Systems Thinking, Leadership Habits, and Organizational Change with Don Gray

In this episode, Don joined Shahin to talk about Systems Thinking, Leadership Habits, and Organizational Change.

The following have been topics of our conversation:

Transitioning from technical skills to people management.

• The importance of people in software development, highlighting their creative force and impact on success and well-being.

• The importance of trusting and empowering knowledge workers, who are closer to the work than managers.


• Jerry Weinberg (author) highlighted the shift from Taylorism (structured tasks) to coaching (personal and process-related goals), with managers becoming more interested in people's educational and career goals.

Leadership development and problem-solving.

• The importance of adapting to change and the need for problem-solving leaders to observe and understand motivation, organization, and information.

Software development, leadership, and personal growth.

• The importance of developer satisfaction, citing the costly consequences of losing experienced developers.


• Find empathetic leadership insights through reading and self-reflection.


• Software development challenges, complexity as the primary issue.

• Agile methodology requires tailoring to individual contexts, rather than following a one-size-fits-all approach.


• Organization must be ready to start software development before investing time and money.

Leadership habits and systems thinking.

• Management prioritizes cost over readiness, despite worker demand for training and success.


• Coach helps team break habits and improve systems in leadership roles.


• The "core habits" for leaders, including sharing the vision, measuring actual delivery, and creating free informational flow.

Systems thinking, agile development, and team dynamics.

• Wardley maps visualize product evolution, highlighting reinforcing and balancing loops.


• The importance of understanding how personal and cultural factors impact decision-making in complex systems.


• Agreeing to try and visioning with team members led to successful product development.

Software development, leadership, and organizational change.

• Using organizational change management techniques to facilitate change within software development teams.


• The increasing presence of women in leadership positions in the tech industry


• The importance of happiness in software development.

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