Alan Fowler – Digital Strategy and AI Enablement

February 10, 2026

Prospective Clients:

Don’t see yourself in this case study? Great! I am always interested with exploring possibilities so please, book in a call.

Alan Fowler is a seasoned professional and now associate at the University of Edinburgh’s Edinburgh Futures Institute (EFI). Alongside delivering complex training sessions (such as the “D4” sessions for The Challenges Group) and mentoring others, Alan is currently writing a comprehensive book. Having lived “two-thirds” of his life before the world became electronic, Alan is highly knowledgeable but self-admittedly resistant to successive waves of technology, preferring robust, traditional workflows.

The Challenge

Alan faced a dual challenge of day-to-day digital friction and a daunting creative project:

Technical Friction: He struggled with recurring university IT issues, such as Microsoft 365 Exchange login loops, SharePoint access, and syncing calendars across his Apple devices. He also found simple formatting tasks, like keeping his email signatures consistent, unnecessarily frustrating.
Creative Roadblocks: His ambitious book project had hit a bottleneck. He needed to convert heavily structured, bullet-point notes from later chapters into the “smooth-flying prose” established in his early chapters, all while meeting his traditional publisher’s strict requirements (e.g., a minimum of 70,000 words, specific fonts, and formatting).

The Solution

I engaged Alan through a bespoke contract (which I now deliver under my Strategy Session(s) package) acting as both an AI Training Consultant and an Operational IT Consultant. This tailored, 1-on-1 collaboration was delivered through a flexible mix of in-person and online meetings, and the specific services were:

AI Book Revision Training: I guided Alan through setting up ChatGPT Plus, immediately disabling data sharing to ensure his intellectual property remained private. We established a prompt workflow where he used a polished chapter as a style reference to rewrite structured drafts into flowing prose. This allowed him to maintain his unique voice while drastically speeding up the drafting process. ChatGPT was chosen due to existing familiarity with the app and because the skills taught apply universally.
Apple Ecosystem & Workflow Optimisation: I trained Alan on leveraging the Apple ecosystem, such as using Universal Clipboard to seamlessly copy and paste research links between his iPhone and Mac. I also resolved persistent Apple Mail bugs, standardising his academic email signature blocks to a consistent 12-point font.
IT Troubleshooting & Security: I standardised his sign-in processes for MS365 and Eduroam by auditing and correcting saved credentials in his Apple Passwords App, ensuring seamless fingerprint and FaceID authentication across his devices without constant login prompts.
Streamlined Client Experience: To reduce administrative overload, I onboarded Alan onto my centralised client portal. This provided him with easy access to AI-generated session summaries, straightforward invoices, and appointment links.

The Results

The tailored Strategy Sessions successfully bridged the gap between Alan’s traditional expertise and modern digital tools.

Accelerated Book Drafting: Alan was empowered to use ChatGPT to rapidly convert structured notes into prose, overcoming a major writing hurdle and achieving a publisher-ready format with authentic writing style that perfectly met his requirements.
Eliminated Tech Frustrations: By fixing his MS365 and Passwords App issues, Alan no longer faced the daily friction of being locked out of his university accounts.
Enhanced Digital Independence: Alan gained confidence in navigating his digital environment, utilising trackpad gestures, password managers, and clipboard syncing to make his research and communication more efficient – and fun!

Conclusion/Takeaways

This collaboration underscores the importance of empathetic, patient tech support when working with highly experienced professionals. By addressing both granular IT frustrations (like password syncing) and introducing cutting-edge AI tools as supportive co-pilots through a hybrid of in-person and online support, his work-flow was transformed from a source of stress into an empowering asset. Alan is now better equipped to share his extensive knowledge, finish his book, and navigate his academic commitments with ease.

“Charlie helped drastically reduce the time and effort needed to respond to re-login requests for University and Microsoft security systems, which was a huge relief.

The purpose of using software and apps is to accomplish work, but technology often ends up demanding attention and time for its own purposes rather than mine. That unpredictably reduces productivity, which is frustrating both for me and for the people I serve. Being helped to remove some of those blocks therefore made a significant difference.

What stood out most to me about his service was the accurate listening to the problem, openness to follow my own way of thinking and work with it, strong technical know-how, focus and follow-through, and the provision of notes for later reference. Those qualities made the support both effective and genuinely useful long after the work itself was completed.”

Elderly man with glasses smiling broadly, wearing a suit and tie.
Alan FowlerDesigning and building futures with people and organisations