We’ve all been there— you think it’s going great with a potential buyer when the deal suddenly dies. And it’s even worse when you find out the buyer went with your competitor even though you have a superior product. So what happened?

Maybe you had a solid sales strategy and you’ve unintentionally stumbled into a common pitfall, like many other sales reps before you. But it doesn’t have to be that way. We looked at some of the biggest sales mistakes that reps make and got some tips and tricks from experts around the business community to help you avoid them.

Sales Mistake #1: Spending too much time talking and not listening to the prospect

Imagine attending a cocktail party and getting trapped chatting with someone who can’t stop talking about themselves. It's awful! But, It isn’t uncommon in sales —many salespeople prioritize talking over listening to their prospects!

By doing so, they risk losing the buyer’s attention. The sales conversation will be over before it even begins.

How do you avoid this sales mistake?

Not doing too much talking during sales calls seems like the obvious answer. But how does a rep begin to quantify what too much even means?

Chris Orlob, the former Director of Sales at Gong, dove deep and analyzed over 25,000+ B2B sales conversations to find out. Chris and his team learned that top B2B sales professionals speak 43% of the time (on average), allowing the prospect to speak 57% of the time (on average).

If your sales team isn't following a similar ratio yet, it’s time to give it a try. Of course, make sure to make the conversation meaningful and relevant to the customer’s needs. Share things about your company that speak specifically to your buyer’s challenges or concerns.

Sales Mistake #2: Not making a follow-up plan during the discovery call

80% of won deals require five or more follow-up calls after a meeting, and planning for this starts during the discovery phase, where it’s critical to move the conversation forward.

Not moving forward can get in the way of closing a deal, yet, when our team at Qwilr polled our webinar audience during “The 6 Deadly Sins of Sales Communication” asking them if they booked a follow-up meeting during their discovery call, 29% answered with a negative response.

How do you avoid this sales mistake?

Remember, the goal of a discovery call is to have another conversation— you should be booking your next meeting during this call.

“Open your calendar during the call and book it in the moment while they are engaged,”

advises Mark Tanner, COO, and Co-Founder, Qwilr.

And what if your buyer replies with something like, “Follow-up with me in three months?”

Kyle Parrish, present VP of Sales at Figma, advised:

“Unless you have a valid reason for delaying the discussion, this is not a real deal. Without a commitment from the buyer, it only wastes your time— blow up the deal right then and there. Your objective as a salesperson is to define if this deal is a winnable opportunity— deals are won and lost in discovery based on the questions you’re asking and the next steps you’re taking,”

Sales Mistake #3: Failure to quantify the buyer’s problem and your solution

Almost all sales decisions rely heavily on the buyer’s return on their investment (ROI). This is why it is so important that sales reps are able to quantify the impact of the solution they’re selling.

In another poll during our Webinar “6 deadly sins of sales communication, 60% of the audience said, yes, they discuss ROI in sales presentations,” while 18% said no, and 22% weren’t sure how to demonstrate ROI.

Not demonstrating and quantifying the value of your product consistently can prevent your sales team from making quota. It's not just about demonstrating how quickly a customer can complete a process using your solution. You've got to go the extra mile and convince your prospect that the value they'll get from your solution is worth the price you're asking.

Now many may confuse ROI as just the monetary value of the product, but there’s more to it.

“ROI’ doesn’t necessarily mean dollars; it can also equate to hours saved or a pain ‘thermometer’ of how the problem is affecting the entire team,”

states Michael McEuen, Head of Growth at Dooly.

How do you avoid this sales mistake?

One way to avoid this mistake is by highlighting the time and cost savings the buyers will enjoy in the long run. By emphasizing the value they'll receive, you'll have them nodding their heads in agreement and happily reaching for their wallets.

Mark Tanner, COO and Co-Founder of Qwilr, states:

“If you’re not understanding your buyer’s problem and putting some degree of quantification towards it, you’ll likely have a hard time closing that deal. ROI isn’t always clean or perfect, but trying to quantify your solution is important to your buyer’s journey. ROI framing is a must when a CFO is involved in signing off on the contract— you have to speak his or her language. The VP and CFO levels need that business justification, and you need to help your prospect put that together,”

One way to accomplish this is by crunching some numbers to figure out the cost of providing the same level of support using another solution and then comparing it to the deployment cost of your solution and calculating their net benefit.

By doing this simple calculation, you'll be able to show your prospects just how much they stand to gain from opting for your solution. It's all about highlighting the value they'll receive and helping them visualize the positive impact on their bottom line.

Need help demonstrating these calculations? Qwilr has a fully customizable ROI calculator your team can use to demonstrate the value of your solution.

Sales Mistake #4: Sending generic sales materials

Qwilr’s Buyer Experience Study conducted in 2021 found that 64% of buyers look for personalized materials, and 25% dismiss generic collateral. It’s true—When it comes to sales collaterals, personalization is the secret sauce that can take your sales game to a whole new level. It's not just about slapping together generic materials and hoping for the best.

When you tailor your collateral to resonate with your specific audience, you're showing your buyers that you truly understand their needs and challenges.

How do you avoid this sales mistake?

The best way to avoid this mistake is to listen to your buyer, show them that you heard their challenges and objectives, and use the information obtained in the discovery call to tailor their sales materials. Kyle mentions,

“Sell to their issues and get them excited about the next step. If you’re not solving the problem that they talked about in discovery, you’ve missed your opportunity, and that’s what loses deals”

For example, if you are sending a proposal, there are two types of personalization: using a generic template and adding basics like name and brand logo. The second level is when your materials reflect the conversations that you’ve had— you’re communicating you listened to your buyer, and you are including the information that speaks specifically to their needs and helps them make an informed decision.

Mark advises spending a few minutes writing a custom intro to show your buyer you care, “that’s the level of personalization that the buyer experience".

Sales Mistake #5: Not acknowledging other stakeholders and deal influencers

According to research by Gartner, an average of 7 people are involved in most buying decisions, yet more often than not sales reps make the mistake of not acknowledging other stakeholders and deal influencers that may join a conversation last minute (think CMOs, CEOs, etc.)

Needless to say, the greater the number of decision-makers, the longer the sales cycle because your sales team would be busy convincing more people than usual, and it gets trickier if you haven’t factored in questions that may be important for the C-suite or other deal influencers.

How do you avoid this sales mistake?

The way to avoid this is by asking who else is weighing in on a deal—as early as possible!

“Right after a demo is an ideal time to understand the full buying committee. Additionally, don’t count on your champion to resell your solution correctly. Their pain points may not be the same as the other stakeholders— it’s in your best interest to get to the other stakeholders and speak about your solution in their language, whether that’s ROI or something else,”

Michael McEuen, Ex-Head of Marketing at Dooly.

As an example, when you’re selling a technical solution, oftentimes, your silent deal killer is operations. To this group, talk about post-sale: the implementation needs to be smooth and the solution reliable,” he added.

When you address the other deal stakeholders from their point of view, you’re less likely to encounter deal delays or vetos.

Sales Mistake #6: Negotiating over email

Did you know that win rates dramatically drop when negotiations are via email? There are a number of reasons for it—it can lead to miscommunication, gives your buyer an infinite amount of time to think, drags out the sales cycle, and more importantly it makes it way easier for your buyer to say “no”!

Bottom line? Negotiating over email is a sin in sales and a mistake best avoided.

How do you avoid this sales mistake?

It may not be via email, but negotiations are still a key part of a sales deal, so how should you handle subtle (and not so subtle) negotiations?

Chris Voss, ex-kidnapping negotiator with the FBI and the author of the acclaimed book Never Split The Difference: Negotiating As If Your Life Depended On It, has many tips up his sleeves on negotiation, but the two that resonate here are building trust-based influence through the use of tactical empathy and working in a way that deactivates negative feelings.

How does it play out during sales negotiations?

Let’s say the prospect expresses concerns about the product's price and its compatibility with their existing systems. To build trust-based influence using tactical empathy, you would listen actively and reflect their emotions.

You could say:

"I understand that you're concerned about the price of the software. It's natural to be cautious when making a significant investment for your business."

From there on, work together with the client to find a mutually beneficial solution.

Similarly, when diffusing negative feelings, you can provide specific assurances or guarantees that address the issues they faced previously. For example, you might say:

"We understand your concerns, and we have a dedicated customer support team available 24/7 to ensure your issues are resolved promptly."

Here’s a tip from our experts— if you’re going to negotiate, get something back. Never give anything without getting something equal or greater in return— don’t make a unilateral concession. That’s hard to do via email. Negotiating live allows you to see a reaction and emotion, but there’s no nuance when you negotiate via email.

Finally, time kills all deals, and email adds time. Discuss concerns with your buyer live whenever possible.

Sales Mistake #7: Insufficient prospect research

Talking about just features more than the value of your product is considered reprehensible in sales, but not giving your prospects what they want or offering solutions based on wild guesses is a bigger issue.

This stems from poor research about your prospects, and while it may seem challenging, it is every bit essential. Prospect research is the name of the game when it comes to having killer sales conversations and sealing those awesome sales deals.

Prospect research allows you to go beyond generic sales pitches and truly connect with your prospects on a personal level. It's all about understanding their pain points, tailoring your approach, and providing solutions that speak directly to their needs. Doing so will increase your chances of closing more deals and building lasting relationships with your clients.

How do you avoid this sales mistake?

It begins with doing your homework upfront, and Julie Thomas, President and CEO of Value Selling Associates—a global sales training company, agrees with the approach.

“ When you understand your prospect’s business, their industry, and their role, you can focus your communication on how you can add value and engage with your prospect rather than pitch to them.”

Julie Thomas, President and CEO of Value Selling Associates

Julie also talks about ‘Warm Call,’ not a phone call necessarily, but a term that means informed sales outreach. It could be a call, or an email, InMail, or even a text.

The difference, she states, is that this time the sales professional will have done their homework.

Remember, top performers in sales prospecting generate 2.7x more sales meetings than the rest. But that’s not all. They also make sure they're of top-notch quality. Imagine creating sales meetings that are bursting with brilliant ideas, profound insights, and genuine value. And you know what that leads to? Fuller pipelines, more sales, and better close rate. By following great prospecting strategies, you fill your pipeline with qualified leads and increase your potential for closing deals.

Sales Mistake #8: Poor Pipeline Management

If you find yourself stuck with stagnant sales and itching to boost your sales performance, it's high time to focus on improving your pipeline management. Having a full and robust pipeline is key to successful sales. Unfortunately, not many salespeople spend enough time on it.

“ Any additional insight a sales team can get into their own sales process is a competitive edge over their competition. This is why every sales org should be tracking their pipeline as closely as possible. Making informed decisions requires good data, and in sales, that good data often stems from high-quality pipeline tracking.”

Dustin Martin, RevOps Manager @ Qwilr

How do you avoid this sales mistake?

Improving your sales pipeline management can help your organization streamline your sales process, prioritize leads, close deals faster, and ultimately boost your bottom line. A few ways to achieve this are setting up the right lead qualification process, focusing on segmentation, recording opportunity data, and automating the sales pipeline.

You can also sign-up as a Qwilr user and explore the new pipeline report and analytics functionality to dive deeper!

Sales Mistake #9: One and done sales training

As a sales leader, you've got a diverse sales team with a range of reps, from those natural-born high performers who seem to win effortlessly to those who consistently lag behind.

Now imagine if even those struggling performers had the tools and knowledge to connect with the right people and have impactful conversations, and that’s where sales training comes into play. According to Taskdrive, Sales training reaps a staggering 353% ROI for the average company.

In a podcast, long-time enablement advocate John Moore discussed the failings of a 'One & Done' or shotgun-style approach to sales training. He stresses that:

“90% of teams prefer this approach, and if the reps fail, it’s on them, instead of making training part of a sustained activity and embedding learnings for the long-term.”

How do you avoid this sales mistake?

The way around this problem is to level the field as much as possible so that lower performers can receive much-needed guidance and direction and top performers can continue to get better at their game.

As a sales leader, a lot of this hinges on you training your team and could cover a wide range of topics, from basic product knowledge to advanced selling techniques. Once empowered, your sales managers will be better equipped at setting sales goals, crafting killer strategies to reach those goals, and highly motivated to support sales reps.

You can fine-tune their skills through targeted coaching sessions, provide actionable insights, and drive profitability to new heights. It’s a win-win for everyone!

Lastly, you can join a sales leadership program that offers opportunities for networking with other sales leaders and learning from their experiences.

Sales Mistake #10: Over qualifying leads

Sales qualification plays a vital role in the sales process by helping sales teams focus their efforts on leads that have a higher chance of making a purchase.

“Not every lead is suitable for every product. But sales reps that over-qualify alienate prospects that really would buy. If they reached out on their own, the interest likely is genuine. No one enjoys just window shopping for SaaS apps.”

Jason M Lemkin, Advisor at SaaSTr

How do you avoid this sales mistake?

It's important to find the right balance when it comes to qualifying leads, so sales reps need to filter out leads that aren't a good fit early on. You wouldn't want to waste time on leads that eventually won’t move forward the way you expected.

To help qualify leads, start by narrowing down your ideal customer profile (ICP). When engaging with prospects who fit the ICP, qualify them by asking the right questions about their goals, needs, budgets, and timelines. Having and using a scoring system can help qualify leads without going overboard. And if used regularly and refined over time, the scoring system can proactively help reps to qualify (or disqualify) leads based on the responses to key questions.

It's all about finding that sweet spot where you gather enough information to make informed decisions without letting it become an obstacle.

Sales Mistake #11: Not writing convincing proposals

This is a big one for us at Qwilr; after all, we have spent years perfecting our sales proposal software that makes creating proposals a breeze for sales teams. As part of this journey, we have also discovered how challenging it is to create a proposal that really convinces a buyer. Unsurprisingly, most salespeople bail out and don’t give enough importance to this sales tool.

Writing a poor sales proposal can have some significant drawbacks that may hinder your chances of closing more deals. Crafting a sales proposal that lacks clarity, doesn't address the client's specific needs, and fails to demonstrate the unique value your product or service brings to the table is a missed opportunity to solve the prospect’s pain point, and they may end up choosing a competitor with a more compelling proposal instead.

How do you avoid this sales mistake?

Creating convincing sales proposals is nuanced and is both an art and a science, and no one knows that better than the sales reps at Qwilr. Here’s a video where they share five elements every proposal must contain to improve your odds of winning the deal!

Sales Mistake #12: Bad sales presentations

Bad sales presentations can derail a deal, which isn’t something that sales teams should take lightly. Apart from a poorly designed and misaligned presentation, think of one that does not capture your brand essence, isn’t effective in conveying your message, isn’t tailored to the unique needs of your buyers, and fails to captivate your prospects from the very start—it’s just wrong.

A well-executed presentation is your opportunity to forge a strong connection, build trust, and demonstrate your expertise as a sales professional, yet many sales representatives often struggle when it comes to delivering impactful presentations that resonate with potential customers.

How do you avoid this sales mistake?

The solution to this problem lies in preparation, an essential step in closing a sales deal. But that’s not all. Sales teams should spend enough time mastering effective communication and delivery, demonstrating product value as well as practicing confident body language to shine during their presentations.

By focusing on these steps, teams can enhance their sales performance and achieve better results in today's competitive marketplace.

Sales Mistake #13: Depending too much on manual processes

How are your sales reps keeping track of all their leads and follow-ups? Well, if they're still juggling a mishmash of flagged emails and printed reports, it's safe to say they're wasting precious time that could be better spent client-facing.

Many sales organizations see this as a problem yet do nothing to streamline it. Considering the best sales tools for the job can be daunting. But not taking action at all is a big mistake.

“Sales reps will need to embrace new tools and channels, as well as a new manner of engaging customers, matching their sales activity to their customers’ buying practices and information collecting needs.”

Cristina Gomez, Managing Vice President for the Gartner Sales Practice

How do you avoid this sales mistake?

By creating a versatile sales tech stack that includes automation and a robust customer relationship management (CRM) tool, you can ensure that your sales team remains efficient and effective, all while keeping up with the ever-changing needs of today's buyers. When choosing the right tools and level of investments, plan for what you need today but also consider what you’ll need as your business grows. Having tools that can grow and scale with you can save you time and money and give you a greater return on your investment.


What are the four most common sales mistakes?

There are several common sales mistakes that salespeople can make. However, the four most common are prioritizing features over value, failing to quantify the buyer’s problem with a solution, insufficient prospect research, and overqualified leads.

What is one of the biggest mistakes salespeople make while selling?

One of the biggest mistakes that salespeople make is not investing time in researching their prospects. Failing to do so results in ineffective targeting, missed opportunities, inaccurate positioning, and weakened credibility.

To mitigate these disadvantages, it's essential for salespeople to invest time and effort into conducting thorough prospect research. This includes gathering information about the prospect's company, industry, recent news or events, and individual stakeholders to enhance the effectiveness of their sales approach.

What causes sales reps to fail?

Sales reps can fail for many reasons. These include insufficient prospecting skills, inadequate product knowledge, weak communication and listening skills, and the inability to build relationships, pushing them to make sales mistakes.

To err is human (in sales too!)

Navigating the world of sales can be challenging, but by avoiding common sales mistakes, your sales team can greatly increase their chances of success. As these sales leaders share their expert tips, it becomes clear that continuous learning, effective communication, and a customer-centric approach are essential for sales success.

"You don't build a business, you build people, and then people build the business."

Zig Ziglar

So invest in your sales team, dodge these sales mistakes, and watch as your relationships with your prospects and customers flourish, and you are able to close deals and take your business to new heights!

Want to avoid some of the common pitfalls when creating collateral, proposals and other sales documents and close more deals? Try Qwilr’s proposal templates to get started easily and focus on customization for your customer base.

About the author

Brendan Connaughton, Head of Growth Marketing

Brendan Connaughton|Head of Growth Marketing

Brendan heads up growth marketing and demand generation at Qwilr, overseeing performance marketing, SEO, and lifecycle initiatives. Brendan has been instrumental in developing go-to-market functions for a number of high-growth startups and challenger brands.