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Why Your Sales Strategy Isn’t Closing Deals: Three Common Pitfalls to Avoid

Writer's picture: Tim CashmanTim Cashman

You’ve done your market research and validated your product-market fit. You’ve built comprehensive messaging frameworks and put together pitch decks. You’ve even honed inbound and outbound marketing efforts to generate the level of demand needed to grow your business. 


Everything seems to be in place. 


There’s only one problem: Your sales strategy isn’t working as expected. 

Why Your Sales Strategy Isn’t Closing Deals

There are plenty of reasons your strategy isn’t netting more closed-won deals. Most often, it’s not attributable to a single cause, but a combination of interrelated factors. This can make diagnosing and addressing the problem more challenging. But the payoff from honing your strategy is absolutely worth the effort. 


Let’s take a look at where to start. 


Symptoms of a Sluggish Sales Strategy

First, you need to spot the warning signs and get ahead of them. Below are some of the most common (and most troubling) symptoms of an ineffective sales strategy. This is not an exhaustive list by any means. But if you’re starting to see the trendline heading in the wrong direction for these key indicators, it’s time to take action. 


  • Longer opportunity lifecycle: The length of every organization’s sales cycle is different. Likewise, every organization has unique guidelines for the conditions and timing that go into creating new sales opportunities in their customer relationship management (CRM) database. That’s why it’s vital to routinely track the amount of time it takes for an identified sales opportunity to become a closed-won deal in your organization. When that timeline consistently exceeds the standard ranges you set, it’s time to take a closer look and determine why. 


  • Spike in opportunity “graveyard” volume: Not every sales opportunity will convert. That’s expected. Your sales team will inevitably need to remove (or “graveyard”) opportunities from the CRM. But when the rate and frequency of this action starts to climb unexpectedly, it’s time to investigate what aspects of your sales strategy need to adapt. 


  • Shrinking average deal size: If the average size of your team’s deals is trending downward for any significant length of time, it’s a clear sign that your customers aren’t seeing the same value in your offerings that they once did. Assuming that your target customer profile hasn’t shifted dramatically, this is likely an indicator that your organization’s sales approach isn’t hitting the mark. 


3 Sales Strategy Pitfalls to Avoid

How can you course correct if you’re seeing these or similar indicators impacting your business? Or, better yet, what mistakes can you avoid to prevent any decline in the first place? 


To set you and your team up for success, avoid falling into these all-too-common traps: 


  • Failure to set clear priorities and goals: Particularly when your organization is competing in a fast-growing market, it’s easy enough to lose focus. It takes discipline to define a clear set of priority initiatives and align measurable goals to those initiatives. Revenue targets are certainly a powerful driving force. But you should also set goals related to things like market penetration rates, cross-sell and upsell performance, and customer renewal rates. The priorities you outline and the specific goals you set become the determining factors in which deals to pursue and what resources are needed to succeed. Without this clarity, your sales efforts will become diluted, inconsistent, and ultimately less effective. 


  • Limited understanding of the buyer journey: Your sales strategy has to be engineered with an outside-in perspective. It needs to identify the steps a customer takes towards conversion, of course, but also articulate what that customer experience feels like every step along the way. It needs to be shaped by a deep understanding of both the practical and emotional elements of the customer journey. 


  • Focusing on transactional selling: There is a time to focus on tactics and details—usually toward the end of a deal cycle. But to get there, it’s essential to build trust and credibility first. This takes time and patience. Because sales teams often mistakenly equate activity volume (number of emails sent, number of calls made) with the value inherent in a more personalized approach, they leave prospects with the impression that the sale is all that matters. Every market, every product, every sales cycle is different. But in general, a transactional sales style is likely to yield only short-term gains, and may actually undermine your organization’s brand and ability to sustain a healthy sales pipeline over time. A successful strategy is one that prioritizes long-term lead nurturing for higher-impact conversion and longer-lasting success. 


Knowing when to monitor your sales strategy more closely and how to avoid the three common pitfalls described above will ensure that you maximize your organization’s chances to accelerate deal cycles and consistently hit your revenue goals. 


Looking for help boosting your lead-nurturing and sales optimization strategies? Let us know. We’d love to help.



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