Three things we learnt this week
Each and every week the Square Holes team are deep in the bowels of a number of projects, working to mine all of the insights that we can to help grow businesses and support thriving cities.
These insights are used by businesses and organisations to innovate their offerings, move into new markets, track their impact and hone their products and output. Each week we will be sharing a broad insight that we have learnt for you to use in your own work.
Let us know what you find valuable!
Ewa: AI takeover of advertising
I’ve just come back from a holiday in the beautiful, remote Cook Islands, and one thing that really struck me was the amount of AI-generated content I was seeing.
Not just on social media, but in printed ads, signs and outdoor advertising. You know the ones: big friendly headlines, little illustrated people, icons, arrows and way too much information squeezed into one image.
Like this one. (This is NOT a real ad. And to Jason I say I’m sorry for breaking all the brand rules – it’s just for illustrative purposes).
Restaurants were using them. All different kinds of businesses were using them. And then I came home and realised I was seeing the same style all over my Australian social media feed. It seems to have appeared almost overnight.
And I really don’t like it.
I think partly because it feels so generic. There’s no real point of view to it. No personality. Just an image that looks like an ad because AI has learned what an ad is supposed to look like. And maybe that’s what bothers me most. It feels lazy. Why bother thinking about how you want your business to look and sound when you can ask AI to make you an ad?
But to every trend there is a counter-trend, and then along comes Port Hughes Fishing Charters with their brilliant post:
Or, more broadly, this real estate agent embracing authenticity.
Dylan: Staying in the loop
This week I’ve been writing about the OODA Loop and mulling over what it says about good decision-making. Organisations often assume that better decisions come from having more information. Still, sometimes the real advantage lies in being able to make sense of what is happening, act, learn, and adapt quickly. The loop reminds us that insight should not be the endpoint. Research can help us see what is changing and understand why, but its value really comes when that understanding feeds into action and creates new learning. Maybe the goal isn’t always to find the perfect answer (which can create decision paralysis), but to make informed decisions decisively and build a better cycle of learning.
Jason: Winning the good in the bad
I ran a workshop this week with livestock producers who had ‘survived’ the severe drought of 2024 and 2025. Now, for many, 2026 is the best year they’ve had in years. One bad year can often be absorbed. Two or more gets harder. Cash flow tightens, energy drops, and it becomes difficult to think beyond the immediate problems.
It reminded me of System 1 and System 2 thinking.
System 1 is fast and reactive, dealing with today’s problems. System 2 is slower and deliberate, maintaining the longer-term strategy, reserves and capability needed to weather the storm. The problem is many leaders get stuck in System 1 for years, or decades – even entire careers. Then when their sector slows or declines, they complain about the pain – much of which better planning, research and System 2 thinking might have eased.
Tough times are inevitable in farming and business.
The danger is becoming so punch-drunk that there’s nothing left when conditions improve.
Maybe the good years are partly won in the bad years.
Square Holes is a cultural insight studio.
We design mixed method explorations of people and culture beyond the category, uncovering the patterns, tensions and shifts shaping behaviour to inform strategy, inspire innovation and enable confident decisions. Our studio model brings together the right mix of thinkers, researchers and specialists for each exploration. If you’re navigating change, entering a new market, or seeking deeper understanding of people and culture, let’s start a conversation >
