How Trust Shapes Our Operating Principle

In this insightful episode of the CEO Show, host Nick Ba interviews Curtis Height, co-founder and CEO of Improving, a $250 million technology services company, to explore the deep-rooted role of trust and culture in building a successful and resilient organization. Curtis shares his personal journey from humble beginnings in Virginia and a disciplined military education at Texas A&M University, through early career experiences marked by loyalty and partnership, to founding and growing Improving. The conversation delves into the concept of “blind spots” in leadership, emphasizing the necessity of self-awareness and openness to feedback for sustained growth. Curtis highlights trust not merely as a value but as a disciplined practice embedded into the company’s infrastructure through rituals, weekly “trust pods,” and shared ownership. He explains how trust accelerates decision-making, fosters accountability, and enhances productivity while nurturing mental health and belonging. The discussion further explores the delicate balance between fostering a culture of trust and driving business outcomes like revenue and profitability. Curtis underscores that culture and character are built deliberately during good times to sustain companies through challenging periods. Rituals such as daily standups focusing on gratitude, values, sales, and recruitment are pivotal in embedding trust and collective involvement. Ultimately, Curtis advocates a “we” culture where loyalty, honesty, respect, and collective success are foundational, contrasting it with a “me” culture, and stresses the importance of conscious leadership to maintain this balance in a living, evolving organization.

Highlights

• Trust as an operating discipline, not just a value on the wall, is central to Improving’s growth and resilience.
• Curtis Height’s early life and military education shaped his leadership philosophy focused on loyalty and accountability.
• Loyalty and trust in early partnerships contribute significantly to long-term professional and personal success.
• Weekly trust discussions based on “The Speed of Trust” embed trust deeply into company culture.
• Talking straight” with respect balances honesty and trust, avoiding destructive bluntness.
• Rituals like daily standups reinforce values, gratitude, and business priorities consistently over 15 years.
• Balancing trust and business imperatives requires conscious leadership and cultural investment during good times.

Key Insights

• Trust as Infrastructure: Curtis Height emphasizes that trust must transcend being a mere aspirational value and instead become a tangible, practiced discipline. By embedding trust into decision-making and organizational rituals, Improving differentiates itself with a culture that withstands pressure, growth, and authority challenges. This approach makes trust a competitive advantage rather than a vague ideal.

• Awareness of Blind Spots: The discussion highlights how leaders often have “blind spots”—areas of reality they resist or fail to see. Curtis acknowledges his own blind spots and stresses that effective leadership and culture-building require humility and openness to seeing these hidden areas. This self-awareness is critical for learning and continuous improvement.

• The Power of Loyalty and Long-Term Partnerships: Curtis’s experience shows that early professional relationships grounded in trust and loyalty often endure throughout a career and significantly impact success. These relationships create a foundation of stability and collective involvement that outperforms the transactional nature of job-hopping often seen today.

• Trust Pods and Behavioral Frameworks: Improving uses structured weekly “trust pods” with about two-thirds of its 1,200 employees participating. These small-group discussions revolve around trust behaviors identified in Stephen M.R. Covey’s “The Speed of Trust,” such as talking straight, demonstrating respect, keeping commitments, and accountability. This institutionalizes trust-building and makes it an active, ongoing practice rather than a one-time effort.

• Balancing Honesty and Respect: Curtis distinguishes between “talking straight” and brutal honesty. Trust is broken when truth-telling becomes an attack. The company culture encourages candid conversations that maintain respect, supporting a psychologically safe environment where diverse viewpoints can be expressed without fear or harm. This nuanced communication is essential for sustaining trust.

• Rituals as Cultural Reinforcement: The daily standup meetings, a ritual maintained for 15 years, are a cornerstone for embedding culture. Each day focuses on a different theme—gratitude, pride, values recognition, sales focus, and recruitment. This repetition ensures values and priorities are consistently top of mind, shaping behaviors and reinforcing collective identity. Rituals formalize culture and make it resilient to change and turnover.

• Conscious Balancing of Culture and Business: Curtis highlights the importance of balancing trust and collaboration with revenue generation and profitability. The company leans into culture-building during good times, knowing that character is revealed (not created) during adversity. Conscious leadership means recognizing when to prioritize cultural investment versus operational focus, maintaining agility without sacrificing foundational values. This balance helps avoid silos and “me cultures” that undermine collective success.

Conclusion

Curtis Height’s leadership philosophy at Improving revolves around trust as an essential, practiced discipline that permeates every facet of the company. His personal story and the company’s rituals reveal how loyalty, respect, and accountability form the backbone of a thriving culture. The use of trust pods and structured conversations based on proven frameworks builds psychological safety and accelerates decision-making. By consciously balancing cultural investment with business imperatives, Improving has created a resilient organization that can navigate market cycles and stresses with integrity and collective strength. This episode offers valuable lessons for leaders aiming to build organizations where trust is lived daily, not just preached—ultimately driving sustainable prosperity and employee fulfillment.