“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.”
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
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
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
“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
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
Are you a Digital Trailblazer, or maybe you have an ambitious and aspiring
leader on your team
ready to step up and become one?
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 2022, 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.