Designing for Chaos

I envy product thinkers who operate within the context of a lean and born-digital startup. Product strategy is never easy, but building technology in this environment becomes fairly straightforward. Write code, test, deploy. Rinse and repeat. Or some variation of this. But try bringing that same approach into a complex physical environment like a retail store, and suddenly you’re not just a product manager – you’re part ringmaster, part therapist, and part exorcist for technology that seems possessed by real-world demons.

I’ve spent the last two decades building tech designed to be used in physical space – first in museums, then in retail organizations – and if there’s one thing I’ve learned, it’s that the gap between the digital roadmap and the reality of the floor is extremely wide.

First, there’s the idealism divide. Most technologists think about users as disembodied entities who interact with software in predictable, often ideal, ways. This is the happy path mentality. Meanwhile, most retail associates are often juggling many scenarios at once: a customer who’s trying to return a swimsuit they bought 6 months ago, a thief trying to steal an expensive piece of outerwear, a random question about product specs, or a manager who’s just informed them they need to be cross-trained on a new area of the store – all while attempting to use enterprise systems on six-year-old hardware.

Then there’s the physical environment itself. That sleek tablet kiosk we designed? It’s now positioned directly under an HVAC vent that drips condensation like a leaky faucet. That in-aisle digital display meant to guide customers? It’s been commandeered as a support pole for seasonal decoration. And the once-white customer-facing payment terminal now bears the fingerprint smudges of a thousand customers.

Let’s not forget connectivity. In the product requirements, the system requires a stable internet connection. In reality, we’re dealing with large-scale Faraday cages that create spotty Wi-Fi at best.

The gap between digital intention and physical implementation creates a special kind of cognitive dissonance. Most product managers are trained to think in terms of user journeys and personas, only to watch customers use the self-checkout as a surface to scratch off a lottery ticket. I’ve grown to love this dichotomy over the years.

Within this chaos lies a peculiar beauty. Unlike purely digital products, retail tech exists in a messy, human world – one where success is measured by metrics, of course, but also the absence of complaints. The most elegant product isn’t the one with the cleanest code or the most impressive AI; it’s the one that works when the Wi-Fi doesn’t, when the user hasn’t slept, and when reality refuses to conform to a carefully plotted customer journey.

I’ve found the best retail tech product managers develop a kind of zen-like mindset. We learn to let go of digital perfection and embrace analog reality. We don’t build for the ideal conditions of the demo environment. We build for the beautiful disaster that is actual retail.

So the next time you’re struggling to operate a seemingly simple piece of technology in a store, know that somewhere a product manager is observing, taking notes, and going back to the drawing board to try once again to bridge the gap between the binary code and the bricks-and-mortar – one humbling iteration at a time.