Self-Reflection in Leadership: The Key to Navigating Uncertainty and Building a Better Future

Perspective by Hera's Co-Founder, Jennifer Rider

The Journey Begins: Stepping Into Leadership with Purpose

Leadership has always been a natural instinct for me. I’ve been drawn to problem-solving, seeing opportunities for improvement, and bringing people together to achieve a shared goal. But as I stepped into senior leadership roles - particularly in positions where I inherited existing teams - I quickly realized that instinct alone wasn’t enough.

True leadership required refinement, structure, and the ability to drive sustainable growth. It required navigating internal and external pressures, aligning people around a vision, and holding both myself and my teams accountable for executing strategies that would move the organization forward.

At the core of my leadership challenges were team dynamics and performance. Stepping into organizations with established teams often meant working with people I hadn’t chosen. Some were deeply invested in the mission, while others were disengaged or resistant to change. I needed to find a way to get the right people in the right seats, build cohesion, and shift the culture toward execution and accountability.

Beyond internal challenges, external factors amplified the difficulty:

Limited resources - We were expected to do more with less, a reality in many mission-driven organizations.
Ineffective or outdated systems and policies - Legacy processes hindered innovation and efficiency.
Internal complacency - A culture of “this is how we’ve always done it” threatened momentum.
External pressures to deliver measurable social impact - Stakeholders, funders, and regulatory bodies demanded data-driven outcomes.

These challenges mattered because they weren’t just operational hurdles; they were barriers to real, meaningful impact. Our world faces complex social challenges, and strong leadership, engaged teams, and an unwavering commitment to purpose are essential to driving solutions.

Investing in Growth: Honing Leadership Skills

Recognizing the gaps in my leadership approach, I proactively sought growth and development. Leadership isn’t just about making decisions - it’s about making the right decisions with confidence and clarity. I knew I had to strengthen my skill set, expand my perspective, and embrace strategic frameworks that would allow me to lead with intention.

Some of the most impactful leadership strategies I employed included:

Returning to graduate school for an MBA - This gave me the analytical and strategic tools to lead at a higher level.
Executive coaching - Receiving mentorship from experienced leaders helped refine my leadership approach.
Situational Leadership Model - Learning to adapt my leadership style to different individuals and situations improved my effectiveness.
The 4 Disciplines of Execution - This framework provided clarity on setting goals, maintaining focus, and ensuring accountability.
Entrepreneurial Operating System (EOS) - Implementing EOS principles helped me create structure, set clear expectations, and drive performance within my teams.

But perhaps the most transformational aspect of my leadership growth was internal:

Self-reflection and personal development - I confronted limiting beliefs that had held me back and actively worked on building confidence in my leadership decisions.
Learning the power of trust and delegation - I realized leadership wasn’t about doing everything myself; it was about empowering the right people to execute effectively.
Holding firm to accountability while remaining empathetic - Balancing high expectations with support created an environment where people felt both challenged and valued.

The Turning Point: Owning the Weight of Leadership

One of the most defining moments in my leadership journey was being given my first CEO role.

This was a moment of both opportunity and pressure. I had spent years preparing, but the reality of sitting in the top leadership seat meant that every outcome - good or bad - ultimately landed at my feet.

It was no longer about influencing decision-making from a senior leadership perspective; it was about owning the entirety of an organization’s success, its people, and its impact.

I quickly realized that successful leadership at this level required three critical shifts:

Clarity in Vision – The team needed not just direction but a clear and compelling reason to rally behind the work we were doing.
Accountability with Empathy – People thrive when they know expectations are high but also feel supported in reaching them.
Relentless Focus on Execution – Big visions fail without disciplined execution and follow-through.

Navigating Internal & External Politics

One of the most underestimated challenges of leadership is managing internal and external politics.

Inside the organization, I often had to balance competing stakeholder interests - board members, senior leaders, and frontline staff often had different perspectives and priorities. Transparency, authenticity, and active listening became my most valuable tools in bridging gaps and ensuring alignment.

Externally, the challenge was even greater. One of the most disruptive forces is happening right now under Trump’s presidency, which is fundamentally reshaping federal funding structures and regulatory demands. Agencies that had once been primary funders for social impact work have been dismantled, cutting off critical resources. Meanwhile, new compliance and oversight measures are creating additional bureaucratic hurdles, making it even harder for organizations to navigate an already challenging landscape.

These external shocks forced me to:

Adapt quickly and find alternative funding sources to keep programs and services alive.
Manage morale internally, as teams grapple with uncertainty about the future.
Stay true to the mission, despite external pressures that make execution more difficult.
Recognize the real-world implications of leadership on communities - especially in a time of increasing social and economic inequality.

The Transformation: What Leadership Achieved

As I implemented these strategies, the transformation was tangible:

Team morale and performance improved dramatically. The environment shifted from stressful and disengaged to positive, collaborative, and motivated.
We went from high turnover to 100% staff retention.
Outcome measures improved in every area.
A culture of accountability, trust, and innovation emerged.

The Lasting Impact of Leadership

This journey reinforced what I have always believed - leadership is not about authority, but about responsibility, resilience, and creating environments where people thrive. The greatest transformations come when leaders:

Face challenges head-on rather than avoiding them.
Align teams around a shared purpose and hold them accountable to it.
Adapt to external disruptions without losing sight of their core mission.
Lead with integrity, transparency, and courage - especially in times of uncertainty.

The impact of strong, ethical leadership is not just organizational - it is societal. The businesses and nonprofits we build, the cultures we shape, and the people we empower will ripple outward, influencing communities and industries far beyond our immediate reach.

Your Leadership Journey: A Call to Action

Leadership is not just about titles or positions - it’s about the impact we choose to have on others and the world around us. As you reflect on your own journey, consider these questions:

What have been your greatest leadership learnings?
How do you navigate uncertainty while staying true to your values?
What do you believe leadership requires in today’s rapidly changing world?

I invite you to share your thoughts, challenges, and insights. Let’s create a conversation about leadership that is grounded in ethics, impact, and purpose. Together, we can build businesses - and a world - that are better for everyone.