The Art of Closing Deals

In large deals, the real competition is rarely another product. It is inertia. The most effective large deals are often shaped early. When the business user begins exploring a problem, and the right conversations start happening at that stage, the deal gradually evolves into a sole-sourced decision rather than a late-stage RFP comparison. Because once a deal reaches a formal RFP stage, many vendors appear to be at the finish line. In reality, the direction of the deal was usually influenced much earlier. Many deals look healthy for months. The champion is engaged. The demos land well. The value is understood. And then, close to the finish line, the deal slows down… or quietly becomes “No Decision.” More often than not, the issue is not price or product. The deal simply never travelled far enough inside the organisation. Large buying decisions are rarely made by one person. They are shaped by a group. The business user evaluates usability. IT looks at integration. Security looks at risk. Finance looks at cost. Leadership looks at long-term impact. Each of them is solving a different problem. If the conversation is only happening with one or two people, the deal remains fragile. This is where relationship mapping becomes one of the most important disciplines in selling large deals. Not just knowing your champion, but understanding the ecosystem around the deal. Who influences whom? Who signs. Who can block progress quietly? Who needs confidence before the decision moves forward? Building that map takes time. It means asking better questions. • Who else will review this internally?  • Who will be responsible for implementation?  • Who owns the budget?  • Who needs to see this before we move ahead? As more people across the organisation understand the value, the deal becomes stronger. It stops being one person’s initiative and starts becoming a shared decision. And shared decisions move forward with far less resistance. The best sellers know that closing large deals is not just about presenting a solution well. It is about shaping the deal early and building alignment across people, priorities, and perspectives. #LargeDeals #Enterprises #SST

The best negotiators rarely talk about price. They focus on everything else. After decades of closing deals across three companies, here's what I've learned. Negotiation isn't about winning. It's about reaching a deal both sides would gladly sign again. Six principles guide every deal I make. 1️⃣ Preparation beats persuasion. The person with the most information wins before the meeting starts. Most sellers show up and hope. Top closers show up and know. 2️⃣ Interests over positions. Positions are what people say they want. Interests are why they want it. A buyer asking for 20% off might simply need budget cover. Solve the real problem, and price stops being the fight. 3️⃣ Silence is leverage. The next person to speak often loses. Ask your question. Then wait. Most sellers fill silence with concessions. Top closers let the silence do the work. 4️⃣ Anchor first. Anchor smart. Whoever sets the first number sets the frame. Anchor high, but make sure you can defend it. Don't let the other side define your value. 5️⃣ Trade, don't concede. Never give without getting. Free concessions signal weakness. Traded concessions create stronger deals. 6️⃣ Protect the relationship. The deal ends. The relationship continues. Negotiate in a way they'd gladly sign with you again. The same buyers often come back around. Six principles. Zero burned bridges. 💾 Save this before your next negotiation.

You think prep is optional. Until the deal tanks and you realise you had no leverage from the start. Why? You didn't define your ZOPA. You didn't pressure-test your BATNA. You walk in negotiating blind. I use a 3-part approach before negotiations: 𝟭. 𝗠𝗮𝗽 𝗺𝘆 𝗭𝗢𝗣𝗔. The range where a deal can happen. Most people guess it. I quantify it! • What’s my ceiling? • What’s their likely floor? • Where’s the overlap, or is there one at all? • If there’s no overlap, I don’t force a deal. • I test assumptions, explore flexibility, or reposition entirely. 𝟮. 𝗦𝘁𝗿𝗲𝗻𝗴𝘁𝗵𝗲𝗻 𝗺𝘆 𝗕𝗔𝗧𝗡𝗔. This isn’t just a fallback. It’s your negotiating power. • If it's a weak BATNA, you’ll rationalise a bad deal • If it’s strong, you can walk calmly and confidently. Before I enter the room, I know exactly what “𝙣𝙤 𝙙𝙚𝙖𝙡” looks like, and I’ve made sure it’s viable. 𝟯. 𝗣𝗿𝗲𝘀𝘀𝘂𝗿𝗲 𝘁𝗲𝘀𝘁 𝗯𝗼𝘁𝗵 𝘀𝗶𝗱𝗲𝘀. Don’t just analyze your own position. Stress test the other party’s too. • What’s 𝘵𝘩𝘦𝘪𝘳 BATNA? • How costly is “no deal” for them? • What internal pressures are shaping their priorities? You don’t need to guess. You need to ask better questions and pay attention to what’s not said. Deals don’t just hinge on numbers. They hinge on trust. It's, clarity, leverage, and relationship strength that shape the agreement. Don’t just hope for a deal. Actively shape it, with precision and control. ------------------- Hi, I’m 𝗦𝗰𝗼𝘁𝘁 𝗛𝗮𝗿𝗿𝗶𝘀𝗼𝗻, and I help you master negotiation & communication for any situation. - Master Facilitator and EQ-i Practitioner - 24 yrs | 44 countries | 150+ clients - Negotiation | Conflict resolution | Closing deals 📩 DM me or hop on a call (link in the Featured section)

When I look back at my early years in enterprise sales, I realize how naive I was. I thought closing a big deal was just about: - showing a killer demo - answering objections smartly - negotiating the right price But the reality hit me hard.  I almost lost my first enterprise deal… not because of the product, not because of pricing, but because I didn’t understand how enterprises actually buy. Here’s what experience has taught me (and I wish I knew this earlier): a. Enterprise deals are not linear. They don’t move from pitch → demo → close. They zigzag through committees, hidden influencers, and endless paperwork. b. Your biggest win is finding a true champion. Someone who sells for you behind closed doors when you’re not in the room. c. Silence is more dangerous than a NO. If updates slow down, it usually means you have lost your internal momentum. d. Procurement isn’t the enemy. Once I learned their priorities, deals started moving faster, sometimes with their help. e. Trust beats everything. Decks impress, but enterprises buy confidence that you’ll stand with them when things go wrong. Today, when I work on large deals, I approach them very differently. With more patience, more empathy, and a lot more focus on people instead of just processes. If I could go back, I’d tell my younger self this one line:  “Enterprise deals aren’t closed, they’re orchestrated.” Curious to hear from others: What’s the hardest lesson you’ve learned in chasing large enterprise accounts? #EnterpriseSales #B2BSales #SalesLeadership #ComplexSales #Sales

Want to close more deals? Get the buyer to feel like your product’s already theirs before they’ve even signed. It’s called the endowment effect—people value things way more when they feel a personal connection to them. How do you tap into that? Think about buying a car - you’d typically get in and go for a test drive. You’d adjust your seat, shift the mirrors, and get comfortable behind the wheel, all the while picturing your daily commute. Suddenly, it’s not just a car—it’s your car. Same goes for anything else. Selling software? Skip the generic demo. Build something tailored to your prospect’s workflow. Let them input real data, customize settings, and see how it fits their world. The key is making it personal. Once a buyer’s test-driven your solution—whether it’s literally or figuratively—they’re not just considering your product; they’re imagining it as part of their life. And when they’re already invested? That’s when the magic happens.

One of the most expensive phrases in 𝗘𝗻𝘁𝗲𝗿𝗽𝗿𝗶𝘀𝗲 𝗦𝗮𝗹𝗲𝘀: "I'll get back to you with another proposal" One of the biggest mistakes founders make when presenting price or negotiating is to chase procurement's request for a better price. 𝗧𝗿𝘂𝘁𝗵 𝗶𝘀— If you're going back to get a better price without context, you're a puppy dog chasing after an impossible ball. You end up: • Guessing what discount percentage is going to get the deal done. • Wondering why the list price you presented doesn't work. • Second guessing the value of your product. • Undercutting the ultimate price you could close the deal with. Skilled negotiators from the competition aren't guessing what discounts or deal structure are going to get the deal done. They're pushing back on nebulous discount requests and are engaging in rich realtime negotiation. So the next time you're asked to come back with a better price, here's what you can do: 1. 𝗥𝗲𝘀𝘁𝗮𝘁𝗲 𝘁𝗵𝗲 𝘃𝗮𝗹𝘂𝗲 𝗼𝗳 𝘆𝗼𝘂𝗿 𝗽𝗿𝗼𝗱𝘂𝗰𝘁 𝗰𝗼𝗻𝗳𝗶𝗱𝗲𝗻𝘁𝗹𝘆 → "The price is the price because..." 2. 𝗔𝘀𝗸 𝘄𝗵𝘆 𝘆𝗼𝘂𝗿 𝗽𝗿𝗼𝘀𝗽𝗲𝗰𝘁 𝗱𝗼𝗲𝘀𝗻'𝘁 𝘁𝗵𝗶𝗻𝗸 𝘁𝗵𝗲 𝗰𝘂𝗿𝗿𝗲𝗻𝘁 𝗽𝗿𝗶𝗰𝗶𝗻𝗴 𝘄𝗶𝗹𝗹 𝘄𝗼𝗿𝗸 → "This is our view but it'd be great to get a sense for how you think about budgeting for a platform like this." 3. 𝗔𝗰𝗸𝗻𝗼𝘄𝗹𝗲𝗱𝗴𝗲 𝘆𝗼𝘂𝗿 𝗯𝘂𝘆𝗲𝗿'𝘀 𝘃𝗶𝗲𝘄 𝗼𝗳 𝘁𝗵𝗲 𝘄𝗼𝗿𝗹𝗱 𝗢𝗥 𝗼𝗯𝗷𝗲𝗰𝘁𝗶𝗼𝗻 𝗵𝗮𝗻𝗱𝗹𝗲 𝗶𝗳 𝘆𝗼𝘂 𝗱𝗶𝘀𝗮𝗴𝗿𝗲𝗲 → "That makes sense so thank you for providing that context" → "I'd view our product in a bit of a different light because..." 4. 𝗔𝘀𝗸 𝗳𝗼𝗿 𝗮 𝘀𝗽𝗲𝗰𝗶𝗳𝗶𝗰 𝗽𝗿𝗶𝗰𝗲 𝘁𝗵𝗮𝘁 𝘄𝗼𝘂𝗹𝗱 𝘄𝗼𝗿𝗸 𝘁𝗼 𝗴𝗲𝘁 𝘁𝗵𝗲 𝗱𝗲𝗮𝗹 𝗱𝗼𝗻𝗲 → "Can I ask what price would work for you? Is there a magic number you have in mind?" 5. 𝗖𝗼𝗻𝗳𝗶𝗿𝗺 𝘄𝗵𝗲𝘁𝗵𝗲𝗿 𝗼𝗿 𝗻𝗼𝘁 𝘁𝗵𝗲 𝗰𝗼𝘂𝗻𝘁𝗲𝗿 𝗽𝗿𝗶𝗰𝗲 𝗶𝘀 𝗿𝗲𝗮𝗹 𝗼𝗿 𝗻𝗼𝘁 → "If we don't miss that price are we in a place where this deal doesn't get done?" 6. 𝗔𝘀𝗸 𝗵𝘆𝗽𝗼𝘁𝗵𝗲𝘁𝗶𝗰𝗮𝗹𝗹𝘆 𝗶𝗳 𝘆𝗼𝘂'𝗿𝗲 𝗮𝗯𝗹𝗲 𝘁𝗼 𝗺𝗲𝗲𝘁 𝘁𝗵𝗲 𝗰𝗼𝘂𝗻𝘁𝗲𝗿 𝗽𝗿𝗶𝗰𝗲 𝘄𝗵𝗮𝘁 𝘆𝗼𝘂 𝘄𝗼𝘂𝗹𝗱 𝗴𝗲𝘁 𝗶𝗻 𝗿𝗲𝘁𝘂𝗿𝗻 → "If we're able to meet that price can we sign the contract this week?" → "If we're able to meet that price, can we move forward with the legal terms as is?" etc. 7. 𝗖𝗹𝗼𝘀𝗲 𝘁𝗵𝗲 𝗰𝗮𝗹𝗹 𝘄𝗶𝘁𝗵 𝗮 𝗰𝗼𝗺𝗺𝗶𝘁𝗺𝗲𝗻𝘁 𝘁𝗼 𝗴𝗲𝘁 𝗯𝗮𝗰𝗸 𝘁𝗼 𝘆𝗼𝘂𝗿 𝗯𝘂𝘆𝗲𝗿 𝗾𝘂𝗶𝗰𝗸𝗹𝘆 𝘄𝗶𝘁𝗵 𝘄𝗵𝗲𝘁𝗵𝗲𝗿 𝗼𝗿 𝗻𝗼𝘁 𝘆𝗼𝘂 𝗰𝗮𝗻 𝗺𝗮𝗸𝗲 𝘁𝗵𝗲 𝗻𝘂𝗺𝗯𝗲𝗿𝘀 𝘄𝗼𝗿𝗸 → "I'll need to discuss with my cofounders but can commit to getting back to you tomorrow" With an approach like this you: • Have an opportunity to reposition the value of your product • Gain clarity around a deal structure that will work • Can accelerate the deal vs. slowing it down Want more sales & negotiation tips? Follow me and check out the resources in my featured section. S/O to Chris Do for the hook and post format inspiration ✨

Over the last 5 years, personally I’ve closed 11 deals that were 7 figures of ARR. Also over those same 5 years, I’ve lost 42 of them. Reality does still exist out here somewhere on LinkedIn. Every one of them (won and lost) had multiple things in common: - Started with cold outreach. Yep… - Took in-person interaction to build progress. Events, onsites, etc - Required maniacal multi threading and an army of teammates working alongside me. - 2 months of contract review and security review. 💰If you want to be closing big deals, prepare to: Research like a maniac, then cold outbound to get then in. Then, prepare to: 1️⃣Lose more than you think. You’ll win, but not as much as you think you will. 2️⃣Be a project manager. You’re not playing hero ball. You’re playing facilitator, except managing execs internally and externally throughout the deal. It’s exhausting, but rewarding. 3️⃣Invest time in person. It’s near-impossible to close these entirely remote. 4️⃣Steel yourself for the absolute buzzsaw of procurement and legal. They will break you or your champion - make it easy for them to get through their process, but keep it on track. It’s longer than you think. 5️⃣ Keep control of a deal by not being controlling. Guide the buying team with clarity. Fight for clarity to drive next steps. Big deals are INCREDIBLE to close and entirely worth it. Be prepared to play the long mental game. Only the sellers with the best process survive. Embrace your process, trust it, win with it.

There’s a reason your deal isn’t closing — and it’s not because of the price. Inside big orgs, decisions follow politics, process, and personal agendas. That’s why closing a deal means helping your buyer 𝘴𝘦𝘭𝘭 𝘪𝘵 𝘪𝘯𝘵𝘦𝘳𝘯𝘢𝘭𝘭𝘺, too. Here’s how: (𝟭) 𝗠𝗮𝗽 𝘁𝗵𝗲𝗶𝗿 𝙞𝙣𝙩𝙚𝙧𝙣𝙖𝙡 influence, not just their title. It’s easy to sell to the person with the right title. But real traction comes when you understand who 𝘢𝘤𝘵𝘶𝘢𝘭𝘭𝘺 moves decisions forward internally. Titles can be misleading—find the person who can champion your cause in the rooms you're not in. They don’t just have access; they have sway. Ask: “Who else needs to say yes?” and “Who really owns the outcome of this project?” (𝟮) 𝗪𝗵𝗶𝘁𝗲𝗯𝗼𝗮𝗿𝗱 𝘁𝗵𝗲 𝗳𝘂𝗹𝗹 𝗮𝗽𝗽𝗿𝗼𝘃𝗮𝗹 𝗽𝗮𝘁𝗵 𝘁𝗼 𝗮 “𝘆𝗲𝘀”. Your champion isn’t always your decision-maker. That’s why our best reps always map out the approval journey: → Who needs to sign off? → What triggers procurement or legal involvement? → At what dollar amount does this escalate to the CFO? When you know the answers, you can preempt roadblocks, and arm your buyer to drive it through. The fastest path to a “yes” is in removing friction from the buying process. (𝟯) 𝗦𝗲𝗹𝗹 𝘁𝗼 𝘁𝗵𝗲 𝗽𝗲𝗿𝘀𝗼𝗻𝗮𝗹 𝗺𝗼𝘁𝗶𝘃𝗮𝘁𝗶𝗼𝗻 𝗼𝗳 𝘁𝗵𝗲 𝗱𝗲𝗰𝗶𝘀𝗶𝗼𝗻 𝗺𝗮𝗸𝗲𝗿. In enterprise sales, you’re asking a person to bet their reputation on you. So make it worth it. Understand what they care about: → What does success look like for them? → How’s their bonus structured? → What are they trying to prove (or avoid)? If your solution helps them win, they’ll go to bat for you because value beats price (especially when it’s personal). 𝗧𝗵𝗲 𝘁𝗮𝗸𝗲𝗮𝘄𝗮𝘆: Don’t just pitch. Partner with the buyer, with the process, and with the politics. Do that, and price stops being the issue.

Coffee is for closers. That line, and the toxic bravado behind it, needs to go. The best consultants and salespeople don’t sell. They start with one simple question: “Why?” And The Wolf of Wall Street is not a how-to sales guide. It’s a cautionary tale soaked in ego and adrenaline. Glengarry Glen Ross? Same thing. A masterclass in manipulation and moral bankruptcy, yet somehow these warped tactics, fast talk, pressure plays, "always be closing" still show up in sales training, and yes, recruitment floors. The recruitment industry, like it's close cousin real estate, is littered with outdated tropes: “Sell the pen.” “ABC: Always Be closing.” “Dominate the room.” Say whatever it takes to close the deal. These tactics are not just outdated. They’re shallow. Real influence doesn’t come from how well you pitch, post, or promote. It comes from how well you listen and whether what you say is backed by substance. Take “Eddie,” a self-proclaimed million-dollar biller with stories spanning Manhattan, London, and beyond. Mate, we all know it’s smoke and mirrors. A performance. You aren’t Brisbane’s own James Bond. The truth? -- The best salespeople don’t push. They pull. -- They don’t dominate the room. They open it up. -- They don’t talk more. They listen better. But not just any questions. They ask the ones no one else dares to. The ones that peel back assumptions, uncover motivations, get to the root of the problem. Most people ask what. Good people ask how. The best ask "why." Why? Because “why” changes the conversation. It unlocks purpose. Invites honesty and builds trust. “Why did that matter to you?” “Why do you feel that way?” “Why” is a shortcut to the truth. I remember sitting in a team meeting years ago. Nick, a sharp and well-respected colleague, was pitching a cost-saving plan that completely missed the mark for our customers. Instead of challenging him directly, I just kept asking “Why?” Five times. Eventually, he paused, and concluded there were better, more customer-focused options. That’s the power of better questions. Not to trap someone, but to help them see more clearly. When you lead with curiosity, you’re building connection. You’re showing someone you care about them, not just the transaction. And that’s where trust happens. That’s what actually drives referrals, sales, and loyalty. Take it from me, someone who spent +20 years getting this wrong. It turns out that the sale is just the byproduct. The real win? Be the person who gets it. Who listens when others talk. Who connects instead of convinces. Be the person who gives it all away for "free." Because you know it will come back around anyway. So next time you’re in a conversation, sales or otherwise, ditch the “pitch script.” Get curious. Ask better questions. Go where others don’t. And above all, ask "Why?" The real magic in winning the deal, doesn't happen when you sell. It happens when you understand. Enjoy the coffee.