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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

The One Technique You Need To Sharpen and Maximize Your Large Language Model

Large Language Models are just that - large. Like much of our work with others, LLMs require a bit of mentoring and coaching. To draw out the best it has to give, we have to train it to think like the rest of our team thinks.

Scott Smeester

August 10, 2023

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The Top Ten Scorecard CIOs Use To Grade Responsible Generative-AI

Generative AI has already proven to be beneficial; and it has already shown signs of concern. Your job is to ensure it is implemented and developed responsibly. What are your peers doing that you can't overlook?

Scott Smeester

July 27, 2023

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Tech and Business: How To Communicate For A Change (The Overview)

You must lead the way for technology and business to communicate for a change. And for the change to mean anything, you are going to have to change the environment in which all this talking is taking place.

Scott Smeester

July 20, 2023

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