Investing in Kindness: 50 Interview Review | Investing in Kindness Blog

Investing in Kindness kicked off at the end of March. I was inspired to start this project after hearing a talk where an investor implied that backing a kind and thoughtful founder was a bad bet. That perspective felt short-sighted. In August, I shared my findings from my first 25 interviews in Investing in Kindness: 25 Interview Review. Between May and July, I completed interviews 26 through 50 with founders, executives, strategists, and advocates from twelve countries.

The first 25 interviewees were from the USA, Brazil, Germany, Italy, Nigeria, Canada, Colombia, Congo, India, Taiwan, and Uganda. They shared how kindness shapes both professional and personal lives. Their roles spanned wealth management, content creation, education, technology, healthcare, and executive leadership, underscoring that kindness is a core leadership principle and a powerful strategic imperative.

This second group included participants from the USA, Bolivia, Brazil, Denmark, Dominican Republic, France, Iran, Israel, Italy, Lebanon, Nigeria, and Romania. Their professional backgrounds ranged from strategy, executive leadership, and coaching to decarbonization, education, and investment.

Together, these new conversations built on the foundation of the first 25 interviews, which established kindness as a disciplined and strategic approach to leadership. The next 25 both confirmed those findings and expanded them. Leaders described how kindness shows up in daily behavior and how it scales into organizational systems, global partnerships, and social innovation. Their insights show that kindness continues to evolve from a moral choice to a measurable strategy for resilience, innovation, and long-term performance.

Below are the themes that remained consistent throughout all 50 interviews, followed by the new insights that emerged in the second set of 25.

Reoccurring Themes

Kindness as Strength and Discipline

Deliberate Action, Not Weakness: Across roles and regions, leaders again rejected the idea that kindness signals weakness. They described it as clarity under pressure — a conscious, disciplined choice rooted in integrity and awareness.
Leadership with Responsibility: A Chief Strategy and Growth Officer noted that leaders carry a “triple responsibility” because their actions affect others at scale. Research supports this view: compassionate leadership has been shown to reduce burnout and increase performance across sectors (BMC Public Health, 2023).
Emotional Safety as a Core Practice: A trauma-informed consultant emphasized that forgiveness is not about what others deserve, but about creating peace and self-regulation — a view consistent with research published in Harvard Business Review (2023), showing that compassionate leadership directly supports employee well-being, loyalty, and performance.
Consistency When Unseen: Several leaders emphasized that true leadership is defined by behavior when no one is watching.

Human-Centered Leadership in Action

Connection Before Agenda: Leaders continue to stress human connection as central to effective management. Some begin meetings with brief personal check-ins, while others design onboarding processes to understand how people think and what they value.
Mentorship as Multiplier: Many credited mentors who invested time without expectation of return — a kindness they now replicate for others. These relationships build loyalty and resilience across organizations.
Empathy in Daily Practice: Interviewees described reframing tense moments by pausing for context and assuming positive intent, reinforcing that empathy is an active, daily discipline.

These insights reaffirm the findings of Kindness and Retention: What the Research Says About Why Employees Stay. Psychological safety — the shared belief that it is safe to speak up — remains a defining factor in team performance. Google’s Project Aristotle identified it as the single most important element of high-performing teams, while MIT Sloan Management Review (2022) found that employees are more than ten times more likely to leave due to a toxic culture than to low compensation.

Kindness Across Cultures

Different Expressions, Shared Value: Leaders working across more than twenty countries emphasized that kindness is expressive in some regions and reserved in others.
Curiosity Over Assumption: Humility and curiosity were cited as essential tools for bridging cultural tension.
Grace for Missteps: One engineer recalled misinterpreting seating customs in China — a reminder of the importance of awareness and patience.
Openness and Respect: Across contexts, interviewees agreed that leading with openness and respect enables true collaboration.

These experiences reflect a universal conclusion across both interview sets: while kindness may look different across cultures, it consistently builds trust, inclusion, and belonging. This aligns with Deloitte’s global research (2015), which found that employees who feel included and respected are significantly more engaged and loyal.

With that foundation established across global perspectives, the following new themes illustrate how kindness is now shaping systems and strategy.

Additional Themes Explored

Kindness as Systemic Strategy

Interviews 26–50 revealed a deeper understanding of kindness as a strategic design principle for organizations and systems — not just a personal leadership trait.

Ethical Innovation and Equity: Founders are redesigning business models with fairness and transparency at their core — from blockchain tools that protect creative ownership to health-tech platforms improving outcomes for children with chronic conditions.
Decarbonization as Compassion: Industry leaders described kindness as accountability to future generations, guiding efforts to reduce emissions, waste, and environmental harm.
Technology in Service of Humanity: Strategists applying AI in healthcare emphasized that technology should extend human care, not replace it.
Expanding Access: Initiatives providing programming kits and internet connectivity for young women in engineering show how small acts of opportunity can create long-term change.
Community Resilience: Nonprofit executives shared models that help mission-driven entrepreneurs build locally rooted, values-aligned businesses.

A Forbes (2025) article and a joint EY & Oxford Saïd (2024) study reinforce these observations. Both identify kindness as an action-based leadership trait that builds resilience, trust, and innovation. Human-centered organizations are shown to be up to twelve times more likely to succeed during major transformations — confirming what these leaders practice daily.

Kindness as Self-Governance and Integrity

Another theme emerging from this phase was the framing of kindness as internal discipline. Leaders described kindness as a form of self-management that prevents reactive or defensive behavior. It requires composure, emotional regulation, and fairness — even under pressure. This echoes evidence that compassionate leaders build stronger, more adaptable teams, as outlined in BMC Public Health (2023) and Harvard Business Review (2023).

Kindness as Investment in the Future

An expanded theme came from leaders working on climate, technology, and education. They viewed kindness as an investment in humanity — a way to safeguard future generations through ethical choices today. This connects personal integrity with systemic impact, extending the project’s early insights on empathy and retention into sustainability, inclusion, and innovation.

This future-oriented perspective connects leadership kindness to intergenerational responsibility — a theme that may define the next frontier of business ethics.

Kindness is a foundational element of effective leadership, resilient organizations, and equitable systems. When practiced with discipline, structure, and accountability, it becomes one of the most measurable and enduring investments in human potential — and a cornerstone of a stronger, more sustainable future.