178 episodes

Leaders need processes and systems to make good decisions. The Systematic Leader podcast interviews leaders (CEOs, Authors, and Enterpreneurs). They share their best frameworks so you can make better decisions in your business.


“Developing the habit of mastering the multiple models which underlie reality is the best thing you can do.” Charlie Munger


I interview experts in their fields so you can learn and apply their frameworks to your business.


Hi, I'm Karl Staib. The creator of the Dig to Fly method and author of Bring Gratitude. I struggled for years with making quality decisions because I didn't have a system in place. Once I developed routines that worked for my personality type that's when my business took off.


I hope you enjoy the podcast and if you have any questions, just reach out at DigtoFly.com.

Systematic Leader Karl Staib

    • Business
    • 5.0 • 43 Ratings

Leaders need processes and systems to make good decisions. The Systematic Leader podcast interviews leaders (CEOs, Authors, and Enterpreneurs). They share their best frameworks so you can make better decisions in your business.


“Developing the habit of mastering the multiple models which underlie reality is the best thing you can do.” Charlie Munger


I interview experts in their fields so you can learn and apply their frameworks to your business.


Hi, I'm Karl Staib. The creator of the Dig to Fly method and author of Bring Gratitude. I struggled for years with making quality decisions because I didn't have a system in place. Once I developed routines that worked for my personality type that's when my business took off.


I hope you enjoy the podcast and if you have any questions, just reach out at DigtoFly.com.

    The Path to Inspired Leadership

    The Path to Inspired Leadership

    In this interview we discuss the importance of setting intentions each morning to bring focus, forgiveness and calmness to the day ahead. Karen Stultz is a coach and podcaster who supports entrepreneurs by shatterning their self-imposed limitations. One of my favorite parts of the interview is the story of how her boss showed her how to lead with empathy, but still help them improve their work.


    Here are the highlights from the interview:


    Empathy and listening as leadership skills


    Karen emphasizes that empathy through active listening is key to effective leadership. Leaders must understand employees' perspectives to inspire them and find solutions together.


    She explains why she was afraid to ask for help and what she did to overcome this fear.


    Inspiring employees through understanding


    Karl stresses the need for leaders to understand why return-to-office pushback occurs, in order to flexibly find compromises like hybrid schedules. Karen agrees understanding contexts fosters inspiration over command-and-control. Understanding your values and how it matters to your employees.


    Setting processes to reduce friction


    Karen advocates documenting the work to justify flexible arrangements. Karen notes clarifying needs and communicating respectfully to tech support helps address challenges directly.


    Finding flexibility through communication


    Karen argues leaders should consider employees' values and happiness. With open communication and caring about people, leaders can inspire loyalty through flexibility and opportunity.


    Developing empathy through self-awareness


    Karen's first boss exemplified empathetic coaching through consistent check-ins. His non-judgmental support helped her improve and find a better role fit, prioritizing employees' wellbeing. It starts with improving your listening skills. An employee must feel heard to trust their boss/manager/leader.


    Morning routines for intention and inspiration


    Karen's daily routine of affirmations, oils, and talismans in bed and on waking prepares her mindset to feel accomplished and help others joyfully, with focused yet flexible intention-setting inspiring motivated action.


    Recommended Book


    Check out the book: One: The art and practice of conscious leadership, written by Lance Secretan


    You can learn more about Karen over at Karen Stultz. You can also connect with Karen over on LinkedIn.


    As always, if you have any questions or want to submit a guest for the podcast that you think would be amazing, just reach out to me on the Dig to Fly website, and I’ll do my best to get them on. If you enjoy the interview, please take 30 seconds to rate the Dig to Fly podcast on your favorite platform. Thanks!

    • 52 min
    The Relentlessly Helpful Approach: Susan Baier on Success through Generosity

    The Relentlessly Helpful Approach: Susan Baier on Success through Generosity

    In this interview, you’ll learn about why emphasizing the importance of understanding audience problems and being relentlessly helpful is so important to success. Susan Baier is a marketing expert that focuses on helping business owners with research. One of my favorite parts of this interview is why it’s so important to be relentlessly helpful.






    Highlights from the Interview






    Thought leadership and building trust with audiences





    Susan explained how research shows audiences want thought leaders addressing new, helpful perspectives from those they trust, advising focusing on problems audiences face rather than self-promotion.






    Developing a clear niche and problem-solving focus





    Susan stressed starting with the problems a niche solves before defining characteristics, advising focusing communication on problems while expanding offerings to problems on clients' journeys. 






    Focusing on the problem that they are struggling with. They will listen to you because they want to learn more.






    Being relentlessly helpful through consistent generosity





    Susan defined being relentlessly helpful as constantly asking "how else can I help?" within business parameters, advising generosity builds trust and differentiation for leaders, employees, and clients.






    Establishing organizational vision, values, and goals





    Susan shared that regularly revisiting goals with teams keep leaders accountable to stakeholders, advising transparency of motivations builds employee commitment to shared missions over profits. She explains that this isn’t easy to do, but very important to keep everyone inspired to do great work.






    Showing gratitude for those who help us grow





    Susan thanked past leader Jay Baer for energizing their work through humor and fearlessness, advising gratitude routines remind people of leaders' positive influences and build connections.






    Favorite Book





    Check out Die Empty: Unleash your best work everyday (Amazon link).






    You can learn more about Susan over at Audience Audit. You can also connect with her on LinkedIn.






    As always, if you have any questions or want to submit a guest for the podcast that you think would be amazing, just reach out to me on the Dig to Fly website, and I’ll do my best to get them on. If you enjoy the interview, please take 30 seconds to rate the Dig to Fly podcast on your favorite platform. Thanks!

    • 59 min
    The Fantastic Five Framework: Transformational Leadership

    The Fantastic Five Framework: Transformational Leadership

    In this interview, you’ll learn a framework that will help ground you when you are pissed off at work. I interviewed Christopher Littlefield, who helps leaders create cultures where people feel valued. Christopher emphasizes the importance of self-awareness and consciously choosing one's mindset to make better decisions as a leader. Leaders must notice where their attention goes and how it affects their energy levels and relationships.


    Here are the top highlights from the interview:


    Building relationships through communication


    Christopher stresses open communication to build understanding between opposing groups. Making assumptions breeds conflict, while empathy opens minds. Leaders must facilitate dialogue to resolve issues and strengthen bonds.


    Practicing gratitude and self-care


    Christopher shares daily practices like gratitude journals and self-reflection to maintain well-being. Leaders must recharge through mindfulness and positivity to avoid burnout while energizing their people. You’ll learn about the “Fantastic Five” framework that will help ground you in what matters. We can shift what we put into the system so we can get better output.


    Mental diet and emotional state


    Christopher notes the impact of one's mental intake on their state, advising leaders to consciously curate healthy inputs. Social factoring and reframing experiences as temporary helps objectively address issues.


    Creating structure and white space


    Christopher emphasizes scheduling recovery periods to stay centered. Leaders must involve their team in planning sustainable routines with clear responsibilities and feedback loops to optimize collaboration.


    Rapid fire questions


    Learn Christopher’s favorite tip for leaders to help people be more empathetic. One cool tip is to help people transition into a meeting. He also shares his favorite book that he most recommends to his friends.


    You can learn more about Christopher over at his website Beyond Thank You. You can also connect with him on LinkedIn. 


    As always, if you have any questions or want to submit a guest for the podcast that you think would be amazing, just reach out to me on the Dig to Fly website, and I’ll do my best to get them on. If you enjoy the interview, please take 30 seconds to rate the Dig to Fly podcast on your favorite platform. Thanks!

    • 52 min
    Financial Growth: Weekly Money Dates with Kendra James-Anderson

    Financial Growth: Weekly Money Dates with Kendra James-Anderson

    In this interview with Kendra James Anderson, the founder of the Finance Femme, you’ll learn how you can take back control of your finances.


    Highlights from the show


    Kendra shared her background in finance and how she transitioned from corporate to entrepreneurship by helping struggling small business owners improve their financial management.


    1. Financial review process


    Kendra outlined her process for regular financial reviews, emphasizing the importance of weekly "money dates" to build familiarity and confidence with one's financial situation.


    2. Growth decisions and personal priorities


    Kendra explained weighing whether to grow her business or stay small based on prioritizing family plans over expansion. She stressed aligning business decisions with personal goals and lifestyle.


    3. Team management through structure and communication


    Kendra cited establishing clear Standard Operating Procedures and communication as key to empowering her productive, hardworking team to function smoothly with minimal interruptions.


    4. Fears around emerging technologies


    While concerned about automation, Kendra focused on strengthening personal relationships with clients, knowing technology cannot replace human understanding and care.


    You can learn more about Kendra James Anderson over at Finance Femme. You can also connect with her on Instagram and LinkedIn. 


    As always, if you have any questions or want to submit a guest for the podcast that you think would be amazing, just reach out to me on the Dig to Fly website, and I’ll do my best to get them on. If you enjoy the interview, please take 30 seconds to rate the Dig to Fly podcast on your favorite platform. Thanks!

    • 55 min
    Solving the Startup Puzzle: Charles Woodin's Journey to Innovative Leadership

    Solving the Startup Puzzle: Charles Woodin's Journey to Innovative Leadership

    In this interview you’ll learn about Charles Woodin's problem-solving approach to leadership, specifically in the context of startups and innovation. You’ll also learn about his personal journey and the unique challenges he faced and overcame.


    Key highlights include:


    1. Charles Woodin's Leadership at Geekdom 


    Woodin discussed Geekdom’s shift in focus towards launching startups and detailed the process of establishing a new podcast studio.


    2. Problem-Solving as a Superpower


    Woodin described his natural inclination towards problem-solving, a trait he identified from childhood, as his key strength.


    3. Incorporating Diverse Inputs for Decision Making


    He emphasized the importance of seeking multiple perspectives to make informed decisions and how forming a board helped him become a better leader.


    4. The Value of Adaptability in Business


    Woodin shared insights on adapting to changes, such as moving Geekdom’s podcast studio to a new location and transitioning to different business frameworks like Six Levers.


    5. Achieving Goals through Team Understanding


    A significant part of the discussion revolved around setting realistic goals, understanding team dynamics, and ensuring everyone is aligned with the organization's mission.


    6. Effective Communication Strategies


    Woodin stressed the importance of clear communication, shared vocabulary, and regular check-ins to keep the team aligned with the company’s goals.


    7 Coaching and Accountability


    The conversation touched upon coaching techniques, understanding employees' motivations, and holding them accountable in a supportive manner.


    8. Importance of Self-Awareness and Feedback


    Woodin highlighted the need for self-awareness in leadership and the value of external feedback in assessing one’s performance.


    9. Book Recommendation


    Woodin recommended “The Hard Thing About Hard Things” by Ben Horowitz for its practical insights into business and leadership.


    10. Future Collaborations and Workshops


    The interview concluded with discussions about potential collaborations and workshops, particularly in process design and efficiency improvement.


    Throughout the interview, Woodin shared practical advice and personal experiences, reflecting on his approach to leadership, the importance of adaptability in business, and the value of a problem-solving mindset.


    As always, if you have any questions or want to submit a guest for the podcast that you think would be amazing, just reach out to me on the Dig to Fly website, and I’ll do my best to get them on. If you enjoy the interview, please take 30 seconds to rate the Dig to Fly podcast on your favorite platform. Thanks!

    • 54 min
    The Cost of Not Listening with Oscar Trimboli

    The Cost of Not Listening with Oscar Trimboli

    The interview with Oscar Trimboli was about deep listening skills to extract insights for leaders to become better listeners and communicators.


    Key Takeaways


    We discuss "what's the cost of not listening?" early in the interview to draw people in.Listen with your whole body - drink water, play music etc. to ground yourself before meetings.Ask for feedback subtly by asking "what's one thing you'd change about this meeting?" rather than directly.

    Topics:


    Oscar's journey to deep listening


    As a teenager, Oscar's protruding jaw made him self-conscious so he learned to ask good questions and listen to avoid drawing attention to himself.Playing card games with diverse nationalities, Oscar learned to read body language and non-verbal cues since they spoke other languages.A pivotal moment was when his Microsoft VP told him he could "change the world" if he could code how to listen well.

    Productive vs unproductive ego


    Ego can be useful to protect us but unproductive when trying to dominate others.Leaders should ask if their ego is being productive or not in conversations.Productive ego invites perspectives from whole group before speaking again.

    Whole body listening


    Listen with your whole body by grounding yourself before meetings (drink water, play music etc.)As host, don't start meetings on the hour - give a 5 minute buffer for people to transition.Do walking 1-on-1 meetings to fully tune in.

    Leaning into emotional conversations


    Don't run from emotional conversations - ask "when did you form this perspective?" to dig deeper.Silence draws out truth; pauses are okay and even powerful.

    Seeking feedback as a leader


    Don't directly ask for feedback from low-trust relationships.Subtly ask "what's one thing you'd change?" or "how would you summarize this meeting?"

    You can learn more about Oscar over at his website, Oscar Trimboli. You can also take the Listening Quiz to learn about how you can improve your listening skills. You can also connect with him on LinkedIn. You can also check out his book, How to Listen (Amazon Link).


    As always, if you have any questions or want to submit a guest for the podcast that you think would be amazing, just reach out to me on the Dig to Fly website, and I’ll do my best to get them on. If you enjoy the interview, please take 30 seconds to rate the Dig to Fly podcast on your favorite platform. Thanks!

    • 57 min

Customer Reviews

5.0 out of 5
43 Ratings

43 Ratings

1201Spring ,

So good!!

This podcast episode featuring Christopher Littlefield is an absolute gem for anyone navigating the complexities of leadership and workplace dynamics. Littlefield's insights are not just practical; they're transformative. His emphasis on self-awareness and mindset is like a guiding light in the fog of workplace frustration. I highly recommend this podcast to anyone seeking to thrive, not just survive, in the modern workplace.

Tanya the Therapist ,

Intimate and Real

I love how Karl engages with his guests. The questions he asks and what he shares creates a very intimate, very real conversation. My favorite way to learn!

Jonathan S. Marion, PhD ,

Interesting and Actionable

Whether through engaging interviews or sharing his own processes, Karl showcases a multitude of perspectives that help make an impact. Most importantly, the broad range of ideas covered are always presented in ways that are both interesting and actionable!

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