11 entrepreneurs and CEOs reveal the best tips for negotiating virtually anything

Sometimes it's worth overpaying.

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Sometimes it’s worth overpaying.
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Getty Images

  • Learning how to negotiate – whether in business or life – is one of the most valuable skills you can have. And anyone can develop it.
  • These 10 top leaders have done all sorts of successful negotiations. They recommend considering tone, emotions, and compromise in negotiations.
  • For Marcello Arrambide, founder of Day Trading Academy and cofounder of SpeedUpTrader, the best outcome isn’t always the best price – he recently happily overpaid by 300% in a negotiation.
  • Visit Business Insider’s homepage for more stories.

The art of negotiation is one of the most valuable skills in life and business. But if it doesn’t come naturally, don’t worry: Anyone can develop negotiation skills. How? By learning from the best.

Here are negotiation tips from 10 master deal-makers and advisors in The Oracles.


1. Let the other person do the talking

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Jocko Willink.
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Courtesy of The Oracles

The key to closing deals is detaching from your agenda and listening to the other person and what they have to offer. Most people are more than willing to talk about themselves, which can tell you a lot about whether they’re a good person with the right intentions.

When you let the other person do the talking instead of playing your hand, you have a competitive advantage that you can use to create a fair deal for everyone. But listening is more than a negotiation tactic. When you’re genuinely interested in what others have to say and their ideas, you just might learn something new. With this approach, everyone wins.

Jocko Willink, retired US Navy SEAL officer, No. 1 New York Times bestselling author, cofounder of Echelon Front, partner in Origin USA, and host of the top-rated “Jocko Podcast


2. Meet them halfway

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Kara Goldin.
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Courtesy of The Oracles

The key to negotiating is understanding who’s at the table and what they want, then working together to come to a solution in a professional but determined way. When I started Hint, I went to the buyers in stores to get my product on the shelves. Early on, we didn’t know that they had to adhere to “planograms” based on product categories: water, sweetened flavored water, soda, and juice. Our product, unsweetened flavored water, didn’t exactly fit into any of them.

By working with the buyers, we got some of them to change the planogram. They wanted to work with us because we showed that we understood the challenges they faced. We helped them argue their case on our behalf. They also liked us. People like to negotiate with people who are working hard to meet them halfway; so stay kind.

– Kara Goldin, founder and CEO of Hint Inc.; creator of The Kara Network, a digital resource for entrepreneurs; and host of the “Unstoppable” podcast; follow Kara on Twitter and Instagram


3. Use this five-step framework

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Roland Frasier.
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Courtesy of The Oracles

First, be crystal clear about what you want; otherwise you will rarely get it. Second, include several “throwaway” asks that you don’t expect to get. That way, you can concede them and fall back on what you really want. Role play the responses you’ll likely get to anticipate objections and counter-asks. Plan exactly when you will give up your extra asks so the other side feels like they are getting something from you.

Fourth, don’t make demands; ask questions, which creates discussion and empathy. For example, instead of saying, “I can’t do that!” try, “How can I do that?” Finally, plan your questions, so you naturally lead them to your desired outcome and it becomes their idea.

Roland Frasier, principal of 30 businesses, including War Room Mastermind and Traffic & Conversion Summit; host of the “Business Lunch” podcast; connect with Roland on Facebook, LinkedIn, and Instagram


4. Use the ‘five U’s’

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Matt Mead.
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Courtesy of The Oracles

Mastering the art of negotiation means “you” need to start mastering the “U’s.” In a world filled with business and cultural sensitivities, we don’t all see situations equally.

First, “understand” the power of the pause: It gives you time to think through your best alternatives and seek counsel.

Second, “untangle” the angles: Negotiations require common ground, so identify the other side’s angles as well as your own. Both sides want the best price, but what gets tangled is each side’s “wants”; untangling these helps you create countermoves.

Third, “unhand” the demands: Don’t start a negotiation with a “my way or the highway” demand-based mindset. Go into it with a “Let’s put our heads together and find a solution” intention.

Next, “un-paint” the picture: A negotiation is like painting a picture; it happens in layers and steps. After pausing and untangling, backtrack all the steps and make sure it “looks good.”

Finally, “uncover” the solution: Listen more than you talk, even if the other side is being assertive. Reframe questions or assertions and repeat back in terms that benefit both sides. Give a little, but always get something back. Don’t be afraid to make the first move or offer, because counter-offers are where the deals happen!

Matt Mead, founder and CEO at Drivonic; cofounder of Mead Holdings Group, The Epek Companies, and Grayson Pierce Capital


5. Make sure everyone wins

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Dottie Herman.
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Courtesy of The Oracles

Start by building rapport. Bring up anything you have in common to keep the dialogue moving and positive. Ask for what you want, then have the patience and discipline to stay quiet and listen. If you pay attention, you’ll always find something that can help you reach your goal.

Never back someone into a corner. Remember: In a successful negotiation, everyone wins. It’s not an “I win, you lose” proposition. There are usually creative ways to compromise, but if you hit a fork in the road, don’t be afraid to walk away. There is power in saying no – which can even turn into a yes. Unless you’re getting divorced, negotiations aren’t personal, so don’t take it that way. If you can see both sides, you’ll likely get where you want to go.

Dottie Herman, CEO of Douglas Elliman, a real estate brokerage empire with more than $27 billion in annual sales; connect with Dottie on Facebook, Instagram, and Twitter


6. Focus on emotions

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Keri Shull.
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Courtesy of The Oracles

The key to negotiating for what you want in life is going deep enough with the person on the other side of the table. Find out how the outcome you are looking for is also a win for them. There doesn’t always appear to be a mutual win on the surface, but if you focus on the core emotions that accompany an outcome, both sides can ultimately win.

For example, when I’m negotiating a land deal for one of our developers, sometimes a client gets caught up on price. But reaching an agreement is usually possible when I get them to focus on what is next for them in life and how selling the land moves them toward their goals.

– Keri Shull, founder of the Keri Shull Team, which has sold over $2 billion in properties; cofounder of real estate coaching business HyperFast Agent; named one of America’s Best Real Estate Agents by REAL Trends; connect with Keri on Facebook


7. Adjust your tone

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Holly Parker.
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Courtesy of The Oracles

All successful negotiations are rooted in truth and trust. Use nonthreatening conversation to find shared interests. Connecting over common ground builds rapport, and it’s less intimidating to ask for what you want once you’re talking. Negotiating isn’t about bullying or threatening the other person. In fact, if you punch too hard, the scales usually tip in their favor. Even if you do close the deal, it will often fall apart. It’s a dance, and both sides must be willing to find balance.

Listen carefully, ask questions, sympathize, and brainstorm options to get over unexpected hurdles. Listening gives you the valuable information you need to overcome obstacles and identify where things are headed. Be aware of your tone of voice, which is powerful but often overlooked. It’s about how you communicate, not just what you say. Start with a calm yet enthusiastic tone, then move to an encouraging tone and then an excited one to cross the finish line.

– Holly Parker, founder and CEO of The Holly Parker Team at Douglas Elliman; award-winning broker who has made over $8 billion in sales; connect with Holly on LinkedIn and Instagram


8. Dig deeper than the bottom line

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Peter Hernandez.
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Courtesy of The Oracles

Being a negotiator requires skill. The economy and geopolitical uncertainty have everyone on edge; so putting and keeping deals together is tough. To keep your negotiations on track, get in the right mindset before every conversation. It’s not about you and your commission; so leave your ego at the door. You must be a calming influence in the situation. Don’t share your client’s emotions with the other party.

The right answer at the wrong time is still the wrong answer; so be patient. Go below the bottom line and dig to find solutions that will make both sides happy. Be solution oriented, not problem focused. Never assume anything, and don’t draw lines in the sand unless you are ready to walk away.

Peter Hernandez, president of the Western Region at Douglas Elliman; founder and president of Teles Properties


9. Visualize all the possibilities

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Torben Platzer.
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Courtesy of The Oracles

My No. 1 tip isn’t actually about the negotiations themselves; it’s about how you make your decisions. We face thousands of choices every day, and the wrong one can really set you back. That’s why successful entrepreneurs weigh their options carefully and evaluate big decisions when they’re negotiating.

What sets humans apart from other animals is that we can visualize scenarios and imagine the potential outcomes. Billionaire investor Charlie Munger emphasizes “assiduity,” when you sit down and think about a situation until you have the solution. That’s what I recommend doing when considering various scenarios in a business deal.

Torben Platzer, cofounder and CEO of personal branding agency TPA Media Group, founder of business education program SELFMADE, and host of the German podcast “SELFMADE“; connect with Torben on Facebook, Instagram, and YouTube


10. Remember that the best outcome isn’t always the best price

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Marcello Arrambide.
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Courtesy of The Oracles

You want the other person to name a price first, which will give you leverage. You must also understand the best outcome for you – which is not always the best price – and be willing to walk away if you can’t make that happen. For example, in one negotiation, I stood firm because I knew that they were ready to sell. But in a recent deal, I overpaid by 300% and was happy to do so.

Why? I was negotiating to purchase the last unit in a building with a fantastic location in the booming tourist city of Medellin, Colombia. My goal was to rebuild it into a hotel, so I needed to own the entire building. I could’ve waited for a lower price, but controlling only part of a property that I couldn’t rebuild would have cost much more than it did to overpay on the last unit. I recouped that investment in just one month.

– Marcello Arrambide, founder of Day Trading Academy and cofounder of SpeedUpTrader, a funding company for aspiring day traders; connect with Marcello on LinkedIn


11. Close the deal quickly

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Alon Rajic.
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Courtesy of The Oracles

Be sincere and straightforward. You don’t have to reveal every bit of information you have; but if you’re asked about something directly, don’t beat around the bush. When you’re candid about your disadvantages, you can present them in an advantageous way.

Stipulate the time frame early in the negotiations so the process doesn’t drag on. Lengthy negotiations are a waste of time and often go around in circles. Short timelines and intense negotiations are likely to bring a more serious and straightforward approach from both parties. This also helps you identify halfhearted buyers or sellers so you can exit negotiations before wasting too much time and energy. I’ve closed dozens of mergers and acquisitions with this approach, often within 30 days.

Alon Rajic, managing director of Finofin, which operates Money Transfer Comparison, a leading foreign exchange guide

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