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Negotiating with Skeptics can be tricky, but it’s not impossible! Based on the article “Change The Way You Persuade” by Gary A. Williams and Robert B. Miller, we’re exploring each negotiation style in detail to help you understand what the best approach is, tailored to increase your chances considerably. If you haven’t read the introduction yet, go do that now and then come back here when you’re done.

Ready to learn the secret to negotiating with Skeptics? Let’s get started.


Identified by their strong personalities, Skeptics are keen on winning and don’t mind if their disagreeable temperament is considered to be offensive. These execs naturally take charge of every situation, working from a place of strong emotions and possibly the thrill of rebellion.

If your boss seems impossible to please and is quick to point out all the flaws in your ideas, they’re likely a Skeptic or a Thinker. Both will have a long list of questions and will poke every possible hole in your argument. The difference is the motive behind these questions. The Thinker wants to understand every angle, but the Skeptic wants to make you sweat. A Skeptic will also freely express how they feel about you and your idea, while a Thinker would never be so straightforward.

You may also notice that your Skeptic boss has little to no regard for your time, possibly looking at their phone while you’re speaking, or even chatting with the person next to them while only half paying attention to what you’re saying. However, if you ever dared to pull the same stunts on them, they’d be fuming.


Celebrity Examples

Steve Case, Larry Ellison, Tom Siebel.


How They’re Convinced

The best way to approach a Skeptic is with calm confidence, making it clear that you’re not deterred by their negativity. Address their concerns head-on, and be prepared with facts and figures that back up your position. Use logic and reason to persuade them, and don’t get drawn into an emotional argument.

Skeptics prefer living in the comfort of their self-curated echo chamber and are more apt to listen to those that they share a kinship with —such as Alumni from the same school. If you’re new to the company or don’t have the right university affiliation on your resume, you’ll be fighting an uphill battle to gain the ever-important credibility. All hope is not lost, however. Having a solid endorsement from someone the Skeptic trusts will act as your golden ticket to gaining their favor. However, be prepared to “verify” your credibility. Name-dropping may get you in the door, but it’s up to you to prove that you can operate on the same level as the Skeptic and deserve to be there.

Of all 5 types of executives, Skeptics need to have their ego stroked the most. They don’t like to be embarrassed, nor do they enjoy feeling inferior, so this can make some interactions feel as though you are walking on eggshells. Always allow the Skeptic to save face if you need to offer a correction; they hate being wrong.

It can be intimidating to negotiate with a Skeptic, but the bright side is that they crave new ideas and aren’t afraid to take risks. Skeptics move fast when making decisions, so make sure you’ve established a strong rapport that will help your chances of having a decision made in your favor.


Helpful Buzzwords

Feel, grasp, power, action, suspect, trust, agreeable, demand, and disrupt.



Skeptics are strong-willed and goal-oriented individuals who crave new ideas and aren’t afraid to take risks. When negotiating with a Skeptic, use logic and reason to back up your claims, be prepared with facts and figures, and don’t let their blunt criticism get to you. Invest in building up your credibility so that you’re seen as trustworthy in their eyes, and always allow them to save face. If you can do all of this, you’re sure to come out on top in any negotiation with a Skeptic.


This is the third negotiation style within a multi-part series based on Gary A. Williams and Robert B. Miller’s article, Change the Way You Persuade (Harvard Business Review, published May 2002).

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