Advance leaders. Accelerate teams.

We are a leadership development firm, designed to advance human performance.

Constant change, complexity, and uncertainty are the new normal. We develop leaders and teams by strengthening their thinking, skills, capabilities and behaviors from the inside-out and the outside-in to unlock full potential and accelerate exceptional results.

Our Clients

To play, press and hold the enter key. To stop, release the enter key.

Our Purpose

We create leaders and leadership teams who energize, engage and inspire their people.

rainbow of people in a circle holding hands

The Enneagram is at the core of all we do. This highly respected personality system is renowned for providing a foundation of deep individualized self-knowledge and growth with progressive levels of life-long proficiency. It is used for personal, professional and group development.

We bring an array of Enneagram mastery, leadership development expertise, gestalt-based team development experience, business acumen, and design thinking knowledge to hasten transformative changes that stick and drive better business results.

Our Services

Leading Matters helps organizations optimize top talent - their greatest assets - for both opportunity and uncertainty.

We deliver Enneagram-based leadership development services.

We expedite the development of leaders to achieve consistently better business results. They learn to consciously choose new, productive thoughts, feelings, behaviors and interactions. They release limiting patterns and build muscle memory of new beneficial ways of leading.

"What got you here won't get you there" - Marshall Goldman

Executive Coaching

Strengthen leaders from the inside out and outside in, setting the stage for next-level results.

Discover how to get out of their own way and bring their fullest talents to bear.

three people helping each other step up onto blocks

Team Development

Fast-track the team's ability to operate as a sum much greater than its parts.
Rapidly build team trust, effective communication, and collaboration.

three people working together to prop up an arrow

Team Coaching

Accelerate becoming a strong united force that drives operational clarity, stability and success.
Learn to leverage the team's collective strengths and mitigate hidden pitfalls.

four business people celebrating with a trophy

Leadership Programs

Expedite development of high-potential talent into the next cadre of leaders.
Quickly acquire key leadership competencies, wield power effectively and strengthen their voice.

Cynthia
Ridley

Cynthia Ridley is in the business of advancing business leadership. She is a masterful executive coach and team development expert with thirty-plus years of experience that combines business acumen, management consulting, and engineering systems knowledge with a passion for inspiring leaders and teams to PLAY BIG.

Cynthia is a highly accomplished executive coach with 17+ years’ of experience. Since 2007, the Enneagram personality system has been her go-to instrument of choice.

She brings a unique combination of experience and expertise to her leadership development work, including senior leadership positions, business strategy consulting, engineering systems knowledge, and a penchant for bringing out the best in people.

“Cynthia asked - Are you playing small? Goosebumps. She knew exactly what was going on and challenged me. I went from 4 deals and $4B in 2018 to 82 deals and $23B in 2021!”

~ Susan Winter, Head or Global Syndications at Silicon Valley Bank