"People often imagine top negotiators as strong, aggressive men"
That’s how Hollywood often portrays them; just look at The Founder, The Godfather, or Boiler Room.
But persuasion and sales are rarely about being combative, loud, or tough.
Using my negotiation skills, I’ve closed six-figure deals over nothing but email and a five-minute phone call, knocked twenty grand off my rent, and saved tens of thousands in health insurance. I built a multi-million dollar business in my early twenties without any investor funding, and forged many lucrative business partnerships with major brands, all without introductions or attending an Ivy League school.
My friends often come to me when they need help negotiating. I teach them how to successfully increase their salary and benefits, as well as paying less when buying houses, cars, or other expensive items. I’ve even helped fellow entrepreneur friends from Y-Combinator and 500 Startups negotiate better terms with famous investors who were trying to screw them over.
All this was accomplished without any aggression or obnoxiousness. Instead, I won with subtlety, diplomacy, profiling, and quickly building game theory models in my head.
I truly believe that women have the ability to out-negotiate most men with a little bit of practice and confidence. Let me explain why:
1. Women are often underestimated
As a nerdy, awkward woman with a high-pitched voice, being underestimated is the story of my life. Although this is sometimes extremely frustrating and annoying, I’ve learned it can work to your advantage. Especially in negotiation.
Whether you’re haggling in an industrial street market in Vietnam or in a boardroom meeting, the element of surprise is powerful. When your opponent lets their guard down, they’re often underprepared. Sometimes, they even divulge information that you can use to defeat them, or at least negotiate much better terms.
2. Why “Bro’s” often miss the most lucrative deals
In my early twenties (and even late teens), I out-negotiated many experienced businessmen who were at least twice my age. I recall one deal where my competitor was a loud and obnoxious “bro” who had an overpowering “frat boy” personality. However, he was actually very off-putting to the decision-maker, who was much more of an intellectual and an introvert.
I immediately picked up on this and also did my own online research on the customer before the meeting. My competition did not, and proceeded to be boisterous and overbearing, which made the customer cringe. He tried to bond over sports, but originally an engineering Ph.D., the customer clearly had zero interest there. My competitor also presumptuously bought the customer a beer and tried to pressure him to drink it, when in fact they did not drink alcohol at all.
The customer abruptly ended our meeting with some probably fake excuse. I didn’t fight it and wished him luck.
An hour later, I followed up with a friendly email, inviting them to a one-on-one over some fine tea in a more quiet place, and they quickly RSVPed. I had noticed their social media profile was full of cats, so we traded stories about their cat and my beloved childhood pet. I also spotted a post about them wanting to take their spouse hot air ballooning in Turkey, and so I made sure to put my makeup bag resembling a Turkish rug on the table. Before I knew it, I was giving them tips and intros to a hot air balloon pilot I knew in Kapadokya and closing an even bigger deal than I had hoped for.
3. Listening skills are so underrated
Online research has always been one of my secret weapons, but so is listening. I’ve seen so many salespeople and executives be too self-focused in meetings. They talk all about their business, all their cool features, and their latest awards, but they don’t listen or let the other person talk.
I try to ask more questions than I talk, and I make sure to remember all the little details I can.
Like their daughter who’s applying to college at my alma mater, UC Davis, or how they went on an African safari for an anniversary with their spouse. I remember their kids’ names, pet names, birthdays, favorite colors, and all the other information that means a lot to them.
To be a good listener you must be curious and empathetic.
4. The power of thoughtful and unique presents
Since I learned most of my negotiation skills from Turkish rug salesmen and shop owners in Middle Eastern bazaars, part of my strategy always involves creating a sense of “reciprocity.” In other words, if you give someone a really thoughtful present, they’re way more likely to do business with you.
This does not have to be expensive, and can often even be a simple gesture, like making a mutually beneficial introduction or sharing actionable advice or insights.
An enterprise salesperson at a very large company recently sent me a “Yeti tumbler” from Amazon. There was no note of who it was from, and it was ugly and generic. I was honestly confused and discomforted—I thought I had accidentally bought it, was possibly being frauded, or maybe even had a stalker.
Once I eliminated the first two possibilities, I gave it to a homeless person and did not take the call with this sales guy.
I hate generic corporate swag so much. I think most of it’s tacky, wasteful, and environmentally unfriendly. Any corporate swag my company has ever ordered has always been high quality, beautifully designed, and utilitarian.
Instead, I often opted for sending the customer something based on their personal preferences, or something I know their children or family can use if they have them. For example, we had plush goat toys resembling our company mascot for kids, and everyone loved them. I still get people emailing me years later saying that it’s still their child’s favorite toy and that now they’re obsessed with goats.
But back in the day, I would just send cool postcards with a thoughtful and genuine message whenever I was abroad. And the response was equally successful; some C-suite executives were even keeping them on their fridge, five years later.
It’s the thought, and the genuine attempt to be thoughtful, that really counts.
Women often do these things naturally, but anyone can use them to become better at negotiating. Just try to be more thoughtful, empathetic, and listen more.