The Dark Art of Negotiation

Posted on December 3, 2009. Filed under: startups | Tags: , |

Note: I wrote this during a particularly bellicose negotiation a few years ago.  I’m not really this mean, but this is an effective way to negotiate against an opponent with an agenda…the best negotiation is actually one that maximizes value for both parties and creates on ongoing and positive relationship (My next post will address the ideal negotiation).  The below is kind of like entrepreneurial Karate…only use it when your back is against a wall.

Train yourself to see motivation and intention in the way a person moves.  When a person is acting outside of their natural state, it is visible.  Perception is multisensory experience.  You can hear confidence or lack thereof when a person makes a statement.  Pick apart a representation and attack the weakest parts.  Doesn’t matter what they are, once an opponent feels that you can see their insecurity, they derail and you are leveraged.

You can see a person’s pleasure or pain in the corners of his mouth.  Adaptation within a message is more effective than adaptation post-response.  Very few will assume you know more than they actively convey.  They presume you act on the information they share, and that their inner monologue is not visible.  Shoot a dart into someone’s pride and tell me they don’t wince.  Eyes will open wide, close half way, then avert the line.  Although there is variation, it is possible to systematically and consciously test an opponent and expose their points of insecurity.

Then listen to the subject matter that elicits insecurity and know that representations of a levered position related to these subjects will fall under stress.  For example, when your potential acquirer tells you “if I don’t buy you I’m gonna buy your competitor”…watch them look down at the table instead of into your eyes…probably means your competitor already turned down the offer.

Watch the way a person waves their hands when they have an agenda.  Look them in the eye as they attempt to execute toward an end.  Make them decide every break in direct eye-contact, and recognize that as a point of opportunity to derail despite a constant stream of words.

Interaction moves too quickly to truly synthesize the words.  Instead attempt to abstract the words into the most significant components of the interaction: 1) intention (what were their goals) 2) efficacy (did they achieve them?) 3) expectations (how did they expect you to respond) 4) actions (how will you respond based on 1-3)

The majority of information you will extract from someone with an agenda will rest not within their “key points,” but in between them.  When someone attempts to develop a rational argument or game plan, they will map out how to get from A to B to C.  It is in the transitions that people stumble, expose a card, not having rehearsed or prepared for the words that are coming out of their mouth.

Every time you sit down at a table with an opponent where pressure exists, they will know or at least feel what they want to happen and what they don’t want to happen.  Sometimes that can be as simple as “I want this person to like me” or “I want to appear attractive, or confident, or smart, or respectful”  Other times it can be “I want information,” “I don’t want this person to know my secret,” “I don’t want to talk about this subject.”

Just as you observe, you are being observed.  Calm, low heart rate, eye contact, relaxed muscles.  Even if the information you take in is alarming, it is important to abstract in the present and defer synthesis and response specifically when it comes to points where you are weak.  Engage only where you feel confident.  Acceptance is an effective short term strategy for where you feel weak.  “I get that, I understand what you mean, interesting point, okay” are all ways to acknowledge while neither contradicting nor accepting your opponent’s leverage.  As a last resort, you can apply silence.  When any response will be weak or admit defeat, do not speak.  Let the person weaken their blow with a follow up comment or question that is more palatable.  If truly defeated, exit without response, regroup, analyze, reengage.

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12 Responses to “The Dark Art of Negotiation”

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If truly defeated, what about a ‘your mom…’ comeback?

Whoa…JTT welcome to the community…

you are channeling sun tzu. and there is irony in reading a blog post about non-verbal physical expression that can only be observed in person. the dark art is a dying arts, or perhaps the art form is just changing. when I started practicing law way back in 1998, in person negotiations were the norm. they were exhilarating–my first negotiation with trained lawyers felt like walking on stage for the first time at the Actors Guild. because the lawyers were method actors, in firm control of their expressions and words. people rarely negotiate face to face now. it’s all through email and conference call–it’s like negotiating with an avatar or playing on-line poker. it’s too bad because people more often take unreasonable positions and dare to be stupid when they don’t have to look you in the eye. so my advice to you, as you are a student of the dark art, is to conduct every important negotiation you ever have in person–you will, through the format alone, be advantaged.

Founders…this is the kind of thoughtful advice you can expect daily if you engage Pat Mitchell at Cooley as your lawyer…dude is smart and cool, happy to intro

I think you make a great point with using silence as a weapon. It may feel uncomfortable but creates a great opportunity for your opponent to make a mistake. It`s a common tactic in tennis, where you put pressure with easy shots without attacking, 80% chance your opponent will make a mistake in first 6 shots.

I hit easy shots in tennis because I can’t hit winners…I think that makes me a “pusher” 🙂

I saw Jordan use elements of this approach many times as we were staring our last company. He’s one of if not the best negotiators I’ve seen. Any analogies to tennis should probably stay off his blog though. If you are looking for a point of weakness for him, ask him about our last tennis match. It was a bloodbath.

Excellent pointers here – especially the one about exposing people during their transitions from one point to another, like that one.

This is one of the big reasons I’m a huge fan of playing poker regularly (preferably face-to-face, not online). It’s perfect training for the skills involved in deal-making. It teaches you to not only call other peoples’ bluffs, but also how to effectively bluff others when you need to, as well as discipline and overall risk management.

Highly recommend “Caro’s Book of Poker Tells”, think you’d like it a lot –

Here’s a good article I remember reading a while back too:

Jordan – interesting strategy. It’s hard to comment without the context of the deal you were involved in. However, I will comment on your use of eye contact. Research has dispelled the myth around eye contact years ago. It is an old-wives tale that someone is more likely to be lying if they break eye contact. In fact, research suggests you are more likely to lock eyes when you are in fact trying to to deceive someone so you can gauge their response. You are observing their reactions to your lie to determine if it has been successful.

thanks for the data andrew…hasn’t been my experience, but would love to read the research if you want to post a link…

Jordan, I don’t have a link, however, the research was conducted by Dr. Paul Ekman and is detailed in his book “Telling Lies”. I highly recommend this book to anyone who considers themselves a negotiator. The concepts discussed are absolutely cutting edge, however, the writing is slow at times due to the clinical tone of the book.

Jordan – I have & have read the Eckman book Andrew mentions. Very interesting stuff. Not really actionable for the amateur though.

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    I’m a NYC based investor and entrepreneur. I think there is one metric that can be used to measure the value of a human life and that’s impact. How did you change things? How many people did you touch? How different is the world because you lived in it and how positive was the change that you affected? (p.s. i don’t use spell check…deal with it) You can email me at


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