September AI Meetup - Making AI Work: Judgment, Experiments, & ROI

Explore how organisations can combine human judgement with disciplined AI experimentation at September’s Second Monday Meetup.
Pamela Simpson will examine how professionals can preserve expertise, accountability, and sound judgement in an AI-enabled workplace. Dan Randow will then put those questions into practice through an interactive simulation where an organisation’s leadership team must choose between competing AI experiments, consider their alignment with business strategy, and decide what to measure to reduce risk and shorten the time to ROI.

Together, the two sessions explore how organisations can make better decisions about what to trust, where to experiment, what to measure, and when to continue, adapt, or stop. Drinks, conversation, and practical ways to think about AI adoption included.

Meet up with your local AI community on the Second Monday of September at EPIC Innovation:

5:30–6:00 pm — Drinks & Networking
6:00–6:45 pm — Pamela Simpson — Human Judgement in an AI World
6:45–7:30 pm — Dan Randow — AI Experiments at Work
7:30–8:00 pm — Drinks & Open Q&A

Human Judgement in an AI World — Pamela Simpson
As artificial intelligence transforms how knowledge is created, shared, and applied, organisations need a deeper understanding, an "epistemological literacy" of how we decide what to trust, what counts as expertise, and how we actually "know" things in a hybrid world.

Pamela Simpson, DBA Candidate at the University of Otago, will share initial insights from her research involving 43 subject-matter experts across professional, corporate, and government sectors throughout New Zealand.

Rather than focusing on technical specifications, Pamela will explore the human side of AI adoption: the shifting tensions between human judgement, professional expertise, and machine-generated outputs.

Key Points:
• The Exploration Mindset: Is the most effective AI collaborator: a "generalists" with the imagination to synthesise competing ideas or 'expert' to validate outputs?
• Enhancement vs. Transformation: Is AI just making existing work faster, or is it enabling genuinely new forms of organisational knowing?
• The Expertise Paradox: How to use AI to boost productivity without falling into the trap of "cognitive atrophy" or eroding the professional formation of the next generation.
• Governance as a Knowledge Problem: Why effective AI governance must preserve epistemic integrity, professional standards, accountability, and trust.

Who This Is For:
This presentation is designed for a broad range of professionals who recognise that successfully integrating AI is ultimately a "people change, not a technology change". Join us to discuss how we can navigate this new landscape not just as tool-users, but as a new society of explorers.

AI Experiments at Work: Reducing Risk and Time to ROI — Dan Randow
Organisations across New Zealand are investing in AI experiments, sometimes without being entirely clear about why, how those experiments support business strategy, or what evidence would justify further investment.

Dan Randow will facilitate an interactive simulation of a leadership team inside a typical New Zealand organisation. A group of participants will consider competing AI investments, debate their alignment with the organisation’s strategy, and choose a small portfolio of experiments to pursue.

The leadership team will also have to decide what each experiment should measure. The rest of the room will watch the decisions take shape in real time as participants weigh value, uncertainty, risk, evidence, and competing priorities.

Key Points:
• Strategic Alignment: Learn how to distinguish interesting AI opportunities from experiments that could create meaningful business value.
• Experiment Portfolio: How leaders can compare competing investments in AI training, automation, agents, knowledge systems, engineering, security, and other emerging capabilities.
• Measure What Matters: How to decide what evidence an experiment needs to produce before committing further time, money, or attention.
• Continue, Adapt, or Stop: How clear measures can reduce risk, shorten the path to ROI, and help organisations avoid disconnected pilots that continue without producing useful evidence.
Who This Is For:
Business owners, leaders, managers, consultants, technologists, and professionals who are deciding where their organisation should invest in AI.
This session will be especially useful for anyone trying to move beyond disconnected pilots, vendor promises, or pressure to “do something with AI,” and towards a coherent programme of strategic experimentation. No technical, financial, or AI expertise is required.

When: Monday, 14 September 2026, 5:30–8:00 pm
Where: EPIC Innovation, 100 Manchester Street, Christchurch

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Sponsored by the AI Coaching Academy. Come have some beer and wine, and raise a glass with your local AI community.
https://ai-coaching.academy/