Lessons Learned From Recent Negotiation Experiences

If you negotiate outside the lines, agreements will be unstable. I've done that before. 1. When I was young(er) and brash(er), I negotiated a comp package too large for my experience. My ambition was so obvious that my boss thought I needed (deserved?) a VP title. Then I thought I needed (deserved?) a corresponding comp package. Based on the higher pay we bought a larger house, and all was good until it wasn't. New funding round, new CEO, and my base pay was reduced by 30%. Now we couldn't afford our larger house. What to do? 2. Much, much later I was CCO at a SaaS company where a large contract was up for renewal. The customer had contractually committed to expand, but they hadn't, and they wanted out of the expansion clause. We didn't let them. We forced them to spend the money on something-- services? Guess what happened one year later? They canceled and moved to a competitor. These agreements--negotiated hard--are not stable. Yes, you can negotiate hard. And you can get what you want. But if you want long-term, sustainable relationships, it's a give and take. It's a win-win. It's a third alternative... and you can't tip the scales too far in your own favor without upsetting the equilibrium and shortening the life of the "contract." My advice is... 1️⃣ Fit first. Make sure there's fit from both sides. If it is no-fit, force-fit, or fake fit, that's a short-term arrangement. 2️⃣ Optimize for IMPACT. *You* want to deliver impact... that's your side of the bargain. That's what you can control, and as long as you are delivering, you increase the stability of your arrangement. 3️⃣ Be realistic. If circumstances change for you or the other party, let them. If it was a great arrangement for you both but now it's not so great for one or the other--have another look with fresh eyes. Don't hold on for dear life to an arrangement that isn't good--that doesn't help anyone. Don't over-negotiate. Add value. Achieve equilibrium with win-wins. Play the long game. 👊

I was a frontline seller at CEB/Challenger Sale for 18 years. At year 19 of my career, I moved to Lavender and became a buyer. Here are the top 5 lessons I learned from being on the buyer side (and wish I learned sooner). 1) Saying "no" sucks. I understand why buyers ghost. You feel like a jerk, even though it's not personal. Especially when the seller has done their job well. 2) When a buyer gives a firm no, they don't want to be "objection handled". No is a decision. The idea is to anticipate and pre-empt objections BEFORE a no is on the table. Often, ghosting happens when WE create a pushy environment where the buyer doesn't feel comfortable telling us the truth. 3) The best sellers play offense, not defense. Ex: if you see an account at an in-flight opportunity announces a new CEO, call out the elephant in the room. "Saw the news re: Mary coming on as CEO. Did some digging and it looks like she came from a company that was using our competitor, ACME. Had a few ideas based on what I learned. Open to talking through those?" PS - always check to see what you can find out about the CEO's former company's competitive buying process in your company's CRM/call recordings. Was the CEO involved? Was she consulted? Who was the one driving the need to change? This context helps to size the potential risk. 4) The very best sellers were SO GOOD at reducing buyer effort. They recognized that decisions are rarely made by one person. They helped frame the problem, the alternative solutions to solving the problem, and were crystal clear about how they solve it. They made the job of socializing the business problem to my bosses easy. They were intentional about putting high-effort tasks on their plate (ex: creating a business case aligned to company objectives vs. copy/pasting standard collateral). 5) A surprisingly large amount of cold emails contained outright lies ("Will told me to get in touch." or "We want to explore a partnership!") or forced personalization ("Saw you went to PSU!"). IMO - seeing my college name in an email is a lazy (+ often automated) attempt to build a connection. Problem relevance > everything else. Sales is hard because there are so many conflicting opinions about what works and what doesn't. This is just my opinion, as someone who was newer to the buyer side. Buyers - what's one thing you've experienced that you wish more sellers understood?

Sick of hearing “no” in negotiations? These five fixes will turn rejections into wins. Understand why your negotiations fail, and gain powerful strategies to flip rejections into confident agreements. After decades of coaching global leaders through tough negotiations, I’ve learned a crucial truth: Most rejections aren’t about your offer, they’re about your negotiation approach. Here are honest lessons from my own painful negotiation mistakes, paired with clear, actionable fixes: 🔴 Mistake #1: Selling instead of solving Early in my career, I passionately pitched a partnership that was quickly rejected, it served my interests, not theirs. High stakes and embarrassment followed. ✅ Action: Never pitch without first asking clearly: “What outcomes matter most to you?” 🔴 Mistake #2: Ego over empathy Confidently proposing strict terms to demonstrate professionalism backfired when the client felt disrespected. Immediate rejection taught me, empathy beats ego every time. ✅ Action: Clearly show respect and collaboration: “Your insights are vital; let’s build this together.” 🔴 Mistake #3: Ignoring their better alternatives A major deal slipped through my fingers because I overlooked my client’s superior alternative (BATNA). My silence made my proposal irrelevant and costly. ✅ Action: Address alternatives directly: “I recognize you have other strong options; here’s why my offer uniquely benefits you.” 🔴 Mistake #4: Threatening their reputation I once had a deal collapse because accepting it would’ve undermined my counterpart’s internal credibility. A painful oversight I won’t forget. ✅ Action: Actively protect their reputation: “How can we structure this deal to enhance your internal credibility?” 🔴 Mistake #5: Losing trust Repeated rejections from a key client taught me they had lost trust due to hidden risks. Transparency became my essential tool for successful negotiations. ✅ Action: Be radically transparent: “These are the risks; let’s address them openly and together.” Rejection isn’t failure, it’s your best negotiation guide when you decode it clearly. What’s your go-to strategy for overcoming negotiation rejection? If this helped you rethink how you handle rejection don’t keep it to yourself! Repost, comment, or tag someone who needs to read this today. ♻️ 

A client of mine asked me to coach a deal recently, I just heard the outcome It was stalled at the executive level, and they were debating priority I noticed there was one key element missing There was a business case, competitive differentiation, and a champion pushing it as a key initiative for them. There was perceived pain at the champion level due to the manual work they had to do. Can you guess what was missing? The executives didn't see, believe, or understand the problem outside the functional area that was telling them about their problem. The feedback was "This looks good, but will the field really use it, and will it actually change anything?" My inference from that statement, the executives viewed the problem as just part of the champion's job. In other words, they didn't want to spend money to just make their lives easier. The solution I suggested? Call a bunch of their field locations, and ask them questions about what they do today, what it would mean if they had a solution like my client's, how often would they use it, and what benefit would it have to them. The rep did just that, he called and spoke to about 20 people. He then put their names and quotes of what they said on a slide, tied it to the outcomes they said, aligned that to the opportunity cost, and expanded it to every field member of the business. The champion took that, met with the exec team again...and...project greenlit! Lessons learned: 1. Functional departments are always asking for stuff, execs are tired of it, you need to make the problem bigger and unignorable. 2. Don't assume or trust functional areas have done the legwork, you, the seller need to do the legwork, speak to enough people, and build a big enough wave with the future user base. 3. Priority changes are never headaches. Executives expect you to not like parts of your job. They have plenty of headaches no one cares about. If there isn't broad impact, cross-function issues, big problems, and broad sweeping solutions, it won't bubble to a priority right now. The rep learned a lot in this deal. They also learned that their actions or lack thereof were the difference between winning and losing. What action can you take in your deal today to move the needle? If I can help you answer that question, let me know.

2 years ago, I was helping close a $385,000 deal. It was a ‘make or break’ deal for quarter-end. But of course:  Procurement was grinding us down on price. THEM: "$385k is INSANE. We only have budget for $200k." We had to bring the focus off price and back to value. Here's what we said next: US: "How familiar are you with the business value we're poised to deliver?" THEM: "I'm familiar. You're going to help us ramp new sellers faster. That's valuable. But not worth $385,000." Dead end? Nope. Then we took it to the next level: US: "Can we walk you through the math we did with your CRO to see if it checks out?" THEM: "Sure." US: "Your AE ramp time is 8 months. At month 9, the avg. rep starts producing $60k in ARR/month after 7 months of ramping up. That sound right?" THEM: "Yep." We were getting closer: US: "Your CRO tells us she's hiring 80 new AEs in the next 12 months." THEM: "Mmhmm." US: "So if you got 80 new AEs up to speed one month faster each: That's 80 * $60k in ARR = $4.8M." THEM: *sitting silent* Then we asked these questions: US (again): "The question then becomes, how believable is it that we can cut a month off your ramp time?" THEM *now the CRO chimes in*: "Very believable. I'm gone deep with them on this." US: "So $4.8M expected return against a $385k spend." Now for the nail in the coffin: US: "Usually when we get price resistance, it's either because: 1) you're not sold on the financial value 2) you do not have the ability to spend the cash. It feels like we covered #1. What's stopping us from here?" They signed 6 hours later. Here are 3 deal-closing lessons from this deal: 1. Get your champion in the negotiation room. Procurement rarely 'gets' the business value. Get your champion in the room when it's time to face off with them. Yes, you won't always be able to. But shoot your shot and at least ask. It will change the tone of the meeting. 2. Price resistance comes from 1 of 3 places: A) Not sold on the value B) Inability to pay C) Just trying to get a better deal. Identify which one you're up against. Then navigate accordingly. For us, it was a combination of 1 & 3. 3. Negotiating is MUCH easier with rock-solid selling skills. We had a few things going for us: - a committed champion - significant business pain  - quantifiable business value Imagine negotiating without those? Would have been a nightmare. That’s all for today. If this either: A) Taught you something B) Inspired you Drop a 💯in the comments. P.S. Learn 6 (WARNING: advanced) SaaS sales techniques I used to earn my first $1M W2: https://lnkd.in/g8mixtVc

We met with the CFO twice, had a verbal agreement, and he asked us for 1 week to finalize between 2 options. A week passed... and nothing. He asked for another 2 weeks. The problem remained: This wasn’t budgeted for and it’s a big investment. What we did not do: Try to hold the timeline against them. 𝗪𝗵𝗮𝘁 𝘄𝗲 𝗱𝗶𝗱 𝗱𝗼: 1. Met with our champion(s) and tried to deeply understand the ‘why’ 2. From there, recommended to take a step back and address their #1 challenge of total cost 3. Partnered in looking through the rest of their current tech stack, and seeing where else we could help provide efficiencies 4. Uncovered they were very unhappy with another adjacent tool and had a renewal within 6 months 5. Created a 3 week evaluation plan to see if we could replace that solution 6. Ran through that evaluation - discovery call, 3 demos, reference, scoping call - and gave them the confidence we could From there, we asked for the CFO’s time with our champions. We built out a cost table that showed the savings and consolidation we would be able to provide. And included in an additional financial incentive in exchange for a longer commitment. It grew our deal size by 30%, saved them money long-term, and got our champions access right away. Negotiations aren’t a battle into who can win the deal. It’s about creating a big win for your buyer. P.S. My 7 rules for negotiation on my blog here: https://lnkd.in/gGAvwSZB

She grilled me for 90 minutes. Argued on price, terms, and payment. Then signed a $120K deal the next day. The negotiation call was scheduled for 30 minutes. It lasted 97. Our first deal of the quarter, and it was going terribly. The VP challenged everything: – Demanded 90-day payment terms when we needed 30 – Pushed for a 22% discount on already-tight pricing – Questioned our data retention periods line by line – Asked for custom SLAs we'd never offered before My palms were sweating. At one point, she said: "This is simply too expensive for what you're offering." I almost caved. Almost offered that extra discount. Instead, I took a breath and asked: "Can you help me understand what specifically your team is trying to build?" What followed was a 40-minute deep dive into their actual problems. The real cost of missed insights in their customer calls. The manual work their team was doing. The tone completely shifted. She ended with: "Let me think about this overnight." I was sure we'd lost it. But at 6:42 AM the next day, the signed contract hit my inbox. With a note: "Thanks for taking the time yesterday. Your team clearly understands our challenges." One year later, they've renewed twice and expanded to a $340K account. That day changed how I view "difficult" negotiations: When someone pushes this hard, they're not trying to kill the deal. They're trying to make it work so that they can buy. Now when negotiations get tough, I see it for what it really is: Not resistance. Commitment. What's a deal you thought you were losing... that became your best customer?