As we brace for the retail juggernaut of Black Friday, Small Business Saturday, and Cyber Monday, there's no denying the stakes. These days aren’t just about sales figures—they’re about shaping the customer experience and forging lasting connections. This week, let’s explore what retail could look like if reciprocity and synergy became foundational principles for merchants.

A Lesson from Aviation

Years ago, while working for an independent airline, I underwent crisis response training. The goal was clear: to prepare for a worst-case scenario—a plane crash. The training wasn’t just about logistical readiness; it was about answering critical questions under unimaginable circumstances:

• How do we respond with empathy and efficiency?
• What must we anticipate that others cannot in the chaos of loss?
• How do we leave a devastating situation better than we found it?

Unexpectedly, this training offered life lessons that transcend aviation. It taught me to think ahead, to act with intention, and to bring value even in challenging situations.

Connecting the Dots to Retail

So, what does aviation crisis training have to do with retail? It’s about foresight, empathy, and action. Stephen Covey’s concept of synergy in The 7 Habits of Highly Effective People offers a perfect lens here. Covey defines synergy as the cooperative interaction of elements to produce an outcome greater than their individual efforts.

Pair this with the principle of reciprocity—giving back in response to receiving something valuable—and you have a powerful framework for reimagining retail. It challenges us to go beyond transactions and step into meaningful relationships.

But how do we cultivate this kind of relationship with our customers?

The Power of Questions

Recently, while presenting to a sock brand about the Art of Connection, I reflected on David Brooks’ book, How to Know a Person: The Art of Seeing Others Deeply and Being Deeply Seen. Brooks emphasizes the importance of asking the right questions.

Did you know the average child asks around 40,000 questions between ages 2 and 5? Children are naturally curious and unafraid to probe deeply. Somewhere along the way, many of us lose this skill, defaulting to surface-level interactions.

Yet, asking questions fosters intimacy. It pushes past unspoken assumptions and helps us see through another’s perspective. If we want to build reciprocity and synergy in retail, we need to start with curiosity.

Asking the Big Questions

Brooks refers to these as “Big Questions”—ones that break routines and encourage reflection. Here are a few examples:

• What crossroads are you at?
• What would you do if you weren’t afraid?
• If you died tonight, what would you regret not doing?
• If we meet a year from now, what will we be celebrating?

When we ask these questions, we move from data collection to meaningful insights. These insights guide transformative relationships—ones that deliver value far beyond the transactional. This is the essence of synergy: creating a combined effect greater than the sum of individual efforts.

Retail as Transformation

So, how can this philosophy manifest in retail? Imagine applying these principles to your brand, your store, or your relationships with customers and reps. What if retail became more about connection and less about the bottom line?

Recently, I asked a client about her experience at a Taylor Swift concert she attended with her daughter. Her response was surprising: “It was pure joy,” she said. From the city’s red-carpet welcome for “Swifties” to the shared camaraderie of fans adorned with bracelets and outfits, the entire event was a celebration of connection.

Think about what Taylor Swift’s concerts do for local economies. My hometown of Indianapolis, for instance, reaped over $100 million during her tour stop. That’s not just good business—that’s synergy. It’s reciprocity on a massive scale, fueled by the joy and connection people experience.

A Call to Action

What if we could create similar moments of joy and connection in retail? How might we invite customers to feel seen, valued, and connected to something bigger than a purchase?

The answer lies in moving beyond assumptions, embracing curiosity, and creating relationships that transform. The question isn’t just how we sell—it’s how we connect. Let’s aim to foster a retail experience that embodies the principles of reciprocity and synergy, leaving everyone better than they were before.

This season, let’s not just sell products. Let’s sell connection, joy, and transformation. That’s the kind of retail worth building.