Growing Business through Enhanced Leadership
If your organization is expanding, you're doing great things. With strengthened management skills, you're ready to lead through the next stage.
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If you are seeking to...
Lead the biggest team of your career
Connect mission to measurable results
Transform accountability with negotiated commitments
Spark meaningful, collaborative dialogue
Work hard in a way that is fun
Rally your team around shared purpose
Take your people, and yourself, to the next level
...this is for you.
Take the Flannel CEO Leadership Assessment
"I'm not dogmatic. These tools aren't novel. They are a straightforward compilation of best practices from numerous sources, tested and honed in real workplaces over two decades.
My goal is to use what's already working for you and help fill in the gaps."
Purpose-Driven Leadership
Mission-Centered Vision
Annual and Departmental Planning
Negotiated, Measurable Commitments
Clear Work Structures Aligned to Goals
Autonomous Performance Cycles
Transparent Accountability
Congruent Compensation
Culture of Continuous Learning
Space for Joy
Clarity at Scale
Vitality and Resilience
The Flannel CEO is a grounded, practical system of leadership, enabling you to support high-performance, purpose-driven teams working collaboratively towards a common vision, in structures that scale with your organization's trajectory.
As a CEO and corporate leader, Garrett has built organizations from a dozen to 700 people, studying leadership and amassing the practices described in the series, The Flannel CEO. Most recently, as CEO of Critical Insight, Garrett led strong growth, repeatedly appearing in Inc 5000 as one of the fastest growing companies and being recognized as one of Washington’s Best Places to Work, including a top-10 ranking in 2021.
Earlier in his career, Garrett served as CEO-in-Residence at Madrona Venture Labs, where he led early-stage teams and built FinTech product concepts, testing them through market engagement for differentiation and viability. Previously, he was Managing Vice President at Capital One, responsible for the ShareBuilder investing business. He continues to serve on the Board of Directors and Investment Committee for ShareBuilder 401k.
With a background as a software and data engineer and as a CFA® Charterholder, Garrett blends analytical rigor with people-first leadership to drive growth, scale, and culture.
Copyright © 2025 by Garrett W Silver - All Rights Reserved
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