Leadership Advisory & Executive Coaching

Where transitions
become traction.

Strategic clarity and disciplined execution for organizations navigating change.

Start a Conversation with Us

About

30+ years at the highest levels of leadership consulting.

Winter Leadership was built on a simple premise: organizations navigating significant change deserve a partner who has been there before, who will do the work personally, and who treats every client's challenge as if it were their own.

Our work spans large enterprise to small and mid-size private and public organizations, including nonprofits, professional sports organizations, and privately held and family-owned businesses. We partner across the full leadership continuum, from the CEO and senior team through directors and frontline people managers.

Our model combines the rigor typically reserved for large global firms with the personal investment and agility of a boutique practice. Every engagement is principal-led, supported by a curated alliance of senior affiliate practitioners selected based on each client's specific needs, business context, and goals.

Boutique practice, global-firm rigor.
Our Model
Discovery before design. Always.
Our Process
Enterprise to nonprofit. Corporate to professional sport.
Our Reach
Deep partnership. Disciplined execution.
Our Commitment

Services

Where we do our best work together.

01

Executive Coaching

Individual coaching for CEOs, C-suite leaders, and senior executives navigating growth, transition, or elevated complexity. Grounded in psychological insight, assessment data, and practical leadership application. Structured, rigorous, and built around each leader's specific context.

02

CEO Succession & Assessment

Independent assessment and succession planning for boards and senior leadership teams. Built on deep experience in executive evaluation, leader succession, and CEO-level assessment across industries and at scale.

03

Senior Team Effectiveness

Facilitated work with executive leadership teams at inflection points: new team formation, strategic pivots, culture challenges, and performance alignment. We design with the organization's strategic moment in mind, not a generic offsite framework.

04

Leadership Development

Custom programs for organizations building leadership capability across levels. From cohort-based director and manager development journeys to enterprise-wide competency frameworks, we design content that fits the organization and the leaders in the room.

05

360 & Leadership Assessment

Multi-rater 360 feedback and validated assessment tools, including instruments such as DiSC and Hogan, designed for depth and utility. Administered with care, delivered with candor. Structured to create real development momentum, not just a report.

06

Speaking & Facilitation

Keynote presentations and facilitated sessions for leadership summits, board retreats, and executive offsites. Substantive content designed around the organization's actual priorities and the specific moment they are in.

Cathy Winter, Founder and Managing Principal, Winter Leadership

Leadership

Cathy Winter

Founder & Managing Principal

Cathy Winter is an executive coach and leadership advisor with 30+ years of experience at the highest levels of leadership consulting. She leads every client engagement personally, supported by a curated alliance of senior affiliate practitioners selected based on each client's specific needs, business context, and goals.

Her background spans a decade at Korn Ferry, where she ultimately served as Partner leading executive assessment, succession, and development engagements for organizations across industries, and five years as President of Premier Sport Psychology, where she led the firm's embedded advisory function serving professional sports front offices across leagues.

She holds an M.A. in Counseling Psychology from the University of St. Thomas and a B.A. in Psychology from the University of Minnesota.

Our Approach

We learn the culture before we design anything.

"Every engagement begins with genuine investment in understanding an organization's culture, history, leadership gaps, and strategic priorities. What leaders carry into the room shapes what we build. That said, discovery does not mean starting from scratch."

Not off the shelf

We bring a deep, tested body of content and methodology developed across decades of practice. What we bring to every engagement is the discipline to draw from that foundation selectively, designing for this organization and these leaders, not the last client.

A partner, not a vendor

There is no account management layer, no hand-off after contract signing. Every engagement is principal-led, with a senior team supporting in defined roles. Design decisions, client relationships, and facilitation stay at the highest level throughout.

Built for complexity

Our work is grounded in behavioral science and adult development theory, and tested against real business results in high-accountability environments where the stakes of leadership failure are not merely financial but reputational and societal.

Contact

Let's talk about what you're navigating.

If you are looking for a leadership partner, we would welcome a conversation. No pitch. We'd love to hear what you're navigating and explore whether we're the right partner.

Email cathy@winterleadership.com
Location Minneapolis, Minnesota