reflections and maps a mid-tenure leadership journey―from recalibrating strategy and accelerating innovation to scaling influence and building lasting impact."
– Martha Heller, CEO of tech search firm, Heller Search Associates and author of The CIO Paradox and Be the Business
“Digital Inside Out can be a tremendous help as CIOs transform their role from new in position to being an impactful leader through the use of numerous real world case studies and check lists to give them the tools needed to be a strategic partner.”
– Ken Hicks, President & Chief Executive Officer, PetSmart
“Digital Inside Out is a masterclass on the most consequential transformation a technology executive can undertake: the evolution from operational IT leadership to true strategic leadership of the business. While few leaders or organizations successfully make this aspirational leap in mindset and influence, Colisto offers deeply practical, substantive, and detailed guidance―delivering hard-won wisdom and clarity from his own exceptional journey as one of the most insightful and high-impact leaders in the Fortune 500".
– Adam Alfi, General Partner, ICONIQ
“Digital Inside Out is the leadership blueprint for the CIOs as technology becomes the ‘business’ from being at the backend. Nicholas Colisto brilliantly reframes IT as a driver of enterprise value―grounded in customer insight, cultural transformation, and strategic agility to deliver superior customer experience and business outcomes. His real-world, experience-led guidance will resonate with any technology leader, who aspires to move to the boardroom. A must-read for those looking to scale impact from the inside out.”
– Anupam Singhal, President & Business Group Head – Manufacturing, Tata Consultancy Services
Editorial Reviews
“Transformation isn’t about technology. It’s about reimagining how a company works and enabling that change through technology. That’s why Digital Inside Out stands out. Nicholas Colisto doesn’t just write about systems or platforms; he focuses on the real engine of change: mindset, culture, and leadership.
– Sven Gerjets, Chief Technology Officer, The Gap
“Digital Inside Out addresses the central question that CIOs – and other transformation-minded executives – face today: How can I become a proactive agent of change, growth, and innovation. With hard-won experience and real-world strategies, Nicholas Colisto aims to help leaders go beyond operational excellence to shaping strategy and building a legacy of success.”
– John Gallant, Enterprise Consulting Director, CIO Magazine
“Nicholas has authored an ultimate playbook for leaders to use for navigation in taking an organization through the journey of technology transformation and digital adoption. Not only does this book provide a roadmap for achieving higher success in organizations, but also lends to finding higher meaning and achievement in one's personal career journey.”
– Brad Marr, CISO & IT VP, MasterBrand Cabinets
In today’s boardroom, technology is no longer just an enabler―it’s the business strategy. In Digital Inside Out, Nicholas Colisto provides a timely and practical guide for CIOs ready to evolve from operational leaders into enterprise change agents. He captures the mindset shift we all experience when we move from managing systems to shaping outcomes. This book is a valuable resource for any digital leader who wants to earn influence at the highest levels and help drive transformation that delivers long-term impact.”
– Mike Anderson, Chief Digital & Information Officer, Netskope
“What I appreciated most about Nicholas’ book is its concise, straightforward guidance. Too often, new CIOs notch early wins and then settle into maintenance mode. Nicholas reminds us that we must never stop pushing the business – and ourselves – forward.”
– Rich Dolce, VP, IT & Americas Information Systems Officer, Fujifilm Holdings America Corporation
“I have been in sales for my entire professional career and the wisdom and knowledge that Nicholas shares in his book, Digital Inside Out has changed the way I think about speaking to executives. Understanding this allows me to meet them where they are in their journey."
– John Sapone, Chief Revenue Officer, NinjaOne