Top Leadership Attributes of Really Successful Digital Trailblazers

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!

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!

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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.