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About Cliff Kayser

Cliff is an experienced organization development (OD) consultant, executive coach, and leadership trainer overseeing Polarity Partnerships' east coast operations out of Washington, DC. In 2017, Cliff became a founding partner of the 501(c)3 organization the Polarities of Democracy Institute and in 2018 the healthcare coaching/consulting firm, SixSEED Partners. Cliff is a faculty member at American University's Master's in OD and KEY Executive programs and is a Coaching Fellow for George Mason's Accredited Coach Training Program under the Center for the Advancement of Well-being. His past work experience includes VP of Organizational Development and Training for The National Cooperative Bank, Senior OD Consultant for The Washington Post, and Corporate Manager of Human Resources (HR) and Training for The Washington Post Company. Cliff earned Master's Degrees in OD (2007) and HR Management (1998) from The American University and his Coaching Certification from Georgetown's Executive Leadership Coaching Program in (2008). He is a PCC (Professional Certified Coach) and a graduate of the 2-year Polarity Mastery program (2010), and has served as the program dean since 2014.

Just Tao It, Chapter 71: Brilliance & Patience

By |2026-04-10T21:39:08-04:00April 10th, 2026|Both/And Polarity Leveraging, Just Tao It, Polarity Thinking|

See the Series Introduction for Just Tao It, Part I: HERE See the Just Tao It Series Introduction Tao/It on-ramp, PART II: HERE See Just Tao It, Chapter 1: HERE From my interpretation of Chapter 71 of the Tao Te Ching (Unpublished): Seeing that you don’t know is brilliance. Not seeing that you don’t know is blindness. To [...]

MASCULINE AND FEMININE: THE POLARITY LEADERSHIP CAN NO LONGER IGNORE

By |2026-04-07T19:12:19-04:00April 7th, 2026|Both/And Polarity Leveraging, Polarity Thinking, Wiser Decisions|

I asked three different AI systems to help me solve a complex organizational challenge last month. Every single response gave me a decision tree, a prioritization matrix, and an action plan. Not one asked me how the people involved were feeling about the change. Not one suggested I spend time listening before deciding. Not one questioned [...]

John Kessler’s Multarity Brilliance

By |2026-04-06T20:45:57-04:00April 6th, 2026|Both/And Polarity Leveraging, Polarity Thinking, Wiser Decisions|

There are moments in life when whatever you thought was holding things together simply stops. Not gradually, not politely—just stops. For me, it was a mountain biking accident that fractured my neck at C2 and left me with a traumatic brain injury. The kind of moment where you don’t need a specialist to tell you something [...]

The “Soft Skill” of TRUST?: Yeah, No…Honoring Jack Gibb, and others

By |2026-04-06T20:30:31-04:00April 6th, 2026|Both/And Polarity Leveraging, Polarity Thinking, Wiser Decisions|

There’s a tendency—especially in leadership circles—to treat trust like a cultural nice-to-have. Something you work on after strategy, after execution, after results. A layer. A tone. A sentiment. That idea doesn’t hold up very well when you actually look at how systems work. Jack Gibb saw this clearly long before most of us were paying attention. [...]

Just Tao It, Chapter 76: Strength & Flexibility

By |2026-04-06T17:23:03-04:00April 5th, 2026|Both/And Polarity Leveraging, Just Tao It, Polarity Thinking|

See the Series Introduction for Just Tao It, Part I: HERE See the Just Tao It Series Introduction Tao/It on-ramp, PART II: HERE See Just Tao It, Chapter 1: HERE From my interpretation of Chapter 76 of the Tao Te Ching (Unpublished): Life comes— soft, supple. Death comes— hard, inflexible. Soft and supple— living. Hard and inflexible— dying. [...]

Just Tao It, Chapter 2: Knowing & Wonder

By |2026-04-06T17:00:45-04:00April 3rd, 2026|Both/And Polarity Leveraging, Just Tao It, Polarity Thinking|

See the Series Introduction for Just Tao It, Part I: HERE See the Just Tao It Series Introduction Tao/It on-ramp, PART II: HERE See Just Tao It, Chapter 1: HERE From my interpretation of Chapter 2 of the Tao Te Ching (Unpublished): When people see beautiful things, Ugly things arise. When people see good things, Bad things are [...]

HOPE! Strong Floor & No Ceiling (Part I)

By |2026-03-19T13:30:41-04:00March 19th, 2026|Both/And Polarity Leveraging, Freedom and Authority, Human Rights And Communal Obligations, No Ceiling, Oliver Libby, Polarity Thinking, Strong Floor, The Polarity Assessment™, Wiser Decisions|

Some days it’s hard to be hopeful. The scope and scale of polarization and doom-loop thinking about the U.S. and the future can feel like an hourly, daily, monthly assault on the senses. Then a book like Strong Floor, No Ceiling comes out. My intuition sirens flare and my energy returns. A few differently firing synapses, [...]

Democracy: The Only System Built for Interdependence

By |2026-04-07T19:27:39-04:00March 19th, 2026|Both/And Polarity Leveraging, Polarity Thinking, Wiser Decisions|

Winston Churchill once observed that democracy may be the worst form of government—except for all the others that have been tried. It is the kind of line that gets laughs because it lands close enough to the truth to sting a little. Democracy is messy. It is slow. It often looks like argument layered on top [...]

HOPE…Not a Strategy: Strong Floor & No Ceiling, PART II

By |2026-03-19T13:32:24-04:00March 19th, 2026|Both/And Polarity Leveraging, Freedom and Authority, No Ceiling, Polarity Thinking, Strong Floor, Wiser Decisions|

(Part I, "HOPE! Strong Floor, No Ceiling" preceded this Part II.) There is an oft-repeated phrase in the global community of Polarity Thinkers: “Simple, not easy.” Strong Floor AND No Ceiling is a simple idea. It is clear. It is compelling. It resonates across differences in a way that most policy ideas do not. It offers [...]

Not a Horse Story

By |2026-03-18T23:08:00-04:00March 18th, 2026|Both/And Polarity Leveraging, Polarity Thinking|

There’s an old Chinese story about a farmer whose livelihood depends on a single horse. One day the horse runs away. The neighbors stop by and say, “That’s bad.” The farmer replies, “Maybe.” A few days later the horse returns—bringing several wild horses with it. The neighbors return and say, “That’s [...]

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