I flew into Toronto for a keynote on Wednesday and a breakout session Thursday afternoon. With Thursday morning free, I planned a trip down to Bloor Street to visit Harry Rosen - the men’s retailer known for its impeccable presentation, thoughtful service, and the feeling that if you walk in there, you belong there.
It wasn’t convenient. The store was about 15 miles from the airport, and Toronto traffic turns that into a 45-minute commitment. But that didn’t matter. I wasn’t running an errand; I was seeking an experience. I wanted to feel good about what I was buying and where I was buying it.
The First Switch: From Outside to Inside
When I walked in, a salesperson greeted me with a simple “Good morning.” No script, no “Welcome in.” Just acknowledgment. That was enough to make me exhale. I relaxed and began to look around with curiosity, rather than guardedness.
That’s the first switch every shopper makes... from outsider to insider. It’s emotional, not transactional. And it’s fragile.
One friendly interaction can make someone feel they’re in the right place. Silence can undo it just as fast.
The Browsing Brain
I started walking through the departments. Considering a jacket here, a shirt there. Each time, the question popped up: Does that look like me?
Sometimes it was yes, but more often it was no.
You're matching your identity, your mood, and comparing it to what you see. You're editing possibilities.
In those moments, the best salespeople know how to engage - not pounce- watching for the micro-signals that say the shopper’s considering. The best can piece together the story from departments the customer stops at, the item they look down at, the ones they feel the fabric of.
The Second Switch: From Browsing to Buying
I walked to the back, glanced at shoes, went upstairs and glanced at suits, and nothing grabbed me. Then looked around the bottom floor. I saw a jacket...modern cut, great fabric, something that felt right.
Now I was in the buying mindset. I wanted to see how it looked.
I took off my jacket, tried it on and looked in the mirror... and instantly imagined myself wearing it on my upcoming trip to China. That mental picture was the second switch flipping: I’d gone from browsing to seeing myself owning it.
I looked around for something that might go with it and spotted a dark green mock turtleneck that seemed perfect.
That’s the moment where a skilled associate can amplify excitement: “That color brings out the fabric perfectly,” or “Let me show you a pair of casual slacks that would complete that look.” A little engagement turns imagination into action.
But no one came.
The Third Switch: From Connection to Isolation
It felt like fifteen minutes had passed but probably only a couple. I was standing there in the jacket, touching the mock turtleneck - waiting for someone to share the moment.
No one did. I began to notice the price tag. I began to feel the silence.
And that’s when the third switch flipped: from belonging to invisibility.
The sale didn’t die because of price. It died because the energy of the moment disappeared. The moment passed.
When no one acknowledges it, it turns to self-doubt: Maybe this isn’t for me after all.
So I stopped touching the turtleneck, took off the jacket and left it on the counter, and walked out on my purchase.
The Missed Story Moment
What I realized later was this: I wasn’t waiting for help. I was waiting for someone to step into my story.
How can you not be curious why, on this particular day, this person walked into your store?
When I found that jacket, I could already see myself wearing it on that trip to China. The picture was alive in my head - the airports the meetings, the confidence it gave me. If a professional salesperson had joined me in that moment, they might have said, “Oh, you’re traveling? I just came back from Hong Kong - you’ll love it there. This fabric wears beautifully on long flights.” Or maybe they’d share a memory about something special they bought abroad that still reminds them of that trip.
We don’t know what would’ve happened next.
That’s the point.
The best moments in retail occur in those unscripted exchanges...the kismet between two people connected by a single item. A jacket. A wall covering. A fountain pen. It doesn’t matter what the product is; it’s the shared spark that turns an ordinary sale into something memorable.
That’s why training matters. You can’t fake that spark...you have to be prepared to risk putting yourself out there, to show genuine interest and humanity.
Great associates consistently do that. They step forward with warmth and curiosity, trusting that if they share a little of themselves, something better than they imagined might come from it.
That’s when retail feels less like commerce and more like connection.
How Online Tries to Replicate the Human Switch
Online, the same thing happens - they’re just flattened into pixels. You’re not wandering through racks; you’re scrolling. You’re not holding a jacket up to your reflection; you’re clicking “View in 3D.”
But shoppers still go through the same steps:
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Curiosity (“I’ll just take a look”)
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Consideration (“That might work for me”)
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Excitement (“I could see myself in that”)
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Hesitation (“Maybe later”)
E-commerce teams try to catch those switches with algorithms: pop-up chatbots, retargeting ads, “You might also like” banners. But even the best sites convert only about 2–3 percent of visitors. Ninety-seven percent leave because the algorithm can’t sense when someone's ready.
It can’t smile, it can’t say, “That looks great on you,” or even the converse, "I think we have something that might work better." It can’t pick up that subtle body language of someone who’s right on the edge of saying yes.
Why Stores Still Matter
That’s why brick-and-mortar retail still matters. In-person selling allows associates to sense the shopper’s energy and connect with their story in real-time. You can see the switch flip- eyes widening, posture changing, excitement rising - and meet it with genuine enthusiasm.
That’s the core of great selling. Not product knowledge, not discounts, but presence.
The Real Lesson
Every shopper walks through invisible emotional stages:
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Outsider → Insider
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Browsing → Buying
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Connection → Indifference
The role of your team is to recognize those transitions and step in before the switch flips backward.
It’s not about hovering. It’s about noticing.
You can’t fix that with signage, markdowns, or marketing automation. You fix it with people who are trained to read shoppers, not just ring them up.
Because no matter how advanced technology becomes, the sale still happens in a single, human moment, when someone feels seen.
