Essay
Changing and (vibe)coding systems
What does it take to replace a system of record?
This is where longer-form thinking, working notes, practical projects and talk run-throughs come together. I like to think of it as being inside an architect's studio, where the work of understanding and shaping the world happens.
The essays are the more polished pieces that have been refined through writing and feedback. The drawing board is where early-stage ideas, sketches and rough work lives. Projects are where I share some of the things I've built, along with the thinking behind them. And talks are where I share run-throughs and notes from some of the sessions I've given. The bookcase is where I share some of the books and podcasts that I have found interesting and that I think others might find interesting too.
Topics
Mode
Essay
What does it take to replace a system of record?
Essay
Being explicit and deliberate with the trade-offs we make in how we use technology
Essay
Sometimes we can speak the same language but mean totally different things.
Essay
A hypothesis on how emerging technologies evolve from doing more to better, different, and sometimes less.
Essay
When we get clear on the differences between vision, mission, strategy, and tactics, we can plan more effectively.
Essay
A practical framing of ambiguity in leadership and how clear definitions improve decision-making.
Early-stage ideas, concept sketches, inspiring quotes and working fragments.
Can a watch be more than a timepiece?
19 days ago
We're not good with probabilities
nearly 2 months ago
AI gives us plenty of coulds. The real value — the thing a trusted advisor gives you — is the should.
nearly 2 months ago
From humans instructing computers, to computers talking to humans — the history of interfaces is really a story of who is adapting to whom.
nearly 2 months ago
Tackling the age old conumdrum.
nearly 2 months ago
AI is the latest in our ability to duplicate. What does that mean for scarcity, value, and authenticity?
8 months ago
Code projects, creative projects, automation projects - a gallery of some of the things I have built, why they mattered to me and what was learned along the way.
Project
Migrating from Tumblr, grown with Eleventy, inspired by digital gardening.
Project
AppleScript utility for changing Mac wallpapers based on active Focus Mode.
Personal opinion or project
Project
A visual archive of Tumblr photo posts and legacy Instagram cross-posts from 2011–2023.
Personal opinion or project
Project
Code for automatically figuring out the Liturgical Season and changing the colour on a website.
Run-throughs of some of my talks with slides, media and notes. Where possible, I will share recordings, along with takeaway guides to make taking action on the ideas easier.
All talks uploaded at the moment are personal ones. You can toggle on personal content to show them:
Capturing some of the books I recommend or want to read next, and some podcasts I find interesting.
Chelsea's book is an excellent, honest, authentic and practical read on how to cultivate resilience and mindfulness in high performance.
View bookChelsea Pottenger
Michael has spent years looking into how we think about change and communication, and 'Mindstuck' is a fantastic distillation of his insights and learnings in this area.
View bookMichael McQueen
I found the Houston Foresight Methodology incredibly enlightening when I studied it. This is the book that gives the detail on that for those who can't get to Houston.
View on Open LibraryAndy Hines, Peter Bishop
This book changed my relationship with decision making and made me understand procrastination on a whole new level.
View on Open LibraryJoseph Bikart
To really embrace the 'organic' nature of a digital garden (and what my desk more likely looks like!), this is a view of the full stream of essays, notes, projects, talks and portfolio media, rather than in separate sections.
Can a watch be more than a timepiece?
19 days ago
Rush Digital | 1 month ago
A positive & practical take on AI, examining the green shoots as we look to the future
A lively discussion with the team from Rush Digital about AI, strategic foresight and the future.
YouTube | 1 month ago
Play videoWe're not good with probabilities
nearly 2 months ago
AI gives us plenty of coulds. The real value — the thing a trusted advisor gives you — is the should.
nearly 2 months ago
From humans instructing computers, to computers talking to humans — the history of interfaces is really a story of who is adapting to whom.
nearly 2 months ago
Tackling the age old conumdrum.
nearly 2 months ago
NZ Tech Podcast | nearly 2 months ago
Conversation with Paul Spain about Xero's partnership with Anthropic.
Conversation with Paul Spain about Xero's partnership with Anthropic.
YouTube | nearly 2 months ago
Play video
Interview series featuring practical AI and innovation conversations with industry leaders.
NZ Catholic Bishops Conference | nearly 3 months ago
More detailsWorkday Blog | 5 months ago
An interview talking about bridging the worlds of startup and enterprise, so that as you scale you get stronger, not just bigger.
News24 | 7 months ago
Partner content focused on small business AI adoption and practical productivity outcomes.
Fear and Greed | nearly 8 months ago
Podcast discussion on practical AI adoption paths for small and medium businesses.
AI Journal | 8 months ago
Practical perspective on common blockers to AI readiness for smaller firms and how to move past them.
AI is the latest in our ability to duplicate. What does that mean for scarcity, value, and authenticity?
8 months ago
Short-form takes on AI, strategy, and leadership.
Instagram | 9 months ago
More detailsAsana | nearly 12 months ago
Resource exploring how smaller businesses can balance AI experimentation, capability, and value realization.
Solutions Review | 1 year ago
My thoughts on how technology isn't an innovation by itself, but is better viewed as a catalyst for true innovation.
LinkedIn | 1 year ago
LinkedIn thought leadership article on Tax Administration 3.0, digital identity, e-invoicing, and AI-enabled tax modernization.
What can we learn from the sea
1 year ago
Data Runs Deep | 1 year ago
Interview with Kendra Vant on my thoughts on where we are heading with AI this year.
Gadget | 1 year ago
Media coverage discussing AI direction, experimentation, and practical use in the small business context.
Elite Business Magazine | 1 year ago
Talking about data that shows productivity on the decline in the UK, and how AI might be able to help
Short-form takes on AI, strategy, and leadership.
Instagram | nearly 2 years ago
More detailsXero Blog | nearly 2 years ago
Data insights article on how AI can augment expertise and improve service quality in accounting workflows.
Guest appearance on Insightful Accountant discussing practical AI adoption in finance and accounting.
Insightful Accountant | nearly 2 years ago
Play video“One of the uber skills of leadership in the 21st century is going to be mastering metaphors”
— Michael Henderson
In a world of synthetic media, authentic content is premium
nearly 2 years ago
How do we set them
2 years ago
Fear and Greed | 2 years ago
Discussion on executive sentiment, practical adoption concerns, and where AI is creating real value.
Do we care about the ingredients?
2 years ago
Can we get the value a different way?
2 years ago
Small Biz Matters | nearly 3 years ago
Conversation on practical technology priorities and market signals from Xerocon 2023.
Interview series featuring practical AI and innovation conversations with industry leaders.
Xero | nearly 3 years ago
More detailsImplications of agentic meetings
nearly 3 years ago
BenefitNews | nearly 3 years ago
Industry perspective on how AI shifts workflows, decision making, and operating models for small business.
Xero Blog | nearly 3 years ago
Research-backed perspective on how small businesses are approaching AI adoption and capability building.