“Leadership is about authenticity, vulnerability, and building strong connections.”

In this episode, Craig Anderson talks with Dr. Debra Chromy, President and CEO of Trellis Company, about her evolution as a leader and the lessons she’s learned over her career. Debra shares her journey from early leadership roles to becoming a CEO, emphasizing the importance of being your authentic self and leading with vulnerability. She discusses how showing up as your true self fosters trust within teams, why curiosity is essential in leadership, and how making tough decisions for the organization, even at personal cost, defines strong leadership. Debra also reflects on the challenges of leading through change, the power of strategic planning, and how surrounding yourself with the right team can help drive success.

After You Listen:

• Connect with Dr. Debra Chromy on LinkedIn

• Check out Trellis Company

• Connect with Craig on LinkedIn

• Subscribe to Craig’s "The Evolving Leader" newsletter
  
  

Key Takeaways:

• Lead with authenticity to build trust and drive results

• Use vulnerability as a leadership tool to foster collaboration

• Surround yourself with the right people to enable success
  
  

Things to listen for:
(00:00) Intro
(01:00) The importance of authenticity in leadership
(03:15) How vulnerability builds trust within teams
(06:30) The role of curiosity in addressing leadership challenges
(09:00) Making tough decisions for the organization’s future
(12:45) The impact of strategic planning on organizational success
(15:30) Debra’s leadership lessons from past experiences
(18:00) Creating a culture of transparency and feedback within teams
(20:45) The leadership advice Debra would give her younger self

“Great leaders know when they’re wrong.”

In this episode, Craig Anderson talks with Ben Pippenger, Co-Founder and Staff Product Manager of Zylo, about the evolution of leadership and the lessons learned from building and scaling a company. Ben shares his journey from an individual contributor to a leader, emphasizing the importance of understanding what truly motivates a team. He discusses how recognition—not just money—keeps employees engaged, why leaders must carve out time for their people, and how making mistakes can be a powerful learning tool. Ben also reflects on lessons from his time at Salesforce, the challenges of maintaining company culture at scale, and why leadership isn’t just about getting things done—it’s about bringing people along with you.

After You Listen:

• Connect with Ben Pippenger on LinkedIn

• Check out Zylo

• Connect with Craig on LinkedIn

• Subscribe to Craig’s "The Evolving Leader" newsletter

Key Takeaways:

• Understand what motivates your team to drive engagement and performance

• Prioritize recognition over money to build lasting team appreciation

• Embrace mistakes as learning opportunities to grow as a leader

Things to listen for:
(00:00) Intro
(01:30) Ben’s transition from contributor to leader
(04:12) The role of motivation in building a high-performance team
(07:28) How Salesforce’s leadership principles influenced Ben’s approach
(10:18) Why leadership isn’t just about more productivity
(14:23) The importance of career paths for non-managers
(18:30) Creating a culture of recognition and peer feedback
(22:45) The one leadership lesson Ben would tell his younger self

“Leadership is about turning people into doers.”

In this episode, Craig Anderson talks with Marc Rust, CEO and Founder of Consequently Creative, about the intersection of creativity, leadership, and vision. Marc shares his journey from creative director to business owner, highlighting the importance of setting clear standards, fostering initiative, and balancing passion with structure. He talks about how hiring people with strong personal passions leads to stronger teams, why fear holds so many leaders back, and how gratitude can open doors to success. Marc also reflects on leadership lessons from Richard Branson, the power of audacity, and why finishing what you start is just as crucial as starting in the first place.

After You Listen:

• Connect with Marc Rust on LinkedIn

• Visit Marc’s website at marcrust.com

• Check out Consequently Creative

• Connect with Craig on LinkedIn

• Subscribe to Craig’s "The Evolving Leader" newsletter

Key Takeaways:

• Embrace audacity and take initiative, even when the path isn’t clear

• Hire people with personal passions and foster an environment where creativity thrives

• Set a clear vision, reinforce appreciation, and don’t let fear hold you back

Things to listen for:

(00:00) Intro
(01:25) Marc’s early leadership journey
(02:38) Lightning round: leadership insights
(09:08) How creativity and leadership intersect
(16:05) Hiring passionate people and building great teams
(20:30) The role of vision in scaling a business
(24:54) Why gratitude and appreciation matter in leadership
(28:15) Leadership advice Marc would give his younger self