Leading Through the Unimaginable: The New York Times' First Female CIO Offers Leadership Wisdom

On the topic of leadership, Cindy emphasised the critical need for trustworthiness. Leaders must earn their people's trust, ensuring teams feel safe, believe in their leader's knowledge, and feel genuinely cared for. A strong sense of purpose is also crucial for employee well-being and motivation. Cindy shared a personal experience of finding retirement emotionally challenging due to a shift in her sense of purpose after leaving her demanding role as CIO.

Another key aspect of leadership she discussed was helping teams navigate mistakes and failures. She recounted a memorable anecdote involving a major printing error during a World Series, when a special full-color section of the newspaper unexpectedly came out in black and white. The team was "devastated" by this public failure, highlighting their passion and commitment. To counter the demoralisation, the CEO was asked to give the team a pep talk, which proved to be incredibly meaningful and restorative.

Reflecting on career growth, Cindy advised that careers are rarely linear, experiencing "ups and downs," but the general trend should be upward. Satisfaction in one's career comes from finding meaningful work, being fairly compensated, and feeling appreciated by management. Setbacks are inevitable but "aren't permanent," a powerful reminder of resilience.

Finally, Cindy addressed the challenge of leaders not knowing everything their team members know, especially in rapidly evolving fields. Her perspective is that leaders and team members are all part of the same team with different jobs. A leader's role often involves providing the necessary tools for the team to succeed, effectively working for them rather than merely directing them.