A storm is brewing outside, and it's a perfect metaphor for today's workshop. I'm speaking to a room filled with business leaders, technologists, and innovators who seek my outside‐in perspective on transforming their business. Some are eager to evolve their organization's digital strategies, while others are apprehensive about changing what works today.

I'm readying the group for the day's first collaborative exercise, and I need everyone's full participation. I'm on my toes, raise my hands, and shift my gaze from one leader to the next to get people's attention as I explain today’s and tomorrow's realities. Outside the conference room windows, I see the sky darken.

“I know you're working harder and faster than you've ever had to before, and your teams are out of breath,” I tell them. “You have the right instincts because the transformation initiatives you're leading are on a treadmill that must accelerate to remain competitive. What was emerging technology two years ago, for example, natural language processing, AR/VR experiences, and real‐time data processing, is becoming mainstream.

“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.”

I pause and look around the room. I need the message to sink in without me saying it. Today's innovations are great progress, but they will become tomorrow's legacy systems. They will need to transform again and again. The treadmill doesn't slow down, but the organization can build up the endurance to run marathons. That's why this next point is so important.

“And your business will need more transformation leaders—what I call Digital Trailblazers—who can lead teams, evolve sustainable ways of working, develop technologies as competitive differentiators, and deliver business outcomes.”

I look around the room and wait till all eyes are on me, then ask everyone a fundamental question.

“Are you ready to take on a digital transformation leadership role in your organization?”

That's the question and advice I share with product management, technology, and data leaders aspiring for greater responsibilities. You must learn to become a Digital Trailblazer. You must develop the skills to define a vision for digital transformation initiatives, lead agile teams, and evolve technology practices. I wrote this book for you to read my stories and learn the lessons that can grow your responsibilities, guide you through handling a transformation's challenges, and accelerate your career.

You've probably already had roles in digital transformations. Maybe you're a product manager and launched digital products, improved customer experiences, and delivered financial results. Perhaps you're a software developer, DevOps engineer, work in IT Ops, or are an architect who has modernized application architectures, automated workflows, or developed customer‐facing applications. You may also work in data science, DataOps, or data governance, paving your company's data‐driven journey. Or maybe you're a business leader committed to learning the more technical aspects of digital transformation.

This book serves as a guide to help you expand your skills and confidence in leading transformation initiatives. Through my collection of stories and lessons, you will see some challenging scenarios unfold without waiting for them to happen to you. In writing this book, I intend to help current and future leaders accelerate their journeys in technology leadership by giving candid accounts of how I handled transformation's challenges.

Product management, agile development, DevOps, and proactive data governance are digital transformation's building blocks. From those starting points, I hope you want to expand your skills and confidence in leading transformation initiatives that will help evolve the business model, target new markets, and deliver innovations. But it's not easy, and program managers and scrum masters must help teams collaborate, improve productivity, and deliver quality results.

I hope you are one of these high‐potential leaders—and maybe you've already experienced some of the challenges, such as addressing technical debt, getting buy‐in for data governance programs, or winning over detractors who hold on to the status quo. I'll be sharing insights around these and many other transformation leadership issues in this book.

Or maybe you're already on your leadership journey. You oversee transformation initiatives and guide multidisciplinary teams but maybe have little experience presenting to the board or the strategic leadership team. When should you create a blow‐up or shock‐and‐awe moment to help teams see opportunities from new perspectives? How do you balance innovation, self‐organizing practices, and standards to evolve your organization's way of working?

You also might be a director, a vice president, or a senior vice president and striving to one day become a CIO, CTO, or CDO (both digital and data).

When I meet people like you in any of these roles, you tell me how hard it is to just keep up with the technical skills required to be employable. And now, you're faced with new leadership challenges that are hard to learn without direct experience.

Let me share how I got here and how my journey can help you accelerate your path to becoming a Digital Trailblazer.

After studying machine learning and medical image processing in graduate school at The University of Arizona, I take a job as a software engineer at a biotechnology company where I develop algorithms to compare genetic samples. I learn the basics of developing commercial software applications, but the Wild West of building internet applications at a startup lures me to New York City, and less than two years out of graduate school, I join this media startup as their director of software development. Back then, working at an “internet company” and joining a startup is a nontraditional career path, but I have a history of taking the off‐beaten trail and just see an adventure into unchartered territory.

The founding CTO hires me to build a natural language processing engine to enable our search algorithms. We are having dinner where he tells me I won the job, then asks me if I want to hire the ex–Russian signal processing expert now cab driver sitting next to us. I do, and we go on to create the foundations of our software development lifecycle. But after a couple of years, several strategic investors come in and refinance the company. The founding CTO goes on to other opportunities, and I land the CTO job.

It's the late 1990s. I'm in my twenties and promoted to CTO of a growing and promising startup. It's still fairly uncommon to see young CTOs, but the internet is evolving from a technology tool to a disruptive business model, and it's my generation that's driving the innovation.

And now, I am the most senior technical leader in my startup and manage an office network, a colocated data center, and dozens of tech vendors. It isn't the first time I have had to figure out new technologies independently, and I am building confidence to manage the new responsibilities.

I report to the CEO and attend our board of directors meetings with highly seasoned executives. I must prove the organizational model and execute my strategy to grow the team, mature the development process, and scale the infrastructure. My responsibilities require creating multiple strategic plans and selling my strategies to colleagues, the CEO, and the board.

I'm young, cocky, and overly confident. Figuring out the technologies isn't the hard part. Managing the team has its challenges, but we're a small organization aligned to our vision. Partnering with other leaders and driving through the murky waters of growth, well, let's just say I have many hard lessons learned from the experience—and that's part of what I want to share with you.

Less than ten years later, I pivot my career and leave the world of being a CTO in startups to one leading transformation as a business unit CIO in an enterprise. Again, I am ahead of the times, a young CIO in his thirties, and entrusted to lead an organization through significant change. I go on to be a transformational CIO in three companies over the next ten years.

I had a front‐row seat to industry transformation and disruption. I watched newspapers, magazines, banks, financial service companies, nonprofits, commercial construction contractors, manufacturers, tech startups, SaaS companies, universities, and other companies struggle with transformation.

I established several best practices during this period and started blogging in 2005 to share my insights. Today, I have over 800 articles published on leading publications for IT leaders, including CIO.com, InfoWorld, The Enterpriser's Project, and my blog, Social, Agile, and Transformation.

That led to my first book, Driving Digital: The Leader's Guide to Transformation Through Technology, an Amazon bestseller. This book shares detailed best practices on agile continuous planning, product management, citizen data science, and others instrumental to the transformations I led. You might have seen me keynote, speak, or moderate panels at one of the 150 events from 2017 through 2021.

I highlight several foundational practices in my roles as a CTO in startups, a CIO in transforming businesses, and now as CEO of StarCIO, a digital transformation consulting and services company.

Many organizational leaders understand top‐down strategic planning. But transformation also requires “bottom‐up” practices, knowledge sharing, innovation, and transformation management. Businesses need the ideas, innovations, and process improvements from everyone in the company to best adjust to market changes, excel with customer experience, and digitally enable the workforce. The essential transformational practices include continuous agile planning, DevOps, product management, becoming a data‐driven organization, citizen technology capabilities, proactive data governance, hyperautomation, and culture transformation.

As I collaborate with more digital and technology leaders, it becomes apparent that as transformation grows in importance across more industries and businesses of all sizes, it is critically vital to groom new transformational leaders. My most vocal supporters are not just the CIOs, CTOs, CDOs, and product leaders but their direct reports and secondary reports. These leaders are challenged by the growing technical skill gaps, which are significant, but they also struggle with the leadership skill challenges and forming diverse leadership teams.

Let's consider how much has changed just over the last five years.

Five years ago, data scientists could get away with being data visualization experts and later learn fundamental statistics and analytics. Today, you need expertise in DataOps, predictive analytics, and machine learning. Organizations look for “full stack” software developers who can build applications from the front‐end user experience all the way through their underlying database architectures. Operational engineers must not only keep the applications, databases, and networks reliable, secure, and high performing, business leaders expect you to automate most of the infrastructure and deployment processes. Product managers can no longer just prioritize backlogs, and you must learn how to research markets, capture customer needs, develop visions, and sell business cases.

But nowhere in these expectations, development needs, and mentoring is an easy path to learn transformation leadership skills. Classroom learning isn't sufficient to help you lead diverse, agile, and innovative teams that drive transformation management and change the culture. You will encounter challenges educating colleagues on leveraging data, intuition, and listening to others when making decisions. And when detractors emerge to transformation programs, how do you sell them on the vision, quell their fears, and win over their support?

And while organizations of all sizes often offer their own leadership programs—or funding for their people to learn leadership skills through conferences and classes—there's only so much you can cover. In fact, my company, StarCIO, has workshops in digital transformation, agile planning, DevOps culture, data‐driven methods, and product management practices, and we help teams select a limited number of learning sessions to cover in any one workshop. But there are only so many stories that I can tell during a keynote, course, or workshop.

That's how the idea for this book came to me. I wanted to tell more of the stories behind my first book, Driving Digital. It's through stories that many of us learn and remember our best lessons. It is why Steve Jobs' presentations are so memorable and why TED Talks are so successful. Before we can learn from our actions, decisions, and mistakes, we learn largely through other people's experiences.

That's what I hope to do here. Each chapter is a mashup of stories from my career, and I jump back and forth in time to expose some of the key learning moments that remain relevant today. The names and characteristics have been changed, some events have been compressed, and some dialogue has been recreated. There are times when I am critical of people's behaviors and approaches—including my own. I mean no harm or disrespect to anyone and hope all will read this in the spirit of learning and improving.

Product, technology, data, and digital leadership are complex responsibilities requiring many skills, practices, and diverse perspectives. It's tough, fast, and can be unforgiving, and that's why I share some of these stories. At the end of each chapter, I conclude and share the underlying leadership lessons, and there are more than fifty transformation leadership lessons published in this book. You can also find more information about these lessons at https://www.starcio.com/digital-trailblazer/intro.

You will learn transformation leadership through your own experiences and hard lessons, but these stories and lessons will help you accelerate the journey to digital trailblazer.