Extreme Anchoring

Timothy Chester

As a CIO, negotiation is part of my daily work—whether it’s advocating for ideas, allocating resources, or diplomatically saying “no.” Fifteen years ago, I took a course from Chester Karrass, a renowned negotiator, after reading about him in an airline magazine. Though the course focused on sales, I walked away with a deeper understanding of topics like concessions, overcoming an impasse, and competitive vs. cooperative negotiations. More recently, I’ve explored Chris Voss’s approach, which focuses on relationship-building and what he calls “tactical empathy.” I’ve found these ideas so useful that for some time now, I’ve led several EDUCAUSE workshops to assist other IT leaders in enhancing their negotiation skills.

Timothy Chester

Today, as I observe President Donald Trump’s first two months in office, I’ve immediately noticed a recurring pattern—he consistently employs extreme anchors, a concept that has been extensively discussed by both Karrass and Voss. Unlike most political leaders, Trump doesn’t start from the middle and negotiate outward—he stakes out an extreme position, forcing opponents to react and shifting the Overton Window toward his agenda. Trump has consistently used this approach to control debate boundaries and dictate engagement in real estate, reality TV, and politics.

Timothy Chester

In today’s , I break down how Trump applies extreme anchoring as a negotiation strategy, why it works, and how to respond when someone attempts to dramatically shift the terms of debate. Understanding this technique isn’t just about politics—it’s about knowing how to navigate high-stakes conversations in any setting.