Digital transformation: How to guide innovation leaders

'Digital Trailblazer' author Isaac Sacolick shares insights on digital transformation, innovation, and leadership
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digital transformation

Every CIO I speak with aims to improve customer experiences, automate workflows, innovate new digital products, and achieve other digital transformation goals.

From my years as a transformational CIO and leading StarCIO, my experience is that technology rarely roadblocks transformation, even for companies with mounds of technical debt. Organizations struggling to deliver ongoing business impacts from data and digital transformations are more likely to struggle to develop experimental cultures, organize multidisciplinary agile teams, and mentor transformation leaders.

Finding leaders ready to take on innovation and transformation programs

I tackle these topics in my new book, Digital Trailblazer: Essential Lessons to Jumpstart Transformation and Accelerate Your Technology Leadership (Wiley, July 2022). I share my stories leading transformation and provide 50 lessons for Digital Trailblazers – my name for the aspiring, innovative, driven, and transformative leaders in an organization.


Digital Trailblazers are lifelong learners and can start their careers in product management, technology, security, or data roles. What sets Digital Trailblazers apart is their ability to ask the questions that challenge people’s thinking and get into the weeds around customer experience, data quality issues, or how to integrate emerging technologies.

[ Also read 9 CIOs share the tips that shaped their leadership style. ]

But finding Digital Trailblazers isn’t easy, and guiding them requires leadership’s commitment to empowering their creativity and collaboration. CIOs who dedicate themselves and their lieutenants to seek and guide aspiring transformation leaders are setting their entire organization up for success for years to come.

Once you identify these leaders, you must encourage them to step out of their comfort zones because many will soon be experiencing firsts such as presenting to leadership, responding to detractors, or making tough calls in setting priorities.

In the book, I tell the stories of what it feels like to be a Digital Trailblazer, knowing they will face many new experiences. I’ll share an excerpt from the chapter “Buried in bad data.” It’s a story about how Donna, a marketer with strong data literacy, partners with the technology team to develop dashboards to guide their lead-generating experiments. It illustrates how you never know where you’ll find Digital Trailblazers in your organization.

Empowering marketers with data visualization tools and agile data practices

When you’re looking for a strategic business partner to experiment and collaborate with, try identifying a team in the marketing department that could benefit from your technical expertise. Make sure you’ve done your business homework and are approaching the conversation with a basic understanding of marketing’s goals and priorities. Ultimately, you can use these collaborations to build champions for your team's transformative work.

Here's an excerpt from Digital Trailblazer:

“I’m about a year into my job as CIO when Alice comes to me with her small data problem. She’s had roles in corporate reporting, and our CMO Eleanor hires her to make sense of all the different marketing campaigns they are running.

‘We’re buying keywords across three platforms and placing ads in several magazines,’ she explains. ‘We run surveys and award the top businesses, which gives us a powerful lens over who may be prospects for our products. But a lot of our work includes buying marketing lists and providing leads to the inside sales team, only they push back when they miss their quotas and claim we’ve given them unqualified opportunities.’

I try to picture what this well-oiled machine looks like and ask Alice if she’ll share with me how this works today.

‘Can I bring in Donna to show you?’ she asks.

Five minutes later, Alice returns with Donna, an early-career marketing analyst, who opens her laptop and starts showing me how she’s doing her work today. ‘I get lists from three providers and merge them into three sheets in this Excel. I then have to merge them into one, but that’s not easy because all we have are names and email addresses with spelling errors and other idiosyncrasies.’

Donna shows me a gargantuan formula that helps merge the list and walks me through several of its components. I am impressed because she has an organized problem-solving approach like a coder, but she’s a marketer, and I wonder if she’s had any computer science training. I ask her to tell me about her background, and I learn she studied anthropology in college and interned with our company the previous summer. This is her first job out of college.”

The secret for CIOs is developing Digital Trailblazers

I complete the story with Donna shifting off spreadsheets to data visualizations, partnering with the tech team to work on data ops, and becoming a product owner for an agile team. A few years later, Donna became director of a large data analytics department.

How could CIOs identify, mentor, and retain people like Donna? Here are some questions to consider:

  • Would your talent development programs quickly identify someone like Donna, or must you take a much more active role in identifying Digital Trailblazers?
  • Do you have training and mentoring programs so people like Donna can learn and apply new technologies in their day-to-day work?
  • Are you ready to assign people to agile teams to experience the full lifecycle of delivering innovations?

Those are great starting points, but the next and often missing link is helping these aspiring transformation leaders become Digital Trailblazers with the breadth of skills necessary to lead change.

Donna had to survive several detractors, including the CEO, who initially missed the big picture of what citizen data science would enable her and the team to accomplish. In the book, I tell stories of other Digital Trailblazers, such as the innovator spearheading agile startup practices when the enterprise was stuck with waterfall strategic planning practices. Other stories are around crisis management, handling P1 incidents, and developing product management disciplines, all circumstances Digital Trailblazers are likely to face but may not yet know how to handle.

I wrote Digital Trailblazer to help you and people like Donna be better prepared and have the confidence to handle what really happens when leading transformations. I hope you will consider reading Digital Trailblazer, sharing it with your team, and discussing its lessons.

[ Leading CIOs are reimagining the nature of work while strengthening organizational resilience. Learn 4 key digital transformation leadership priorities in a new report from Harvard Business Review Analytic Services. ]

Isaac Sacolick is the president and founder of StarCIO, a technology learning company that guides leaders on digital transformation. A lifelong technologist, Isaac has served in startup CTO and transformational CIO roles.