Systematic Leader

In this interview, Mark shared his methodology of developing self-awareness through questioning to uncover limiting beliefs. He focuses on feeling shifts through future envisioning to program new responses. One of my favorite parts of this interview is when he talks about getting more truthful with yourself so you can notice the patterns.

Highlights from the interview

Developing self-awareness and catching limiting beliefs:

Mark discussed using pointed questions to reveal where people are limited, then shifting those beliefs through truthful self-reflection on underlying issues of shame, blame, guilt, and hate. Tuning into your thoughts and emotions so you can ask yourself better questions.

Case studies of individual and business transformations:

Mark shared how he transformed frustrated clients by addressing underlying emotions, including a business that grew 350% annually after the owner resolved childhood issues limiting him. It starts with noticing your thought patterns, and he explains how to work with them.

He also shares a case study from Stanford that showed how complaining damages your brain. It makes you dumber.

Transforming behaviors through body-led feeling shifts:

Mark shares how feeling future success through visualization and intention setting produces biochemical changes, allowing new behaviors versus conscious thinking, which is too slow.

Creating coachable moments. How you can turn difficult moments into growth. You’ll also learn how laughing at yourself is a powerful tool that will help you turn tough situations into positive experiences.

Shifting mindsets through future envisioning:

Mark stressed envisioning a better future self handling adversity automatically versus past failures. Remembering lessons from a successful future self reprograms the subconscious. He walks me through building the confidence to give a great presentation.

Addressing adversity through future-focused problem-solving:

Roleplaying, Mark demonstrated curiosity, appreciation, and solution-finding over blame. He emphasized accessing wisdom from a future self who has already solved issues.

You can learn more about Mark over at Encompass Life. 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!

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!

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

1. 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.

1. 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.

1. 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.

1. 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.

1. 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.

1. 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!

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!

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!

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!

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!

Highlights in the interview:

• Tim’s passion for creativity.
• Understanding the challenges that you need to overcome to reach your goals.
• Setting the standards for our work.
• The power of the lean startup framework.
• The importance of experimentation in our business.
• Utilizing your natural skills so you grow your career with purpose.
• Leveraging persistence in your career.
• How to work with your inner voice so you tackle the hard projects that grow your business.
• Understanding what a business's problems are.
• The framework that he teaches people to solve problems.
• How Tim co-designs a project for a client.
• Utilizing strategic suggestions.
• Taking an active leadership role as a freelancer.
• The exercise he used to figure out his strengths and passions so he could do work he was good at and he loved.
• What routines that help him keep moving forward when he feels stuck.
• Using Pareto’s 80/20 rule to help you focus on the projects that move the needle.
• How to build a better relationship with employees and contractors by creating clear expectations of what you expect and why you expect it.
• How to deal with perfectionism.

You can learn more about Tim over at FreelanceGPS. You can also connect with him on LinkedIn.

In this interview, you’ll learn about building a business that fits your unique skillset. Josh Spector is an entrepreneur who teaches experts how to use writing to grow their businesses. One of my favorite parts of this interview was when he talked about finding his niche by looking at his past.

Highlights in the interview:

• Josh ability to keep his focus on what matters.
• How to create content that provides maximum value.
• Why paying someone by the hour is bath for employers and employees.
• Keeping your messages as concise as possible.
• How to narrow down your business offerings.
• Focusing on who you want to work with, not what you want to do.
• Attracting your ideal people.
• We break down my niche.
• How to speak directly to the people you help in your business.
• Figuring out what you are good at and creating leverage in your career.
• How he looks at his past to help him understand himself better.
• Why it’s important to just do things so you can learn about your strengths and how to utilize them out in the business world.
• Taking action unlocks part of you that you wouldn’t have expected.
• Why it’s important to crossing things off your list that you don’t want to do in your business and career.
• The framework that helps you figure out how to do the things you love.
• Why assuming success is a framework
• Building confidence in yourself.
• Struggles are a part of business and why you should look at struggles as a puzzle.
• Iterating and improving the things that we work on.
• Working on not taking failures personally.
• Book he most shares “Tribes” by Seth Godin, podcast “Social Media Marketing Podcast”

You can learn more about Josh over at his website Josh Spector. Check out his amazing newsletter For the Interested. Here are his Skill Sessions if you want to check them out. 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!

In this interview, you’ll learn about how meditation helps you clear your inner noise so that you can make better decisions. Dal Balcauski is the founder of Product Tranquility. You’ll enjoy his story about asking specific questions to get to the heart of a product and how to price it.

Highlights from the interview:

• How Dan got into software at a young age.
• How he dealt with undiagnosed ADHD in his career.
• The balance of perfection and good enough.
• How he looks at ADHD differently than most people.
• Adjusting his career to better utilize his strengths.
• How he got into meditation.
• How meditation and exercise helps him reduce stress and improve his mental state.
• Creating space to process your thoughts and emotions.
• Not getting caught up in our emotions so we make better decisions.
• Doing a better job of choosing our actions.
• Building awareness when making decisions.
• How meta meditation and prayer have a lot in common.
• Getting out of his own way and clearing out the inner noise.
• How our distractions can hold us back and what to do it.
• What we say “yes” to and “no” to on a daily, weekly, monthly basis and how we can learn from these decisions to make better future decisions.
• Framework to help with pricing a product.
• Understanding our relationship with money and how it helps us understand the value of products.
• Using frameworks that actually work in business.
• Clear views of product fit.
• Aligning the value we are creating with the customer.
• The value of different customer segments.
• Any process should be in service of a goal.
• Most recommended books for life, AI, and pricing.

You can learn more about Dan over at Product Tranquility. 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!