071: The Human Work Behind Strategy

In this thoughtful episode, Elena Armijo welcomes Teri Riddle, CEO and founder of the Crossland Group, to reflect on leadership, trust, and the deeper forces shaping organizations today. With more than twenty five years of experience guiding leaders across the public and private sectors, Teri brings a rare combination of strategic clarity, humanity, and lived wisdom to the conversation.

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Elena opens with a coaching reflection centered on a question many leaders are quietly holding right now: when everything feels uncertain, what does trust require of me? She reflects on trust as something built slowly through ordinary moments of follow through, honesty, and repair. Alongside trust, she names three other forces that often move through organizations at the same time: joy, grief, and change.

Teri brings a powerful layer to this reflection. Early in her career she worked in hospice care, an experience that profoundly shaped how she understands transition and loss. In organizations, change always carries a form of grief. When that grief is ignored, it often appears in other ways such as disengagement, conflict, or burnout. Naming what is ending alongside what is beginning can help leaders guide people through change with greater honesty and care.

Teri also reflects on how these ideas shape her own leadership practice. Inside her firm, practices such as eliminating time tracking, offering annual sabbaticals, and prioritizing well-being are rooted in a simple belief that trust must be lived, not just discussed.

These values have also shaped the evolution of the Crossland Group itself. Over twenty five years, periods of reinvention became defining moments in the firm’s journey. One pivotal shift involved moving beyond traditional organizational charts and focusing instead on purpose, strategy, and the shared responsibility leadership teams hold for the success of the whole system.

The conversation closes with reflections on mentorship, generational responsibility, and the importance of illuminating truth as leaders navigate an increasingly complex world.

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This podcast was produced by the following amazing team:

Ulrich Wolvaardt, Audio Engineer

Aaron Boykin, Musician & Artist (Get updates about Aaron’s music via Instagram)

Jo van Eeden, Project Manager

Elena Armijo