Closing sales deals is harder than ever. 

You’ve prospected, pitched, and followed up relentlessly—only to watch the deal stall or disappear. Sound familiar? You’re not alone. 

While 42% of sales pros say prospecting is the hardest part of their job, a close second—36%—struggle most with closing itself, according to HubSpot. And in today’s B2B landscape, where it takes on average 62 touches across at least three channels to seal a deal, it’s no surprise that sales close rates hover around just 29%. 

36% of sales pros struggle to close sales deals. — HubSpot

The truth? Most reps aren’t losing deals because they lack effort. They’re losing them because of preventable mistakes. Whether it’s poor qualification, weak follow-up, or misaligned messaging, these errors pile up—and deals slip through the cracks. 

The solution lies in helping sales reps improve their execution, and that happens when sales leaders and reps can recognize the warning signals. When sales leaders and reps know what to watch for, they can fix what’s broken. 

In many cases, struggling teams make one of 10 common mistakes that prevent reps from closing sales deals:

• Weak discovery
• No personalization
• Chasing wrong deals
• Misalignment with the buyer’s journey
• Value not clearly communicated
• Poor content delivery
• Mishandling objections
• Inconsistent follow-up
• No internal champion
• Lack of coaching and feedback

Continue reading to learn how those mistakes derail deals. Plus, you get strategies to overcome them, win more consistently, and finally stop wondering what went wrong. 

Why Closing Sales Deals Often Falls Apart

What’s really getting in the way of closing sales deals? Below are 10 of the most common mistakes reps make—each one a potential deal-killer if left unchecked. 

Mistake #1: Weak Discovery Undermines the Close

Great closers don’t wing it—they earn the right to close by running a strong discovery process. When reps rush through discovery or ask surface-level questions, they miss the insights that drive deals forward. 

It isn’t enough to identify the buyer’s pain points. Reps need to dig deeper during their discovery calls: What’s the root cause? What’s the cost of inaction? Who else is affected? What outcomes does the buyer truly care about? 

Without these answers, it’s nearly impossible to tailor a compelling solution or build a persuasive business case. And when it’s time to close, the rep ends up guessing—relying on generic pitches instead of value-driven conversations. 

A weak discovery sets the stage for a weak close. 

✅ Pro Tip: Use structured frameworks like MEDDIC or SPICED to guide your discovery. Train reps to treat discovery as an ongoing process—not just a box to check on the first call. 

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Coach Reps to Start Closing Sales Deals Faster

Fixing sales mistakes starts with better coaching. This handbook shows you how to use AI-driven insights to deliver personalized, scalable coaching that helps your reps close more deals—faster. Download the eBook now.

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Mistake #2: No Personalization = No Connection

Buyers can smell a templated pitch from a mile away—and they tune it out just as fast. In today’s market, personalization isn’t optional. It’s a competitive advantage. 

When reps rely on generic messaging, they fail to show that they understand the buyer’s business, challenges, and goals. That lack of relevance erodes trust early and makes it harder to build momentum later in the deal cycle. Even the most compelling product demo falls flat if it’s not grounded in the buyer’s world. 

Personalization doesn’t mean writing a custom novel for every prospect. It means aligning messaging with industry trends, role-specific pain points, and real business outcomes.

If a buyer feels like they’re just contact #47 in a sequence, don’t expect them to return your call—let alone sign a contract. 

✅ Pro Tip: Equip your reps with access to role-based messaging frameworks, case studies by industry, and relevant customer stories. Sales enablement platforms make it easier than ever to personalize at scale—use one. 

Mistake #3: Chasing the Wrong Deals

Not every opportunity deserves your team’s time. But when reps skip proper qualification, they end up spending weeks—or even months—on deals that were never real to begin with. 

Sometimes the contact isn’t a true decision-maker. Other times, there’s no urgency, no budget, or no actual fit. Without a clear qualification process, reps confuse interest for intent and fill their pipeline with false positives. 

This doesn’t just hurt close rates—it drains resources, inflates forecasts, and creates friction between sales and leadership. 

Effective qualification helps reps focus on the right buyers, shorten sales cycles, and increase win rates. It’s not about disqualifying leads for the sake of it—it’s about prioritizing the right ones. 

✅ Pro Tip: Implement a consistent qualification framework like BANT, CHAMP, or MEDDIC. Use deal reviews and pipeline coaching sessions to reinforce the discipline of qualifying early—and revisiting qualification throughout the deal. 

Mistake #4: Misalignment with the Buyer’s Journey

Even the best sales process will fall flat if it doesn’t match how your buyers actually make decisions. 

When reps push for next steps too early—or lag when buyers are ready to move—they create friction. That disconnect leads to stalled deals, ghosting, or worse: a competitor swooping in with better timing and alignment. 

To close more deals, reps need to guide—not drag—buyers through the decision-making process. 

Today’s buyers are more informed and more cautious. They expect value at every stage and want a partner, not a pitch. Reps who fail to recognize where the buyer is in their journey risk offering the wrong message, content, or call to action at the wrong time. 

To close more deals, reps need to guide—not drag—buyers through the decision-making process. 

✅ Pro Tip: Encourage reps to ask discovery questions that reveal where the buyer is in their internal process. Support them with digital sales rooms or guided selling tools to share relevant content and keep stakeholders aligned throughout the journey. 

Mistake #5: Value Not Clearly Communicated

If your reps can’t articulate value, they won’t close the deal—no matter how good the product is. 

Too many reps focus on features and functions, forgetting to answer the one question every buyer is asking—“So what?” Buyers don’t just want to know what your product does. They want to understand why it matters to them. What business problem does it solve? What results will it deliver? What’s the risk of doing nothing? 

When reps can’t answer that, the deal stalls—or gets reduced to a pricing conversation.

The best sales reps connect your solution directly to outcomes the buyer cares about: driving revenue, reducing costs, increasing efficiency, or mitigating risk. That’s the difference between being seen as a vendor and being trusted as a partner. 

✅ Pro Tip: Build your team’s messaging around the buyer’s perspective, not just your product’s capabilities. Every value proposition should pass the “So what?” test. If it doesn’t, rework it until it does. 

Mistake #6: Poor Content Delivery

Content can make a deal—but only if it’s delivered at the right time, to the right people, in the right way. 

When reps don’t know what content to use, can’t find it, or share irrelevant assets, they miss critical opportunities to influence the buying decision. And in B2B sales, where more than six people are typically involved in a purchase, failing to deliver tailored, impactful content can quickly derail momentum. 

When reps don’t know what content to use, can’t find it, or share irrelevant assets, they miss critical opportunities to influence the buying decision.

The right content helps reps build trust, reinforce value, and move buyers forward faster. And high-performing sales teams are more likely to say their content is easily accessible and aligned with their sales process, helping them close more deals and shorten sales cycles. 

✅ Pro Tip: Equip your team with a centralized, searchable sales content hub that surfaces the right content for each stage of the sales cycle. Even better? Integrate content recommendations into the tools reps already use so it’s seamless, not siloed. 

Mistake #7: Mishandling Objections

Buyer objections aren’t deal-killers—they’re opportunities. But only if reps know how to handle them the right way. 

Too often, reps get flustered, go on the defensive, or try to dodge the question. Worse, they overreact and start discounting or overselling in a panic. That doesn’t build confidence—it erodes it. 

Your team should know the most common objections—whether it’s about price, timing, or competing solutions—and have clear, buyer-focused responses ready. 

Buyers raise objections because they’re weighing risk. They’re looking for reassurance, not a rebuttal. Reps who anticipate objections and address them with calm, confidence, and clarity are the ones who keep deals moving forward. 

The key is preparation. Your team should know the most common objections—whether it’s about price, timing, or competing solutions—and have clear, buyer-focused responses ready. 

✅ Pro Tip: Build an objection-handling library and practice it through role-plays or peer coaching. Better yet, use call recording and coaching tools such as conversation intelligence to review how reps respond in real conversations—and help them improve in the moments that matter. 

Mistake #8: Inconsistent Follow-Up

Follow-up isn’t just a task—it’s a discipline. And when it’s inconsistent, deals die. 

Reps often assume that silence means disinterest. But in reality, buyers are busy, distracted, and juggling multiple priorities. Without timely, thoughtful follow-up, even the most promising deals can slip through the cracks. 

And here’s the kicker: It takes an average of 31 touches to close a B2B deal. That means giving up after three emails or one call isn’t just premature—it’s a lost opportunity. 

What hurts even more? Generic “just checking in” emails that add no value. They don’t move the conversation forward—they make the rep look like they’re just going through the motions. 

Effective follow-up is strategic. It’s about providing value at every touchpoint—sharing a relevant resource, offering insight, or prompting the next step. The cadence matters. The content matters. And the timing? That matters most.

✅ Pro Tip: Set up structured multi-touch follow-up sequences that combine personalized emails, value-based check-ins, and call touchpoints. Equip reps with tools to automate reminders and track buyer engagement so no deal goes dark unnoticed.

Mistake #9: No Internal Champion

If your reps don’t have someone on the inside advocating for your solution, guiding them through the buying process, and rallying internal support, the odds of closing drop dramatically. 

Champions help navigate complexity. They give insight into decision criteria, internal politics, and the timeline—things you won’t find on a discovery call or in a CRM field. Without that guidance, reps are selling blind. 

In addition, deals stall because reps focus on the most responsive contact, not the most influential one. And in today’s B2B landscape, where 6 to 10 stakeholders are typically involved in a purchase decision, relying on a single point of contact is a risky play.

✅ Pro Tip: Train your reps to identify true champions—not just friendly contacts. Champions have influence, credibility, and a vested interest in your solution’s success. Use multithreading strategies to engage multiple stakeholders and avoid single-threaded deals.

Mistake #10: Lack of Coaching and Feedback

Even top performers need sales coaching. When sales teams don’t have a system for ongoing feedback and skill development, performance plateaus—and deals slip through the cracks.

Many times, coaching happens only when there’s a problem: a missed quota, a blown forecast, or a big deal gone cold. But the best sales organizations treat coaching as a continuous process, not a corrective one. They review calls, refine messaging, and practice key moments in the sales cycle—before they’re make-or-break.

The best sales organizations treat coaching as a continuous process, not a corrective one.

Modern sales teams use tools like asynchronous video coaching and real-time feedback to help reps improve faster. It’s not about micromanaging—it’s about giving reps the support they need to win.

✅ Pro Tip: Build a coaching culture that reinforces core skills and sharpens deal execution. Use call recordings, peer reviews, and manager-led sessions to provide targeted feedback. Make coaching part of the rhythm—not just a reaction.

Start Closing More Sales Deals Today

Closing sales deals isn’t just about having the right pitch or product. It’s about executing consistently across the entire sales cycle—and avoiding the common pitfalls that silently sabotage success.

From weak discovery to inconsistent follow-up, each of these mistakes can cause deals to stall, slow down, or disappear. But the good news? Every one of them is fixable.

Start by identifying which of these issues show up most in your team’s process. Coach around them. Equip your reps with the tools, content, and guidance they need to execute with confidence at every stage.

Because when your team avoids these 10 mistakes, they don’t just close more deals—they close the right deals, faster.

✅ Next Step: Share this list with your sales team during your next pipeline review or coaching session. 

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About the author: Erik Fowler is Chief Revenue Officer of Allego where he is responsible for the company’s customer acquisition and sales goals. He has 20 years of sales leadership experience, focused on maximizing sales opportunities through strategic planning and streamlined sales processes.

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Coach Reps to Start Closing Sales Deals Faster

Fixing sales mistakes starts with better coaching. This handbook shows you how to use AI-driven insights to deliver personalized, scalable coaching that helps your reps close more deals—faster. Download the eBook now.