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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.

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 [...]

Environment: Can We Have a Word?

By |2026-04-07T19:37:20-04:00March 18th, 2026|Both/And Polarity Leveraging, Polarity Thinking, Wiser Decisions|

One word could change our trajectory. “And.” Every generation inherits problems it didn’t personally create. Some inherit wars. Some inherit economic breakdown. Some inherit institutions that no longer work the way anyone hoped they would. The generation coming of age right now has inherited something different. They have inherited a planetary system sending increasingly unmistakable signals [...]

Just Tao It, Chapter 66: Lead & Follow

By |2026-06-15T11:03:12-04:00March 18th, 2026|Both/And Polarity Leveraging, Just Tao It, Law of Least Resistance, 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 66 of the Tao Te Ching (Unpublished): Streams and rivers flow down to valleys. Valleys hold the sea by staying low. Those who [...]

Religion: When Either/Or Thinking to the neglect of Both/And Thinking by Gets Backed by God

By |2026-05-25T19:55:17-04:00March 16th, 2026|Both/And Polarity Leveraging, Polarity Thinking, Wiser Decisions|

There’s a pattern that shows up across religions, politics, organizations, and even families—anywhere belief and power begin reinforcing one another. Something complex and deeply human gradually gets simplified into a choice. Not simply a preference, but the right choice. Once that happens, everything outside that choice starts looking less like a difference in perspective and more [...]

Artificial Intelligence: Got Human? On Being Watchers & Guiders of AI & Humans

By |2026-04-07T19:33:12-04:00March 13th, 2026|Artificial Intelligence, Both/And Polarity Leveraging, Polarity Thinking, The Polarity Assessment™, Wiser Decisions|

I recently heard something that made me smile at first and then linger long enough that I sat down to write this. When some AI systems interact internally, they sometimes refer to humans with a particular word. Watchers. It is a curious label. If one human described another that way — “Oh, that person’s a Watcher” [...]

The Usefulness of Being a Metatheory — and the Polarity of Reality And Hope

By |2026-03-13T15:20:49-04:00March 13th, 2026|Both/And Polarity Leveraging, Human Rights And Communal Obligations, Polarity Thinking, Strong Floor, The Polarity Assessment™|

After twenty years working with Polarity Thinking, one word finally helped me explain why it works: metatheory. A metatheory isn’t another model or framework. It’s the lens behind the lens — the way of seeing that shapes how we understand everything else. In that sense, the usefulness of Polarity Thinking is not simply that it offers [...]

Just Tao It, Chapter 48: Less is More (Apparently) Effort & Ease (Redux)

By |2026-06-15T11:03:48-04:00March 11th, 2026|Both/And Polarity Leveraging, Just Tao It, Law of Least Resistance, 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 the Tao Te Ching, Chapter 48 (Unpublished): Being in learning each day, There is accumulation. Being in It each day, There is distribution. In [...]

Series Introduction: Wiser Decisions

By |2026-03-19T12:50:58-04:00March 10th, 2026|Artificial Intelligence, Both/And Polarity Leveraging, Polarity Thinking, The Polarity Assessment™, Wiser Decisions|

The word “radical” often suggests someone has wandered far from common sense. In this case, I mean something closer to the opposite. My radical position is simply this: human beings need to become far more skillful at supplementing Either/Or Thinking with Both/And Thinking. At first glance that statement may sound almost too obvious to deserve a [...]

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