My father taught me to ask “Is this helpful?” three times before acting.
Seemed weird when I was a kid. Felt like overkill. Why ask the same question three times?
Then I spent 30 years as a performance coach and realized: he wasn’t teaching me a decision-making technique. He was teaching me how to wait for the thing underneath the thing.
The first answer is surface level—reactive, what you’re “supposed” to say. The second answer goes slightly deeper—what you actually think. The third answer? That’s the truth you’ve been avoiding.
The gap between the first answer and the third is where transformation lives.
The Bottleneck Nobody Talks About
Here’s what nobody tells you about AI collaboration: the technology isn’t the bottleneck. Your willingness to sit with the uncomfortable truth is.
Tomorrow at AICO Toronto 2025 (November 28 at Microsoft Canada HQ), I’m keynoting on “Hybrid Intelligence: Connecting Human Intuition with Artificial Intelligence.”
But here’s the real talk: most organizations are implementing AI solutions to problems they haven’t actually named yet.
They know something is wrong. Productivity feels hollow. Meetings multiply. Everyone’s busy but nothing’s moving. The old playbook stopped working.
But nobody wants to say it out loud.
The Refusal of the Call
So they do what the hero does in Campbell’s “Refusal of the Call” stage—they get busy with adjacent problems.
“Let’s implement this AI tool.” “Let’s optimize our processes.” “Let’s hire consultants.”
All true. All helpful. All not the actual problem.
The actual problem lives in the space between what everyone knows and what everyone’s allowed to say.
When the Hammer Breaks
Heidegger called these moments “breakdowns”—when the thing that was working invisibly suddenly becomes visible through its failure. The hammer breaks, and suddenly you see that you’ve been hammering wrong all along.
AI is creating systematic breakdowns in how organizations think about thinking itself.
Not because AI is bad. Because AI reveals what was already broken but compensated-for through human effort:
Meetings that exist because we don’t trust asynchronous communication. Reports that nobody reads because they answer questions nobody asked. Processes that survive through institutional inertia, not actual value.
AI doesn’t break these things. It just stops pretending they work.
The Wound and the Light
As Rumi wrote: “The wound is the place where the Light enters you.”
Your organization’s AI adoption struggles aren’t technical problems. They’re disclosure events—moments when what-was-hidden becomes unavoidable.
The question isn’t “How do we implement AI better?”
The question is “What truth about how we actually work has AI made impossible to ignore?”
What I've Learned From 2,000 Executives
I’ve coached over 2,000 executives through these moments. The pattern is always the same.
They come wanting tactics. They leave having named something they’d been avoiding for years. The tactics matter—but only after you’ve sat with the truth long enough to stop flinching from it.
This is where “Is this helpful?” becomes more than a question. It becomes a practice. And that’s where the real work begins.
Join Us Tomorrow at AICO Toronto 2025
📅 Date: November 28, 2025
📍 Location: Microsoft Canada HQ, Toronto
🎟 Register: Event Registration
🗓 Full Schedule: View Schedule
Come if you’re ready to stop optimizing around the breakdown and start learning from it.
Come if you suspect your AI strategy is solving the wrong problem beautifully.
Come if you’ve been waiting for permission to name what everyone already knows.
The wound isn’t the problem. The refusal to look at it is.
See you tomorrow.
Opher Brayer is Co-Founder and Chief Scientist at Impro.AI, where he leads research on hybrid intelligence methodologies that connect human intuition with AI capabilities.
