SERIES: Passing the Baton

Linley McConnell

[Photo above: Linley and her father, Rob McConnell. The two are part of the ongoing leadership transition at Gibson’s Cleaners in Toronto. Want to know how it’s going from the other side of the table? Read Rob’s perspective here.]

When I joined Gibson’s, our family’s dry-cleaning business, in 2018, I came in fresh from the corporate world with a head full of ideas and a lot of (over)confidence. Like most multi-generational businesses, Gibson’s had decades of institutional knowledge, deeply held processes, and a team of people who had long since earned their trust.

This month, I want to explore the generational dynamics that come up when the ‘new’ and ‘old guard’ work side by side. What I’ve learned is that both sides have something the other needs.

Here are three phrases I’ve heard more times than I can count, and what I’ve learned from each of them.

“We’ve tried that. It doesn’t work.”

Have you ever been to a dinner party where someone keeps sharing unsolicited business advice your way? Looking back, I’m certain that’s what our senior leadership felt like when I first walked through the door. Loyalty programs, new service categories, rebranding ideas—I had a lot of thoughts. And often, the response was some version of: “We tried that. It didn’t work.”

That phrase can feel like a door slamming. But it doesn’t have to.

What the Old Guard can do better

• Pause before responding. Before defaulting to experience as a reason to shut down an idea, absorb it. Ask clarifying questions (open-ended ones). The context in which something was tried five or ten years ago may be very different from today.

Not long ago, wash and fold was a service that no reputable dry cleaner would touch. Today, it’s everywhere. If we had stayed locked in “we tried it, it won’t work,” we would have missed one of the most significant shifts in our industry. Timing, collaboration, and communication matter just as much as the idea itself.

What the New Guard can do better

• Research before you blurt. I’ll be the first to admit I’ve walked into rooms with half-formed ideas and expected them to land. A well-constructed argument is far more persuasive than enthusiasm alone.

“That’s How We’ve Always Done It.”

This one is a close cousin of the first, but it’s less about past failure and more about present comfort. And comfort, while human, can quietly become the enemy of growth.

What the Old Guard can do better

• Call out the discomfort. Resistance to change is often less about logic and more about what feels safe. Acknowledging that can help create more openness to new systems and processes.
• Consider what ageing out of your customer base means for a business. The businesses that thrive are the ones that continue to challenge their own assumptions, even when it’s uncomfortable.

What the New Guard can do better

• Understand the ‘why’ before changing the ‘how.’ I’ve made the mistake of updating a process in the name of efficiency, only to discover the original way existed for a very good reason. The repercussions of that kind of change can be costly.
• Earn the right to change things. Get curious about the existing system, build trust with the people who run it, and then introduce your ideas. You’ll get a much better reception.

“It’s Going to Be Too Much for the Team.”

This one hits closest to home. Legacy businesses often have long-tenured employees who are deeply embedded in the culture and rightly protected by it. At Gibson’s, we have a beloved team member who remembers the day I was born. That kind of history means something. It also means that asking the team to stretch can become a personal matter among senior leaders.

What the Old Guard Can Do Better

• Protect your people, but don’t protect them from growth. If a core goal of the business is to evolve, asking more of your organization—imperfectly at first—is one of the only ways to move forward. Many long-tenured employees want to learn, adapt, and grow. Don’t assume otherwise.
• Think ahead when hiring. If certain roles need to evolve, consider which skills and mindsets will be needed as you bring in new people.

What the New Guard can do better

• Respect the expertise in the room. There aren’t many skilled pressers walking in off the street. Your team is your quality and your reputation.
• Ask what’s in it for them. Before rolling out a new initiative that affects your team, think about their motivators. Change lands better when people understand what’s in it for them, not just what’s in it for you.

Generational change in a business isn’t something that happens to you; it’s something you navigate together, conversation by conversation, and sometimes, phrase by phrase. The businesses that get it right aren’t the ones where one side wins; they’re the ones where both sides decide to keep showing up.

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