How to Be a Master Negotiator

\"\"I’m not feeling too bullish on the fate of humankind. It seems that in a few years, every aspect of our lives will be ruled by the internet. We’ll be myopic from staring at screens and more sedentary than potted plants. A minor power outage could be an extinction event.

One interesting aspect of our over-reliance on technology is the sharp drop in interpersonal interactions. Not so long ago, our daily lives forced us to deal nonstop with our fellow humans – and it was more than just answering, “Do you want fries with that?” You’d need to share information with other people, and you might even need to convince them to do something. You would need to talk and listen, and you might have to react – in just a few seconds! – to something unexpected from your counterpart.

That quaint art of “talking” with strangers is mostly behind us. Nowadays, if you so desire (and many do), you can go through an entire day with almost no meaningful live-action dealings with anyone. You might see people and say some words, but there’s little uncertainty or mental resources required.

You can buy almost anything you need online. Returns are online too. If you do have to communicate, it’s by email or text or Instagram or Facebook or twitter, so you don’t have to think on your feet. We don’t have to worry about l\’esprit de l\’escalier anymore; now everyone has l‘esprit du clavier (a term I just coined). And if you don’t understand something someone’s written, you can just google it 🙂

Even dating has become far simpler. In the past, you might need to talk for hours before things got busy, and folks would get all judgey and disinterested if you couldn’t talk coherently. Now, you just go to Tinder, swipe right, text something funny, watch some Netflix together, hook up, and then say goodbye forever (I believe this is exactly how Tinder works). A once intricate dance has been reduced to an app and about 30 words.

The more our social muscles atrophy, the more we want to further limit human contact with strangers. Cashierless stores? Waiterless restaurants? Sign me up! It’s already a challenge for an average person to hold a simple conversation with a stranger, and it’s going to get worse.

However, the goal of never having to talk to a stranger again won’t be met in my lifetime. Unique, complex, or significant problems will still require old-school, in-person, real-time discussions. Discussions that most of us – since we no longer hone our craft in daily dealings with others – will be woefully unprepared to have.

And therein lies the opportunity. The bar to becoming a master negotiator has been lowered. Dramatically.

In my youth, successful negotiation required huge preparation, careful evaluation of your and your counterpart’s best alternatives, and lightning wits in the contest. Today, skills have deteriorated to the point that becoming an expert dealmaker is surprisingly easy. Almost no one has the belly for a fight. And by “fight”, I mean, “conversation”. I haven’t done anything to improve my skills, but over the last ten years or so, I’ve achieved much better outcomes in my negotiations.

I’ve done detailed analysis of countless recent negotiations and spent untold hours breaking down the critical keys to success. Are you ready?

In order to be a master negotiator in today’s world, you need to:

1. Ask for something; then

2. Stop talking.


Ask for Something – A Critical First Step

You will not get what you don’t ask for. That’s always been true, but it really needs repeating today. I’m no shrinking violet, but even I find myself increasingly loath at times to ask for things I want. Engaging with a stranger is stressful, and the less we do it, the less we want to do it.

However, that cuts both ways. No matter how afraid you are of asking for something, the other person is probably WAY more afraid of you. Because not only are you talking to them – they know they’re going to have to talk back!

If you can communicate your desire in a polite, clear, grammatically correct, verbally delivered sentence, you’re suddenly one of the world’s greatest negotiators. You don’t need to offer a lot of explanation or support – just ask for what you want, plus maybe one sentence as to why.

As soon as you ask for something – short, clear, concise – you have them exactly where you want them. Their heart rate will surge and they’ll start to sweat. Whirling confusion will reign in their head as they try to formulate a response. With increasing horror, they’ll realize they’re going to need to respond – with spoken words! – and soon. It is at that point that you must execute on the the most critical step in master negotiation. You must…

Stop Talking

After you’ve made your ask, simply stop talking.

Even though we’re chasing the dream of not needing verbal communication anymore, our DNA will compel them to respond. Sit quietly, and the other side will take care of things. If there is a long, uncomfortable pause as the jumbled words and memes sort themselves out in your counterpart’s head, embrace it and enjoy it. Do not start talking.

In the past, asking for something would lead to a knowing smile and a quick shot back from your counterpart. People were ready for the duel, and it showed.

Nowadays, few can think on their feet. When faced with the grim specter of talking to a stranger, folks will just start babbling. Even if they have a script, it’s a shaky crutch at best and they’ll be even worse than most as soon as they go off it.

Recently, I’ve noticed that I can often see directly into people’s brains – they will start voicing what should be an internal monologue.They’ll restate my request, explain to themselves what it means, talk about different ways to respond, and then finally get to the words they should have said to start. It’s amazing, and they’ll often arm me with the best retort with their own unfiltered thoughts.

While they’re weaving all over the road, you’ll have plenty of time to prepare a tight and powerful response. As they finish and hope for a chance to catch their breath, surprise them with a quick volley. Sometimes, if you’re in a sporting mood, you can even say, “I don’t fully understand what you mean” and then repeat your request verbatim.

Results will vary, but most of my recent negotiations have gone quite well. The most common trait in my counterparts is a visceral desire to exit the negotiation as fast as possible. Negotiating – and talking to strangers, for that matter – takes most people out of their comfort zone. They’ll fold just to make you go away.

Negotiations Galore

After you’ve mastered what it takes to be a world-class negotiator, you need to ply your craft. You may not be presented with too many chances to negotiate in our modern world, but you can create your own. Try to reduce your internet bill. Buy a big-ticket product the old-fashioned way, in a store from a human. Convince your Tinder date to watch what you want on Netflix. Whenever you’re presented with something less than ideal, speak up and try to change it. You’ll be surprised how many opportunities there are, and you’ll be amazed how often it works.

It is unfortunate that we’re moving to a less social and interactive (at least in person) culture, but that has lowered the bar for you to become a master negotiator. In the land of the blind, the one-eyed man is king 🙂


Do you love old-school horse trading and have some wins to share, or will you do anything to avoid a negotiation? Let me know in the comments. 

Picture courtesy of Jana


2 thoughts on “How to Be a Master Negotiator”

    1. Au contraire – from the experiences you describe, I think you’re the prototype for a modern-day master negotiator. The tentacles just add to the other side’s fear!

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