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I’ve learned as much from the good bosses I’ve had as I have from the bad. The good ones challenged me, empowered me, helped me to see the bigger picture- showing me the 10,000 foot view when I was still wading through the surf, gave me perspective, objectivity, genuinely cared about me and saw my potential. But guess what? The bad bosses did too, for the most part. It was just less pleasant, and sometimes downright painful. All of it was instructive.

That was my earliest lesson in leadership. By watching, learning and listening, I thought about who I did and didn’t want to emulate. I found I’d work twice as hard, twice as long, and deliver better work for leaders who helped me understand why we were doing something, why it mattered, showed me the greater purpose and how I could make a difference. That was the leader I wanted to be.

In the first brand I worked for, I’d worked my way up from an entry level role to a leadership one. It had been an amazing journey. When I was offered an opportunity for a new role, managing the transition to digital commerce, I was all in. I’d been the one who pitched our CFO on moving to digital design, saving hundreds of thousands of dollars. Selling online was the dream. But one long time mentor said, “Why would you leave? It’s a huge risk. What if it fails?”

It wasn’t unreasonable. These were early days for E-commerce: picture Amazon as a mostly text site full of blue-underlined links. If this new business didn’t drive results, we could get shut down, and then where would I be? I called a trusted C-level executive and asked for advice. Was I making a terrible mistake? He said, among other things: “You have to think about what’s going to make you excited to get out of bed in the morning. What do you WANT to be doing?”

One was the voice of fear, the other, the voice of empowerment. One encouraged me to stay in my comfort zone, the other, to grow. My most inspiring mentors in that time expanded my worldview in a way that felt a little bit like helping me to leave home. Exciting- but scary. And ultimately led me to find my niche and passion in the world: digital commerce.

I’ve sought to do the same for others that worked for me over the years. Be approachable. Listen. Teach. Provide context and the bigger picture. And just like I’ll never forget the mentor who empowered me to find my dream, I occasionally hear from someone whom I’ve helped. One day, I got a text from a former team member saying,

“I don’t think I ever told you how grateful I am that you hired me, supported and developed me. You changed my life and gave me so many gifts!! I’m very appreciative and want you to know the amazing impact you had on my life. Thank you.” Wow. Just wow.

I still hear the voices of the ones who were most meaningful to me, who helped me become the leader I am today. I continue to learn from trusted colleagues and mentors to this day. And I will keep paying it forward. I hope you will, too.

About Jess Blogs:

Jessie Jackson is an eCommerce leader, with a passion for making the websites we use better.

Better for customers = better for business.