10 Questions on Leading Gen AI and Driving Digital Transformation

I recently recorded an episode of the Politely Pushy podcast with Eric Chemi, sponsored by Bospar. We discussed how to make digital transformation a core competency, a favorite topic, and the heart of what I do at StarCIO.

10 Questions on Leading Gen AI and Driving Digital Transformation

Organizations must reinvent themselves every couple of years because of market, customer, and technology transformation opportunities and potential disruptions. Top company executives recognize that continuous transformation requires new leadership competencies, organizational practices, and cultural principles.

This week marks the second anniversary of publishing Digital Trailblazer, so it’s befitting that we started the interview by reviewing who Digital Trailblazers are, what digital transformation is today, and how Gen AI is impacting digital strategy.

The videos embedded below are clips of my responses during the interview. The links to the full interview are at the bottom of this post.

Who are Digital Trailblazers

Executing a digital strategy requires planning transformation initiatives, delivering innovative capabilities, and leading change management programs. Transformation leadership requires blending several skills, including product management, program management, solutions architecture – and disciplines, including agile planning, design thinking, DevOps, data science, and data/AI governance.

Digital Trailblazers build breadth and depth around these leadership skill sets, thus forming unparalleled transformation experiences and building confidence to lead larger-scale initiatives.

What is Digital Transformation in 2024+?

Two quotes from two books:

Driving Digital by Isaac Sacolick

“Digital Transformation is about looking at the business strategy through the lens of technical capabilities and determining how technology can improve the way companies operate and generate revenue.” – from Driving Digital.

Digital Trailblazer by Isaac Sacolick

“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.” – from Digital Trailblazer.

In the interview, I explain the history of digital transformation and how market, customer, and technology evolutions require organizational leaders to reimagine their businesses and realign transformation strategies.

How Generative AI Impacts Digital Transformation?

Generative AI introduces capabilities we’ve all been seeking for decades – the ability to ask questions in non-technical languages, make sense out of huge knowledge bases, and automate thinking steps that used to require significant time researching and processing.

While Generative AI delivers productivity improvements, its long-term value must go beyond this low-hanging fruit and deliver innovations, transformed customer experiences, and significant business model evolutions.

In the interview, I share the industries that stand most to gain – or become disrupted by gen AI.

Watch the full interview

Below are seven more questions I answered during the interview.

  • Is the size of the company a factor in digital transformation?
  • How do people learn about the uses of AI?
  • What skills should students focus on for a gen AI future?
  • What should CEOs, CIOs, and Boards care about regarding Gen AI?
  • What tech companies are excelling at their own gen AI transformations?
  • What are the most important areas to invest in outside of AI?
  • What areas should businesses review if they have to reduce costs?

You can see the full interview here and subscribe to the Politely Pushy podcast on Spotify, Google, Apple, and others.

My thanks to Ronan Sacolick for his help on this post.

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, 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.