About 35 years ago, high above the Big Piney River in the Ozarks, I learned how to see in the dark.
No night vision goggles. No ninja training. Not a single magic mushroom! Just a strange skill we picked up in Army Basic Training…
Oblique Vision…
You’ve probably done it. You try to see something in the dark (like a coffee table… a chair… the cat…). But when you focus on where you think it is, you still can’t see it.
::: stub toe… see red… [expletive!] :::
But, if you look off to the side of it, your peripheral vision helps you see its dark shape, so you can edge around it. It has to do with rods and cones in your retina… but I won’t bore you with details.
The Army taught it to help us navigate at night.
But years later, I realized it was just as useful in broad daylight…
Oblique Strategies
In the 1970s, Brian Eno and Peter Schmidt created a deck of cards called Oblique Strategies. Each one had a strange little prompt printed on it:
- “Honor thy error as a hidden intention.”
- “What wouldn’t you do?”
- “Turn it upside down.”
- “Water”
At first glance, they look absurd… like something out of a riddle.
But they work because they force you off the obvious path. And sometimes, the real answers (the honest ones) live just off to the side.
[…and yes, there’s now an app for it… Happy to share it if you’re interested :)]
…Which brings us to you, the product rep.
Why product reps keep stubbing their toe
Most reps face the same problem as that coffee table hiding in the dark…
If you stare straight at the obvious, you’ll miss what’s really there.
And what ends up happening is you…
- Fall into transactional conversations [“Here are the specs. Here’s the warranty. Later!”]
- Struggle to stand out because competitors have almost the same PowerPoint deck
- Miss the deeper cues about what an architect really cares about on a project
That’s where oblique thinking comes in. When you step sideways and ask unexpected questions, you can uncover what the architect might not say directly.
In other words, sideways questions are trust tools.
When an architect pauses, laughs, or shares something unexpected, the relationship shifts. You’ve just stepped out of the “just another vendor” positioning.
You’re now the collaborator who helped them see their own problem differently.
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How to use oblique thinking with architects
Three practical ways you can apply this framework to your day-to-day work:
1) Incorporate “failure” as a tool
Ask: “If this product or this detail failed beautifully, what would it look like?”
It can get the architect talking about risks and frustrations. Then, it gives you a chance to address them before a competitor does.
2) Imagine extremes
Try: “What if this building had to last 300 years instead of 30?” or “What if the budget doubled?”
You’re meeting them in big-idea mode, which earns respect.
3) Bring in other worlds
Architects like strong analogies. Try asking: “In the auto industry, they solved a similar ventilation problem by doing X. Can we find a parallel here?”
It shows you think beyond your product and positions you as a creative partner. [So keep your eyes & ears open for those parallel ideas!]
[Want more of these weird little trust bombs? I made a one-page toolkit for you… You’ll find it here. (No log-in needed)]
Your next move
Choose one sideways question from the toolkit above.
Drop it in a meeting, call, or email this week.
Don’t overthink it. Just try it once and watch what happens.
Does the architect pause, laugh, or tell you something they didn’t mean to say?
That’s the sideways moment where trust sneaks in… and the architect starts selling themselves on working with you.
That’s it for this week!
Here’s to building trust, not just buildings. Catch you next week!
Neil “Lookin’ sideways” Sutton
Architect | Speaker | The Product Rep Coach
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