[10] The Art of Negotiation (Or How I Learned to Stop Discounting Myself...Most of the Time)
Let’s talk about negotiations — or as I like to call them, corporate emotional rollercoasters disguised as “deal strategy.”
Negotiation is so much more than asking for a discount or pushing for a higher price. It’s one of the most important skills you can learn in sales. Why? Because the final result of a negotiation sets the tone for the entire relationship with your customer.
Now, before you start sweating through your silk blouse, remember this: negotiation isn’t just about haggling over price. It’s the power move that defines how your customer sees you, your product, and your boundaries. It’s giving Beyoncé energy with Excel tabs. It's strategy meets sass.
You want a discount? Great — I want something in return. Maybe that’s a signed contract by the end of the week. Maybe it’s a case study. Maybe it’s you sending a singing telegram to my boss explaining what a pleasure it was working with me. (Okay, fine, maybe not that last one — unless you’re serious?)
Here’s the deal: every give needs a get. That’s not you being a diva — that’s you being a professional with a backbone (and maybe a killer pair of heels). Bend too far and suddenly you're the discount rep — and no one respects the discount rep. Not even the customer who asked for the discount. Wild, right?
Set boundaries. Write them into contracts. If they want a better price, hold them to deadlines. If they miss a deadline, the discount comes off the table. Period. This will lead to some deals lost. But it will also lead to you being known as someone who knows their worth, protects their product, and sets clear expectations.
Let’s Get Real: Negotiation is Hard (and Also Emotional Damage on a Google Calendar)
For me, this is the part of the deal cycle where I start pacing. The deal is so close. I can see quota on the horizon. But then comes that dreaded email:
“We love {{your product/offering}}, but can you knock 30% off just because?”
Sir. This is not Kohl’s. You don’t get 30% off just for showing up with a coupon code called “WE TRIED.” 😅
From conversations with other reps, reading up on LinkedIn, and real-life trial by fire, I’ve found there are a few core principles that consistently come up when it comes to mastering negotiation:
Preparation
Positioning
Patience
Active Listening
Emotional Control
Creativity
Clarity
Courage
Let’s take a beat with creativity. This is where I shine. If a customer wants something, I start mentally flipping through the bag of goodies:
You want onboarding help? Sure — I want a case study.
You want to delay payment? Cool — let’s get that contract signed now and future-date your invoice.
You want a multi-year discount? Love it. I want it prepaid.
Negotiation is not a tug-of-war.— it's more like a Texas two-step. Sometimes you lead, sometimes you follow, but if someone starts stompin' on your boots? You best believe you speak up and let 'em know. Bless their heart, but you didn’t show up to get danced all over.
Lean into the silence. Let the prospect sit with your counteroffer. Let them talk first. It feels unnatural at first, but remember — the person who speaks first usually loses leverage.
And no, sending 3 follow-up emails in a row because they “opened the doc” isn’t negotiation. That’s anxiety with a Send button.
Step One: Know Your Floor (and I Don’t Mean My Favorite Dance Move)
Before you even think about talking numbers, you need to know your walkaway point — your “no thanks” zone. This is your sacred floor. Your holy ground. Your Beyoncé lemonade boundary.
Figure it out like this:
What’s the lowest deal that still helps you hit quota without sobbing into your iced latte?
What’s the cost to your team — implementation, support, time, therapy?
What’s the market rate — not because you’re matching it, but because you’re better and can prove it.
Time-to-close — are we flexing for speed or playing the long game?
Once you’ve got that floor? Tattoo it on your soul. Or at least put it in Salesforce and bold it like your life depends on it.
Sticking to your floor takes guts. But remember: you are not everyone’s bargain bin. This isn’t a garage sale — it’s premium pricing for premium vibes.=
Step Two: The Give/Get Game
The only thing worse than a discount with no strings attached is a brunch with no bottomless mimosa option.
Every “give” should come with a “get.” Here are some of my faves:
💅 Give: A 5% discount
💌 Get: Signed contract by end of month
💅 Give: Free onboarding
💌 Get: Case study within 60 days
💅 Give: Multi-year pricing
💌 Get: Pre-paid upfront commitment (hello, cash flow!)
Get creative. This is where you show them you’re not just another sales rep — you’re a business partner with main character energy.
Step Three: Embrace the Awkward
Negotiations are awkward. But so is wearing heels through TSA, and yet here we are.
Let the silence sit.
Let them stew in your counteroffer. Let them talk first. The first person to speak usually loses leverage — and also probably impulse-buys unnecessary skincare products. (Just me?)
Try this:
Count silently: One Mississippi… all the way to seven. Hold the line.
Sip your coffee: Calm energy, hydrated queen.
Doodle or jot a note: Keeps the nerves in check.
Smile and nod: Looks confident. Says “I’m unbothered.” Bonus points if your lip gloss is poppin’.
Mute yourself (in virtuals): Honestly, lifesaver. Just don’t forget to unmute unless you want to be that rep.
Step Four: Surprise — You’re Doing It Already
You negotiate daily. You just don’t realize it.
Job offers? Ask the hard questions. Don’t just take the salary and run. Ask about flexibility, bonuses, equity, growth tracks — you’re not a charity case, you’re a revenue generator with a fresh blowout.
Social plans? "Where are we eating?" is code for negotiation. Speak up. (Also: if someone suggests Applebee’s for the fifth time, it’s okay to exit the friend group.)
Relationships? Forget sales deals — try negotiating closet space with a partner who thinks one drawer is “plenty.” Spoiler alert: it’s not. You deserve more room for your power blazers and backup heels.
Every time you hold a boundary, ask for more, or simply say “nah” to something that doesn’t serve you? You’re negotiating. You’re advocating. You’re showing up like a boss
Final Word: Be a Closer — But Make It Cute
You can be high-performing and high-heeled.
You can close six-figure deals and still throw in a “just circling back 💁♀️” emoji.
That’s the whole Deals in Heels vibe. Powerful and playful. Sharp and sparkly.
So the next time you’re in a negotiation — whether it’s a $200K renewal or convincing your roommate it’s their turn to buy paper towels — remember:
You are not just selling software. You’re selling you. And baby, you’re full price.
And if they want a discount?
Cool.
I want a signed agreement, a case study, a testimonial, and a LinkedIn post that says I make spreadsheets look sexy.
💋 Recap: Close Like a Pro (In Heels)
Negotiation isn’t just about price — it’s about power, presence, and protecting your worth. Whether you're sealing six-figure deals or convincing your partner to take the trash out without turning it into a TED Talk, the rules are the same:
✨ Know your floor (and don’t dance below it)
✨ Make every give come with a get
✨ Silence is golden — embrace the awkward pause
✨ You’re negotiating daily — own it
✨ You can be charming and firm. Soft smile, hard boundaries.
And most importantly: You are full price, always.
📬 Let’s Keep the Magic Going
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💬 Want to talk deals, sales careers, or what to do when a prospect ghosts you after asking for a “small” 40% discount?
DM me — I’m always down for a quick chat (and yes, I’ll bring snacks).
🔥 Save These 5 Negotiation Tips
Never negotiate against yourself. Make your offer and stop talking. Let them fill the silence.
Write your must-haves down before you get on the call. Future you will thank you.
Ask what’s most important to them — sometimes you can give a “win” without losing value.
Tie concessions to timelines. “I can do X if we sign by Friday.” Period.
Smile while you say no. It’s disarming. It’s powerful. It’s ✨ iconic ✨.
Now go get your bag, protect your value, and strut into that next call like the deal-closer you are. 💼💅