What I Learned about Digital Transformation from Speaking to Hundreds of Leaders


You learn a few things when you spend a chunk of the year on the road attending and speaking at conferences targeting CIOs, CTOs, CDOs (Chief Digital and Data Officers), CISOs and some CMOs. I’ve attended and spoken at over twenty events this year to share insights and lessons from my book, Driving Digital: The Leader’s Guide to Business Transformation Through Technology and presented on several topics around digital transformation, enabling the data driven organization, driving business value with emerging technologies, enabling a culture of transformation and innovation, and creating business and IT collaboration with agile practices.

I recognize that most of you can’t afford to be on the road twice a month, so let me share some insights with you from the presentations I’ve attended, questions I’ve fielded, and discussions I’ve had this year with millennials just entering the job force to CXOs of Fortune 100 companies. I’ll be updating this posts with links to these articles when I publish them. If you’d like to be notified when one of these posts is online, please consider signing up for my newsletter.

Insights from Leaders on their Transformation Challenges


Over my next several posts, I’ll continue this story and cover the following themes

  1. Developing a Strategy for Putting People First in Transformation Programs

  2. We Are Doing Agile, but are not Agile

  3. Financial Practices are outdated for the Transformation Era

  4. We are More Successful Onboarding New Tech Versus Maturing It

  5. If Data is the new Oil, We’re Still Digging Wells

  6. What to do When My CIO Still Doesn’t “Get It”

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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, CIO.com, 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.