Drive has 700+ articles for digital transformation leaders written by StarCIO Digital Trailblazer, Isaac Sacolick. Learn more.

At a recent Coffee with Digital Trailblazers, we discussed who are the right people to lead digital transformation initiatives in their organizations – leaders that I call Digital Trailblazers. I chose this topic as an extension to Chapter 8 of Digital Trailblazer, where I ponder the advice from boards of directors and CEOs on finding the right leaders to oversee the organization’s digital transformation initiatives.

From the discussion, we captured fifty attributes of Digital Trailblazers that I grouped into five competencies:

Digital Trailblazers Top Competencies and Attributes

  • Leadership skills and mindset: How Digital Trailblazers inspire, influence, and change mindsets.
  • Personal Competencies: The learned characteristics, behavioral traits, and other acumens.
  • Transformation: How Digital Trailblazers manage up and collaborate with other leaders and their peers to challenge the status quo and transform the business.
  • People skills: How Digital Trailblazers collaborate with teams, partners, and people.
  • Digital skills: The technology, data, and other skills Digital Trailblazers use to develop solutions, select MVPs, plan initiatives, deliver releases, and transform experiences.

Once categorized, I interviewed several executive Digital Trailblazers to weigh in on their top attributes for each competency. You can watch the episodes on the Driving Digital Standup’s playlist, with stellar advice from Martin Davis, Joanne Friedman, Tyler Johnson, and Joe Puglisi.

I’ll release a white paper and dashboard on these competencies soon. Please sign up for the Driving Digital Newsletter, and I’ll notify you when it’s available.

Top Digital Trailblazer leadership skills and mindset

As a preview, here’s how respondents voted on the top leadership skills and mindset of Digital Trailblazers. Each respondent was asked to select two from the list of attributes.

Digital Trailblazer Leadership Attributes

When reviewing the data for all five competencies, a pattern emerged separating attributes. I segmented the top 25% quartile and labeled it “Top” and the bottom 25% quartile as possibly “Less Important” based on the respondents’ selections. I labeled the middle 50% segment as “Situational,” as they are likely attributes needed for specific culture, goals, or types of transformation initiatives.

Digital Trailblazers are value-driven strategic thinkers

Career checklist for data leaders The results say that, above all leadership skills and mindset, Digital Trailblazers are strategic thinkers and spearhead value-creation in their organizations. They can be product managers brainstorming new customer-facing products, services, and capabilities, architects demonstrating how consolidating platforms leads to improved experiences and productivity, or data scientists who connect hypotheses to analytics and actions that improve profitability.

These are just some examples, and the takeaway is that Digital Trailblazers are innovative, question-asking, customer-driven, and strategy drivers in their organizations.

The situational attributes are ones that Digital Trailblazers are likely to need at different points in planning, delivering, and driving transformation change management. Many will have training in design thinking to conceive optimal experiences, are servant leaders when collaborating with agile teams, and will leverage their situational awareness skills when presenting their big ideas to executives.

I was surprised to see teacher and transparency attributes at the bottom, but perhaps respondents are saying these are table stakes for Digital Trailblazers, thus making it less important to call out as a top attribute.

StarCIO Vision Statement Template

If you lead digital transformation initiatives, use these guidelines to self-evaluate your mindset, skills, and behaviors. How are you delivering value to customers, and why is your initiative strategically important? Use the StarCIO Vision Statement Template if you need help in these areas.

More to come on Digital Trailblazer Competencies!

Published on:

Leave a Reply


StarCIO

My company, StarCIO, provides leadership, learning, and advisory programs for companies looking to accelerate delivering business value from digital transformation. Contact me if you’d like to learn more about partnering opportunities.


Isaac Sacolick

Join us for a future session of Coffee with Digital Trailblazers, where we discuss topics for aspiring transformation leaders. If you enjoy my thought leadership, please sign up for the Driving Digital Newsletter and read all about my transformation stories in Digital Trailblazer.


Coffee with Digital Trailblazers hosted by Isaac Sacolick

Digital Trailblazers! Join us Fridays at 11am ET for a live audio discussion on digital transformation topics:  innovation, product management, agile, DevOps, data governance, and more!


Join the Community of StarCIO Digital Trailblazers

About Drive

Drive Agility, Innovation, Transformation

Drive is the blog for digital transformation leaders brought to you by StarCIO and Isaac Sacolick.

Agility, Innovation, and Transformation are the three primary digital transformation core competencies that every StarCIO Digital Trailblazer must champion in their organizations. Learn more About Drive.


About the StarCIO Digital Trailblazer Community

StarCIO Digital Trailblazer Community

Revolutionizing traditional learning, networking, and advising experiences.

Visit the community


About StarCIO

StarCIO

About Isaac Sacolick

Isaac Sacolick

Author, 1,000+ articles, keynote speaker, Chief StarCIO Digital Trailblazer. Full bio


Driving Digital Newsletter

Driving Digital Newsletter

StarCIO Guides

StarCIO Agile Planning Guides

Digital Trailblazer

Digital Trailblazer by Isaac Sacolick

Driving Digital

Driving Digital by Isaac Sacolick

Driving Digital Standup

Driving Digital Standup

Coffee with Digital Trailblazers

StarCIO Coffee With Digital Trailblazers

Recognition

InfoWorld 2025 Judge
InfoWorld Technology of the Year 2024 Judge
Thinkers360 Top 10 in IT Leadership
Thinkers360 Top Agile Thought Leader
Thinkers360 Top DevOps Leader
Thinkers360 Top in Digital Transfomation
Thinkers360 Top in Analytics
Thinkers360 Top in Product Management

Discover more from StarCIO Digital Trailblazer Community

Subscribe now to keep reading and get access to the full archive.

Continue reading