Confessions of an Implementer:

"The Mindset Shift Every Family Business Needs" with Adam Hill

Podcast: Confessions of an Implementer
Host: Ryan Hogan
Guest: Adam Hill
Date: October 1, 2025

Episode Overview

In this episode, host Ryan Hogan sits down with Adam Hill, fourth-generation CEO of Hill Brothers, to explore the unique challenges and breakthrough moments faced by family businesses—particularly those with a deep legacy. Adam recounts his journey from growing up in the shadow of his family's century-old business to spearheading its transformation through the Entrepreneurial Operating System (EOS). He shares how a shift in mindset, embracing vulnerability, and implementing structured systems helped Hill Brothers break through stagnation, regain profitability, and drive sustainable growth. The episode offers powerful insights into leadership, organizational change, and the complexities of family business dynamics.

Key Discussion Points & Insights

1. The Legacy and Evolution of Hill Brothers

• Background: Hill Brothers was founded in 1923 and has spanned four generations (01:38–02:24). Adam notes the family’s long-standing presence:

  “By the time I was born in 1979, it was already well over a 50-year-old company.” (01:40, Adam Hill)

• Family Dynamics: Adam describes the experience of company picnics doubling as family reunions and the presence of multiple family factions (02:27).
• Business Growth: The company evolved from being co-managed by four brothers (each taking key operational roles) to a more professionalized model under Adam’s father (04:49–10:08).

2. Leadership Transition — The Realities of Climbing the Family Ladder

• Misconceptions: Adam dispels the myth of a “guaranteed path to the top” for family members:

  “The idea of this kind of escalator to the top…isn’t quite the realistic story for most family businesses.” (04:49, Adam Hill)

• Professionalization: His father professionalized the business by “hiring to his weaknesses,” building a leadership team that enabled significant scaling (10:30).

3. Early CEO Struggles and Breaking the "Sacred Cows"

• Initial Challenges: Upon becoming CEO in 2018, Adam felt unprepared and isolated as previous mentor relationships turned transactional (12:12–15:00).
• Company in Decline: Hill Brothers faced its first signs of decline, including discussions of layoffs for the first time in nearly a century (15:01).
• The Problem of Sacred Cows: Adam explains the resistance to change in long-standing businesses:

  “There’s this terminal uniqueness…‘we’re different because we’ve been around for so long, we’ve already figured everything out.’” (15:55, Adam Hill)

4. Discovering and Implementing EOS – The Mindset Shift

• The Catalyst: Adam’s introduction to Gino Wickman’s "Traction" occurred during a period of crisis; he describes overcoming skepticism and hiring an EOS implementer (16:30–17:14).
• Value Creation: EOS implementation resulted in a 50% revenue increase and returned the company to profitability (17:14).
• Key unlocks: Adam credits two core EOS elements for the turnaround:
  • Vision: Creating and sharing a clear company vision across the organization (18:05–21:02)
  • Traction: Instituting disciplined weekly meetings and execution frameworks (“level 10 meetings”) (18:05)
• Quote:

  “…the combination of [vision and discipline] were the key to really driving most of the results…” (19:33, Adam Hill)

5. Navigating Family Dynamics and Leadership Change

• Leading Former Leaders: Adam discusses the awkwardness and necessity of leading team members who once mentored him—likening it to “command rotations” in the Navy (22:05–25:47).
• Role of EOS: Implementing structured systems helped depersonalize difficult decisions and shift accountability to roles, not relationships (23:04):

  “It’s not really me that’s making this decision. It’s the position, it’s the chain of command, it’s the nature of the accountability chart…” (24:04, Adam Hill)

6. Personal Resilience and Support Systems

• Overcoming Adversity: Adam shares openly about his journey through alcoholism and how seeking community and therapy were essential to building his resilience as a leader:

  “Community is the best source of building mental health when it’s the right community.” (29:45, Adam Hill)

• Three Levels of Breaking Ceilings: He highlights that EOS helped him break through “ceilings” as an individual, a leadership team, and organization (32:24).

7. Convincing the Team to Change

• Pushback and Adoption: Implementing EOS required both persuasion and, at times, decisive leadership:

  “It definitely took some convincing, but I will honestly say that it was a bit forced down the throats of the leadership team too.” (35:56, Adam Hill)

• Embracing Healthy Conflict: Letting go of “artificial harmony” was challenging but necessary for growth:

  “…it was more of a discomfort for me…to protect that artificial harmony. And so it was a lot of anxiety for me to see the conflict start to erupt, but then it was…relieving…” (36:50, Adam Hill)

8. Realities of Team Turnover During Implementation

• Leadership Transitions: As is common with EOS, some key leaders left during the first 12 months, requiring Adam to temporarily take on multiple roles (38:34):

  “We did lose a couple of [key leaders]. And I took over…so it took some time for me to…stop wearing all the hats.” (38:34, Adam Hill)

• Visionary vs. Integrator Roles: Adam still occupies both the Visionary and Integrator roles, acknowledging it's not ideal but reflective of both personal and organizational readiness (39:33–41:39).

9. Lessons on Culture and Value Creation

• Moving Beyond Timecard Culture: Adam challenges the outdated notion that time spent equals value:

  “…it's not necessarily the time you put in that’s driving the value. It’s the amount of return on whatever investment that you’re looking at that's driving that value.” (41:01, Adam Hill)

• Building for Succession and Exit: He underscores the importance of installing systems to create business value, whether for succession or sale (43:57–46:27).

10. Adam’s Approach as an EOS Implementer

• Ideal Clients: He looks for open-minded, growth-oriented owners—especially next-gen leaders in family businesses, or founders looking to exit (43:57–46:27).
• Common Obstacles: Nearly all implementations feature “elephants in the room” or “sacred cows” that must eventually be addressed for true transformation (47:06).
• Geography: Adam works with in-person clients in Colorado and Southern California, but also virtually (48:20).

Notable Quotes & Memorable Moments

• On Family Business Myths:

  “The idea of this kind of escalator to the top…isn’t quite the realistic story for most family businesses.”
  — Adam Hill (04:49)

• On Breaking Through Ceilings:

  “There’s things that are deemed untouchable…the longer a business is in business, the more sacred cows develop. But until we question those things, they’re going to remain obstacles to our growth.”
  — Adam Hill (32:24)

• On Vulnerability and Growth:

  “Community is the best source of building mental health when it’s the right community…mentorship…a cohort…all specific to an individual thing.”
  — Adam Hill (29:45)

• On Implementing EOS:

  “Having a system in place…takes the weight of the decision off [the leader]…it’s for the greater good of the organization.”
  — Adam Hill (24:04)

• On EOS Results:

  “Over the next two years our revenues grew by 50%. We became a nine-figure business for the first time and…broke through that ceiling.”
  — Adam Hill (17:14)

Key Timestamps for Reference

• 00:00–01:40 – Hill Brothers family business origins
• 10:30–12:12 – How Adam’s father professionalized the business
• 12:12–16:30 – Adam’s transition to CEO, early struggles, hitting company ceiling
• 16:30–19:33 – Discovering EOS, skepticism, and initial impact
• 21:02–25:47 – Family dynamics, leading former mentors, and value of EOS for structure
• 29:02–32:24 – Adam’s personal resilience: overcoming alcoholism, value of mentorship and community
• 35:56–37:59 – Convincing the team to adopt EOS, embracing conflict, moving from artificial harmony
• 38:34–41:39 – Leadership turnover; occupying Visionary and Integrator roles; culture change
• 43:57–47:06 – Keys for successful EOS clients, common obstacles in implementation
• 48:20–49:16 – How to find Adam as an EOS implementer

Conclusion

This episode provides a candid, nuanced look into the mindset shifts required for generational family businesses to survive and thrive. Adam’s journey is an example of how vulnerability, a willingness to challenge tradition, and a disciplined approach to leadership systems can catalyze transformation in even the most established organizations. His story offers encouragement and tactical lessons for any leader navigating the intersection of family, legacy, and the need for change.

Contact Adam Hill:

• Website
• Email: adam@eosworldwide.com

(Summary compiled directly from podcast transcript, reflecting the speakers’ original tone and language.)