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The Founder’s Transition: A Personal Reflection on My Eight Trailheads

The Founder’s Transition: A Personal Reflection on My Eight Trailheads

  • Timothy O'Keeffe
  • Huyett

As a person of Irish descent—and married to a Quinn—I was once struck by a Gaelic saying: “A son’s job is to kill his father, and the father’s job is to let him do it.” As stark as it sounds, this phrase has lingered with me throughout my journey as a founder, leader, father, and husband. It has become something of a compass as I reflect on my career and, more importantly, on the delicate and complex work of transitioning my role.

I am 63 years old. I have five children, none of whom are currently employed in our business. For 33 years I have poured my energy into building what started as a tiny company of one into an organization of 250. We have built more than a business—we have built a culture we call our “Culture of Excellence.” We post our financials on the plant wall. We publish pay rates and practice transparency. We share profits, not as a slogan, but as a reality. These choices have not only shaped performance but have signaled who we are at our core: an Evergreen® company built to endure.

But endurance is not automatic. It must be stewarded, particularly through succession. For the last three years, I’ve been intentionally preparing for transition. And what I’ve learned is that transition is not only about corporate charts, valuations, or estate planning. Those are the “above the line” elements: necessary, visible, measurable. Just as critical, and perhaps more so, are the “below the line” dimensions—family dynamics, relationships, communication patterns, even the echoes of personal history.

Because my family members are not directly in the business, the challenge sharpens: how do I prepare a non-participant family to embrace responsibility for an Evergreen enterprise? How do I sustain the Culture of Excellence once my daily presence fades? And how do I, as founder, come to terms with stepping aside?

The Role of a Family Therapist

One of the most important choices I made was to invite a family therapist into this process. For some, this might feel unusual. Businesspeople are comfortable hiring consultants, lawyers, accountants—but a therapist? Yet this decision has been transformative.

Our therapist works with both my family and my executive team. Her role has been to uncover patterns—habits of communication, unconscious dependencies, and the subtle ways founder influence can overshadow growth. At first, it was uncomfortable. Therapy has a way of holding up a mirror. But with time, it has helped us speak more honestly, listen more carefully, and move toward trust.

The therapist observed me, my family, and my team in action. From this vantage point, eight recurring “trailheads” emerged. Each one represents a path that must be explored if transition is to succeed. They are personal, sometimes raw, and always challenging. But perhaps, in sharing them, other Evergreen leaders might recognize echoes of their own journeys.

Trailhead 1: Transparency Does Not Equal Trust

At Huyett, transparency is a deeply held value. But I’ve learned that transparency can be distorted into something less helpful: information dumping. Posting financials is easy; building trust is harder. People sometimes confuse access to data with the presence of trust. But real trust comes from relationships, integrity, and follow-through—not just visibility.

This realization has pushed me to ask: when I practice transparency, am I truly building trust, or am I hiding behind numbers?

Trailhead 2: Deference to Brilliance

My CliftonStrengths highlight thinking and strategy. Empathy, tellingly, sits at the very bottom. My default is to value intellect, problem-solving, and vision. These are strengths, but also blind spots. Too often, brilliance can overshadow relationships.

I have had to learn—slowly—that being brilliant is not the same as being effective, and that being right is less important than being kind. Transition demands a recalibration: relationships first, insight second.

Trailhead 3: Work as Worth

This is perhaps my most personal trailhead. I grew up in a household marked by dysfunction. My brother died by suicide. Out of that pain, I became what the Enneagram calls a “Competitive Achiever.” For decades, I measured my worth by work. I out-hustled, out-produced, and out-drove those around me. It built a business—but it also communicated, intentionally or not, that worth equals output.

That is not the message I want for my people. They are valuable for who they are, not only for what they produce. This trailhead calls me to separate identity from productivity, to reset the culture so worth is not confused with work.

Trailhead 4: Heroic Leadership Stimulates Dependency

Founders often become “heroes.” We run fast, solve crises, carry burdens others cannot. But this creates dependency. When one person is always the problem-solver, others fail to develop.

As I transition, I must resist the hero instinct. My real work is not solving problems myself but creating the conditions where others grow strong enough to solve them without me.

Trailhead 5: Pseudo-Openness

We celebrate openness. But in practice, openness sometimes means rushing to solutions. Problems are spotted quickly but rarely explored deeply. We leapfrog to fixes without living long enough in the questions.

This pattern is seductive because it feels efficient. But it undermines learning. True openness means slowing down, engaging in disciplined problem solving, and letting issues breathe before jumping to solutions.

Trailhead 6: Psychological Assessments as Protection

We use tools like StrengthsFinder, Enneagram, PCM, and Wonderlic. At their best, these assessments open doors of self-understanding. At their worst, they become shields: “That’s just who I am.” They can also be used to label others, boxing people into categories.

In transition, these tools must be reframed. They are not excuses but invitations—to grow, to adapt, to imagine new possibilities.

Trailhead 7: Family of Origin Echoes at Work

We carry our histories into the workplace. My drive to achieve is rooted in my family story. For others, different echoes emerge. These patterns shape culture in ways often unseen.

Acknowledging them allows us to loosen their grip. By naming the influence of family of origin, we create the possibility of change. For me, this has meant facing the ways my own history of proving myself has shaped not only me but my company.

Trailhead 8: Reforming Servant Leadership

I move fast. It has been both my strength and my liability. But as the proverb reminds us: “If you want to go fast, go alone. If you want to go far, go together.”

Servant leadership requires slowing down, listening, empowering others, and walking at the pace of the group. Transition has forced me to unlearn speed and relearn patience. It is not about how far I can carry the company, but how far we can go together.

Reflections on the Journey

These trailheads are not checkboxes to complete. They are ongoing journeys. Some days, I see progress. Other days, I stumble into old patterns. Transition, I’ve learned, is less about “handing off” and more about “becoming a different kind of leader”—one who lets go, who trusts others, who creates space.

Recently, one of my sons joined the firm part-time as a Family Advocate. This is a small but significant step. Perhaps, in time, he or his siblings will take on more. Perhaps not. But what matters is that the company—our people, our values, our Evergreen commitments—remains strong.

When I think back to that Gaelic saying—that the son must “kill” the father—I now hear it less as brutality and more as invitation. To be succeeded is not to be destroyed, but to be released. My job is to let go, with grace, so that others may lead with strength.

This is the work of a founder. This is the true transition.

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