Article Library

Digital Transformation

Industry Articles

CIO Coaching Playbook: Align Legacy, Cloud, And Talent

This article outlines how CIO coaching drives enterprise value by aligning legacy systems, cloud strategy, and talent. It shows how modern CIOs can sharpen board communication, govern transformation with measurable outcomes, and build influence across the C-suite. Through coaching cadence, clarity, and confidence, CIOs turn technology alignment into business advantage.
Scott Smeester
November 11, 2025
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Avoiding Pitfalls In A Digital Transformation

Critical pitfalls to avoid during digital transformation – from methodology fixation to skills gaps – with actionable strategies for successful implementation.
Scott Smeester
November 19, 2024
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Ending the Isolation: A Conversation with Scott Smeester on Modern CTO

Scott Smeester's discussion on the Modern CTO podcast with Joel Beasley addresses the isolation often felt by tech leaders and the importance of community and mentorship in overcoming it. Highlighting key leadership skills like effective listening and strategic questioning, Scott emphasizes the need for tech leaders to extend beyond technical know-how to embrace innovation and collaboration. This conversation underlines the transformative power of support networks for personal and professional growth in the tech industry.
Scott Smeester
March 14, 2024
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Leadership Blogs

How CIOs Keep Their CEOs From Quitting

CEOs are quitting. A major reason cited is because they don’t have the skills to lead their company into transformation. The problem is, people misunderstand transformation. CIOs don’t. And that is why the CIO needs to help keep their CEO from quitting prematurely.

Scott Smeester

April 20, 2023

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How To Lead And Manage Your Company’s Use of ChatGPT and Generative AI.

The use of ChatGPT and generative AI has flooded companies with questions and concerns. CIOs are being asked for their perspective and for policies. How do you lead both reactively and proactively while encouraging calm and confident ways forward?

Scott Smeester

April 13, 2023

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The Problem May Not Be Technology Debt

Tech debt is a real cost. But there is a greater debt companies should fear, and on the flip side, it’s the one investment that must be made regardless of economic conditions.

Joe Woodruff

March 30, 2023

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