The Reward of Confounding Expectations: An Interview with Jennifer Smith

I met Jennifer Smith at a fund and friend-raising gala for Gillette Children’s Specialty Healthcare. She was just hours off the plane from a trip to Rwanda and Uganda, and I was impressed that she and her husband Brooks were awake. But Gillette is both a customer and cause Jennifer cares about, so awake she was.

When we sat in her office a few weeks later for this interview, our conversation started with stories of the women small business owners she’d met in Africa. We Jennifer_Smithshared a mutual admiration for these women who were at the very earliest phases of business maturity and yet were so completely advanced in their discipline and commitment to making their firms and families successful. As it turned out, these would be just the first examples I would hear of expectations dashed during our conversation.

Jennifer is CEO of Innovative Office Solutions. Reading the phrase “Office Solutions,” you likely envision a sleepy or struggling firm in a dying industry, among a million small businesses competing against big box players like Staples, led predominantly by men. You’d be right… and wrong. I left our conversation with several principles that underlie Jennifer’s history of defying the odds:

Absorb the positive

It started early. Jennifer was just 12 when she developed a severe form of encephalitis. She spent weeks in the hospital, and her mother was told she would die. Inherently outgoing and raised with the idea that no one has boundaries, Jennifer found that the experience “accelerated everything” about who she wanted to be, and what it would take to fight back. By the time she was in high school, she was running track. Sports were big in the small college town where Jennifer grew up, and TEAM became a mantra for her. She ran for a coach who had each person say goals out loud every day. As I listed to Jennifer’s story, I observed someone who absorbed the positive energy around her and used it as fuel to defy expectations.

Make your own luck

In Jennifer’s first executive role, she was often the youngest person and only woman in any company, customer or industry meeting. “I wasn’t afraid to admit ‘I don’t know’ to anyone” and always felt she could get help. Her practice is simple: “Be keenly aware – both of yourself and what others in any given situation need or want – then make your own luck.” Using a clear awareness of needs with a persistent philosophy of win-win vs. zero-sum gain in any situation, Jennifer has won over partners and competitors by simply asking for their help.

I asked Jennifer if she carries the loneliness we’ve heard about from others in our bold leader conversations. Her response: “I’ve never felt alone!” Her approach leaves her feeling connected to staff, partners, customers and even competitors. When faced with a wall, her instinct is to rally the right posse to work together. (I imagine in the dictionary next to the word collaborative, there is a photo of Jennifer Smith.)

Think “freedom to…”

Imagine you lead an office supply company in this century. Many of the products you sell are in decline, as the love of all things digital means less paper, folders, and filing cabinets are needed. The words “commodity” and “price” fill your day. What can you do?

Jennifer decided to stop selling office supplies and start solving something new. Today, she imagines what the next generation of the workforce will be like, and her company as a catalyst to make it successful. The shift in focus changes everything: Product categories are changing. Her team is more human centered and design driven. New partnerships are emerging. And rather than craving freedom from the dated and even depressing nature of the business, her team capitalizes on the freedom to do what pulls both customers and the company forward. The result has made Innovative Office Solutions the fastest growing independent dealer in the industry – growing even during our recent economic trough.

Be intentional

The changes over time have come with lessons (like every bold leader I’ve met, Jennifer is a voracious learner). Her natural philosophy of finding reward in seeing people help each other to create something great is still a guiding principle, but now Jennifer says, “I’ve learned I need to be intentional.” Having recently completed a large acquisition, Jennifer reflected on how an intentional, proactive focus on the newly combined customer experience and internal culture was key. “Core values don’t simply happen; they’re acted out in the choices we make every day.”

Since our conversation, what sticks with me is Jennifer’s history of confounding expectations. “I think the odds against something can make it exciting,” she said. Yes, she wants her company to hit the next revenue milestone. Yet it’s more about the unheard of nature of the thing than it is about the $ number. “What if you took a dying business in a shrinking industry and reinvented it to improve lives for people?”

What if, indeed, Jennifer. What if, indeed.