Terrence Cummings - Executive Coaching

Whether one-on-one or with a full team, my coaching starts with trust, candor, and clarity. I help leaders and teams uncover what’s holding them back, unlock what’s already within them, and build the confidence and cohesion to move forward with purpose.

1:1 Leadership Coaching

A Safe Place for Bold Growth.

In my one-on-one coaching, I create a space grounded in safety and honesty where leaders can explore both their strengths and their struggles without fear of judgment. I’m what I call a “lockbox.” If you share something with me, it stays with me. That sense of psychological safety allows clients to go deeper, to name what’s really holding them back, from career decisions to personal challenges that show up at work.

I balance vulnerability with accountability: I will listen deeply, but I’ll also challenge you to push past self-imposed limits and expand what you believe is possible. My approach blends curiosity with pattern recognition. I learn fast, connect dots across disciplines, and help you see your challenges through new lenses that unlock action.

My coaching draws on principles of Conscious Leadership, helping leaders grow their awareness of how they think, feel, and react — and to lead from choice rather than reactivity. I also built a proprietary coaching program inspired by the Co-Active model while at Guild, blending its human-centered foundation with the rigor and practicality needed in high-growth environments.

The result is coaching that’s grounded and growth-oriented, equal parts reflection and real-world momentum.

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Terrence has a remarkable ability to help you see yourself and your potential with new clarity. Through his coaching, I learned to challenge my own assumptions, build confidence, and lead with greater purpose.

LeShanda Davis

Senior Director

Teams Coaching

Build Teams That Move as One.

Great teams don’t just work together — they trust each other, challenge each other, and move in the same direction with speed and clarity. I help teams build alignment, autonomy, and momentum so they can perform at their highest level at pivotal moments.

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The best leaders know how to make people feel both valued and challenged, and the best teams know how to be honest with one another. My work creates the conditions for that honesty — surfacing what’s unsaid, strengthening communication, and helping teams replace friction with forward motion.

I use a mix of skip-level conversations, team diagnostics, and pattern recognition to help leaders see their culture clearly. I don’t come in to prescribe solutions; I help teams reveal the truths that unlock their own. When those truths come to light, leaders make better decisions, trust deepens, and performance compounds.

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Terrence blends empathy with edge. He invites every voice in, frames the right questions, and doesn’t let us lose the thread. Our team communicated better, made decisions quicker, and actually enjoyed the process.

Kristie Griffin

Head of Talent

Terrence's blend of candor and care is what separates good coaches from transformational ones. He doesn't just diagnose problems or recommend solutions—he creates the conditions for leaders to do the hard work themselves and come out better with every interaction.

Alana Brandes

Chief People Officer