Executive Evolution

"Leadership is about building others up while getting out of their way."

In this episode, Craig Anderson talks with Peter Dunn, founder and CEO of Your Money Line, about what it really takes to grow into a leadership role. Pete shares candid reflections on how he went from a self-focused leader to someone committed to empowering others through trust, transparency, and support. He opens up about past missteps, the guilt he carries over early leadership choices, and the ongoing work of becoming someone worth following. Pete also explores why feedback is an act of care, how empathy and performance go hand in hand, and why the mission behind Your Money Line is so deeply personal. Whether you're a new leader or a seasoned executive, Pete's story is a reminder that leadership is less about having the answers—and more about asking the right questions.

After You Listen:

• Connect with Peter Dunn on LinkedIn

• Check out Your Money Line

• Connect with Craig on LinkedIn

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

Key Takeaways:

• Feedback is an investment in someone's growth

• Empathy makes hard conversations more effective

• Leadership is about helping others shine, not just hitting goals

Things to listen for:(00:00) Intro (01:11) Seeing leadership potential in others (02:15) Pete's book for HR leaders (03:00) The difference between givers and takers in leadership (04:06) What it means to truly empower your team (05:39) Creating a coaching tree inside your business (07:00) Pete's leadership role model (08:11) Learning from a strong executive team (09:56) Valuing teammates' career journeys (11:22) Pete's first leadership experiences (13:25) Recognizing privilege and using it for good (15:10) Identifying and developing high-potential team members (17:11) Leadership lessons from unexpected places (18:34) Telling the truth with empathy (20:07) Leading with curiosity and compassion (21:17) The impact of mission-driven leadership (26:11) How culture reinforces the mission (27:18) The advice Pete would give his younger self (28:53) The role of self-awareness in leadership growth

"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

"What you put out as a leader will be heard and will affect every level of the organization."

In this episode, Craig Anderson talks with Ian McCoog, Assistant Professor of Medical Education at Geisinger Commonwealth School of Medicine and author of Leadership Bites. Ian explores the challenges healthcare professionals face when transitioning from clinical expertise to leadership roles. Drawing from his book and personal experience, Ian shares how leadership theories can guide decision-making and foster team collaboration. He also emphasizes the importance of self-care for maintaining balance in high-pressure environments and discusses how storytelling can make leadership lessons stick.

After You Listen:

• Visit Ian's website at ianmccoog.com
• Connect with Ian McCoog on LinkedIn
• Get a copy of Ian's book, Leadership Bites
• Connect with Craig on LinkedIn
• Subscribe to Craig's "The Evolving Leader" newsletter

Key Takeaways:

• Build confidence by understanding that everything you say or do as a leader has an impact on your team and organization
• Develop competence by leveraging leadership frameworks and reflecting on lessons learned from experience
• Maintain calm by finding moments for self-care, even during hectic and demanding days

Things to listen for:

(00:00) Intro (01:38) Ian's early leadership journey (02:38) Lightning round: leadership insights (07:51) Challenges in medical leadership (16:01) Leadership theories and applications (18:24) Maintaining equilibrium in medicine(20:17) Resident leadership as a paradigm

"A good leader is someone who is helping others become the best of themselves."

In this episode, Craig Anderson sits down with Brook Gratia, President of Edgewater CPA Group, to explore the realities of leadership, scaling a business, and the challenges of integrating new teams. Brook shares her journey from launching her firm to leading a team of 20, reflecting on key leadership lessons—like hiring the right people, adapting to team dynamics, and navigating the emotional complexities of leadership. She opens up about the difficulties of merging company cultures, setting clear expectations, and balancing the demands of running a business while supporting employees.

After You Listen:

• Connect with Brook Gratia on LinkedIn: https://www.linkedin.com/in/brook-avey-gratia-54275b6/

• Check out Edgewater CPA Group: https://www.edgewatercpa.com/

• Connect with Craig on LinkedIn: https://www.linkedin.com/in/craigpanderson/

• Subscribe to Craig's "The Evolving Leader" newsletter: https://clearpathcoaches.com/stay-in-touch

Key Takeaways:

• Hire the right people from the start to save time, stress, and money

• Separate your identity from employee decisions while still showing care

• Build structured processes to keep teams aligned and accountable

Things to listen for:

(00:00) Intro

(02:10) Best leadership book

(05:03) Leadership inspirations

(08:45) Defining leadership

(11:42) Early leadership roles

(15:54) Challenges in growing a business

(27:13) Get out of the weeds and lead

"Oftentimes, positive reinforcement training ability translates well to humans too."

In this episode, Craig Anderson talks with Mandy Stetzel and Kathleen Schonsheck, Co-owners of Uptown Pup, about how they built a successful pet care business by prioritizing transparency, trust, and a strong team culture. Mandy and Kathleen share their journey from passionate dog lovers to business owners despite having no formal business or leadership training. They discuss how they learned to lead, the importance of hiring and mentoring the right people, and how staying true to their values has helped them grow a business that serves both people and pets. They also explore how positive reinforcement—used in training dogs—can apply to leadership, the role of financial transparency in building team trust, and why leading by example is the best way to create a thriving workplace.

After You Listen:

• Visit Uptown Pup's website at uptownpupindy.com
• Follow Uptown Pup on Instagram: @uptownpupindy
• Like Uptown Pup on Facebook: Uptown Pup
• Follow Mandy & Kathleen on BlueSky: The Uptown Girls
• Connect with Craig on LinkedIn
• Subscribe to Craig's "The Evolving Leader" newsletter

Key Takeaways:

• Trust your instincts and learn from experience—even when you make mistakes
• Invest in leadership books, mentorship, and financial transparency with your team
• Know yourself, recognize your triggers, and prioritize self-care to be a better leader

Things to listen for:

(00:00) Intro

(01:02) Meet the owners of Uptown Pup

(01:52) Lightning round: leadership books

(05:01) Lightning round: leadership crushes

(09:11) The early days of building Uptown Pup

(12:47) Hiring and team building strategies

(16:29) Growing into leadership roles

(22:36) Maintaining culture and vision

"It's our job to make sure that we hire someone who is the right fit. Because not being a good fit is a terrible thing for someone who you offer a job to."

In this episode, Craig Anderson sits down with Jack MacKenzie, President of CollegeAPP to discuss his journey as a leader and the lessons he's learned from building successful teams. Jack reflects on stepping into his first major leadership role as a student body president and leading a fast-growing company, sharing insights on hiring challenges, why a 50% success rate can be a win, and the importance of addressing misalignment early. He also emphasizes the power of creating a vision that inspires belief and drives alignment, offering practical advice for cultivating transparency, trust, and accountability within teams.

After You Listen:

• Connect with Jack MacKenzie on LinkedIn

• Connect with Craig on LinkedIn

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

Key Takeaways:

• Trust your instincts in hiring; red and yellow flags often point to deeper alignment issues

• Lead with vision and conviction to inspire belief and motivate teams toward shared goals

• Balance vulnerability and confidence to build trust while staying true to your vision

Things to listen for:

(00:00) Intro

(01:52) The lightning round

(09:36) Believing so strongly others follow naturally

(13:13) Lessons from leading a student government

(15:39) Biggest takeaways on building strong teams

(22:30) Spotting red flags and trusting your gut

(28:14) Why leaders shouldn't take themselves seriously

"You can't build trust without relatability and authenticity—when your team knows you're genuine, trust naturally follows."

In this episode, Craig Anderson sits down with Kyle McDowell, author of Begin With We and founder of Kyle McDowell Inc., to discuss his evolution as a leader and the principles that have shaped his leadership philosophy. Kyle shares how his transformative journey led to the creation of his "10 We's"—a set of principles designed to foster trust, authenticity, and collaboration within teams.

Reflecting on the highs and lows of his corporate career, Kyle opens up about the mistakes that shaped his leadership style, the challenges of stepping away from the corporate world, and the lessons he learned about relatability and building a culture of excellence.

After You Listen:

• Connect with Kyle McDowell on LinkedIn

• Connect with Craig on LinkedIn

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

Key Takeaways:

• Earn trust by leading with authenticity and relatability

• Inspire teams by removing barriers and empowering them to excel

• Foster a culture of excellence through shared principles and accountability

Things to listen for:

(00:00) Intro

(02:10) Leadership lightning round

(07:30) Lessons from leadership mistakes

(13:40) The power of self-reflection in leadership

(18:15) The "10 We's" and their impact on team culture

(23:10) Overcoming skepticism and earning trust

(30:00) Balancing empathy and accountability as a leader

(37:00) Advice for new and experienced leaders alike

"You can't lead an organization unless you have people coming alongside you to accomplish that task."

In this episode, Craig Anderson sits down with Christiana Thornton, CEO of Granite Edvance, to talk about her evolution as a leader and the pivotal moments that shaped her leadership philosophy. Christiana reflects on her journey, from stepping into her first major leadership role to assembling a high-performing team that drives organizational success. She shares the challenges of navigating isolation as a new leader, balancing people-pleasing tendencies with the need for decisiveness, and learning to trust and delegate effectively.

After You Listen:

• Connect with Christiana Thornton on LinkedIn

• Connect with Craig on LinkedIn

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

Key Takeaways:

• Build trust with your team by fostering confidence and collaboration to unlock greater potential

• Lead with confidence by making tough decisions and acting decisively, even when it's unpopular

• Delegate effectively and empower others by leveraging your team's strengths to achieve more together

Things to listen for:

(00:00) Intro

(02:10) Leadership lightning round

(07:01) The power of trust in leadership

(10:16) Overcoming isolation as a new leader

(13:30) Lessons in delegation and collaboration

(17:45) Balancing ambition with boundaries

(22:20) Building aligned teams for long-term success