The Role of Questions in Negotiation

I've watched over 2,500 discovery calls in the last few years. There's one thing I'm convinced of: Top salespeople get to the "heart of the problem" FASTER than their peers. SPEED to uncovering the 'real' problem matters. Here's why: Avg salespeople don't uncover even the tip of the ice berg until late in the call. So they never get a chance to go beyond the surface. They run out of time. Great salespeople get to the heart of the matter fast. That gives them TIME: Time to peel back the onion. Time to explore negative impact. Time to diagnose the root cause. Here are four questions (in order) that get to 'the heart of the deal' fast: 1. Tell me about your biggest challenges when it comes to X? Easy enough. Just enough to kickstart the conversation in the right direction. But not enough by itself. Customers will (almost) always give surface level answers to the first question. 2. What's going on in the business that's driving [what they shared] to be a priorty. Ask this, and your customers will CHUCKLE half the time. Why? Because you are striking a CHORD when you ask that. You're getting to the 'need behind the need.' That's where big money lives. Getting closer. 3. What metric is suffering most as a result of that? Avg sellers struggle to quantify pain. You walk into a different world when you go from expressed pain to quantified pain. Your customer's urgency ramps up. And spending money to solve the problem begins to look REAL good. 4. What's driving you to solve all this now rather than later? Ask this too early? And the answers will be weak. BUT... If you ask this AFTER those first three questions... Your customer now has the FULL CONTEXT of the problem top-of-mind. And now... their answers to THIS question will be far, FAR richer. Give those 4 questions (in order) a try. P.S. Here's 39 more questions that sell: https://lnkd.in/g-VRcCsq

What you learn depends on what you are willing to learn. When in a discussion, negotiation, or team project, the way you ask a question shapes the answers you receive. Your framing doesn’t just influence the response—it determines what possibilities open up (or shut down). Consider these two scenarios: (1) Team decision-making: Asking "Who is responsible if this fails?" creates defensiveness. Asking "What can we do to set ourselves up for success?" shifts the focus to proactive problem-solving. (2) Negotiation: Asking "Can you lower the price?" leads to a yes/no answer. Asking "What flexibility do we have on pricing and value?" invites creative solutions—maybe a better package, a longer-term deal, or additional perks. Here are three simple shifts to unlock better insights: (1) Ask open-ended questions. Instead of "Is this possible?" try "How might we make this work?" (2) Frame questions toward learning, not blame. Instead of "Why did this go wrong?" ask "What can we learn from this?" (3) Expand the lens. Instead of "Should we do A or B?" ask "What other options haven’t we considered?" Curiosity isn’t just about what you ask—it’s about how you ask it. #Curiosity #Learning #Leadership #Asking #Growth #Reflection

Here's a discovery question that helped me sell my first 7-figure Enterprise deal as an AE. Prospect was looking for negotiation training. The company I was working for didn't sell negotiation training. Instead of trying to convince her negotiation wasn't the right answer, I sought to understand why they were looking to solve for negotiation. I asked, "How did the leadership team arrive at negotiation as the right problem to fix?" Her: "Because we sell a commoditized product. Customers don't see a difference between our parts and our competitors'. We keep losing to low-cost competition. Every deal is turning into a price war." Me: "This may be an awkward question, but, is there actually a difference?" Her: "When it comes to our ability to outperform on reducing plant downtime - yes." Me: "And, how often are customers factoring the cost of excess downtime into their decision?" Her: "Not enough. They're usually just looking for the cheapest replacement part." Me: "Does the negotiation phase feel like the right time to raise that?" Her: "No - it's too late in the sales cycle." Boom. That was the magic moment. That was the moment SHE introduced doubt that negotiation was the right problem to solve. It became her a-ha moment. Her realization. Her idea. It opened the door for me to share a different POV on an alternative root cause of the known problem. That led to a meeting with the ELT to discuss root causes, not solutions. TLDR: People hate to be told they are wrong. Help them revisit their own beliefs/assumptions by seeking to understand HOW they arrived at a conclusion. There's a lot of insight to be gained by asking, "How did the team arrive at X as the right problem to solve?".

Management isn't about having all the answers. It's often about using a perfectly timed question. Here are 7 questions for the hardest management moments (and tactics you can apply to any situation)... Why are questions superior to directives? - Engage: Your team wants to help & to be heard. - Empower: You're role-modeling vulnerability & respect. - Enlighten: You'll generate more data for better decisions. You'll notice I use a similar pattern: Label + Question - Label: It's a negotiation tactic. If you say "It seems like you're upset" they pause to question if that's true, diffusing the emotion. - Question: I make them open-ended. I want to get them talking and surface data, ideally their underlying 'Why.' ⬇️⬇️⬇️ 1. Moment: Your star employee just told you about a competing offer. Question: Jen, I appreciate that you feel comfortable discussing this with me. What role would you like me to play in reviewing this possibility with you? 2. Moment: You just gave critical feedback, and they’ve clearly shut down. Question: Bill, I sense I’ve upset you. What piece of feedback was most off of the mark? 3. Moment: You’ve found a great candidate you want to hire, and they’re about to leave for the day. Question: Sally, I know you are almost out the door, and it’s been a long day. If we made you the offer to come on board, what would stop you from saying 'Yes'? 4. Moment: Your idea has been called out as stupid by a subordinate in a large meeting. Question: One of the things I like most about working with Amanda is that we have agreed to always tell the truth. Amanda, let me have it. How did I mess this up? What did I overlook? 5. Moment: Your boss just asked you to take on work your team has no capacity for. Question: Gina, this sounds like a top priority. Given that the team is already overcapacity, which of our current initiatives do you think we should pause to make space for it? 6. Moment: You just finished delegating a critical piece of work. Question: Jim, it sounds like you're ready to give this a go. What is the best way for me to stay close enough to help ensure your success?" 7. Moment: You just gave a raise, and your employee is disappointed. Question: Sahil, I'm sensing you feel there's some distance between this raise and what you think you deserve. Help me understand how you thought about what was fair and what I may have missed. ⬇️⬇️⬇️ Play the game yourself: Think back to a sticky, awkward moment. Replay it, only this time: -> Don't react (with words or body language) -> Acknowledge & diffuse by labeling their reaction -> Offer a question that surfaces as much info as possible Better or worse outcome? If you found this helpful, you'll like my free newsletter even more. Subscribe: mgmt.beehiiv.com Get 70+ practical playbooks to help you manage more effectively. And please repost ♻️ and follow Dave Kline for daily leadership coaching.

Are your direct questions killing your deals with indirect buyers? Most sales reps approach every conversation the same way. Direct questions. Pushy tone. Bad timing. I learned this lesson the hard way selling to “softer” personas like HR, generally speaking. I'd ask "What's driving this to be a priority?" and watch them instantly close up. What changed my results was what I call the Triple T approach: 1️⃣ TACT: Frame questions through a third party lens ("I typically find that leaders like yourself...") 2️⃣ TONE: Slow down, soften your voice, appear thoughtful and curious rather than interrogating 3️⃣ TIMING: Build rapport first, then ease into business questions gradually Here's a practical example: BEFORE: "What's your pain point? Why now? What's your budget?" AFTER: "What's interesting is... usually when I talk to HR leaders like yourself who are considering a change... I find there's something happening in the business driving this to be key priority for them. What's that look like in your situation?" Same core question. Completely different response. This approach creates psychological safety for indirect buyers to open up about their real challenges. Since implementing this method, I've uncovered 10X more pain points and closed deals other reps couldn't touch. The best part? This works in ANY high stakes conversation (personal or professional). - Want to run better discovery than last time? You’d be foolish not to check this out: https://lnkd.in/gexS_66B

Here are 5 *slightly-awkward* discovery questions I like, that signal you're different than the typical AE who's never thinking post-sales. That you're up to dig into what happens after the contract's inked. (Especially key if you're selling complex / enterprise deals.) 1. Unexpected Outcomes "Obviously, [ your main product benefit ] is the goal. But if your biggest win came in a totally different area we didn't initially expect, where would a win like that show up?" → Start it off with a win scenario, and get them thinking past the first use case into (potential) expansion areas. 2. Past Failures "Could you walk me through a time your team invested in something that technically worked, but didn't deliver the outcome? What happened?" → Finds their real definition of success, internal change management / political dynamics, and what metrics actually matter. 3. Resource Check "If this gets approved, what's one resource your team will have to 'borrow' from another team to make it successful—and how comfortable are you having that conversation?" → Cross-department dependencies are very real. Best to call out delivery roadblocks now, they haven't planned for later. 4. Executive Sponsorship "When you show this to [ exec sponsor ], what's 1 question they might ask, that you're hoping they don't... and what would your honest answer be?" → Often, what someone's telling you and what they know internally about an exec's concerns / skepticism are different things. 5. Six Months Later: "Let's say it's 6 months from now and you're in a QBR. Someone asks, 'Was this worth it?' What do you pull up on your screen to prove it was? And what would make you nervous about showing that?" → Helps you define real success metrics, and how they'll be tracked. Okay okay, I said 5 questions... but here's one more: 6. Plan B "What's your Plan B if this doesn't get approved?" → What's funny is I've found that my deals tend to be less "real" if there's no Plan B. Not the other way around. If something's truly important, there's always another option they're looking at. Could you see yourself testing one of these? PS, Olli the AI Agent we built is crazy good at crafting disco questions. If you'd want to put him to work on some of your toughest deals, drop a note & I can get you access.

Don’t be so blinded by your end goal that you miss serious 🚩 flags in your interview process! Here are the most common warning signals you'll encounter, along with questions you should be asking: 1. Too many departures / bad Glassdoor reviews Identify the impetus behind the churn – is this a symptom of a recent leadership or a major company pivot? It’s more likely to subside in that case (unless there’s a strong history of said changes). If it’s a longer tail churn that’s been around for a while, and you’re not getting any clear answers, you need to dig a little further: ❓ “What’s your temperature check on the current company climate? ❓ "What are you hopeful about, what are you less certain about?” ❓ “How do you personally view some of the recent departures and changes that the company is facing?” ❓ “Is there a common thread behind the changes? If not, what's your take?” 2. Role flip-flopping Do you seem to get a different response about what the role actually entails from each interviewer? The buck typically stops at the person in charge – aka your manager, major stakeholder, or CEO. Get clarity from these folks with the following Qs: ❓ “From your perspective, what’s the top priority you expect this person to focus on? What do you foresee this person tackling 6-12 months from now?” ❓ “I've noticed a few priorities have popped up from the team in my interviews (list them) – how would you rate the level of importance or urgency on these?” ❓ “What problems do you want this person to own vs support?” 3. Unclear culture Are you getting vague terms like “we’re a family” or “work hard, play hard” but not quite getting a clear picture of what any of that actually means in practice? Make sure you ask culture questions in EVERY interview to get as many perspectives as possible, and don't be afraid to ask for extra time later if you're presented with an offer: ❓ “How would you describe the work culture – what is encouraged, what’s discouraged?” ❓ “Does the team have any norms or rituals that are important?” ❓ “What kinds of behaviors or values are celebrated by leadership? Do they ever discourage any particular behaviors?" ❓ “How do people typically take time in regards to PTO, sick, or personal situations?” Do the necessary vetting on your end to make sure you’re going in eyes wide open!

12 High-Impact Questions That Ignite Buyer Urgency. I was coaching a salesperson the other day who kept losing deals late in the sales cycle. Something kept slipping through the cracks. I asked, “Walk me through your discovery questions.” He rattled off the usual, generic, yet important, qualifying questions: ➤ How do you typically budget for this kind of project? ➤ What timeline are you working with? ➤ What solution are you using now? ➤ What keeps you up at night? I then asked if he ever used this question. “What happens if nothing changes over the next 6 to 12 months?” He said, “I’ve never asked that.” The next call, he did. The prospect paused. Took a breath. Then said, “Honestly? We’ll fall even further behind. I’m already under pressure to fix this or we risk losing the account.” That deal closed a week later because he asked questions that made it personal, emotional, and uncovered the cost of inaction. That’s why urgency can’t be told. It has to be discovered by the prospect through implication questions. You don’t need better scripts to create a better outcome. You need better questions. #sales #selling #presentations #salescoaching

This one question helped me get $15K more during salary negotiations. “What are the key challenges of this role?” Most people ask questions like: ❌ “What do you like best about working here?” ❌ “What’s the company culture like?” Those are fine… but they’re not strategic. When I ask about key challenges, I’m not just being curious. I’m hunting for an opening— --> A moment where I can say, “Here’s how I’ve solved that exact problem before. --> A chance to connect my skills directly to their pain points. And here’s where it pays off: When we got to the negotiation stage, I reminded the interviewer of that moment. "You mentioned [X challenge], and you said my experience doing [Y] was exactly what you needed." That alignment? It helped me land $15K more in base salary. So yeah, ask smart questions. Not to check a box, but to position yourself as the only person who can solve their problems.

This clarifying question has CONSISTENTLY gotten me more valuable information from prospects. It’s so basic I wish I’d started using it sooner… Whenever someone tells me something they want or need that is remotely up for interpretation, I ask: “What does *that* mean/look like, to you?” Examples: CEO: “My number one problem is discoverability.” Me: “What does discoverability mean, to you?” CEO: “I want more people to know about us. I want my company to be the first thing people think of when they’re evaluating our category.” VP of Sales: “We need more pipeline coverage.” Me: “What does more pipeline coverage look like, to you?” VP: “We’re at a 2.5X multiple right now. We need to be at 5X to hit our revenue targets.” This question is effectively “mirroring” my prospect, but (to me) feels less manipulative. It also helps me: 1) further quantify the business impact, and 2) build more trust through understanding Try it on your next disco call. #sales #discovery #salestips