How to Negotiate in Real Life

Getting to “Yes” in a less than rational world

Image for post
Image for post
Image by Sasin Tipchai from Pixabay

Picture this:

Your employee walks into your office and says with great determination,

“I need a raise.”

You look up, one eyebrow raised.

“I need to buy a house and there’s no way I can make the payment on my current wage.”

You probably felt an immediate visceral reaction to this statement. The flawed argument is immediately obvious to us. Yet, we do this all the time in boardrooms and in our personal lives.

“We need a change order — we overspent and we’re hurting.”

“I need you to stop peeling oranges that way because it annoys me.”

Here are the two flawed premises that the majority of people base their arguments on that is the reason most negotiations fail:

  1. The other party should care about how I feel — If I describe my suffering in enough detail, they will agree to what I want (hot tip — they care more about how they feel).

A big part of my job involves unpacking projects that have gone wrong and negotiating a solution with the stakeholders — both on our side as well as the client side. And lots of travel. In essence, it involves constantly negotiating in situations where the variables are always changing — the stakes, the people, the time frame and the availability of background information.

Here are some of the tactics I’ve learned about negotiating that get results irrespective of how much the variables change.


Take the time to develop a strategy for negotiation. Preparation counts.

  • Identify the opportunity in every situation — Winston Churchill famously said, “Never let a good crisis go to waste.” Too often, we approach negotiations purely from an “Us versus Them” viewpoint or from a perspective of damage control. However, negotiations can often be a catalyst for beneficial change. Start by re-framing the situation — “Can this be an opportunity to access senior leadership on the other side, to introduce new options, to rebuild bad relationships, or to remove an obstructive person/situation?”
Image for post
Image for post
Created by the Author
  • Don’t send someone in who is not the right person to negotiate — This is the flip-side of the point above. You would not send your 12-year-old son to negotiate your power bill so don’t send a junior level person to negotiate a major issue. Recognize the limits of your authority. It is often more effective to bring a senior level person in to negotiate with their senior level person.
Image for post
Image for post
Created by the Author


This is where the sausage gets made, and this part is about achieving alignment between both parties. It is often helpful to follow a process to help to stay focused on the outcome:

  • Diffuse emotions — If emotions are present, the first step is to diffuse them. Nothing meaningful or rational can be exchanged until this is achieved. Often the easiest solution is to give the other party a chance to vent and to validate their right to feel that way without defending yourself.
Image for post
Image for post
Created by the Author
  • Clarify how to get to a “Yes!” — Ask the question, “What would need to happen for you to say yes?”


A good negotiator is only measured by how well she can close the deal. Most people focus too much on the process of negotiation and don’t have a strategy to arrive at a productive outcome. Here are some strategies for closing that have been highly replicable:

  • Guide them into the obvious solution — Telling people what to do is usually a bad tactic (in the boardroom or in life). Instead, it is often better to lead people into an obvious conclusion by asking leading questions — e.g. “I agree with your thinking. How do you think we should manage x issue?”

“Diplomacy is the art of letting someone else have your way.” — Sir David Frost

  • Understand the concept of “saving face” — If your solution involves some admission of fault on your client’s end, help them come up with a plausible way to deliver the news to their management that is palatable to them.

For the future

One of the most important lessons I’ve learned is that the situation leading up to the negotiation has a significant impact on the outcome (e.g. how much bad blood has already been spilled before you get to the negotiation table). So, it’s important to bear the next points in mind to help future negotiations go easier.

  • Start negotiations early — Negotiations are like taxes, if you know you’re going to need to do it regardless, it’s best to do them as soon as possible. We often negotiate when the damage has been done as opposed to when we sense there might be damage coming. By that point, you’ve made people angry and lost all leverage.

Remember, at the end of the day — you need to win the person, not win the facts. Don’t go in wanting to be right, stay focused on the outcome.

A successful negotiation is when both parties walk away feeling good. Use negotiations as a valuable event in building relationships.

“Let us never negotiate out of fear. But let us never fear to negotiate.” — John F. Kennedy

I love hearing feedback and personal stories. Please feel free to reach out through my website or on

Written by

Experiments in living intentionally and connecting deeply. I want to hear from you! — Website — Facebook — MojoMint

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store