The Heart of Transformation

“How do organizations stay relevant in a world that's changing faster than ever? By embracing transformation that starts from the heart – and the questions we dare to ask.”

1. Exploring Before Executing

Organizations often find themselves caught in the cycle of execution – tirelessly repeating strategies that once worked but may no longer be effective in today's changing landscape. Leckie emphasizes that before companies launch into action, they should explore and question whether their systems and plans are still relevant.

This process begins with curiosity. Leaders need to challenge past assumptions and remain open to new perspectives. By pausing to genuinely explore ideas, businesses can uncover creative solutions to modern problems rather than defaulting to outdated strategies. Exploring doesn’t mean avoiding action but ensures the actions taken are well-informed and aligned with current needs.

To explore effectively, leaders can pose five specific questions to ignite fresh thinking. These questions encourage individuals to be curious and identify blind spots, embrace diverse perspectives, and go beyond surface-level solutions. Leaders must embrace the discomfort of asking, "What if we're wrong?" to drive meaningful transformation.

Examples

• Asking employees, “What are we assuming is true?” to uncover hidden biases in business strategies.
• Identifying missing voices in decision-making to break free from echo chambers.
• Encouraging unconventional ideas by requesting “third-best” solutions instead of default answers.

2. Learning Before Knowing

In the digital age, knowledge itself is no longer the primary asset – the ability to learn constantly and adapt matters most. Leckie highlights the need for organizations and individuals to shift their focus from simply knowing to continually learning.

This shift forces leaders to let go of rigid certainty. They should instead embrace feedback and critiques, using them as opportunities to grow. Encouraging teams to question outdated practices and sparking honest conversations about blind spots builds a learning culture. It's less about defending what you already know and more about being nimble and receptive to new possibilities.

Leckie outlines the mindset needed to foster this culture. By asking, “How is my idea wrong?” or “What don't I yet know?” leaders demonstrate humility and adaptability, enabling organizations to keep pace with rapid innovation and industry changes.

Examples

• Leaders seeking feedback by asking, “When was I last proven wrong?” as a way to embrace reflection and adaptability.
• Acknowledging blind spots during team meetings to uncover areas of improvement.
• Encouraging employees to pursue learning opportunities rather than sticking only to their established skill sets.

3. Changing Before Protecting

Organizational stagnation often stems from fear – fear of losing control or admitting that past methods no longer work. Leckie argues for embracing change rather than clinging to the status quo.

Change requires grappling with uncertainty. Leaders must honestly assess the risks of inaction by asking tough questions, such as, “What’s the cost of staying safe?” This insight fosters an understanding that complacency often carries greater risks than trying something new. Further, leaders must model this mindset by openly acknowledging their fears and taking bold actions.

Little changes, enacted person by person, create meaningful organizational shifts. Leaders who lead by example and involve others in the change process make adaptation more approachable and achievable.

Examples

• A manager admitting fears about a new business approach and encouraging team feedback to address concerns.
• Comparing the risks of sticking to old processes versus innovating to highlight hidden costs.
• Publicly advocating for a transformation initiative and demonstrating commitment through personal actions.

4. Pathfinding Before Path-Following

Rigid guidelines may give structure, but excessive adherence can stifle creativity. Leckie encourages organizations to focus on pathfinding by supporting values-driven decisions and empowering employees to take initiative.

Pathfinding allows teams to embrace shared goals while defining their own means of achieving them. Rather than prescribing exact steps, leaders should clarify the organizational "North Star" – values and ultimate objectives – and trust employees to navigate the journey. This fosters self-reliance and a sense of ownership among team members.

Instead of strict oversight, engaging questions like, “What is most important?” and, “Are our actions aligned with our values?” help companies stay true to their mission while allowing this flexibility.

Examples

• A company allowing teams autonomy to decide how to meet cost-cutting goals instead of mandating specific cuts.
• Leaders using “What’s most important?” discussions to ensure team values match the company mission.
• Encouraging open dialogue about tough decisions by asking questions like, “Can we discuss our differences?”

5. Innovating Before Replicating

Leckie asserts that businesses often focus more on replicating past successes than pursuing new ideas. True innovation requires a willingness to experiment, fail, learn, and play the long game.

Jeff Bezos's approach with Amazon exemplifies this. Choosing growth over short-term profits, Amazon endured losses to understand customers better and develop innovative solutions. Companies must shift their focus from simply replicating old models to actively challenging what they know to create something better.

Learning from failure is fundamental to innovation. Leaders can ask themselves questions like, “What have I learned from my mistakes?” and strategize ways to avoid repeating them in the future.

Examples

• Experimenting with new markets or products instead of sticking solely to historically profitable ones.
• Analyzing patterns of failure to identify areas of consistent underperformance.
• Considering new business models by asking, “How would I disrupt myself?”

6. Humanizing Before Organizing

Organizations often define employees strictly by their roles, but Leckie highlights the importance of recognizing the full person behind the position to unlock their potential.

Leaders who show genuine care for their teams foster trust and collaboration. Asking questions like, “What’s most important to you?” or “How can we work better together?” deepens connections and encourages open dialogue. This approach helps people feel valued, increasing their willingness to contribute their full abilities.

By getting to know what drives their colleagues inside and outside of work, leaders can create a culture that promotes honesty, support, and shared success.

Examples

• Understanding an employee’s personal motivations to assign work matching their strengths.
• Addressing issues early by discussing “How will we know when things have started to go sideways?”
• Asking team members, “When are you at your best?” to optimize productivity patterns.

Takeaways

1. Foster curiosity by consistently questioning existing assumptions and approaching challenges with the mindset of exploration over execution.
2. Encourage a learning environment by embracing feedback, recognizing blind spots, and being willing to admit to being wrong.
3. Invest in building trust and humanizing your workplace by seeing employees as individuals beyond their roles and involving them in meaningful decisions.