--- title: "Episode 28: Rethinking Digital Transformation with Cheryl Smith Part II" description: Explore how Duncan McGregor tackles customer business challenges with cloud migration, private networks, and 5G technologies in Episode 1 of Enterprise Intelligence for Innovators. image: https://jasonwdcassidy.com/hubfs/AI-Generated%20Media/Images/The%20image%20depicts%20a%20modern%20office%20environment%20with%20a%20sleek%2c%20minimalist%20design.jpeg --- [Skip to main content](https://jasonwdcassidy.com/blog/ei-episode-28-cheryl-smith#main) [![Jason Logo](https://jasonwdcassidy.com/hs-fs/hubfs/logo50x200-1.png?width=200&height=50&name=logo50x200-1.png) ![logo50x200-1](https://jasonwdcassidy.com/hs-fs/hubfs/Logos/logo50x200-1.png?width=200&height=50&name=logo50x200-1.png) ![logo50x200-1](https://jasonwdcassidy.com/hs-fs/hubfs/Logos/logo50x200-1.png?width=200&height=50&name=logo50x200-1.png) ![logo50x200-1](https://jasonwdcassidy.com/hs-fs/hubfs/Logos/logo50x200-1.png?width=200&height=50&name=logo50x200-1.png)](https://jasonwdcassidy.com) Open main navigation Close main navigation - Search - [Recent Posts](https://jasonwdcassidy.com/blog) [Recent Posts](https://jasonwdcassidy.com/blog) Search # Episode 28: Rethinking Digital Transformation with Cheryl Smith Part II ![Jason W. D. Cassidy](https://jasonwdcassidy.com/hs-fs/hubfs/Headshots/jason-casual-outdoors.jpg?width=50&height=50&name=jason-casual-outdoors.jpg) by [Jason W. D. Cassidy](https://jasonwdcassidy.com/blog/author/jason-w-d-cassidy) Mar 10, 2022 [https://youtu.be/dv-ZfmuMR9c?si=Al7bu58HRq9IWZ\_U](https://youtu.be/dv-ZfmuMR9c?si=Al7bu58HRq9IWZ_U) In this episode of Enterprise Intelligence, host Jason Cassidy welcomes Cheryl to the show for the second part of their conversation to talk about the process of co-authoring the book as well as the opportunities and challenges she sees for organisations in the years to come. [Check out Part I here](https://jasonwdcassidy.com/blog/ei-episode-27-cheryl-smith). Do great leaders create the times, or do the times create great leaders? That’s the question Cheryl Smith asks in her leading book, The Day Before Digital Transformation: Unlocking digital transformation for business leaders. As an IT expert and experienced business leader consultant, there is perhaps no one better qualified to make the vague concept of Digital Transformation easier to understand and take action on. Cheryl Smith has led IT at Fortune-ranked companies for 20 years. She was the global CIO at McKesson Corporation, KeySpan Energy (now National Grid), and WestJet Airlines, was the VP of Strategic Systems at Verizon, and a Principal at EY. On top of being a co-founder of the CIO Institute at UC Berkeley’s Hass School of Business, Cheryl has helped to create a leadership program at the Professional Development Academy (PDA) with General Colin Powell, and has served on several Advisory Boards including IBM and Oracle. For more of Cheryl’s insights, follow her on LinkedIn: [https://tinyurl.com/bdcuk9ep](https://www.youtube.com/redirect?event=video_description&redir_token=QUFFLUhqbDYxOWYzVlRRaTFvcDVhRUdFUU9pcHloRDZuZ3xBQ3Jtc0tuTWExbHdQN0ljWGk3NGNpNFB0dzExSGpFc1E4enRkX21hUE5LV2hBT0tpTGZNNG5INzdVaVVnUUhpbDBUaVRiUXdKTjhCc01KZWhGdDVqbGFkSFJZNDl4WTNXQU5WbVJIREtoenJ2SnRDYkpYSGk5UQ&q=https%3A%2F%2Ftinyurl.com%2Fbdcuk9ep&v=ehWu3i5e8K0)  **Tags:** [EI,](https://jasonwdcassidy.com/blog/tag/ei) [Podcast](https://jasonwdcassidy.com/blog/tag/podcast) ![Jason W. D. Cassidy](https://jasonwdcassidy.com/hs-fs/hubfs/Headshots/jason-casual-outdoors.jpg?width=50&height=50&name=jason-casual-outdoors.jpg) Post by [Jason W. D. Cassidy](https://jasonwdcassidy.com/blog/author/jason-w-d-cassidy) Mar 10, 2022 CEO at Shinydocs Corporation | Document and File Analysis Software | Privacy | AI | Cybersecurity | All your Documents, Files, and Records | Digital Transformation for Legal, Government, and Business [Follow me on my website](https://shinydocs.com) [Follow me on Facebook](https://facebook.com/jasonwdcassidy) [Follow me on LinkedIn](https://linkedin.com/in/jcassidy/) [Follow me on Twitter](https://x.com/JasonWDCassidy) ### Related Articles ##### [![EI 2024 - Artificial Stupidity](https://jasonwdcassidy.com/hs-fs/hubfs/ei/ei2024-1366x796.png?width=520&height=294&name=ei2024-1366x796.png) EI • Aug 05, 2024 EI 2024 - Artificial Stupidity 1 min read](https://jasonwdcassidy.com/blog/ei-2024-artificial-stupidity) ##### [![EI 2024 - Status Quo, Status Quo, Status Quo, Giant Leap!](https://jasonwdcassidy.com/hs-fs/hubfs/ei/ei2024-1366x796.png?width=520&height=294&name=ei2024-1366x796.png) EI • Jul 29, 2024 EI 2024 - Status Quo, Status Quo, Status Quo, Giant Leap! 0 min read](https://jasonwdcassidy.com/blog/ei-2024-status-quo-status-quo-status-quo-giant-leap) ##### [![EI 2024 - Tech; time to buy or time to sell?](https://jasonwdcassidy.com/hs-fs/hubfs/ei/ei2024-1366x796.png?width=520&height=294&name=ei2024-1366x796.png) EI • Jul 15, 2024 EI 2024 - Tech; time to buy or time to sell? 0 min read](https://jasonwdcassidy.com/blog/ei-2024-tech-time-to-buy-or-time-to-sell) ### Comments ###### Categories - [Podcast](https://jasonwdcassidy.com/blog/tag/podcast) - [EI](https://jasonwdcassidy.com/blog/tag/ei) - [Learning](https://jasonwdcassidy.com/blog/tag/learning) - [Success Stories](https://jasonwdcassidy.com/blog/tag/success-stories) - [Local Government](https://jasonwdcassidy.com/blog/tag/local-government) ###### Recent Posts - [How to Succeed at The 3 Content Use Cases Where Most of us Are Failing](https://jasonwdcassidy.com/blog/how-to-succeed-at-the-3-content-use-cases-where-most-of-us-are-failing) - [What Principles Guide Your Cyber Security and Governance Controls?](https://jasonwdcassidy.com/blog/what-principles-guide-your-cyber-security-and-governance-controls) - [Can you use Controls to Measure the Success of Governance and Cyber Security?](https://jasonwdcassidy.com/blog/what-tools-measure-the-success-of-governance-and-cyber-security) - [Are You Really Covered? Why Most Organizations Only Have Cybersecurity for Some of Their Content](https://jasonwdcassidy.com/blog/are-you-really-covered-why-most-organizations-only-have-cybersecurity-for-30-of-their-content) - [Cyber Security and Governance:  How to be the Hero saving Money, Time, and Reputational Risk](https://jasonwdcassidy.com/blog/cyber-security-and-governance-how-to-be-the-hero-saving-money-time-and-reputational-risk) ![JasonWDCassidyLogo220x50](https://jasonwdcassidy.com/hs-fs/hubfs/Logos/JasonWDCassidyLogo220x50.png?width=220&height=50&name=JasonWDCassidyLogo220x50.png) Caffeine, Curiosity, Creativity ©2026 Jason W. D. Cassidy All rights reserved. [Privacy Policy](https://jasonwdcassidy.com/privacy-policy) - - - - - ```json { "@context" : "https://schema.org", "@type" : "BlogPosting", "author" : { "@type" : "Person", "name" : "Jason W. D. 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