Although Millennials are often referred to as an entrepreneurial generation, not every one of them is starting his or her own business. Many Millennials are opting for more traditional career paths.

Millennial LeadersBecause we’ve featured several entrepreneurs during this year’s Millennial Momentum series, I was excited to speak with Millennial leader Madeline Caldwell for a little different perspective. For the past four and a half years, Madeline has been working for TBC, a full service, marketing firm in Baltimore. I couldn’t wait to hear the perspective of a Millennial leader working within a larger organization.

When I admitted my excitement to Madeline her response surprised me. She explained, “It’s funny you bring that up. I think the most successful employees in an agency environment are actually entrepreneurial.” According to Caldwell, in order to advance within an agency, employees must do more than just meet deadlines and get work done. They must be collaborative, proactive and have a passion to forge their own path.

Madeline Caldwell: Millennial Entrepreneur in DisguiseMadeline admits that in true Millennial fashion, she has an entrepreneurial mindset. One might even argue that she is an entrepreneur in disguise. She said, “There’s usually a process and a way things have been done in the past that people tend to follow. But it doesn’t mean that that can’t change. Often the change is for the better. Looking for opportunities to improve, rather than falling in line is an entrepreneurial characteristic that can help anyone in any work environment.”

That mindset has served Madeline well. She believes it is partly responsible for her success. She’s advanced much more quickly than expected and earned a leadership role relatively early in her career.

Madeline admits that her age can, at times, be an obstacle to overcome. She explained, “The nature of public relations is that you’re typically working with a company spokesperson who tends to be at a higher level within an organization. It’s critical to learn quickly how to interact with individuals who are much more tenured than you are.” She admits that she’s dealt with push back because of her age. But she’s found that quality work – and confidence in that work– is the best way to answer those concerns. Madeline wisely said, “If you’re able to do excellent work and gain a client’s trust that removes any age barrier.” {tweet this}

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3 Book Recommendations from
Madeline Caldwell
to Give You Momentum

  1. Lean In: Women, Work, and the Will to Lead by Sheryl Sandberg and Nell Scovell
  2. Girl Boss by Sophia Amoruso
  3. The Confidence Code: The Science and Art of Self-Assurance by Katty Kay and Claire Shipman


On-The-Job Leadership Training

Like so many other Millennial leaders, Madeline’s leadership training is coming on the job. She relies on a variety of resources to continue her education. There’s a mentor she can call on when she needs advice – she believes it’s important to find a mentor outside of your organization. She regularly seeks feedback from current team members and learned valuable lessons from one team member’s exit interview. She admitted, “I feel like I’m always trying to improve. I hit some speed bumps in the beginning of my time as a leader. So I definitely look to external resources for help. I read a lot.” She said she often finds articles on LinkedIn and also reads plenty of leadership books.

When leaders ask for feedback, everyone on the team has a voice.

Leadership is an evolution and Madeline has a vision for the type of leader she wants to become. She explained, “These qualities are important to me because I respect leaders who exhibit them.”

  • Be a Giver of Trust: Early in her tenure as a leader one of her team members said they felt she didn’t trust them. She admits it was hard to hear because we all know how it feels to not be trusted. She never wants to be a micromanaging leader.
  • Be Collaborative not Self-Centered: Leading a team of Millennials, Madeline has found they enjoy working side-by-side on projects. While she knows leading by example will always be necessary, she recognizes leading from the top down won’t be affective on her team.
  • Be Self-Reflective: Madeline has found it is important to make a distinction between feedback and approval. Seeking outside approval can be tempting. But successful leaders seek feedback not approval.

That important distinction between seeking collaborative feedback for growth rather than outside approval is key. It ensures that Madeline will continue to give her team a voice. It positions her to be a leader who actively listens for the benefit of her team. And it foreshadows a bright future for this successful Millennial leader.