Overcoming Objections

After coaching the #1 sales reps at companies like Salesforce, HubSpot, and dozens of Fortune 500s…. I've noticed a pattern. Elite performers don't get better at handling objections, → They get better at preventing them. Here's how they handle the 7 most common deal killers. 1. "Your price is too high" This objection means one thing: perceived value < price. Average reps respond by desperately defending their pricing: "Well, we're more expensive because of X, Y, Z..." (creating more resistance). Elite reps prevent this by running a discovery process that quantifies: → True cost of inaction (what happens if they do nothing?) →Opportunity cost (what are they missing out on?) →Potential ROI (10X value compared to price) 2. "I need to think about it" This classic stall tells you nothing about what they're actually considering. Elite reps respond: "I completely understand. To make sure I'm giving you what you need, can you share specifically what you're thinking about?" Then they shut up and listen. The prospect's answer reveals the actual objection that needs addressing. 3. "I need to run this by my CEO first" If this surprises you, you missed uncovering all stakeholders early in your process. Elite reps ask: "If it was only up to you, would you move forward?" If they hesitate, they're not truly sold. If they are convinced, coach them for the conversation: "When you talk to the CEO, what concerns might they have? How will you address those concerns?" This transforms your champion into a prepared advocate who can sell internally for you. 4. "We don't have budget" When prospects truly see 10X value, they find the money. Personal example: When my parents found out I needed surgery for a broken finger as a teenager, they had zero budget for it. But the cost of inaction (permanent damage to my hand) was so high they found thousands of dollars. If your prospect truly believes your solution solves a critical problem, budget objections disappear. 5. "This isn't a priority right now" Average reps can only sell to prospects with active pain. Elite reps transform latent pain into active pain by helping prospects see the true consequences of inaction. If you're consistently hearing "not a priority," you're failing to elevate pain levels in your discovery process. 6. "We're considering Competitor X" Never trash talk competitors. Elite reps ask: "Based on what you've seen so far between us and them, which way are you leaning?" Their answer will reveal exactly what matters most to them and where you need to differentiate. 7. "I need to speak with your customers first" This is an uncertainty objection. Find out what they're really uncertain about: "I appreciate that. When you speak with our customers, what specifically do you want to find out?" Their answer reveals what you missed building confidence around earlier. When you thoroughly uncover pain, quantify impact, and build value upfront, objections rarely surface.

Most people fight objections. I turn them into leverage. Here’s what I’ve learned: Objections 𝘧𝘦𝘦𝘭 like attacks. You feel the heat rise. You want to push back. But when you fight them, you lose control. I learned this the hard way on the streets of Glasgow. Where words were weapons, and reading people was survival. Now, I train professionals how to keep their cool, even when the boardroom feels like a pressure cooker. I’ve trained thousands of people in high-pressure roles. Here’s what works: 𝟭. 𝗦𝗲𝗽𝗮𝗿𝗮𝘁𝗲 𝘁𝗵𝗲 𝗽𝗲𝗿𝘀𝗼𝗻 𝗳𝗿𝗼𝗺 𝘁𝗵𝗲 𝗽𝗿𝗼𝗯𝗹𝗲𝗺. → Don’t take it personally → See the human behind the heat. Most people aren’t trying to provoke, they’re trying to protect something. 𝟮. 𝗙𝗼𝗰𝘂𝘀 𝗼𝗻 𝗶𝗻𝘁𝗲𝗿𝗲𝘀𝘁𝘀, 𝗻𝗼𝘁 𝗽𝗼𝘀𝗶𝘁𝗶𝗼𝗻𝘀. → Ask: “𝘞𝘩𝘢𝘵’𝘴 𝘣𝘦𝘩𝘪𝘯𝘥 𝘵𝘩𝘪𝘴 𝘱𝘶𝘴𝘩𝘣𝘢𝘤𝘬?” → Look for the 𝘸𝘩𝘺, not just the 𝘸𝘩𝘢𝘵 → Get curious, not defensive 𝟯. 𝗥𝗲𝗱𝗶𝗿𝗲𝗰𝘁 𝘁𝗼 𝗼𝗽𝘁𝗶𝗼𝗻𝘀 𝗳𝗼𝗿 𝗺𝘂𝘁𝘂𝗮𝗹 𝗴𝗮𝗶𝗻. → Ask: “𝘞𝘩𝘢𝘵 𝘸𝘰𝘶𝘭𝘥 𝘢 𝘨𝘰𝘰𝘥 𝘰𝘶𝘵𝘤𝘰𝘮𝘦 𝘭𝘰𝘰𝘬 𝘭𝘪𝘬𝘦 𝘧𝘰𝘳 𝘣𝘰𝘵𝘩 𝘰𝘧 𝘶𝘴?” → Explore. Don’t defend. Create space for joint problem-solving. 𝟰. 𝗥𝗲-𝗴𝗿𝗼𝘂𝗻𝗱 𝗶𝗻 𝘀𝗵𝗮𝗿𝗲𝗱 𝘀𝘁𝗮𝗻𝗱𝗮𝗿𝗱𝘀. → When emotions spike, reach for facts. → Use criteria both sides recognise. Timing, risk, fairness, precedent. → Neutral ground restores calm. 𝗔𝗻𝗱 𝗶𝗳 𝘁𝗵𝗲𝗿𝗲’𝘀 𝗼𝗻𝗲 𝘁𝗵𝗶𝗻𝗴 𝘁𝗼 𝗺𝗮𝘀𝘁𝗲𝗿 — 𝗶𝘁’𝘀 𝗹𝗮𝗻𝗴𝘂𝗮𝗴𝗲 𝘂𝗻𝗱𝗲𝗿 𝗽𝗿𝗲𝘀𝘀𝘂𝗿𝗲. Use lines like: → “𝘏𝘦𝘭𝘱 𝘮𝘦 𝘶𝘯𝘥𝘦𝘳𝘴𝘵𝘢𝘯𝘥 𝘸𝘩𝘢𝘵 𝘮𝘢𝘵𝘵𝘦𝘳𝘴 𝘮𝘰𝘴𝘵 𝘵𝘰 𝘺𝘰𝘶 𝘩𝘦𝘳𝘦.” → “𝘓𝘦𝘵’𝘴 𝘭𝘰𝘰𝘬 𝘢𝘵 𝘸𝘩𝘢𝘵 𝘸𝘦 𝘣𝘰𝘵𝘩 𝘯𝘦𝘦𝘥 𝘵𝘰 𝘮𝘰𝘷𝘦 𝘧𝘰𝘳𝘸𝘢𝘳𝘥.” Because every time you do this, objections lose their sting. They stop being threats and start becoming tools. This works in contract disputes, boardroom deals, cross-functional stand-offs, anywhere pressure runs high. Objections become clarity. Clarity becomes leverage. And you stay in control. Objections aren’t the enemy. They’re a map if you know how to read them.

I bombed my first investor meeting because I couldn't answer a basic objection. That experience led me to build a framework that helped me close my $780K pre-seed round 👇🏾 Fundraising is (basically) just sales. In sales, customers give you reasons they can't buy; in fundraising, investors give you reasons they might not invest. Our objections at Chezie fell into two categories. Here's exactly how we addressed each one. MARKET & COMPETITIVE RISK The objection: "The market feels too small." What this really means: the investor can't do the math from your ICP to $100M in revenue. They're not saying the market doesn't exist, they’re just saying it’s probably not big enough to build a big business. How we handled it: I built the math directly into our Market Opportunity slide. 57,000 companies globally have ERGs. Our pricing at maturity puts average contract value around $50K. 2,000 customers at $50K each gets you to $100M. Once the investor could run that math themselves, the objection mostly went away (plus I got brownie points for doing bottoms-up market sizing 💅🏾). TEAM & EXECUTION SIGNAL The objection: "We're not sure the team can pull this off." What this really means: the investor isn’t confident that the team has either the right domain expertise OR has the personnel to actually build the product. How we handled it: We showed our hiring plan, named CTO candidates we were already in conversations with, and let our traction speak louder than our org chart. At that point we had $120K ARR across seven enterprise customers. That signal said more about our judgment than any answer about a CTO search could. THE FRAMEWORK Every objection an investor throws at you is just uncertainty on whether or not you can execute. There’s a two-step process on how to handle them. 1. Acknowledge it directly. Don't deflect or get defensive; if the concern is legitimate, say so.  2. Show action. Either point to something you've already done that addresses the concern, or explain specifically what you'll do once you close the round. - - - I put together a cheat sheet covering the 10 most common VC objections with plain-English translations and example responses. Click "Visit my website" above to grab it for free. And if there's an objection you keep hearing that's NOT on the list, drop it below. Happy to help you work through it 🤝🏾

There’s a big difference between handling objections and understanding them. Handling sounds like this: Prospect: “The other agent will sell my home for 2%, not 3% like you.” Agent: “I understand how you feel. Many people felt the same way. But what they found was that they ended up leaving money on the table because the lower-fee agents didn’t market the property as aggressively or negotiate as strongly.” When you’re convincing, you’re losing. Of course you’re going to say that. You’re biased. You have commission breath. Convincing comes across as dismissive. Understanding sounds like this: “You want to make sure you’re getting a fair deal and aren’t overpaying on commissions.” That hits differently, doesn’t it? It names what the person actually cares about. Not just the words, but the feeling behind them. When people feel understood, they relax. They stop bracing for the rebuttal. They open up because they feel like you’re with them, not against them. That’s why understanding is better. Because objections aren’t walls to climb. They’re windows into what someone values. Once people feel understood, then you can poke the bear. Ask a question that illuminates a potential knowledge gap. Examples: “With a reduced commission, the pool of agents eager to bring buyers through your door can shrink. How are you thinking about handling that trade-off?” “Part of the commission goes toward attracting buyer’s agents to your property. If that piece is reduced, it can impact exposure. How are you making sure your home still gets full visibility?” “Sometimes that 1% savings looks great on paper, but if it means your home doesn’t get as much attention or as many strong offers, it could end up costing you much more than you save. How are you weighing that trade-off?” No pushing. No pressing. No persuading. Just illuminating a knowledge gap without leading people to a desired answer. Because the goal isn’t to persuade. it’s to let people persuade themselves. Buyers have the answers. Sellers have the questions.

A friend has been helping me with one of the trickiest parts of running a business... when a prospect seems interested, then starts backpedaling. For the longest time, I assumed objections meant I’d said something dumb or successfully sold them on doing absolutely nothing. If a prospect pushed back on price, asked for more time, or questioned whether my approach would work for them — I figured all hope was lost. So I’d either: - Try to “explain harder” (never helps) - Take their hesitation as a polite no - Wrap up the call before things got awkward Then my friend dropped a little bomb on me: "Silence is the death knell, Jay. Objections mean they’re still considering it." That completely flipped my perspective. Instead of panicking from objections, I used them as a signal to dig deeper. Here are the 3 objections I hear most, and how I’ve been managing them: 1. “I'm too busy right now.” - Power question: “Totally get it. What's taking precedence over this?” - Why it works: It forces them to name what’s actually taking up their time — and whether it’s truly more important than solving the problem you've spent the entire conversation digging into. Aren't they delaying the inevitable? 2. “I need to think about it.” - Power question: “Totally understandable. What’s holding you back from deciding today?” - Why it works: Instead of accepting a vague delay, it prompts them to voice real concerns—so we can actually address them. 3. “I’m not sure this will work for me.” - Power question: “What specifically are you unsure of?” - Why it works: It gets them to define their own success criteria, so I can connect the dots between what they need and what I offer. Sure, I definitely win more deals these days. But I also feel a lot more comfortable when objections come up. No more panic and cold sweats. Now I treat objections as a natural part of the conversation. What’s an objection you hear during client discovery calls? How do you handle it?

Some demo calls never lead to the next step. You walk out thinking it went well. The prospect asked a bunch of questions. You answered them all. But then…nothing. No follow-up. No urgency. No deal momentum. This happens more often than most sales teams care to admit. And in my experience, the root cause is almost always the same: poor objection handling. Now, I don’t mean price objections or late-stage pushback. I’m talking about the way we handle the everyday questions prospects ask during a demo. The subtle ones. The ones that sound simple, like: “Do you have modeling capabilities?” Most reps hear that and immediately jump into features. They pull up the dashboard, walk through how it works, and try to impress with detail. But they’re answering the wrong question. Because what the prospect is asking might be: “My CFO is frustrated with the forecasting data we provide.” Or, “I need to justify this purchase internally, and I’m not confident in the reporting.” When you answer too quickly, without probing, you stay on the surface. And surface-level answers don’t close deals. Here’s what I would recommend instead: Step one: Answer the question. Yes, provide value. Respect the ask. Nobody likes being met with a question when they’re expecting an answer. Acknowledge their point and give a concise, confident response. Step two: Get to the real reason. Right after answering, ask something like, “Would you mind sharing what’s prompting that question? Is there a specific situation you’re trying to solve?” This shift in approach changes everything. When you give them the space to reflect, most prospects will open up. They’ll explain the internal pressure, the stakeholder needs, and the actual pain behind the question. That’s where the real selling begins. That’s where you stop being a feature provider and become a problem solver. And that’s why I believe objection handling isn’t something that's simple question and answer. It’s a skill that determines whether you truly understand and can accommodate your customers real-life pains... or are you just going through the motions.

The wrong way to train objection handling: "When they say this, you say that." "Use this framework to overcome price objections." "Here's how to handle 'I need to think about it.'" But what if objections are a symptom, not the problem? What if objections mean you're having the wrong conversation? I've learned that objections usually arise from two places: → Lack of understanding → Lack of trust If prospects truly understand their problem and trust you can solve it, objections disappear. Instead of teaching objection handling, I teach objection prevention. For understanding: → Ask deeper questions about their current situation → Help them quantify the cost of their problems → Paint a clear picture of what success looks like → Confirm understanding before moving forward For trust: → Share relevant case studies and examples → Be transparent about what you can and can't do → Address concerns before they become objections → Listen more than you talk When I get to the investment conversation, the prospect already knows: → They have a problem worth solving → The cost of not solving it is significant → I've helped others in similar situations → Working with me is their best option The "objection" conversation becomes: "When can we get started?" Instead of: "This is too expensive." The timeline conversation becomes: "How quickly can we implement this?" Instead of: "I need to think about it." Great salespeople prevent objections from happening in the first place.

Stop “Overcoming” Objections. Start Advancing Readiness. We’re often asked, “How do you overcome objections?” But here’s the truth: If you’re trying to overcome objections, you’ve already missed a step. Objections aren’t walls. They’re signals. They tell you where the family actually is—not where you want them to be. “We’re not ready yet.” “We need to think about it.” “It’s just not the right time.” These aren’t barriers. They’re indicators of readiness—and when you listen closely, you realize they’re not pushing you away. They’re inviting you in. The best salespeople aren’t objection handlers. They’re readiness guides. They slow down, go deeper, and build the kind of trust that clears the emotional clutter. Instead of pushing forward, they pause and ask: • What part of the decision feels most unclear right now? • What’s holding your heart back even if your head says yes? • What would make this feel like the right time—for you? The goal isn’t to close the family. The goal is to advance them—emotionally, practically, relationally. Progress beats pressure. Discovery over defense. Guidance over persuasion. So the next time someone says “We’re not ready,” Don’t “handle” it. Understand it. And walk with them through it. That’s how we move people forward—not with tactics, but with trust. #SeniorLivingSales #PersonCenteredSelling #EmotionalReadiness #ModernSales #TrustTheProcess #SalesLeadership #SherpaSelling #MoveInWithMeaning

Founder-Led Sales Bootcamp #6: Objection handling like a pro Objections aren’t personal attacks. They’re symptoms pointing to missing information or hidden risk. When you treat them with curiosity, you turn friction into trust and keep the deal alive. What great objection handling looks like: ☑️ Calm first reaction A pause and a nod show you aren’t rattled. Buyers watch your face before they hear your words. ☑️ Root-cause questions “Walk me through why that’s a concern.” The goal is to unpack the real issue, not swat the surface comment. ☑️ Shared diagnosis You restate the objection in their language and ask if you got it right. Agreement here proves you’re listening. ☑️ Evidence or story Facts, metrics, or a quick customer example replace opinion with proof. Stories stick better. ☑️ Check the pulse “Does that address it, or is there more we should explore?” This closes the loop and surfaces any lingering doubts. ☑️ Document for the team Log new objections in your CRM so marketing, product, and future reps learn from that objection and how it was handled Action plan: 💡Write your top five objections and crisp answers on one page. Review before every call. 💡 Use “tell me more” once per objection to dig past the first layer. 💡Collect one new proof point this month - a measurable win or testimonial to strengthen your answers. 💡End each call with a loop-close question: “Anything else we should cover before we end?” 💡Share fresh objections in Slack so the whole team levels up together. Follow me if you want the full Founder-Led Sales Bootcamp Series delivered to your feed daily