Are you a Digital Trailblazer? Develop the Skills and Confidence to Lead Transformation

She was a developer with an innate talent for UX. A leader with big ideas but trapped supporting a website on an outdated content management system. She learned agile, led offshore development teams, and developed her confidence to become an architect on several modern SaaS platforms.

Isaac Sacolick - Digital Trailblazer

He could have just been another software developer on one of our teams, trying to navigate his way through legacy code and hopefully make an impact with his innovations. But inside him was an architect, a delivery leader, and someone that scores of teammates admired. Years later, he became an SVP of technology and a technical advisor at several startups.

She was a community leader that I met at a conference, and one day, I bet she will be an editor of a major website, an author, a CMO – or maybe all three, driving impacts no matter what she elects to do.

Who are the leaders driving digital transformation?

I meet people like them while leading workshops, keynoting conferences, partnering with technology companies, or guiding leaders on centers of excellence programs. Some have already earned their “C” titles and are looking to expand their leadership skills, while others are early in their careers and want to learn how to take on roles in transformation initiatives.

I call them Digital Trailblazers. They are aspiring leaders, drivers of transformations, and people who continuously step out of their comfort zones. Over the years, I have learned to recognize the signs of their potential that may not be easily identifiable to the executives they report to or show up in their yearly performance reviews.

And I tell some of their stories in my new book, Digital Trailblazer: Essential Lessons to Jumpstart Transformation and Accelerate Your Technology Leadership. They include a data analyst who learned Tableau – she went on to lead a BI program at a Fortune 100 enterprise, and a product manager who now is a CTO at a major data and analytics company. The book covers many of the difficult situations leaders face when stepping up into transformation roles where they are often learning on the job. Each chapter has my hard-learned stories, and then I share five key lessons learned for digital trailblazers.

As I write this post, I am coming home from my first keynote where I introduced why Digital Trailblazers are the key to successful digital transformations. At the end of my presentation, a leader asks me, “Isaac, how do you find them?”

I thought for a second and answered, “They find me.”

Digital Trailblazers challenge the status quo

Isaac Sacolick - Digital Trailblazer

It’s true. A Digital Trailblazer’s desire to learn more, take on greater responsibilities, and find ways to excel at what they set out to do is a beacon.

They find me by asking hard and challenging questions in ways illustrating they are ready to share their expertise while being humble about what they don’t know. They are lifelong learners, always looking to improve the depth of their skills and the breadth of their knowledge. For example, I met a Digital Trailblazer a few weeks ago, a project manager trying to learn test automation and how it might improve the speed and quality of their deliverables.

When I meet them, they may not be experts on scrum or agile methodologies, but they are developing an agile mindset and are ready to experiment. They are driven but also empathetic. They embrace diversity by getting to know people from the inside out, learning about the experiences that shape their teammate’s opinions, and identifying people’s strengths and interests.

What Digital Trailblazers do differently to lead transformations

The Digital Trailblazer’s decision-making is deliberate, instinctive, and most importantly, balanced in which lever to pull, when, and how hard. They think about when to be fast, when to be safer, and what areas to drive innovation. Digital Trailblazers ponder which capabilities improve customer experiences, when to increase operational efficiency, or what technologies to invest in a POC. They are data-driven but aren’t waiting for perfect information or consensus.

And they aren’t afraid to get in the weeds and roll up the sleeves to get something done. But they do this selectively and in ways where their efforts lead to sustainable and evolving ways of doing work. They are learning, driving, and teaching all at the same time.

Are you a Digital Trailblazer?

Being a Digital Trailblazer requires developing a broad perspective around the future and the grit to drive transformation. It’s not easy and can be stressful, but you can develop the skills and confidence by learning, questioning, and experimenting. As one CIO told me, you must develop the muscles to drive transformation – and that requires a commitment to developing your leadership skills, a willingness to challenge yourself, and an openness to collaborate with diverse-thinking teams.  

As I prepare to launch my book Digital Trailblazer, I plan to share more stories, advice, and tools for Digital Trailblazers and their executive sponsors. I will publish some of it here on this blog and some for people who sign up for previews of Digital Trailblazer. Whether you’re already a Digital Trailblazer and want to strengthen your skills or seek to cultivate more Digital Trailblazers on your team, this ongoing series will help you broaden your perspectives on what’s required to drive transformation.

To start, please watch this week’s episode of 5 Minutes with @NYIke where I share three critical leadership skills of Digital Trailblazers.

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About Isaac Sacolick

Isaac Sacolick is President of StarCIO, a technology leadership company that guides organizations on building digital transformation core competencies. He is the author of Digital Trailblazer and the Amazon bestseller Driving Digital and speaks about agile planning, devops, data science, product management, and other digital transformation best practices. Sacolick is a recognized top social CIO, a digital transformation influencer, and has over 900 articles published at InfoWorld,, his blog Social, Agile, and Transformation, and other sites. You can find him sharing new insights @NYIke on Twitter, his Driving Digital Standup YouTube channel, or during the Coffee with Digital Trailblazers.