The Art of Mentoring: Asking Questions, Being Curious, Building Confidence

The Art of Mentoring: Asking Questions, Being Curious, Building Confidence

The Art of Mentoring: Asking Questions, Being Curious, Building Confidence | Kathleen Duffy

One of the best parts about being an entrepreneur is the opportunity to help others on a similar path. Mentoring has always been part of my life, whether at home as a parent, as the leader of my company, or as a member of boards and committees in the community. In 2005, I was fortunate to serve as a member of the first formal mentoring program for the National Association of Women Business Owners (NAWBO), the voice of America’s 10.6 million women-owned businesses. In that role, I helped emerging women business leaders take that important next step in their ventures. 

Today, I serve as a mentor for Seed Spot, a nonprofit and support system for young entrepreneurs, giving them access to resources, community partners, capital sources, and more. These experiences have taught me as much as I have hopefully imparted to my mentees. But there’s a fallacy in mentoring that is worth sharing. It’s that as mentors, we must have all the answers. After all, by virtue of our experiences and jobs, we are problem-solvers. So why not tell our mentees how to address the pain points they are facing in their careers or entrepreneurial ventures?

My approach is a bit different. Rather than telling my mentees what they should do, I ask questions. Being curious goes a long way in helping people tell their stories, share their goals – and yes – solve problems. Chances are good that they have the answers. It may be that they just need some time to step back and reflect. 

I can still remember the feeling of angst as I worked to get my company started in 1991. Can I do this? Am I good enough? Will people want to hire me? Confidence can be a big issue for entrepreneurs and career-minded individuals, too.  As such, it is critical for mentors to build confidence in their protégés. This made a world of difference for Megan Epley, a young entrepreneur, and CEO of StARTem, a nonprofit that improves student engagement and STEM (Science, Technology, Engineering, and Math) test scores through interactive art education. Megan had a winning idea but she doubted her ability to turn it into a viable enterprise. Asking questions, listening, connecting her to resources, and lifting her up was a reminder that she had what it takes to succeed. Fast-forward four years and Megan’s company is well on its way to improving the academic performance of K-8 students in Arizona. 

More recently, I began mentoring an entrepreneur who was starting a business but was stuck on how to move forward. Despite her pedigree – an Ivy League education and a stint at one of the largest and most reputable consulting firms in the nation – I sensed that she didn’t believe in herself. She wanted my opinion on what tools she needed – a PowerPoint deck, perhaps? – to help share her idea with potential clients. After much discussion, she realized that she had a solid network of prospects. She simply needed to call them and pitch her idea. In this case, my encouragement was a bit more direct: The people you are calling will pick up the phone. Remember, it only takes one successful call to get started.

Being a constant source of support is an important part of being a mentor. And watching your “students” realize their dreams is the biggest reward.