Digital Transformation: How to Drive its Best Practices as Competitive Core Competencies

 I wrote the post the #1 reason digital transformations fail nearly five years ago. I shared, “The number one reason digital transformations fail is because executives fail to embrace that it’s a bottom-up transformation that will require change across the organization over a 3 to 7+ year period.”

Digital Transformation as Organization Core Competency in Digital Trailblazer by Isaac Sacolick

I feel this statement is true today as much as it was then, in March 2018, when many organizations were in rounds one or two of their digital transformations. Back then, it was common to hear executives tout their digital transformation strategies and watch their town hall performances. But too many organizations underestimate the effort involved in engaging and inspiring their staff, and that’s one reason why many digital transformations fail to deliver business outcomes.  

Of course, what I didn’t know at the time is that we’d face a pandemic starting in 2020, a “new normal” of hybrid work in 2021, inflation, supply chain disruption, and war in Eastern Europe beginning in 2022, and now you decide which economist to believe whether we’re in a global recession or not.

Digital transformation is not a destination or journey; it’s an organizational competency 

In the five years since that post, I believe most companies rewrote their digital strategies several times, accounting for these macro conditions, let alone what was happening in their industries and changes in business strategies. Early last year, I wrote a post about digital transformation 2.0 to reckon with and advise business, technology, digital, and data leaders about the next wave of transformation.

It was around the time of that post when I finished the writing and editing of Digital Trailblazer. One of my pivotal statements in the book summarizes my feelings on digital transformation and why it’s more important than ever for leaders – i.e., people I title Digital Trailblazers, to continue driving their organizations:

“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.” – Isaac Sacolick, in the preface to Digital Trailblazer

I share my aha moments, blow-ups, and other stories you’ll likely face while leading digital transformation initiatives. I also identify fifty transformation lessons, starting in Chapter 1 with, “Step out of your comfort zone and broaden your perspective by seeking outside‐in learning opportunities,” and ending in Chapter 10 with, “Accelerate bottom‐up transformation and grow middle adoption.”

You must apply both these lessons if “you will always be transforming.”

Evolving from Driving Digital practices to transformation core competencies

StarCIO Centers of Excellence

If transformation requires growing middle adopters and you will always be transforming, what does it mean to “establish transformational practices as essential core competencies.”

I describe transformational practices in many of the agile, devops, data-driven, product management, and low-code posts on this blog and in detail in my first book, Driving Digital. My company, StarCIO, offers Center of Excellence and Digital Trailblazer Advisory programs to guide organizations.

Going from practice to core competencies requires organizations to

  • Assign responsibilities to transformation leaders (Digital Trailblazers) who empower self-organizing teams while driving standards
  • Write and update vision statements so that initiatives have a customer and strategically driven north star
  • Build feedback mechanisms through inclusive conversations, brainstorms, customer engagements, outside-in learnings, experiments, KPIs/OKRs, and metrics
  • Define decision-making principles and authorities
  • Commit to continuously improving driving digital practices through a regular release cadence

In my most recent Driving Digital Standup video, I provide an update on what it means to be a Digital Trailblazer and one way to build digital transformation as a core competency — more to come in future posts and the monthly Driving Digital Newsletter.

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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.