What truly defines a leader isn’t found in the calm between storms. It’s revealed “in the squeeze,” or what Kevin A. Weishaar calls the Orange Test of Leadership. Founder of Weishaar Strategic Partners, with more than two decades of executive experience leading both for-profit and nonprofit multifamily housing organizations, Weishaar has built his career around one core belief: leadership is about preparing for pressure, not reacting to it.
His Orange Test of Leadership was inspired by a memorable lesson from Dr. Wayne Dyer, whose vivid analogy left a lasting impression on Weishaar early in his career. “He came on stage holding an orange and asked, ‘If I squeeze this orange, what comes out?’ The audience laughed and said, ‘Orange juice,’” Weishaar says. “Then he asked, ‘Why orange juice? Why not apple or grapefruit?’ The answer is obvious, because that’s what’s inside.”
The metaphor reveals a profound truth about leadership: pressure does not create character, it exposes it. “In property management, budgets tighten, markets shift, and residents call with urgent issues,” he says. “When you’re squeezed, what comes out isn’t about the pressure itself—it’s about what you’ve been cultivating inside all along.”
Leading from the Inside Out
After overseeing more than 100 properties across 21 states and leading hundreds of staff, Weishaar understands that emotional steadiness is not a soft skill, it’s an operational advantage. “If you’re frantic, your team will feel frantic. If you’re grounded, they’ll find steadiness in your presence,” he says. “Your tone sets the temperature of your team.”
That philosophy drives the work of Weishaar Strategic Partners, where he now advises organizations on executive leadership, operational design, and team alignment. His firm helps leaders bridge the gap between strategy and execution by focusing first on the people who bring plans to life. He calls this approach “people-first and outcome-driven,” balancing empathy and accountability to turn clarity into results. “people-first and outcome-driven,” a balance of empathy and accountability that turns clarity into results.
Habits That Prepare Leaders for Pressure
Weishaar challenges leaders to see composure under stress not as a personality trait but as a habit of preparation. “The best leaders I’ve coached don’t just hope they’ll be calm under pressure. They practice it,” he says. He points to several daily disciplines that help leaders stay centered when things get tough:
- Reflection: “Even five minutes of asking, ‘What filled me up today? What drained me?’ can change how you show up tomorrow.”
- Curated input: “Be mindful of the voices and information you let in. What you consume shapes what comes out.”
- Emotional rehearsal: “The strongest leaders visualize stressful moments and practice how they’ll respond. When the real pressure comes, they’re ready.”
- Gratitude practice: “Some executives start meetings by naming one positive outcome from the week. It shifts the emotional fuel of the team.”
These small, intentional actions create leaders who respond to adversity with focus and grace rather than tension or frustration. “Curiosity, stillness, and gratitude are not luxuries,” Weishaar says. “They’re leadership fuel.”
Leadership Under Pressure
In both market-rate and affordable housing, Weishaar has led teams through complex transformations, guiding organizations to scale responsibly while maintaining their culture and mission. He believes that the key to thriving through uncertainty lies in preparation. “Leadership is forged in pressure but it’s shaped in preparation.”
That preparation is both structural and personal. It means investing in systems that bring clarity before confusion arises and nurturing the mindset that keeps leaders steady when others waver. “If patience, empathy, and resilience aren’t inside you, they won’t appear under stress,” he says. “But if they are, no amount of pressure can take them away.”
Turning Pressure into Purpose
Ultimately, Weishaar encourages leaders to see difficult moments as diagnostic. “If what comes out when you’re squeezed is stress or doubt, that’s feedback, not failure” he says. “It’s an invitation to build stronger foundations.”
Through his work with Weishaar Strategic Partners, he helps executives and organizations do exactly that: align teams, optimize systems, and lead with the kind of clarity that endures under pressure. His mission is to equip leaders not just to survive the squeeze, but to grow because of it.
For more insights from Kevin A. Weishaar, visit his LinkedIn.
