Why I Wrote a Fearless Book to Inspire More Digital Transformation Leaders

“The pace of technology change is increasing, and you must reevaluate your digital strategy and priorities. Frequently. You will always be transforming, and your organization must establish transformational practices as essential core competencies.”

Digital Trailblazer quote by Isaac Sacolick

That paragraph on page one of Digital Trailblazer exemplifies why I wrote the book. Leaders will often say, “transformation is a journey,” but what’s not said enough is that the current wave of innovation,  customer experience improvements, and data-driven practices will give way to more evolutions.

Businesses will always be transforming, and I believe digital transformations backed by new technologies, competitive data capabilities, and company culture evolution will be front and center for most businesses for at least another decade. I make my case for how digital transformations are different from crisis management and strategic transformations in the final chapter, Transforming Beyond Crisis and Becoming a Digital Trailblazer.”

My journey from digital practices to guiding transformation leaders

Before you get to chapter 10, I leave Digital Trailblazers with chapters of my real stories leading transformations and over 50 lessons learned.

When I became a CTO in my late 20s, there were no playbooks or stories for developing a collaborative business-tech-data culture or creating sustainable innovation programs. When I transitioned to CIO in my 30s, there was little guidance for aspiring transformational leaders on bringing agile to enterprises or launching data governance programs.

In 2017 I published my first book, Driving Digital, and shared many of my best practices around agile, DevOps, data cultures, agile PMOs, product management, and culture transformation. It became a bestseller and helped me launch StarCIO, where I lead center of excellence programs for transforming SMBs through large enterprises and provide evangelist services for digital-trailblazing technology companies.

Your questions drove me to write Digital Trailblazer

After publishing Driving Digital and speaking with thousands of tech, data, and business professionals, the questions started coming in.

  • “Isaac, how can we create diverse teams when everyone is competing for the same talent?” 
  • “What can we do to help employees who hold onto legacy ways of working learn new practices and technologies – and avoid having them become detractors to transformation programs?” 
  • “We want to adopt startup-like agile and devops practices, but how do we create a playbook that works in larger companies with decades-old business models, defined brands, and mountain ranges of technical debt?”

When I started writing Digital Trailblazer in early 2019, I confess that these questions were not top of mind. I started by writing stories that truly shaped my leadership style and transformational practices with no firm goal. I wasn’t sure I would get another book out or use the stories as blog posts, but by the end of 2019, I made a firm commitment to write a second book. When the pandemic hit in 2020, I had more time to finish it.

Or so I thought. I had busy years in 2020-2021 as more business leaders recognized technology and data’s importance to their business and future of work. Emails, meetings, and taps on the shoulder were replaced with low-code applications, data visualizations, and automations. Ecommerce and retail became holistic experiences seeking loyal customers and subscription services. Companies grappled with supply chain issues, growing security threats, and now a looming recession. Remote work became a hybrid model and led to the great resignation.

Organizations need Digital Trailblazers to drive innovation and transformation

It became clear to me that organizations needed more than technology and driving digital practices to accelerate transformation. Boards, CEOs, CIOs, and CDOs need leaders who drive transformation while reading the tea leaves, knowing that “transformation requires saying yes, no, maybe, do more, do less, pivot, and stop” – one of the many quotable phrases in Digital Trailblazer. Are you a Digital Trailblazer, or maybe you have an ambitious and aspiring leader on your team ready to step up and become one?

Transformation requires saying

I develop my stories into a raw, first-person narrative of what goes on behind the scenes in leading transformations. I share what it was like answering questions at one of my first board meetings and how to develop consensus on a new product’s minimally viable product. I reveal several very personal stories, including what it was like to lead a startup in lower Manhattan during 9/11.  

More importantly, I target the book toward aspiring transformation leaders. I have several people and personas in mind – some lifelong learning CIOs always looking to improve their strategies, but many others who aspire to lead transformations and accelerate their careers. To help translate my stories into best practices, I add 50 leadership lessons to the book, five at the end of every chapter.

Digital Trailblazer: Read the book, join the community

In September 2021, an editor at Wiley expressed interest in publishing Digital Trailblazer, and I agreed to finish the manuscript by the end of the year. I partnered with Ginny Hamilton to help me edit the book. Some chapters only needed small tweaks, and others required full rewrites. We wrestled over the book’s title and cover. Thank you, Ginny and Wiley!

The book debuted last week, and I am excited to share it with the world. Like transformation, the book is the start of a journey, and readers will find ways to get access to the StarCIO Digital Trailblazer Community.

I believe hope you will read Digital Trailblazer readers will enjoy reading my stories and reflecting on the lessons I share. I look forward to your feedback.

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