Why I Wrote Digital Trailblazer: A Leadership Guide on Digital Transformation

You know that look people make when they’re trying to understand a concept? Their head is tilted, their eyes are squinted, brows furrowed.

For me, there’s nothing like watching confusion melt when they truly comprehend a new concept. I love seeing the look in their eyes when they reach that magical moment of “getting it” and experience that “aha” moment of why it’s important.

Isaac Sacolick: Digital Trailblazer: Essential Lessons to Jumpstart Transformation and Accelerate Your Technology Leadership


Some of my favorite writers, including Chris Laping (People Before Things), Helen Yu (Ascend Your Start-Up), and Adam Grant (Think Again), encourage people to answer their “why” when embarking on a transformational journey. And my book writing mentors, including Dan Roberts, Ginny Hamilton, Jason Burns, Linda Brennan, Jay Cohen, and many others, encouraged me to answer my why about writing Digital Trailblazer

So here it is: 

My why is helping people have those aha moments when I guide them on methods for leading and driving digital transformation in their organizations.

How come? Because I was fortunate to have so many of those aha moments myself starting from when I was a teenager. At that age, I was already deeply interested in learning more about innovation and growing businesses thanks to my dad’s stack of BusinessWeek and Scientific American magazines. At 14, I once took the subway up to midtown New York City and bought my first textbook on entrepreneurship from the McGraw Hill building on 47th street. It was a text that would lead me to have aha moments about product development, organizing teams, and financing innovation. Twenty years later, I would find my way back to that building – riding the elevator to my office at Businessweek, where I served as head of technology and CIO. 

I’ve never stopped seeking those aha moments. I uncovered them while studying machine learning at The University of Arizona, the digital disruption of newspapers as a startup CTO, the construction industry’s digital transformation opportunities as a CIO, and now working with leaders in many industries, including financial services, healthcare, nonprofit, manufacturing, retail, higher ed, and others.

I extended my learning to sharing – through writing, speaking, advising, and mentoring. And that’s when it happened with more regularity – I started seeing those aha moments unfold before my eyes as I shared my experiences with new audiences and clients. Ever since, I’ve been on a quest to inspire as many of those aha moments as I can.

Digital Trailblazer is a book written to deliver aha moments to anyone looking to advance their technology leadership skills in this new normal of nonstop transformation. 

A Guide to Lead Digital Transformation 

Isaac Sacolick - Digital Trailblazer

Today, most businesses understand the need for continuous improvement. We’ve reached a point where the best organizations embrace learning cultures, seek experimentation, become more data-driven, innovate with new products, and align on hybrid agile ways of working.

The challenge is that there isn’t a framework for driving successful transformations that can be applied prescriptively across all businesses and circumstances. That’s why I choose to provide guides, and they all start with people – people who take the initiative, leave their comfort zones behind, and drive transformation. 

People I call Digital Trailblazers.

Aspiring Digital Trailblazers are drivers – people who want to lead their businesses to tomorrow’s business models, differentiating customer experiences, and data-driven practices. They’re comfortable with not always knowing the right answer, but they’re brave/bold enough to speak up anyway because their questions and ideas trigger new ways of thinking. Digital Trailblazers are continuous learners, have agile mindsets, and seek to make long-lasting impacts.

With so much information constantly coming at us, there’s so much to learn and often too little time to invest in yourself. I hear this throughout organizations – from software developers, data scientists, product managers, IT professionals, and the VPs leading agile and IT operational teams – all the way to CIOs, chief data officers, and chief digital officers.

And professionals like you see the need to develop the ability to lead transformation as a core competency – because you know that what you master today will be obsolete in just a few years. Digital Trailblazers embrace transformation not only in their own work, but in their own lives.

I wrote this book for aspiring Digital Trailblazers and people leading or aspiring to lead digital transformations.

Agile, DevOps, Product Management, DataOps, Data Governance, Low-code

I share the challenges you will likely encounter in the stories and scenarios on your transformation journeys. I hope executives and managers will read this book, assign it to teammates, and recommend it to their colleagues in other parts of the business. I hope it will spark conversations and develop the confidence needed both personally and at all levels of an organization to lead successful transformation initiatives.

My new book, Digital Trailblazer: Essential Lessons to Jumpstart Transformation and Accelerate Your Technology Leadership, will deliver many “aha” moments on areas including: 

  • Evolving your organization’s agile way of working and delivering innovative experiences because being agile is foundational to leading transformation
  • Transforming the culture with empathetic, diverse, data-driven teams because these are the types of teams you need to be successful
  • Navigating the C-suite and growing leadership’s commitment to digital transformation because if you can’t collaborate and cultivate executive sponsors, your best laid plans will likely fall short

Isaac Sacolick speaks on Digital Transformation

To write Digital Trailblazer, I had to look back into my career as a CTO, CIO, and now leading StarCIO. I called upon some of my most challenging and inspiring moments – from debugging code as a young developer to my seat at a tense board of directors meeting as a CTO. Instead of talking about leadership guidelines in the abstract, I take a story-led approach so you can learn from these real-world experiences. You will see yourself in these stories, and ultimately the storytelling approach I take will help you recall the lessons when you need them the most.

At the end of each chapter, I share five key takeaways – hard lessons learned that can help guide you. There are 50 of them in the book, and I can’t wait to hear from you how many aha moments you have.

It Takes a Village: A Community for Digital Trailblazers

I’m thankful to the many people I include in my stories, the friends who provided advice on the topics: Ginny Hamilton, StarCIO’s chief feedback officer and the book’s editor; Wiley, the book’s publisher, and the over 20 people who provided endorsements.

One of those endorsements came from R “Ray” Wang, CEO of Constellation Research. He says, “Digital Trailblazer is the must-go-to playbook for not only leadership advice, but also real-world stories on how to handle the toughest challenges in culture, process, and technology.” I love Ray’s characterization of the book. Thank you, Ray! 

Digital Trailblazer is just the start! Stay tuned for new programs to help accelerate your technology leadership journey.

Please visit Digital Trailblazer to pre-order, learn more, and join the community. I hope the book sparks some aha moments for you and your teams. 

Isaac Sacolick: Digital Trailblazer

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