How to Negotiate For What You Want And Still Make Friends

When you are going into a negotiation at an disadvantage how do you get what would want while keeping the relationship intact.

How to Negotiate For What You Want And Still Make Friends
[Photo: lenetstan via Shutterstock]

I still remember the first week of my first job out of college. Picture a group of handpicked young men and women gathered in a conference room for what was nicknamed “influence training.” “People automatically form a first impression of you and this first impression affects your ability to do your job,” the trainer told us. “Which traits create the most credible and persuasive first impression? Tall, Caucasian, brunette, a deep voice and male,” nodding to the winners of the genetic lottery. “For you,” she paused, addressing me, “it’s not going to be so simple.”


She was right. I’m 5-foot-4, not male and not Caucasian. Through no fault of my own, I will never start at the same starting line as my male counterparts in any meeting, much less a negotiation. Ample evidence suggests that negotiation is more challenging for women. Too often, we don’t even try to negotiate or, if we do, we are penalized for not acting in a way women are expected to.

Add those disadvantages to situations where a negotiator of either gender isn’t asking for something: a raise or promotion, negotiating a partnership deal as a young company, raising venture dollars–and you have the very definition of an underdog.

Here are six tips for underdogs looking to successfully negotiate:

1. Understand Your Disadvantage.

I’m glad someone told me these unconscious biases early on, instead of claiming that I did have equal footing. Use this knowledge to your advantage, and develop your negotiation tactics accordingly.

2. Beware Of Overcompensating.

I spent almost a decade trying to overcompensate in ways that weren’t helpful. As the first female investor at two successive private equity firms, I forced myself into a Type-A negotiator personality–more bluntly, I was a hardass. I earned the reputation for being aggressive but every time I pushed as a Type A, I would lose–sometimes the negotiation or more often, the relationship. I found the harder I pushed, the harder the world pushed back.

3. Remember This Likely Won’t Be Your Only Negotiation With This Person.

How can both sides walk away from the negotiating table liking and respecting each other more?


Very few negotiations are once-and-done. The majority of negotiations occur as a necessary part of an important ongoing relationship. Most people prefer to have relationships with people they actually like.

I found more success as a female negotiator when I recognized the unconscious expectations that the other side had of me. A softer, more approachable Type-B style allows underdog negotiators to truly understand what drives the other side’s behavior, what is truly important to them. I invest the time to think through motivations and to rank negotating points in order of priority. It’s still a learning process for me and a “helluva 3D game of chess” as one of my company’s investors commented.

4. Seek The Win-Win

Do not make it a zero-sum game. The end game is for everyone to win. This does not mean that both parties get 100% of what they want. It may even mean that you don’t get 100% of what you want.

In Getting To Yes: Negotiating Agreement Without Giving In, the authors stress the importance of going soft on people but hard on the problem. If both sides started with three issues on the table, it may be worth exploring the underlying reasons those issues are important as well as identifying more issues that could be traded off against each other. This way, both parties cooperate to create white space for a win-win to occur.

5. Start With The Data.

Focusing on the win-win does not mean that you should go into any negotiation with a soft pitch. Come to the table with data that helps you make your case and expect the other party to do the same with a completely different interpretation of the same facts. Still, data can be a really great starting point, and it’s not limited to facts and figures.

In fact, the question “why” helps the underdog negotiator get the most important kind of data–why the other side feels the way they do, why they have adopted a position that on first glance, seems contrary to your own interests.


Your conversation will not end with a spread of convincing data (you wish!). However, it is helpful to clearly communicate all the facts, if only to help both sides figure out where the creative white space might be.

6. Keep Both Side’s Emotions In Check

Negotiations are always highly emotional–you’re entering an uncomfortable situation voluntarily because you really, really care. This is not a conversation that should turn into a temper tantrum; it’s a pragmatic conversation between adults. But there is an appropriate time to let your passion show, particularly if you can do so sparingly. Showing your commitment, and how much this matters to you, is an important signal to your boss, investors, partners. Remember that the other side will leverage emotions, too, including negative emotion. Do not respond in kind but instead channel positive energy into asking clarifying questions and diffusing the anger.

After all, the goal is to reach agreement, yes, but to also trust and respect each other when it’s all said and done. Both parties should think: “I would definitely do business with this person.”

Michelle Lam is the founder of the innovative, data-driven bra retailer True&Co. Before transforming the world of women’s undergarments, Lam was an investor at Boston Consulting Group, Microsoft Corporate Strategy and was Bain Capital Ventures’s first female principal.