Common Sales Mistakes

Your sales team isn’t lazy. They’re just lost. As a leader, you’ve tried everything. Bigger targets. More calls. Extra pressure. But the numbers aren’t moving. Here’s the real problem: Many times , team doesn’t know what to do next. Too many tools. Too many steps. Not enough clear direction. So they guess. They skip follow-ups. They chase easy leads. They avoid the hard stuff. Not because they don’t care —Because the system is confusing. The fix? Make things simple. → Give them one clear way to work → Show them small wins every day → Train them in 5 minutes, not 50 → Help them focus on what matters → Most importantly, free them to do what they’re best at: selling This isn’t about working harder. It’s about making their job easier to do right. People want to succeed. They just need the path to be clear. Don’t push your team harder. Clear the path → and watch your team do their best work. That’s how "Sales" do their best work.

I’ve managed 100+ AEs and run probably 100,000 deal reviews. If I got $1 every time we crowned our Main Contact our ‘Champion’, I could've bought a Tesla Model X by now (the meme Will Aitken made for Aligned nails it👇). Here are the 8 biggest mistakes AEs make when selling with champions—and the fix: 1. Main Contact ≠ Champion I admit, it feels good having someone update you on every detail of a deal and doesn’t give you a hard time. But that doesn’t necessarily make them a champion. Can they truly influence execs? Are they willing to fight politics and budget? Motivation is great, knowledge is great—but not enough to close a deal. 2. Settling for One Champion While having a real champion is great, you shouldn't stop there. Latest stats show deals involve 11 stakeholders—That’s a lot of opinions… When two more people make the case together, decision risk drops, and they’re far more likely to get everyone on board. Also, champions can leave or lose political battles—If you can, don't settle on one. 3. Thinking Execs Will Care Executives are busy, stay high-level, and rarely have time for your 25-slide pitch. They need to hear a concise, compelling case—fast. If you don’t help your champion distill it down to a crisp 1-pager or bullet-proof 10-minute deck, the exec will pass or default to “Let’s hold off.” 4. Overestimating Champion Motivation More often than not, reps send champions 5 decks, 4 white papers, and 7 case studies, overestimating their motivation. And if they do have that level of time, are they even real champions? Keep resources minimal, targeted, and easy to share internally. Less confusion = more clarity = faster decisions. 5. ‘Blue Bird’ Champion? Not a Strategy Letting your champion 'work their magic' while you watch from the sidelines is wishful thinking. Co-sell with them: schedule joint calls, get their feedback on internal pushback, and arm them with tight value narratives. 6. Zero Internal Coaching Building on #5, your champion will present your solution in front of their team—have you coached them on your solution’s top 3 outcomes? Do they know how to handle “We have no budget” or “We tried a similar tool before”? Don’t let them wing it. 7. No Mutual Plan, Just Hope Feeling good about your champion being strong enough to lead the way? That’s how deals die. Yes, they know their internal politics, but you know how to buy in your category. Combine both skills. A mutual plan > following hope. 8. ‘Decision Maker’ Myth It’s 2025, and committees rule. There’s rarely a single all-powerful Decision-Maker. Identify both ATL (exec-level) and BTL (manager-level) stakeholders. Use your champion to bring them into the conversation early and build consensus from the ground up. First on the problem, then on the solution. —— Buying decisions happen when you're not in the room. You either influence them by building Champions right, or dance around in circles with a Main Contact. Choose which salesperson you want to be.

I just deleted 147 cold emails without reading them. Here’s what they all got wrong: Every morning, my inbox looks the same. A flood of pitches from people trying to sell me something. Most days, I just mass delete them. But this morning, I decided to actually read through them first. Within 5 minutes, I spotted a pattern. Everyone was making the exact same mistake. They were all trying to close the deal. ALL IN THE FIRST MESSAGE 🥵 Let me show you what I mean (with two small examples): APPROACH A: "The Wall of Text" Send 100 cold emails with full pitch, calendar link, and case studies. • 3 people open • 0 responses • 0 intros This looks exactly like the 147 emails I just deleted "Hi [Name], I noticed your company is scaling fast! We help companies like yours optimize their marketing stack through our proprietary AI technology. Our clients see 300% ROI within 90 days. Here's my Calendly link to book a 15-min chat: [LINK]. Looking forward to connecting! Best, [Name]" BORING!!! APPROACH B: "Micro Conversations" Same 100 prospects, broken down into micro-convo's. Email 1: "Do you know [mutual connection]?" • Send 100 • ~40 open • ~20 respond Email 2: "They mentioned you're scaling your marketing team. I'd love to connect about [specific thing]." • Send to 20 who responded • ~15 continue engaging Email 3: "Would you mind if they made an intro?" • Ask 15 engaged prospects • ~10 intros Final score: • Approach A: No intros • Approach B: 10 intros How to Apply These Lessons (Tactical Summary): 1. Focus on Micro-Conversations: Break your cold outreach into smaller, manageable steps. Build rapport before making any asks. 2. Personalize Everything: Reference mutual connections, specific company milestones, or shared interests in every message. 3. Play the Long Game: Aim for replies in the first message.. not conversions. If you’ve been struggling with cold outreach, you might just need a new approach. Give this one a try and lmk how it goes.

I almost fired our best SDR last year. It wasn’t personal. He was a good guy, worked hard, and always showed up on time. But month after month, his numbers weren’t improving. Emails went unanswered. Calls never connected. Demos? Non-existent. We were both frustrated. I started to wonder if he was the problem. Maybe sales wasn’t his thing? Then one afternoon, we grabbed coffee. Instead of talking numbers, we talked openly. I asked him straight-up: “Why isn’t it working?” He took a deep breath and replied: “I’m following our playbook. I send hundreds of emails, but honestly, I’m just guessing. I don’t really know who’s ready to talk, so I try everyone.” It hit me like a ton of bricks. We’d built a system based on volume and hope, not precision. It wasn’t him. it was us. We’d given him the wrong tools, the wrong strategy. So instead of letting him go, we completely changed how we did outbound. We stopped guessing. We started paying attention to signals: Who’s visiting our LinkedIn profiles? (Tracked via Teamfluence™) Who’s engaging silently with our posts? (Tracked via Clay) Who’s spending serious time on our website? (Tracked via RB2B) Suddenly, our SDR wasn’t sending cold messages. He was following signals that said, “Hey, I’m interested. Talk to me.” Within a month, his reply rate doubled. In two months, he became our top performer. Today, he leads our outbound team. It wasn’t about effort. It was about timing and having a system that showed him exactly when to reach out and who to reach out to. Outbound isn’t about sending more messages. It’s about knowing exactly when and how to engage. If your SDRs are struggling, ask yourself: Are they failing you or are you failing them? It might change your perspective. It certainly changed ours. #Outbound #SalesLeadership #SDRlife #RevOps #LinkedInSales #SalesLessons #GTMStrategy #B2BSaaS #SmartSelling #GTMEngineering #AIOutbound #Teamfluence #Clay

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 ⏳.

WORD OF WARNING JOB SEEKERS! A dear friend of mine was recently contacted by someone presenting as a recruiter about a role with a well-known software company. He provided very specific details — the role, company, salary, and benefits. He even boasted that the candidates he puts forward “always get interviews” because he prescreens their references and submits both the resume and the references to the client. Trusting the process, she provided several references. Soon after, all of those contacts received calls — not about her candidacy, but with sales pitches for the recruiter’s services. Here’s what she uncovered: there was no job. When she called the company directly, they confirmed they weren’t hiring for that role and had never heard of his recruiting firm. She documented everything with screenshots and reported him to LinkedIn. Red flags to watch for: • Requests for multiple references before you’ve had any interview or confirmation of candidacy. • A recruiter who emphasizes “prescreening” or “special access” to gain your trust. The job market is challenging enough without tactics like this. Sharing this as a reminder to all candidates: protect your network, and trust your instincts.

"Mirage PMF" is one of the most common startup killers. Here's what it looks like: You hit $1–2M ARR. Growth is fast, VCs are lining up with term sheets, and you double down—scaling pipeline gen and ramping up AE hiring. But soon, the rocketship starts to rattle. More often than not, it explodes. The root cause is usually a failure to focus—an undefined Ideal Customer Profile (ICP). In the rush to grow, you end up with a hodgepodge of customers, each using your product differently. It feels like optionality, but really, it leads to a scattered product roadmap, unfocused GTM, and an overwhelmed CS team. ⏳ Building a successful startup is like navigating an hourglass. Early on, you experiment broadly, testing different customer profiles to find where your product solves the most acute pain. You can reach $1–2M ARR serving a mix of personas. But once you hit this milestone, the game changes. Now, it’s time to analyze your customer data relentlessly: Where is your PMF strongest? What specific company traits and buyer personas give you 75%+ confidence you’ll both close the deal and truly delight the user? This is the moment to narrow your focus—and it feels hard. Saying no to potential revenue is never easy. But alignment around a clear ICP is what enables you to scale efficiently. Product, marketing, sales, and CS all row in the same direction. Only then do you earn the right to methodically expand to new ICPs, growing your TAM in a disciplined way. “Mirage PMF” has always been a risk for early-stage startups. But it’s getting worse in the GenAI era, where hitting $1–2M ARR is faster than ever. I expect even more post-Series A implosions as a result. -- I'm thinking of writing a series on the most common reasons startups fail after Series A. My goal: help founders avoid these traps (even if it’s a bit of a cautionary tale). Let me know what challenges you want me to cover—and if you’d find this series useful! 

There’s a sales trainer out there who swears his cold calling method is the method. Best-selling book. Best approach. Best results. The problem? Overconfidence bias. Overconfidence bias is when someone puts too much faith in their own knowledge or method while ignoring the complexity of reality. Sure, his approach worked for him. Maybe even for some of his clients. But calling it the best ignores all the variables that shape success: The rep. The tone. The timing. The market. The context. The product. The marketing. Listening. Empathy. Luck. That’s the danger of overconfidence bias in sales. It makes you believe there’s a silver bullet. A single formula. One way. But selling is messy. What works for one person, in one moment, might flop for another. If you ever hear, “My way is the best way,” you’re experiencing overconfidence bias. The antidote to overconfidence bias? Curiosity. Experimentation. Adaptation.

Outbound isn’t about volume. It’s about timing. Like most people in sales, I’ve been through the “do more” mindset: - More emails. - More calls. - More sequences. - More “touches” across channels. And sure - consistency matters. But the truth is, the right message at the wrong time still gets ignored. A few weeks ago, I re-sent a message to a prospect who’d ignored me for two months. Same company. Same use case. Slightly tweaked subject line. This time? She replied within 15 minutes. We booked a call. What changed? Not the product. Not the pitch. Just the timing. She had just started exploring AI for customer support. She was finally ready to hear it. And that’s what outbound really is: - Being present at the moment someone is ready to listen. - Being patient enough to follow up with value - not pressure. - Being consistent enough to earn a response when the timing is right. So no, I’m not chasing massive volume anymore. I’m chasing relevance + timing - and it’s made all the difference.

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.