Experiential Learning: Lessons from Battle-Tested Leaders

True leadership capability isn’t developed in a classroom—it’s forged through experience, challenge, and practical application. You learn by doing, and more often than not, by failing.

The military’s approach to leadership development, as a result, emphasizes the critical role of experiential learning in building effective leaders.

The Power of Experience

Leadership development through experience differs fundamentally from traditional academic learning. While theoretical knowledge provides a foundation, it’s the practical application of leadership principles in real-world situations that truly develops leadership capability.

And it’s not really a matter of years of experience, but rather the quality of experiences gathered. It can, and does, happen fast sometimes. Sometimes it never happens.

This approach to leadership development parallels how technologies mature through TRL stages in our technology development series, where theoretical concepts must be proven through practical demonstration and real-world application. To develop as a leader, you need to be in sitautions where your basic ideas and values are challenged and tested.

Military Leadership Development

The military’s approach to leadership development has been refined over centuries of experience and as a result is a very effective model.

The model emphasizes progressive responsibility, structured challenges, and continuous feedback. Leaders learn through a combination of formal training, mentorship, and increasingly complex assignments that test and develop their capabilities. The emphasis on this is rarely seen in the corporate world, but is no less important there.

The military model is, again, not unlike the process we put our technologies through. In the same way you as a tech lead might develop technology, you can as a manager develop leaders (or yourself).

Diverse Experiences in Leadership Development

So what are we actually talking about when we say “experiential learning” in the context of leadership development. There are really 4 categories we’re exploring. These experiential learning approaches differ in context and impact:

• Challenging Situations:
  Leaders often find themselves in high-pressure environments where difficult decisions, resource constraints, and unexpected obstacles are the norm. These direct challenges force rapid decision-making and foster resilience, sharpening both problem-solving abilities and adaptive leadership skills. Think of this as “trial by fire”. This is sometimes an ad-hoc thing that just happens, but can also be a purposeful “special project” assigned to someone for the purpose of growth.

• Structured Progression:
  Unlike random encounters, structured experiential learning involves deliberate challenges with clear objectives, measurable milestones, and regular assessment. This systematic approach ensures that each experience builds on the last, creating a coherent developmental pathway for a leader. These look more like regular career development and progressions.

• Simulated Field Training:
  Particularly prominent in military leadership development, simulated exercises and field training provide a controlled environment for practicing decision-making. These safe-to-fail simulations offer immediate feedback, enabling leaders to experiment with different approaches and build confidence without the weight of real-world consequences. This is what most think of as “leadership development”, it could be training courses, executive coaching, or other classroom-oriented venues focused on the training, not on the actual deliverable.

• Real-world Application:
  The ultimate test of leadership comes in actual operational settings where stakes are high and consequences are real. In these scenarios, leaders must integrate all their skills to navigate the complexities of limited resources and time-critical decisions while maintaining team cohesion and effectiveness. This is the day-in-day out demonstration of skill within one’s own regular job function.

Each of these experiential types contributes uniquely to the overall leadership journey, ensuring that leaders not only learn but also apply, adapt, and grow when facing real challenges.

The Feedback Loop

In all of these learning modes, continuous feedback forms an essential part of the experiential learning process.

Through structured after-action reviews, leaders gain insights into their own performance and decision-making processes. Peer feedback provides valuable perspective on team dynamics and leadership impact, while mentor guidance helps connect individual experiences to broader leadership principles. Regular self-reflection and performance assessment complete the learning cycle, ensuring that lessons are truly internalized and applied to future situations.

The process of experiential learning naturally builds resilience as leaders encounter and overcome various challenges. By facing failure and recovery in controlled environments, leaders develop the emotional and psychological strength needed for long-term success. The experience of managing ambiguous situations and unexpected challenges creates adaptive capabilities that serve leaders well throughout their careers.

Beyond individual growth through this experience->feedback loop, effective leaders recognize their responsibility to help others learn from their experiences. This can be through mentoring, coaching, writing, or otherwise building organizational systems that capture the learnings for others.

Practical Applications

Experiential learning remains the cornerstone of effective leadership development.

As a leader yourself, it’s important to actively focus on developing a next generation of leaders and to understand your own role in that. Future leaders need experience in order to develop, and there are a variety of ways to provide that experience. Classroom training alone will not get it done.

Actively plan and provide special projects, increasing responsibility, simulated exercises, and clear, timely feedback for yourself and your team.