Common Sales Mistakes

The worst cold email I received this month started with: "I'd love 15 minutes to introduce myself and show you what we do." Nobody cares about your introduction. Nobody has time for a generic pitch. After analyzing thousands of outreach sequences, I've discovered a psychological shift that's doubling meeting rates for innovative sellers. The best performers aren't focusing on their product. They're focusing on buyer psychology. Here's what's actually working in 2025: 1. The Curiosity Gap When you write "Other VPs in your space are seeing X trend" instead of "We help companies do Y," you create an information gap buyers want to fill. Our brains hate incomplete information. Use this. 2. Relevance Triggers Generic outreach gets generic results. When you mention a buyer's LinkedIn post or recent initiative, you're bypassing their "sales defense system." Relevance is required. 3. Specificity Signals "This could help you grow revenue" gets ignored. "Companies like yours are seeing 22% reduction in CAC" gets attention. Specific numbers signal you actually know what you're talking about. 4. Miniature Commitments Don't ask for 30 minutes. Ask for feedback on one specific insight. Small asks lead to bigger conversations. 5. Value-First Mindset Position yourself as a resource, not a vendor. Share insights without expecting anything in return. Reciprocity is powerful. The old playbook of "smile and dial" is dead. Meeting quotas in 2025 requires understanding human psychology. What psychological principle has worked best in your outreach?

If you're a CMO struggling to hit pipeline numbers, it's probably not your strategy, team, or tactics. It's the broken system. For over a decade, B2B had a playbook that worked. Budgets were predictable, buyers were reachable, and marketing automation (mostly) tracked the journey. We built careers on nurtures, MQL handoffs, and attribution models. Then that foundation cracked.  Here's the data to prove it. THE BUDGET SQUEEZE Marketing budgets dropped from 11% of revenue pre-pandemic to 7.7% today (Gartner). Meanwhile, WordStream reports Google Ads CPL hit $70.11 in 2025, up 31% from $53.52 two years ago. B2B tech companies now routinely pay $200+ per lead. We're doing more with less, while the price of every click, impression, and conversion climbs relentlessly. THE INVISIBLE BUYER 6sense shows 70% of the buyer journey now happens anonymously, outside systems you can track. Gartner found 75% of B2B buyers actively avoid sales contact until they're ready, and when you do connect, Digital Commerce 360 reports 1/3 go silent after initial contact. Buying groups expanded to 6-10 people on average, sometimes up to 16, according to Gartner. Most of those people will never appear in your CRM. They're researching and forming opinions in the dark — and traditional marketing automation can't reach them there. THE BROKEN INFRASTRUCTURE Cookie deprecation and privacy regulations blocked the known, tracked visitors underpinning marketing automation, breaking traditional scoring methods and making the journey even harder to track. And meanwhile, the legacy MAP vendors were mostly stagnant, raising prices without adding new functionality. THE TRAGEDY OF THE COMMONS Backlinko reports content exploded to 6M blog posts daily.  Algorithm InSights 2025 found LinkedIn organic reach collapsed to 1-2% in 2025 — half of prior levels.. Email isn't faring better. Infraforge says cold email open rates dropped from 36% to 27.7% in one year. Reply rates fell from 7% to 5.1%, meaning 19 out of 20 cold emails are now ignored. It's a tragedy of the commons. We abused every tactic until buyers tuned out and opt out. THE MEASUREMENT BREAKDOWN Meanwhile, Televerde and Anteriad report many companies haven't updated MQL definitions in over five years. We're optimizing for metrics sales doesn't value, while what really drives revenue impact (strong brand awareness and preference) stays invisible. THE BOTTOM LINE Today's B2B marketers operate with smaller budgets against higher costs, trying to influence larger anonymous buying groups through noisier channels with weaker reach, measured by outdated metrics — all while buyers demand authenticity and avoid our outreach. I'd argue your pipeline misses are probably not an execution failure. The system fundamentally changed and the old playbook broke. What part of this broken system is hitting you hardest: the budget pressure, the invisible buyer, or the broken infrastructure? And do you have other stats on this?

In my 20 years of Sales and Marketing Professional Career, I learnt that “Sales isn’t about pressure — it’s about process”. 🔄 In the rush to hit targets 🎯, it’s easy to fall into the trap of pushing harder and moving faster 🏃♂️💨. But just like trying to cook a meal on high flame 🔥 can burn the outside and leave the inside raw, rushing the sales process often backfires — leading to weak execution ❌, broken trust 🤝💔, and lost deals 📉. Top-performing sales professionals don’t rely on pressure. They rely on patience 🧘, consistency 📆, and a clear strategy 🧭. Because real, long-term success in sales doesn’t come from shortcuts 🚫 — it comes from doing the right things ✅, the right way 🛠️, over time ⏳.

The toxic negotiation myth that nearly destroyed my career.   28 years ago, I was that young "trainee" sitting across from a sales director who'd scream:   "DO NOT BLINK FIRST! STAND YOUR GROUND AND TAKE IT TO THE BRINK!"   Back then, negotiations were a war.    "Coffee is for closers" wasn't just a movie line - it was my brutal reality.   But here's what most negotiators get dead wrong:    Winning isn't about crushing the other side.  It's about creating mutual value.   The real negotiation paradox:   - Aggressive tactics destroy long-term opportunities - Fear-based strategies guarantee failure - Zero-sum mindsets kill relationships   Most people approach negotiations with three deadly misconceptions:   1. Negotiation is a competition 2. Someone must lose for you to win 3. Pressure tactics guarantee success   The truth? These beliefs are negotiation poison.   Collaborative negotiation isn't soft. It's strategic.    It requires:   - Deep understanding of underlying interests - Long-term relationship building - Creative problem-solving - Emotional intelligence   Your BATNA (Best Alternative To a Negotiated Agreement) isn't just a backup plan. It's your negotiation north star.   Who's ready to transform their approach from combative to collaborative?   Drop a 👇 if you've ever felt trapped in the old "win-at-all-costs" mindset.   --------------------------------- Hi, I’m Scott Harrison and I help executive and leaders master negotiation & communication in high-pressure, high-stakes situations.  - ICF Coach and EQ-i Practitioner - 24 yrs | 19 countries | 150+ clients   - Negotiation | Conflict resolution | Closing deals 📩 DM me or book a discovery call (link in the Featured section)

Here's an avoidable mistake I made with inbound leads when I was an AE for The Challenger Sale. I'd get an inbound lead. They'd tell me they were looking at us + 2 of our competitors. I'd ask discovery Qs to understand why they were evaluating solutions and to understand the need. Then, I'd explain our differentiators and why those made us a better option for their needs. Here's where I fell down. I never slowed down to see if there were other priorities and categories of spend I was unknowingly competing against. As a result, I lost a lot of inbound deals to "We've decided to put a sales training investment on hold. Instead, we're going to invest in sales tech / do a re-org, etc.". After losing enough of them, I learned to add a step. Directly ask buyers 2 Qs: 1) "How did the leadership team arrive on X as the right solution to this problem?" - X = the category of spend. In my case, sales training. Listen for "I" vs "we" language. If I'm hearing "I" language - it might be a signal that they don't yet have buying group alignment on this problem or category of spend. 2) "What other investments/priorities were or are the the business considering?" - Language choice is important here. It's not "Were there other...". This is where we lean into assumptive language. Buying is not linear. Buying groups change their mind, back up, and hit restart. Assume this was not the only solution category they were/are considering. If I hear "none!" - that's a red flag. Most importantly, make it easy for them to be honest with us. Don't rush to convince them to prioritize our category of spend, before we deeply understand the others. "Objection handling" erodes buyer trust here.

Your agenda doesn’t matter more than the buyer’s confusion. That’s a lesson technical sellers have to learn quickly. I’ve watched sellers keep moving through a presentation when the buyer had already checked out. Not because they didn’t care. Because they had prepared. They had a flow.  They had points to cover.  They had slides to get through.  They had technical details they believed mattered. But the buyer’s face had already changed. The energy shifted. The questions got shorter. The buyer stopped leaning in. And instead of pausing, the seller kept going. That’s where deals get lost quietly. Not always because the solution is wrong. But because the seller missed the signal. When you detect doubt, stop. When you see confusion, simplify. When you feel resistance, ask. Don’t push through it. Don’t explain over it. Don’t pretend it’s not there. Name it. You can say: “I want to pause here. I can tell this may not be landing the way I intended.” Or: “Before I go further, what questions are coming up for you?” Or: “I may have gone too technical. Let me connect this back to the business issue you raised.” That’s not weakness. That’s skill. The best technical sellers don’t just know the product. They know how to read the room while they’re in the room. Because buyers rarely tell you the moment they get confused. They show you. And if you miss it, your presentation may keep going while the deal is already slipping away. What buyer signal do you think sellers miss most often? 

Sales is won or lost in discovery. Here are the Top 5 reasons why discovery meetings often fail (and how to fix them) 1. Lack of preparation: If you don't do your research on the prospect and their business before the meeting, you won't be able to ask relevant questions or provide valuable insights. This can make the prospect feel like you don't understand their needs and can damage the relationship. 2. Poor communication: If you don't set clear goals for the meeting or communicate them effectively to the prospect upfront, you may end up talking past each other or not covering important topics. Frame the meeting before starting so they know the focus is on discovery, rather than showing them your product or service. 3. Asking the wrong questions: If you ask closed-ended questions that don't encourage the prospect to share more information, you may not get a clear understanding of their needs or challenges. 4. Not listening actively: If you're not actively listening to the prospect during the meeting, you may miss important details or opportunities to build rapport. 5. Focusing too much on selling: If you're too focused on selling your product or service during the meeting, you may come across as pushy or not interested in the prospect's needs. This can damage the relationship and make it harder to close the deal later on. If you want help building stronger relationships with your prospects, avoid these common pitfalls and set yourself up for success.

One pattern keeps repeating in Enterprise Sales right now. I hear it from every Sales leader, CRO and Sales Rep I speak to. Some are calling it 'Deal Slippage' Others "Elongated Sales Cycles' or simple 'Do Nothing' outcomes. But the premise is the same, deals getting stuck mid-pipe. These deals are a killer for morale, for forecast accuracy and of course for quota attainment. You know the deals I'm talking about...The client is strongly engaged in the early stages, there's a genuine problem to be solved, good traction with their team and then something happens. The momentum disappears, the can quietly gets kicked a bit further down the road. These Zombie deals never quiet die do they?...Instead they just lurch from quarter to quarter, with just enough life to keep them in CRM. If you're dealing with this issue, either personally or across your sales teams, here are 10 Client Red Flags we're consistently seeing in our Client Loss Reviews at the moment. Avoid these 🚩 and you just might put the breaks on your deal slippage problem... 🚩No Genuine Exec Sponsor: If no-one internally has stepped up to defend your deal in the boardroom, or better yet sell the value on your behalf, that's a big red flag. 🚩Lack of Resourcing Depth – Delivery Risk is a huge concern to clients at the moment. If your team feels light or lacking in real-world experience, its a big red flag. 🚩Transition Cost Ambiguity – Hidden, deferred or unclear costs over the life of a project are huge red flags for procurement, who will usually assume the worst and penalise you accordingly. 🚩Top Heavy Team – When sales reps or senior leaders do all the talking, but the delivery team stays quiet, buyers immediately lose faith. 🚩Generic Industry Stories – If client case studies and references don’t sound exactly like their lived experiences, it's a big red flag that you haven't done this before. 🚩Q&A Avoidance – Dodging the hard questions or glossing over the risks, makes buyers assume you can’t answer their critical questions or worse, you don't want to. 🚩Rigid Pricing Models – One number, no options, no flexibility, means buyers feel boxed in and misunderstood, suggesting heighted risk, not certainty. 🚩Governance Gaps – “We’ll work it out post-award” is code for chaos, poor governance and delivery risk. Avoid at all costs! 🚩Slow Responsiveness – Slow response times, suggest slow delivery times, a lack of urgency and poor internal process. Clients think "If this is what you're like before we sign, how slow will you be after we buy" A huge red flag for enterprise clients. 🚩Risk Blind Spots – If you can’t name, explain, manage and mitigate their risks, clients will assume you haven’t seen them or worse, have intentionally ignored them. I could easily share another 20 client 🚩 we often uncover on a daily basis. Instead I'd love to hear one red flag you always look out for, as a sign a deal maybe straying off course?

Salespeople: Your business case will make or break your Q4 deals. Yet most business cases have these 9 mistakes. Here's how to avoid them (and what to do instead): 1. Sending case studies. Nothing wrong with case studies. But they aren't a business case. A lot of sellers think they are. Buyers will say: "We need a business case." Many sellers respond with: "I've got a few case studies to send!" Wrong move. A case study is not a business case. It supports a business case. One's the case. The other is proof of the case. Different things. 2. Using "industry research." This is worse than the first mistake. Many companies have Forrester Reports. Those reports have ROI numbers. Many sellers use that as a business case. Wrong move. These can support a business case. But they aren't a business case. A business case is specific to a buyer. A Forrester Report isn't. 3. Leading with ROI. Great business cases ignore the solution and ROI. At least, for the first half. They define: - the problem - financial impact - root causes Then (and only then) do they transition to the solution. Problem first, ROI second. Do this well? The rest of the business case is 10x easier. 4. Skimming past the root cause. If you don't define the root cause of the problem? You have no bridge to a solution. Root causes define required capabilities. Required capabilities define the solution. Don't skip this. If you do? You just created an opportunity for someone else to win the business. That's called "unpaid consulting." 5. Being the 'author.' Your champion should be the author. Not you. A great business case reads like an internal document. Not a seller-generated marketing PDF. Feel free to be the ghost-writer. But make your buyer the author. 6. Only getting one champion's perspective. Most business cases are written through the lens of one person. That person can't see the full picture. They see a tree. They don't see the forrest. If you get multiple perspectives? Now you have the 'forrest.' That's much more likely to resonate with finance. 7. Projecting only one ROI scenario. Executives think in terms of ranges and scenarios. Executives DON'T think in terms of one possibility. - worst case - base case - best case Project all three. 8. Making it seem too easy. If you intentionally overestimate how easy this will be? You kill your credibility. Be real about it. Spell out what's required to deliver the return you're projecting. 9. Making your business case too long. Aim for 1-2 pages. Most sellers create 15-slide decks. Long business cases show sloppy thinking. Short business cases show clear thinking. As the saying goes: "Sorry I'm writing you such a long letter. I didn't have time to write a short one." Focus on the vital few. Cut the trivial many.

Last month, I received FOUR DocuSigns from a popular vendor—without even understanding their product, let alone approving a business case. It blew my mind. Don’t get me wrong… I love grit and bold moves. But some moves just kill your deals. Here are 7 closing moves that scare buyers (and what to do instead): 1. Premature DocuSign In many cases, AEs don’t meet the Economic Buyer (EB) but influence them through champions. EBs are often not involved in the details and will only spend 15min discussing the project, asking questions like “Do we really need this?” and “Why can X vendor deliver?”. This is a hesitant distant buyer that you only get *one shot* to win. Don’t kill it. Before a DocuSign, confirm they’re ready to sign. 2. Premature Order Form Nobody likes an assumption. If the buying stage is still about ROI and business case, I don’t need your full T&Cs yet. Instead, send a concise proposal or (better) a Deal Room link with a dedicated proposal tab covering the executive summary, business impact, terms, onboarding timeline, and relevant proof—so I see WHY I should buy, not read terms. 3. Aggressive Exploding Offer Deadline discounts are a risky game that should only be played with tact and empathy. If there is readiness to buy, it is fair that in a give-and-get negotiation a vendor asks for a timeline commitment. But there’s a way to do it tactfully, and there’s a way to kill a deal—e.g. ”John, I haven’t heard back from you. As a reminder, on X this offer will expire”. Threats don’t make buyers want to buy. 4. Bypassing Champions (Irresponsibly) I’m all in for multithreading. But imagine this; You’re a CxO that’s unaware of any project going on. Your VP is speaking with a vendor, but waiting for the right moment to bring it up since there’s a sensitive ask. You then get approached by a seller, and it hurts the ask of the VP champion. What to do instead? I have just one rule of thumb—Tact. Every situation is different. Use your EQ and IQ, not a hard multithreading rule. 5. Nonstop “Are We Good?” Follow-Ups Yes, time kills deals. You should text, call, and keep the momentum. That being said if you’re bombarding buyers daily just to ask if they’ll move forward, know that with each ping, their frustration grows. While follow-up is key, constant nagging without adding value is a recipe for ghosting. Share onboarding overview, offer a tentative kickoff, etc. Every buying stage can be supported. 6. The “Price-Shame” Maneuver Tying closing follow-ups to business pain is great. But there’s a fine line between a helpful “We wanted to hit X goal by Q2, is that still the plan?” and a pushy “Don’t you care about solving X?”. One drives partnership; the other feels like a guilt trip. —— A ‘Move’ is not a substitute for doing the work. I won’t magically buy from a DocuSign. Deals close when buyers actually want to sign. If done wrong, moves will destroy months of trust. The difference is your focus: Inward or outward. Choose wisely.