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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.
“Working with Charlie has been an excellent experience. He was always quick to respond to my questions, queries, and any problems that came up, often resolving things within just a few hours.
That level of responsiveness made a huge difference. It built a real sense of trust — I felt respected and listened to, which meant I was comfortable asking for help whenever I needed it.
That mutual trust is incredibly valuable, and it’s what really stood out to me about working together.”
