Talking to your boss about money is the second-most-awkward conversation you can have with your boss — the first being that time your date slapped his/her ass during the Christmas party conga line, obviously. I remember the first time I asked my boss for a raise. I rehearsed the conversation for hours in front of the mirror… but when I faced Mr. McGregor, I just threw up in my mouth and cried and actually got a pay decrease. And then I actually thanked the bald prick when it was over.

There’s got to be a secret to taking the edge when it comes to showing the boss who’s boss. So I found the most badass expert I could. Now, I’m not a particularly religious guy — so I don’t believe in Star Wars. That being said, when I ended my call with Christopher Voss, I had the lingering suspicion that I had just experienced Jedi mind tricks firsthand.

“High-stakes negotiation is emotional intelligence on steroids. Knowing how to negotiate correctly is a powerful tool, in any situation,” he told me in his cool, stoic voice.

If Liam Neeson’s character in Taken got kidnapped himself, the FBI would bring in a guy like Chris Voss — and Voss would have way better catchphrases, probably. An FBI agent for 24 years, by the time he left, he was the FBI’s lead International kidnapping negotiator. His training background is rarified: he claims to be the only negotiator trained by the FBI, Scotland Yard, and Harvard. He also teaches classes at Harvard and Georgetown, and now runs a negotiation-consulting company, Black Swan. He also has a dedicated Wikipedia page. Respect.

This is a man who made a living using his words to influence people, under the most stressful, dire consequences. And now, he makes a living teaching people how to apply this same high-wire diplomacy in everyday situations. I asked Voss to give me the rundown on asking for a raise, without vomiting, or even crying.


Ask the right questions, and influence people

“The dynamic between hostage-takers and bosses is the same on several levels. When you walk into your boss’ office and ask him for a raise, you’re going to feel tension and anxiety. Any time you feel tension, you’ve been taken hostage on some level. You are afraid of losing something, and that feeling has taken you hostage. So, you need some hostage-survival technique: make sure the other side sees you as a human being. The more they recognize you as a human being, the more likely they are to treat you well,” Voss detailed.

“You need to tie everything back into the company’s future, and how you personally will assist its prosperity — do this by asking ‘how’ and ‘why’ questions. An excellent ‘how’ question is ‘How can I become more valuable to you and the company? How can I put you in the position to make the company more successful?’ Basically — you’re saying, ‘how can I make you pay me more money,’ without outright saying it. Or, asking something like ‘How do you think I’ve helped the company grow over the last quarter?’ Immediately, your boss will be recalling all of the positive things you’ve done. This will subconsciously put you in a positive light, in your boss’ mind.”

Voss refers to these types of question as loaded: they make the listener feel powerful, and it burdens the other side to make a decision and give out some insight… but they don’t perceive it as giving up any semblance of power. More often than not, the listener will play along.

This method is akin to the Ben Franklin effect — by asking someone to do you a favor, you give them a little slice of control and empowerment. People will like you better, because they feel like they did you the favor because they like you, even if that’s not the case. It’s a mind trick, for sure, and another instance of humanizing yourself.

“This makes people forget you are the actual source of the power, it gives them the illusion that they are the source. There’s great power in deference. The first thing hostage-takers want to do is have control, and they are mostly used to having to struggle to maintain that control. When we would come into a hostile situation, and give the illusion that we’re just ‘giving them control,’ it catches them off guard. It throws them off their game. It would be easy to use a similar tactic when dealing with an employer in that type of a situation. This empowers the other person: it makes them want to talk to you, in real human terms.”

Focusing too much on “yes questions” is another crucial error people commonly make, according to Voss.

“If you go into your boss’ office and say something like, ‘Haven’t I been a good employee?’ they’ll immediately put up their guard — again, rely on the ‘how’ and ‘why’ questions. Put the ball in their court, make them come to their own conclusions. Also, if you have any ‘land mines’ — problems your superiors have with you that you might not know about — this will draw those out. These are things you need to know about if you are trying to secure a raise. You’re better off, you’re smarter. You are in a better position to negotiate because you have more info.”






In banking, it’s simple. You don’t negotiate with your own boss, you negotiate with your competitor’s boss and offer him not your service, but your current clients’ potential revenue. You get him to pay what you can convince him that your current bonus would be, get your next two bonuses guaranteed, because you’re bringing him your clients.

At the end of this two year cycle, either he gives you a massive bonus, a big pay rise and new title, or you repeat the process.

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