Forget “Winning” — The Real Art of Negotiation

Scott D. Clary
Scott D. Clary
7 min readMay 23, 2024


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Forget “Winning” — The Real Art of Negotiation

Let’s talk about something every entrepreneur loves (and hates) to do: negotiate.

Most people think of negotiation as a battleground. You’ve got your side, they’ve got theirs, and someone’s gotta “win,” right?


That’s amateur hour.

And if you’re reading this, you’re not an amateur.

You’re playing the long game, building empires, not sandcastles.

So, let’s reframe this.

Negotiation isn’t about winning. It’s about creation.

It’s about forging deals that don’t just benefit you, but elevate everyone involved.

The Win-Win Fallacy

Now, before you roll your eyes at the whole “win-win” cliché, hear me out.

I’m not talking about kumbaya and compromising until everyone gets a participation trophy.

I’m talking about crafting agreements so ingenious, so mutually beneficial, that the concept of “winning” becomes irrelevant.

Think of it like this: You’re not just dividing a pie, you’re baking a bigger one.

The more value you can create for the other side, the more you’ll ultimately get yourself.

The Judo Move: Using Their Strength Against Them

Great negotiators don’t just know their own strengths, they intimately understand the other side’s.

What are their fears, their desires, their hidden pain points?

Once you know this, you can use their own momentum against them.

It’s like judo: You’re not trying to overpower your opponent, you’re using their force to your advantage.

If they’re terrified of missing out, create a sense of scarcity.

If they’re ego-driven, appeal to their sense of legacy.

Beyond Price: The Currency of Relationships

Remember, money is just one form of currency.

In the world of high-level entrepreneurship, relationships are often worth far more.

A strong relationship can open doors, create opportunities, and smooth over rough patches.

So, don’t just focus on squeezing every last dollar out of a deal.

Focus on building trust, rapport, and a reputation for fairness.

That’s the kind of currency that pays dividends for years to come.

Your Next Steps: Reframe, Research, Relate

The next time you’re heading into a negotiation, try this:

  1. Reframe: Shift your mindset from “winning” to creating value.
  2. Research: Dig deep into the other side’s motivations and concerns.
  3. Relate: Build a genuine connection with them, beyond the transaction.

Negotiation Tactics: The Advanced Playbook (Not Your Average Haggling)

Now, let’s get tactical.

Buckle up, because we’re about to go beyond basic bargaining.

This is the advanced playbook, the stuff they don’t teach you in Negotiation 101.

Tactic 1: Anchor High (But Be Reasonable)

First impressions matter. The initial offer sets the tone for the entire negotiation.

So, don’t be afraid to anchor high. This doesn’t mean being ridiculous — you want to aim for ambitious yet justifiable.

Why? Because it gives you more room to maneuver.

Think of it as starting a hike at a higher elevation.

Even if you descend a bit, you’ll still end up above where you would have started if you anchored low.

Tactic 2: Trade, Don’t Concede

When the other side pushes back, don’t just give in. Look for opportunities to trade concessions.

For example, if they want a lower price, offer it in exchange for a longer contract or faster payment terms.

This keeps the negotiation dynamic and allows you to capture value on multiple fronts.

Remember, every concession should be a calculated move, not a surrender.

Tactic 3: The Power of Silence (and Strategic Pauses)

In the heat of negotiation, silence can be your most potent weapon. After making an offer, resist the urge to fill the void.

Let the other side stew for a bit. This creates a sense of anticipation and can lead them to make concessions they hadn’t planned on.

Strategic pauses within your speech can also be effective. They add emphasis and allow your points to sink in.

Tactic 4: BATNA: Your Walk-Away Power

Never enter a negotiation without knowing your Best Alternative To a Negotiated Agreement (BATNA).

This is your safety net, your Plan B.

Knowing your BATNA gives you confidence and leverage.

If the negotiation isn’t going your way, you can walk away without fear. This often prompts the other side to sweeten the deal.

Tactic 5: The Columbo Tactic (Play Dumb… But Not Too Dumb)

This tactic is named after the famous TV detective Columbo. He appeared bumbling and disheveled, but his apparent cluelessness disarmed suspects and led them to reveal more than they intended.

In negotiation, you can use a similar approach.

Feigning a lack of understanding on certain points can encourage the other side to explain things in more detail, potentially revealing valuable information.

Bonus Tip: Emotional Intelligence (EQ) Over IQ

While these tactics are powerful, remember that negotiation is ultimately a human interaction.

Emotional intelligence (EQ) is just as important as tactical skill.

Pay attention to the other side’s emotions and body language. Build rapport, show empathy, and find common ground.

This will not only make the negotiation more enjoyable, it will increase your chances of reaching a mutually beneficial agreement.

Master the Art of Negotiation: Complex Deals and Curveballs

Now, let’s tackle the real-world challenges you’ll face as an entrepreneur navigating complex deals and unexpected curveballs.

Challenge 1: The Multi-Party Negotiation

Negotiating with multiple parties adds layers of complexity. Alliances shift, hidden agendas emerge, and consensus becomes elusive. Here’s how to handle it:

  • Map the Terrain: Before entering the negotiation, identify each party’s interests, priorities, and potential coalitions.
  • Build Coalitions: Look for opportunities to form alliances with parties who share your goals, even if only partially.
  • Play the Long Game: Multi-party negotiations rarely happen in a single sitting. Be patient, persistent, and adaptable.

Challenge 2: The High-Stakes Negotiation

When the stakes are high, emotions run hot, and the pressure to perform is immense. Here’s how to stay cool under pressure:

  • Prepare Relentlessly: Leave no stone unturned in your research and preparation. The more you know, the more confident you’ll be.
  • Manage Your Emotions: Take breaks, practice mindfulness, and avoid reacting impulsively.
  • Focus on the Process, Not Just the Outcome: Even if the deal doesn’t go your way, you can still learn valuable lessons and build relationships.

Challenge 3: The Unexpected Curveball

Negotiations rarely go exactly as planned. Unexpected information, sudden demands, or unforeseen events can throw you off balance. Here’s how to stay agile:

  • Don’t Panic: Take a deep breath, assess the situation calmly, and avoid making rash decisions.
  • Reframe the Problem: Look for creative solutions that address the new information or demands.
  • Don’t Be Afraid to Walk Away: If the deal no longer makes sense, don’t hesitate to walk away. There will be other opportunities.

The Art of the Counter-Intuitive Move

Sometimes, the most effective negotiation tactic is the one that seems counterintuitive. Here are a few examples:

  • Revealing Weaknesses: Selectively sharing a minor weakness can build trust and make you appear more human.
  • Offering a Concession Upfront: This can create a sense of reciprocity and encourage the other side to be more flexible.
  • Asking for Advice: Showing humility and seeking input can disarm the other side and open up new possibilities.

The Never-Ending Journey of Mastery

Negotiation is a skill that takes a lifetime to master. There will be setbacks, challenges, and moments of self-doubt. But with every negotiation, you’ll learn, grow, and become a more effective leader.

Remember, the best negotiators are not just skilled tacticians, they’re also empathetic listeners, creative problem solvers, and relentless learners.

The Art of Negotiation: Your Path to Mastery (and Beyond)

We’ve journeyed together through the intricate world of negotiation, from reframing your mindset to mastering advanced tactics and overcoming real-world challenges.

Key Takeaways:

  1. Value Creation Over Winning: Remember, the best deals aren’t won, they’re created. Focus on expanding the pie, not just your slice.
  2. Preparation is Key: Do your homework, research the other side, and know your BATNA.
  3. Emotional Intelligence Matters: Build rapport, show empathy, and read the room. EQ is just as important as IQ in negotiation.
  4. Embrace the Unexpected: Be adaptable, creative, and willing to walk away if necessary.
  5. Negotiation is a Journey: Mastering this skill takes time and practice. Embrace the challenges and learn from your mistakes.

The Path to Mastery:

  • Practice, Practice, Practice: Seek out negotiation opportunities in all areas of your life, from business deals to everyday interactions.
  • Learn from the Masters: Study the negotiation styles of successful entrepreneurs, diplomats, and historical figures.
  • Get Feedback: Ask trusted colleagues or mentors to observe your negotiations and provide constructive criticism.
  • Experiment with Different Tactics: Don’t be afraid to try new approaches and see what works best for you.

Beyond Mastery: The Art of Influence

As you continue to hone your negotiation skills, you’ll discover that you’re not just becoming a better dealmaker, you’re also becoming a more influential leader.

The ability to persuade, inspire, and motivate others is essential for any entrepreneur who wants to build a lasting legacy.

And it all starts with mastering the art of negotiation.

Until next time,




Scott D. Clary
Scott D. Clary

👋 | Host @ Success Story Podcast 🎙️ | I write a newsletter to 321,000 people 👉