The Most Humbling Lessons Of Leadership

As a young girl growing up in Portland, Oregon, Jill Nelson’s mother had one cardinal rule: no coloring books. An avant-garde artist, Jill’s mother wanted her daughter to embrace her creativity. Jill was afforded an easel, paints, and a blank canvas — but it was up to her to create the art.

“The idea of me coloring between someone else’s lines offended her,” says Jill. “She provided me with every possible art supply, but never anything with rules.”

These were the early beginnings of an entrepreneur. As she navigated high school and college, Jill followed a path defined by big ideas, free expression, and plenty of rule breaking. Like many entrepreneurs, Jill left a trail of failed day jobs and dissatisfied managers in her dust; unable to thrive in an environment where she wasn’t following her own vision. After working as a receptionist herself for a small business, Jill came up with the idea for a personalized, live virtual receptionist services company, Ruby Receptionists. She started the company in 2003 and Ruby has enjoyed success ever since, experiencing year over year growth and expanding to three locations with more than 450 employees.

“My chaotic upbringing is one of the reasons I thrive in an entrepreneurial environment,” says Jill. “I had to learn to survive in unpredictable environments and be independent. My safety net was removed pretty early on in life.”

When Jill was just sixteen years old, her mother, who suffered from mental illness, committed herself to an institution. Though her father was already quite absent from her life, he passed away from a heart attack just two years later. With independence thrust upon her, Jill found herself left to her own devices to figure out what was next. Despite her circumstances, she felt unusually prepared to tackle the unknown and find her way.

 “I feel that the whole experience has given me strength and the ability to thrive on my own,” says Jill. “I have the confidence and willingness to live in chaos and the unknown — and I’m very thankful for it.”

Although Jill’s natural calling was to entrepreneurship, she sees herself as a late bloomer to leadership. While Ruby Receptionists was a growing, profitable business, Jill was eight years into the business before she deeply considered what leadership really meant. She had started a company, written a business plan, and built her team. She never once considered that employees would do anything other than what she’d hired them for — she didn’t spend much time thinking about training, management, or the role of her own leadership.

“It has taken my entire career to realize it’s all about leadership,” says Jill. “I should’ve known better because I certainly never did what people asked me to do.”

In 2011, Ruby hit the 100 employee mark and something changed. Someone treated Jill differently simply because she was a leader. They regarded her as if she was on a pedestal, and Jill immediately felt uncomfortable. In her head, she was just like her employees. They were in it together, and she was no different than any of them — so why would they give her special treatment?

Another team member helped her understand the distinction. “Someone made the observation that most people want and need a leader. If someone is going to invest their time in a company, they want to invest it in someone they believe in and who’s taking them somewhere they want to go,” recalls Jill. “I realized that it’s my job to be that leader and step up and own it — even if that might not be who I am up close every day.”

Jill had to reframe the whole idea of what it meant to be a leader. She came to understand that her employees were looking to her for guidance, support, and motivation, and that ultimately they were coming to work for her. It wasn’t a role that she was entirely comfortable with, and even today, she’s remained open and vulnerable to learning the challenges of leadership.

In 2015, Jill brought in a private equity partner and, after a successful transaction, she attracted great new talent and built out her leadership team. Though her company was entering a new stage, Jill was still leading the way she used to. Her new team often felt as if they were delivering on Jill’s vision and not their own. While they had hired key people to fulfill key roles, Jill found herself managing in a way that impeded their roles. It didn’t take long for it to come to her attention that there was a problem.

“My entire leadership team had lost faith in me,” says Jill. “They didn’t feel supported by me and they felt like I wasn’t letting them into their own organization. It had already made its way to the board and I was walking around ignorant of it.”

For entrepreneurs who are as passionate about their business as Jill, this is an incredibly humbling experience. The people that directly reported to her didn’t believe in her ability to lead, and Jill wanted to understand why. She was able to speak individually with each member of her leadership team and talk openly about the recent transitions, her leadership style, and what they hoped would change. She realized that she needed to find a new way to lead.

“After I heard everything, I knew that this is not how I wanted to be — I needed to recover from this,” says Jill. “I let each person know that I heard them, I told them what I thought I heard, and what I would do better in order to move forward. I asked if I had their faith to give me another try.”

The conversations were difficult, but Jill knew she needed to have her team on her side. She wanted them to be honest if her efforts would be as interpreted as too little, too late. But they were willing to stick by her as she tried to grow into a new stage of leadership.

“I love bottoming out because that’s where you get to see progress. You get to dig yourself out and conquer things,” says Jill. “I learned so much from this and emerged a better leader. We’re all in a much better place.”

When Jill’s team challenged her, she remained open and positive. She embraced the chaos of leadership and chose to be honest with her team about who she is and the mistakes she’s made. The team rode out the bumps in the road together and ever since, Ruby’s culture has flourished. Today, they are a four-time winner of Fortune’s Top 5 Best Small Companies to Work For, Inc.’s Best Workplaces 2017, and a Portland Business Journal’s Fastest-Growing Companies in Oregon for the past 10 years.

“I’ve learned that leadership is key to culture,” says Jill. “Our lives are a blank canvas — never think that you have it all figured out. We have to remain authentic, because that’s how we learn. ”

To hear more of Jill’s story and interviews with other purpose-driven leaders, tune into my Growing with Purpose podcast.

The article can be found here.