Key Questions to Ask for Persuasive Negotiation

You don’t need “better discovery questions.” You need bolder, much more direct questions. These 10 make buyers stop and think out loud (which is what you want): 1. “Who loses if this goes forward?” Some wins create a loser. This surfaces blockers and turf wars before they kill your deal in procurement. 2. “Who gets credit if this goes well?” This reveals who wants to be the hero. People support what they help champion, and what they can add to their promotion narrative. 3. “What’s the last project you regret saying yes to?” Uncovers emotional baggage and past vendor trauma - which shapes how they see YOU. A great way to adjust your pitch and tone before it’s too late. 4. “If I talked to your CFO tomorrow, what would they push back on?” You don’t need the CFO in the meeting to start selling to them. 5. “What’s already been tried?” If you pitch what’s already failed, you lose credibility before you start. 6. “What’s your boss’s favorite metric?” Reveals the hidden KPI that actually gets budget - and who really holds the purse strings. 7. “Who gets fired if this goes wrong?” Blunt, but powerful. It reveals where the risk (and decision power) really lives. 8. “Is this something you want, or something your boss wants?” Gets to the real power center. Are you selling to influence, or just echo? 9. “What’s the internal politics I should know about here?” Not "who’s involved," but who’s gunning for whose budget, who hates change, who needs a win. Every deal has landmines. This question helps you spot them before you step on one. 10. “What’s at stake for you personally if this works?” This is where discovery gets real. People buy for the business, but move for themselves. These aren’t silver bullets. They shouldn’t all be used during disco. But IMO they’re 10x better than “What keeps you up at night?” These also aren’t all warm and fuzzy, but if you want better deals, ask bolder questions. At the end of the day, fake urgency, false champions, and fluffy timelines don’t kill deals. Polite discovery does.

Yesterday, I delivered my final workshop of 2024 to my favorite client, G2. AEs & AMs brought Q4 deals at-risk for losing to status quo. We worked through tactics to reduce deal risk + re-engage execs at stalled opportunities. Here are the 4 Qs we worked through on their deals: 1) Can I quantify the cost of inaction (COI)? This is not ROI. This is not, "Every day you wait, you're missing out on the opportunity to improve X by 425%". Humans make stupid decisions constantly. Buyers are humans. We rarely assume risk to realize a benefit. ROI = by doing something, you MIGHT see this return. COI = by changing nothing, you ARE seeing this unintended cost/risk. 2) Do I know what other priorities and categories of spend I'm competing with? This is not "which of our competitors am I up against?". This is, "What other investments/priorities might take precedence over this one?". Ask your buyer this question directly. Make it easy for them to be honest with you. Don't rush to convince them to prioritize yours, before you deeply understand the others. 3) Do I know the 11.2 stakeholders involved in making the decision? Sometimes it's more. Sometimes it's less. But it's rarely just 1 person. Do you know who they are? More importantly, does your BUYER know who they are? We should be having this candid convo with our buyers. "In other companies i've worked with, here is how and where CXO tends to get involved, and here are the places where they typically push back. How might that look different with your CXO?". 4) Does my buyer have the skill and will to rally those other 10.2 stakeholders to give a sh*t about this spend? We could have the perfect solution to an expensive problem. But, our success/failure often lies in the hands of the messenger (our champion). Do the heavy lifting to help your buyer craft a narrative that will inspire them to advocate COI effectively. The key here is effort reduction. Job #1 is for the buying group to agree that this is a problem worth solving, and worth solving now. A big part of being great at Sales is being willing to put our egos aside. The reason I call G2 my favorite client is because there is ZERO ego on this team. They want to learn. They don't cut each other down. They're not stuck in "but this is how we've always done it". They APPLY what they learn (same-day in their sales calls). We laugh a lot in our workshops. A big part of that has to do with the learning culture G2 has created for their commercial org. It reminds me a lot of where I grew up learning how to sell (CEB). And, a ton of that credit goes to the women pictured below. When I think of the BEST of Sales Enablement leadership - I think of Emily Hyde. It's no surprise her team is just as A+. Eric Gilpin - thank you for being a CRO who invests in their Sales team's development and sets the bar high for what great leadership looks like. Now for a 3 week break before SKO (sales kickoff) season kicks off!

Weak questions bore brains. Let’s crank the voltage. Afraid to dig deep? Let sharper queries unravel. By the end of this post, you’ll have a toolkit to ask questions that spark curiosity, reveal hidden opportunities, and guide conversations like a master negotiator. After years in negotiation, I’ve learned that asking the right questions isn’t just an art—they’re a game-changer. Here are 5 types of questions to elevate any conversation: 𝟭. 𝗘𝘅𝗽𝗹𝗼𝗿𝗮𝘁𝗼𝗿𝘆 𝗤𝘂𝗲𝘀𝘁𝗶𝗼𝗻𝘀 📌 𝗣𝘂𝗿𝗽𝗼𝘀𝗲: Dig deep. Understand the big picture. 🛠️ 𝗔𝗽𝗽𝗿𝗼𝗮𝗰𝗵: Use open-ended “what,” “how,” or “why” questions to encourage free sharing. 💡 𝗘𝘅𝗮𝗺𝗽𝗹𝗲: “𝘞𝘩𝘢𝘵 𝘧𝘢𝘤𝘵𝘰𝘳𝘴 𝘢𝘳𝘦 𝘮𝘰𝘴𝘵 𝘪𝘮𝘱𝘰𝘳𝘵𝘢𝘯𝘵 𝘵𝘰 𝘺𝘰𝘶𝘳 𝘵𝘦𝘢𝘮 𝘸𝘩𝘦𝘯 𝘤𝘰𝘯𝘴𝘪𝘥𝘦𝘳𝘪𝘯𝘨 𝘢 𝘱𝘢𝘳𝘵𝘯𝘦𝘳𝘴𝘩𝘪𝘱?” 𝟮. 𝗖𝗶𝗿𝗰𝘂𝗹𝗮𝗿 𝗤𝘂𝗲𝘀𝘁𝗶𝗼𝗻𝘀 📌 𝗣𝘂𝗿𝗽𝗼𝘀𝗲: Reveal patterns and relationships. 🛠️ 𝗔𝗽𝗽𝗿𝗼𝗮𝗰𝗵: Ask how people, ideas, or events influence each other. 💡 𝗘𝘅𝗮𝗺𝗽𝗹𝗲: “𝘏𝘰𝘸 𝘥𝘰 𝘺𝘰𝘶 𝘵𝘩𝘪𝘯𝘬 𝘺𝘰𝘶𝘳 𝘴𝘪𝘴𝘵𝘦𝘳 𝘷𝘪𝘦𝘸𝘴 𝘥𝘦𝘤𝘪𝘴𝘪𝘰𝘯-𝘮𝘢𝘬𝘪𝘯𝘨 𝘪𝘯 𝘵𝘩𝘦 𝘤𝘰𝘮𝘱𝘢𝘯𝘺?” 𝟯. 𝗥𝗲𝗳𝗹𝗲𝗰𝘁𝗶𝘃𝗲 𝗤𝘂𝗲𝘀𝘁𝗶𝗼𝗻𝘀 📌 𝗣𝘂𝗿𝗽𝗼𝘀𝗲: Inspire self-awareness and critical thinking. 🛠️ 𝗔𝗽𝗽𝗿𝗼𝗮𝗰𝗵: Gently challenge assumptions and help connect actions to outcomes. 💡 𝗘𝘅𝗮𝗺𝗽𝗹𝗲: “𝘞𝘩𝘢𝘵 𝘸𝘰𝘳𝘬𝘦𝘥 𝘸𝘦𝘭𝘭 𝘪𝘯 𝘵𝘩𝘢𝘵 𝘱𝘳𝘰𝘫𝘦𝘤𝘵, 𝘢𝘯𝘥 𝘸𝘩𝘢𝘵 𝘸𝘰𝘶𝘭𝘥 𝘺𝘰𝘶 𝘤𝘩𝘢𝘯𝘨𝘦?” 𝟰. 𝗚𝗲𝗻𝗲𝗿𝗮𝘁𝗶𝘃𝗲 𝗤𝘂𝗲𝘀𝘁𝗶𝗼𝗻𝘀 📌 𝗣𝘂𝗿𝗽𝗼𝘀𝗲: Unlock creativity and spark innovation. 🛠️ 𝗔𝗽𝗽𝗿𝗼𝗮𝗰𝗵: Ask forward-looking or “what if” questions to inspire out-of-the-box thinking. 💡 𝗘𝘅𝗮𝗺𝗽𝗹𝗲: “𝘞𝘩𝘢𝘵 𝘪𝘧 𝘸𝘦 𝘳𝘦𝘪𝘯𝘷𝘦𝘯𝘵𝘦𝘥 𝘰𝘶𝘳 𝘱𝘳𝘰𝘤𝘦𝘴𝘴 𝘦𝘯𝘵𝘪𝘳𝘦𝘭𝘺 𝘵𝘰 𝘵𝘢𝘤𝘬𝘭𝘦 𝘵𝘩𝘪𝘴 𝘤𝘩𝘢𝘭𝘭𝘦𝘯𝘨𝘦?” 𝟱. 𝗦𝘁𝗿𝗮𝘁𝗲𝗴𝗶𝗰 𝗤𝘂𝗲𝘀𝘁𝗶𝗼𝗻𝘀 📌 𝗣𝘂𝗿𝗽𝗼𝘀𝗲: Align actions with long-term goals. 🛠️ 𝗔𝗽𝗽𝗿𝗼𝗮𝗰𝗵: Focus on weighing options and balancing risks and rewards. 💡 𝗘𝘅𝗮𝗺𝗽𝗹𝗲: “𝘏𝘰𝘸 𝘥𝘰𝘦𝘴 𝘵𝘩𝘪𝘴 𝘢𝘭𝘪𝘨𝘯 𝘸𝘪𝘵𝘩 𝘰𝘶𝘳 𝘭𝘰𝘯𝘨-𝘵𝘦𝘳𝘮 𝘨𝘰𝘢𝘭𝘴, 𝘢𝘯𝘥 𝘸𝘩𝘢𝘵 𝘳𝘪𝘴𝘬𝘴 𝘴𝘩𝘰𝘶𝘭𝘥 𝘸𝘦 𝘱𝘳𝘦𝘱𝘢𝘳𝘦 𝘧𝘰𝘳?” Great questions aren’t random—they’re your most powerful tools for influence, innovation, and clarity. Master them, and you’ll master the room. What’s one question you’ve asked that completely changed a conversation? Drop it below—I’d love to learn from you. (𝘗.𝘚. 𝘐’𝘷𝘦 𝘢𝘴𝘬𝘦𝘥 𝘮𝘺 𝘧𝘢𝘪𝘳 𝘴𝘩𝘢𝘳𝘦 𝘰𝘧 𝘢𝘸𝘬𝘸𝘢𝘳𝘥 𝘲𝘶𝘦𝘴𝘵𝘪𝘰𝘯𝘴 𝘵𝘰𝘰. 𝘉𝘶𝘵 𝘩𝘦𝘺, 𝘵𝘩𝘢𝘵’𝘴 𝘩𝘰𝘸 𝘺𝘰𝘶 𝘨𝘦𝘵 𝘣𝘦𝘵𝘵𝘦𝘳!)

The "#1 Rule of Compensation Negotiation" isnt what you think! If you’ve spent time on career blogs or scrolling through job search advice on social media, you’ve probably seen one common piece of advice: “Always negotiate.” But here’s the truth: that oversimplification has led a lot of people down the wrong path. Some career coaches and self-styled experts go as far as saying “everything is negotiable.” and that mindset had put new hires in very uncomfortable positions, and occasionally even getting offers pulled. Not only is "everything is negotiable" simply not true, some areas like ERISA-regulated benefits and retirement plan participation are legally locked in. Trying to negotiate them shows you don’t understand how compensation packages work, and can weaken your credibility. The Real Rule of Thumb: Always Ask Instead of “always negotiate,” the smarter approach is to always ask. Negotiation starts with curiosity and understanding what’s actually on the table. Good questions to ask include: “How is performance reviewed, and how often do raises occur?”  "Does this company share Comp-Ratios? And if so, what is the CR for this offer?" "What is this companies general compensation philosophy?" “What does the bonus structure look like are there guaranteed components or performance-based?” “How does this offer compare against recent hires made in similar leveled roles?" Notice the difference: you’re not demanding; you’re asking questions that clarify the total package. This opens the door to a productive discussion instead of a standoff. Successful negotiations aren't about saying “I need more because my rent is high” or “I deserve it because of personal circumstances.” Instead, they’re strongest when tied to business value. “Based on the market data for this role and the responsibilities outlined, I believe a range of X–Y is more aligned with the value I’ll bring.” “In my last role, I increased revenue by 20%. I’d like to understand how that type of impact is rewarded here.” The most effective negotiators aren’t necessarily the boldest or most aggressive. They’re the ones who combine asking the right questions with providing concrete examples of their impact. Instead of going in with the mindset of “fight for every dollar,” go in prepared to learn, clarify, and connect your skills to measurable results. That’s where real negotiation power lives and as the one who has approved contracts in the several-million dollar range, I can tell you this works!