How to Negotiate Like a Boss

How to Negotiate Like a Boss

One of the key things I decided to be more intentional about this year is negotiation. I am actually good at it but I decided to step it up a notch and help you step yours up too.

I learned that with negotiation, it is about knowing what you want, going after it while respecting the other person/party in the process.

With negotiation, you always win when you have the right mindset. How?

  • You get a price cut, salary increase, or higher revenue
  • You get an extra gift or compensation (life and health insurance, travel perks, remote work days, new position title, something intangible but valuable etc.)
  • You build relationships and get a confidence boost
  • You build rapport and capacity
  • You gain knowledge by learning a new way to negotiate and a new way not to negotiate.

The best negotiation ends in a win-win situation where both parties get value. So the big question is How can you negotiate for best results and end in a win-win situation?

5 ways to Negotiate:

  1.  Observe: This is the first step to a successful negotiation. Observe the environment. Your negotiation strategy in a market will be different from your strategy in a supermarket. Observe the person – is the other party, friendly, irritable, sad, happy, eager, etc.? Pay attention to the body language and the people surrounding them. Know your seller/the other party. If you understand where they’re coming from, you can also explain things in terms that are meaningful to them, and you will be better prepared to adapt to the dialogue as terms change. Observe the mood of the environment. If the other people around that person are tense, they might dissuade your seller or the other party.
  2. Be Realistic: Price is what you pay, value is what you get. Make a mental estimate – what is the best price to pay for this service or product in comparison to the value you will get? Or what is the best price you should be paid for the value you’re bringing? In fact, put yourself in the seller’s/ other party’s shoes. Don’t be inconsiderate (e.g. Don’t ask them to sell an iPhone to you for $100. Be realistic or 1 billion naira salary). Don’t put yourself in an unrealistic situation.
  3. Connect on a Personal Level: Say hello, be polite. To begin with, ask about their day. Compliment the person, genuinely care. Once you can connect, they will be more open to listening and negotiating with you. Information creates trust. When you keep your cards too close to your chest, people become wary. Open up and share as much information as you can with people to give them the full scope of your thinking. Don’t share your execution strategy or too personal info.
  4. Be confident: Know When to Play your cards: Based on your observation, you will know what negotiation strategy to apply. Should you demand like it’s your right? Should you playfully ask and throw in a few compliments? Do you just beg and admit the person is doing you a favor? (Please this does not apply to your job if you deserve what you’re negotiating for) Would it be better to just add more products, benefits and get a mass bargain? You need to know.
  5. Know When to Push and When to Walkaway: Many people can’t deal with the pain of initial rejection. When they hear their first no, they give up. Others just keep pressing without threshold.

Bonus: Offer a little bit more value. Leverage on the concept of underpromising and over-delivering: If you were required to do 3 things and you can do 6, throw in one more and tell them you can do 4 and when you are hired, do 5. Do it when you know how you can get back value from your investment of time and resources.

Let me explain, Beyoncé was paid between $3 million to $4 million for headlining Coachella according to Business Insider, but she spent a large chunk of her money on the stage, costumes, and rehearsed for up to 11 hours on some days with an insanely strict diet. She promised a performance but she delivered beyond everyone’s expectations and focused on the higher goal of making the performance into a whole production. She went on to sign a $60 million naira deal with Netflix for that production – Homecoming. Be value-minded, think big, think of what you can offer, think of other ways you can gain and if this deal might just be a stepping stone, think deep. It’s not always about the money you get now.

Remember Jason Weaver, the singing voice for Young Simba character in Disney’s The Lion King. He turned down a $2 million deal from Disney when he was 19, and opted for $100,000 and lifetime royalties instead. He receives cheques every year and considering the iconic movie is still a cult favorite more than two decades later, he’s still raking in the royalties.

Another Bonus: Don’t say yes to the first offer, except it’s what you want. Even if it is what you want, push a little for more.

Most importantly, be Daring. As a matter of fact, dare to ask for what you want, dare to negotiate. Finally, if you do not intend to compromise, you should not even bother negotiating (Negotiation is a back and forth, not an express decision between two parties)

If you have any questions, ask me in the comment section


I am a multi-faceted creative driven by the need to create lasting solutions to key problems faced by you and your business. Ask me anything about business, branding, communications, or life and we will figure out the answers together. Drop a comment.

  • Ajana Oluwatomiwa April 7, 2020

    This was really helpful, thanks for sharing

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