The ROI of Psychological Safety in Business with Donald Thompson

Successful leadership requires balancing strategic excellence with an empathetic, people-first mindset, as demonstrated by Donald Thompson's journey from a coach's son to a global executive advisor.

In this episode of From the Top with Chad Hesters, host Chad Hesters connects with Donald Thompson, a multi-exit entrepreneur and award-winning CEO, to explore his career path spanning software, marketing, and corporate leadership. Their conversation unveils insights on why being "underestimated" can be a strategic advantage and how "hustling with humility" allows leaders to accelerate their professional development. They dive deep into psychological safety as a critical risk management tool, strategies for professional persistence in conservative cultures, and the evolving role of AI in shaping modern employee engagement.

What You’ll Learn:

The "Hustle with Humility" Framework: How to turn limited resources and lack of traditional credentials into competitive advantages by becoming an insatiable learner who asks thoughtful questions of experienced leaders—and why most successful people are eager to mentor those who genuinely seek their perspective.

How to Position Yourself as a Learning Leader: The specific technique of finishing meetings five minutes early to ask one or two substantive questions of senior executives, starting with low-stakes inquiries ("What are you reading?") before advancing to deeper strategic questions that demonstrate genuine curiosity.

Psychological Safety as a Risk Management Imperative, Not Just Feel-Good Culture: Why the real ROI of engagement lies in preventing costly mistakes—stopping production lines when specs are outdated, surfacing unpopular ideas before decisions are made—rather than simply boosting morale.

How to Navigate Hierarchical Organizations Without Direct Confrontation: Practical techniques for proposing alternative viewpoints in conservative, top-down cultures, including asking permission to speak freely, framing ideas as "pre-meeting stress tests," and knowing when to advocate privately rather than publicly.

The Leadership Inflection Point: How recognizing your own limitations—in Thompson's case, his hard-charging sales mentality burning out talent—and choosing to evolve toward empathetic leadership without lowering performance standards is the difference between good results and elite performance.

AI's Role in Reframing Employee Engagement: Why the conversation shouldn't be about "losing headcount" but rather how to grow revenue with 30% less hiring—transforming AI adoption from a fear narrative into an opportunity narrative that energizes rather than threatens your workforce.

About the Guest(s):

Donald Thompson is an award-winning CEO, multi-exit entrepreneur, and Managing Director for the Center of Organizational Effectiveness at Workplace Options, bringing decades of experience in building high-performance teams and scaling businesses. Recognized as an Entrepreneur of the Year, Forbes Next 1000 honoree, and three-time Inc 5000 Chief Executive, Thompson has guided companies from bootstrap phases to successful acquisitions by Adobe Systems and private equity firms. In this episode, Thompson shares transformative insights on employee engagement, inclusive leadership, and navigating organizational culture in the age of AI—providing C-suite executives with practical strategies for building trust, reducing turnover, and driving psychological safety without compromising performance standards. His philosophy of "hustle with humility" and commitment to empathetic yet excellence-driven leadership resonates deeply with strategic decision-makers seeking to cultivate engaged, loyal teams that speak up when it matters most.

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Quotes:

"Anything that you're gonna do big and significant requires a team to execute it through. You can have an individual vision, but in order for that vision to have value at scale, you have to be able to be resilient." - Donald Thompson

"Winning through people is going to be the enduring element of business success both now and the future." - Donald Thompson

"You endure pain because the promise is so much greater." - Donald Thompson

"I turned that lack into kind of a limited resource to really be a competitive learner." - Donald Thompson

"Hustle with humility is finding people to help you with the things that you need to work on." - Donald Thompson

"The risk factor is that most leaders are making decisions on a lower percentage of insight than they have in the organization because people are afraid to speak up." - Donald Thompson

"Psychological safety is, do you create an environment where the best ideas surface in time for you to execute them properly?" - Donald Thompson

"Every time I enter a discussion, I have seniority power in most rooms that I'm in, so it sounds like a dictate even when I'm just trying to add to the dialogue." - Donald Thompson

"When you are an elite leader, an elite performer, then that means there's always more to grow, learn, and improve." - Donald Thompson

"AI is not the technology. It is about how do we adopt this technology in a manner that doesn't create fear but creates enthusiasm and opportunity to have a better, more profitable future." - Donald Thompson

Episode Highlights:

[02:28] The Underestimated Advantage

Donald explains how lacking a traditional path led him to become a "competitive learner".
He defines "hustle with humility" as finding leaders who have already succeeded and asking for their thought processes.
This approach allows emerging leaders to apply the wisdom of others to "jump the line" in their success base.

[11:07] The Journey to Empathetic Leadership

Donald reflects on a time when his "hard edge" in sales led to high turnover and employee burnout.
A leadership coach challenged him to decide if he wanted to stay at "reasonable" results or strive to be an "elite" leader through empathy.
This shift allowed him to maintain high standards of excellence while adopting a people-first mindset.

[14:51] Strategies for Professional Persistence

In conservative or hierarchical environments, Donald recommends asking permission to "speak freely" to honor authority while providing feedback.
He suggests using "pre-meeting notes" to stress-test contrary ideas privately before bringing them to a group session.
These techniques help manage environments that are top-down while ensuring the best interests of the business are met.

[20:30] Psychological Safety as Risk Management

Leaders often view psychological safety as "touchy-feely," but Donald frames it as a tool to surface the best ideas in time for execution.
Without a safe environment, employees may remain silent about production errors or strategic blind spots due to fear of consequence.
Leaders must learn to ask smarter questions to avoid creating an "echo chamber" of their own thinking.

[28:11] AI and Modern Employee Engagement

Employee engagement is now a dynamic concept influenced by the "tsunami" of AI tools.
The goal for CEOs should be using AI to increase profitability and efficiency rather than strictly reducing headcount.
Leaders must frame AI adoption as a way to create a better, more opportunistic future for the entire organization.

Episode Resources:

LinkedIn Profiles:

Chad Hesters' LinkedIn: https://www.linkedin.com/in/chadhesters/
Donald Thompson's LinkedIn: https://www.linkedin.com/in/donaldthompson/

Websites:

Donald Thompson's Website: donaldthompson.com
Workplace Options: workplaceoptions.com

Books:

Underestimated by Donald Thompson
The Employee Engagement Handbook by Donald Thompson (February 20, 2026)

Organizations:

Adobe Systems – Software company (acquisition partner)
Hugo Boss – Global fashion company
Center for Organizational Effectiveness – Donald Thompson's division at Workplace Options