sales challenges

The road to success in sales is filled with challenges, highs and lows. Many variables come into play. As we note in our book, Listen to Sell, “It can be easy to feel that given the right factors—the market, the product, the tools, the data, the competition, a natural sales ability—selling would be easier, and success would be inevitable.” 

Listen to Sell Book

But this is a passive and, ultimately, self-defeating way to view and approach the profession of sales. Not only are many of these factors outside the salesperson’s control, they’re also constantly in flux. This is why we say the most significant variable in your sales success is you. The conditions will never be perfect. Success comes down to your view of your role and what you are doing to overcome the sales challenges you’ll most certainly have to confront at various points along the way.

Here are 12 essential sales challenges that salespeople commonly face and what they need to do to overcome them to have both a higher level of success and a greater sense of personal fulfillment in their careers.

Inneffective Prospecting

When it comes to sales challenges, ineffective prospecting is increasingly a significant barrier to long-term success. As sales cycles have grown longer and more complicated, a reluctance to prospect, along with poor prospecting habits, can hold salespeople back and put them at a huge disadvantage. Especially in a volatile and competitive market, salespeople need to expand their books with new business, and that requires shifting customer acquisition strategies so that there’s a better balance between maximizing existing accounts and developing new ones.

One of the reasons prospecting can be so challenging is that salespeople are often hampered by psychological barriers, emotional challenges and unconscious beliefs that keep them from doing what they know they need to do. Effective prospecting isn’t just about learning new techniques; it also requires confidence, skills and inner motivation.

Connecting With Your Prospects

This is why changing mindsets about prospecting is key to overcoming this challenge. To get past these barriers, salespeople need to change the lens through which they view prospecting. Instead of expecting an immediate payoff, they should recognize that the activities they’re doing are laying the groundwork for their future success. Follow a structured approach and diligently protect the time to do it, and the investment will pay off. 

It’s also important to remember that prospecting isn’t selling; it’s about making connections. The goal is simply to create enough interest to begin building a relationship. It doesn’t require pushing a product or getting to a decision. It does, however, require conviction — a belief in and deep knowledge of your solutions and the value you bring, communicated in personalized ways that resonate with specific audiences. Similarly, effective prospecting requires you to know your market, your audience, their needs & point points, and also their audience and what’s important to them.

Accessing Decision-Makers

In B2B sales, getting to the decision maker is one of the big challenges salespeople grapple with. Traditionally, B2B salespeople have approached sales by casting the proverbial wide net. They pull in everything they can get, sift through it all to isolate the leads and accounts that align, and then throw everything else back. Now, though, we have the benefit of a variety of sales enablement technology and tools that make it possible to throw a spear and catch exactly what you want. 

This fine-tuned approach allows salespeople to be much more productive and effective at targeting decision makers, yet complexities in the customer buying process have presented new challenges. In many organizations today, a sprawling group of decision makers, each with diverse needs and interests, is (directly or indirectly) involved in the buying decision, leading to longer and more complicated sales cycles.

As the buying process has evolved, salespeople can no longer simply rely on the “lead” to pull them through and up the chain to a decision. The traditional lead is often a lower-level person who has been tasked with doing some fact-finding and information-gathering on behalf of key decision makers. For example, they may have attended an event or downloaded a white paper, which is how they’ve landed on the salesperson’s radar. But sales reps who focus purely on this kind of lead aren’t doing the work necessary to engage at an account level or get an audience and develop relationships with the actual buying committee members. 

Today’s salespeople must understand the broader Ideal Client Profile (ICP), be able to get connected with each of these likely decision-makers and take on the role of facilitating agreement internally among them. This is how successful salespeople create and add real value, build more durable relationships with clients and expand their overall reach. 

Creating Value in Initial Meetings

One of the common challenges and complaints in sales is the difficulty of getting a second meeting with a prospect or advancing the opportunity beyond the initial discussion. Dig a little deeper, and you can find some common pitfalls that are creating this roadblock.

The Challenge of Understanding the Customer Perspective

Often, salespeople have trouble generating momentum and interest after the first meeting because, from the potential customer’s point of view, there wasn’t much substance to the initial discussions. Customers want to get some tangible value out of participating in a meeting with the sales rep, not hear the same trite questions they’ve been asked over and over again, like “what keeps you up at night.” At best, they’ll find the sales rep isn’t memorable or doesn’t stand out enough to warrant a next meeting. At worst, they’ll think the salesperson wasted their time.

Getting a second meeting or moving the opportunity forward requires creating value early and repeatedly, and successful salespeople do this by doing their homework in advance. They come to the table having already researched to understand the organization, the people they’re speaking with, their industry and customers, and broader market conditions. As a result of their prep work, these sales reps are able to engage in a higher level of conversation, one that adds tangible value right from the start and differentiates them from the competition.

Key to instilling this commitment among salespeople is building a customer-centric culture that is relentlessly focused on making sure every employee understands clearly how the value proposition makes a difference for customers. When a salesperson views selling through the lens of how they’re helping create value for people, they approach the entire process differently. They recognize that value can be assessed in various ways, depending on the customer and their needs, and that different things are valuable for different people and purposes. Beyond doing their homework, this motivates them to ask good questions, actively listen, and uncover needs and problems that they can help the customer solve. Those behaviors — that genuine desire to create value — come through to the customers in every discussion, helping to create momentum that propels opportunities forward.

Building Trust With Buyers

Trust is the cornerstone of any successful business relationship, and it’s particularly important in sales. Now more than ever, buyers want to work with someone they can count on to operate with integrity, honesty and transparency and who they believe has their best interests at heart. The most successful salespeople recognize that trust is central to a human-centered selling approach and it’s what sets them apart. The trust they’re able to build becomes the foundation for strong, sustainable customer relationships.

Being prepared, truly listening to understand the customer’s needs, facilitating connections among the various stakeholders and focusing on creating value all go a long way toward building trust with buyers. At a tactical level, it includes things like using what you’ve learned in your research and interactions with the client to personalize your outreach and make it meaningful to that individual. It also includes using that knowledge to ask substantive questions that help the customer dig deeper and think about their problems in novel ways. 

This entails spending more time on the sales discovery process, because that’s where the salesperson and the customer can find out what they don’t know and then work collaboratively to determine the right solution. (Sometimes your solution won’t be the right fit — and being transparent about that is another powerful trust builder.) It’s also important to hold yourself accountable for what you say you will deliver. Track promises made and promises kept so you can develop a record of dependability. And remember, trust-building is an ongoing process that cannot be taken for granted; it doesn’t end just because the initial deal has been signed. 

Inadequate Sales Training

One of the ways organizations seek to head off sales challenges at the pass is by sending their reps through sales training. Unfortunately, these initiatives often fail to achieve their intended outcomes. How bad is it? Sales training has been referred to as a “black hole,” where “so much is spent for so little return.”

There are a number of reasons sales training fails, ranging from taking a one-and-done approach to the content quality, learner experience, and the overall business strategy behind it. For starters, you can’t teach people to sell by teaching people to sell. Education is important, but knowing what to do doesn’t mean someone will do it. Developing new skills, while critical, doesn’t necessarily mean the person will remember and consistently apply them, particularly when the pressure is on. 

Most sales leaders know this. They acknowledge that other factors, like Achievement Drive and inner beliefs, are far more influential when it comes to long-term sales performance. But their training doesn’t address them. And the sales metrics they focus on don’t reflect them. 

Effective sales training addresses both the skillset and the mindset that create sustainable sales success, and it builds accountability for reaching specific behavioral, performance, and financial milestones. Sales training has to be a process that is repeated and reinforced over time, grounded in principles that build relationships and a commitment to helping salespeople understand their purpose so they can stand out and become irreplaceable.

Lack of Formal Sales Process

An effective, value-based sales process provides the roadmap and framework for success. Too often, when salespeople don’t have a formal process to rely on, they end up rushing through (or completely overlooking) important steps, or falling back on old habits, like product features & benefits dumping. 

Even if you have a formal sales process in place, it’s a good idea to review it to make sure it’s emphasizing the behaviors and actions you want every customer to see. Effective sales processes emphasize the importance of mastering sales conversations and actively listening, as well as downstream skills like effective negotiations. They should help the salesperson create relationships across the account, not just with one person.

Finally, you have to hold people accountable to adhering to the process and integrate it into the culture. A common language and a sales culture that support the process will reinforce the importance of following it and drive consistency.

Handling Sales Objections

In sales, objections come with the territory. That’s why handling objections is one of the 15 essential sales skills top salespeople focus on mastering. More than just a skill, though, handling objections is also a factor of mindset, self-belief and perspective. 

Whereas some reps will personalize the objections, lose confidence or stray off course from the process when they get a negative response, the best salespeople welcome objections. They view questions and concerns as a gift, because they’re a signal that the buyer needs more information to clarify their own thinking so they can take the next steps. 

Rather than trying to respond with a comeback that proves the customer’s concerns are unimportant or wrong, a successful salesperson will ask questions to understand their concerns and listen without interrupting. They’ll work to shift the focus to solutions. And they know that some people simply won’t be moved. But most will respond positively to their efforts and value their attempts to help them.

Sales Motivation

Keeping motivated when objections and rejections are part of the job is no easy task. Longer, more complex selling cycles that ebb and flow make it even more challenging to stay engaged and positive as the process drags on.

One of the ways top salespeople keep themselves motivated is by focusing on progress, not just numbers. Big goals are great, but they can also become demoralizing if it feels like they’re so far from your reach. By focusing on the smaller, incremental steps along the way, salespeople can see tangible evidence that their efforts are making an impact. It also gives them a clearer line of sight to how the activities they’re doing are adding up to wins that will lead them closer to the big goal.

It’s also true that sometimes the limits to success are self-imposed. Salespeople are having conversations with themselves every day about what’s possible for them to achieve and whether they have what it takes to be successful. This is the mindset aspect of sales. When salespeople are constantly telling themselves they aren’t capable of getting there, those doubts will eventually self-sabotage their ability to sell.

By the same token, breaking through the self-limiting behaviors is a powerful motivator. Salespeople who are aware of these inner conversations and are able to get to the root of the issues behind them will be able to develop new self-beliefs that drive positive, productive behaviors and actions.

Sales Anxiety and Mental Health Challenges

Considering the myriad challenges salespeople face, it’s perhaps no surprise that research shows more than 70% of sellers struggle with their mental health. The impact of anxiety and mental health issues can be far-reaching, ranging from burnout, fatigue, disengagement, lower productivity and increased mistakes to numbing behaviors like shopping, gambling and substance abuse. 

Over time, there’s a compounding effect that can lead to more cynicism and negativity about the company’s products and services as well as the job itself. As a result, a sales target that might seem totally achievable to someone who’s well-rested and in a positive frame of mind can seem overly challenging and even punitive to someone who’s feeling exhausted and stressed out.

Since sales reps are continually dealing with uncertainty and the natural ups and downs of the role, leaders need to recognize that supporting and building resilience is vital. This includes setting a positive example and creating an environment that emphasizes personal well-being and encourages people to prioritize their mental health. 

One strategy is controlling the things you can control by starting the day with a “startup routine.” If you can prime your day with more certainty, and also build in micro-moments throughout the day to reset, you can feel more in control and contain the chaos.

Discussing Price Increases With Customers

One source of anxiety for many salespeople is broaching the topic of price increases with their customers. The first step in making this process easier is avoiding the common pitfalls. Some salespeople will take an apologetic tone as a way to show empathy or offer a short-term fix of rebates or discounting to “make the customer whole.” While these approaches may be well-intended, they devalue the organization and its solutions, and they can damage the rep’s credibility, leaving the customer wondering what’s really going on.

This is another area where the salesperson’s skillset and mindset both come into play. Just like any good sales conversation, a discussion of price increases should focus on customer value, exploring what’s important to the customer and how the company’s solutions create relevant value based on their needs. These shouldn’t be treated as adversarial, us vs. them discussions.

From a mindset standpoint, salespeople need to be aware of how their own inner beliefs might be creating barriers. If they don’t believe in the value of the product or its ability to address the customer’s needs, or they don’t believe in their ability to have effective conversations around pricing, they’re more likely to end up defaulting to apologizing or offering discounts. Having confidence in what you’re providing is key. It fuels a genuine desire to ask questions, understand concerns and work to address them with the customer.

Inaccurate Sales Forecasting

Even with the advent of sophisticated new technologies, sales forecasting accuracy remains a persistent challenge that vexes sales leaders and complicates the process of running a successful sales organization and driving predictable sales pipeline and growth. Many sales leaders complain that their reps too often base forecasts on emotion, gut feelings and even wishful thinking, or that they simply don’t understand what the factors are that contribute to whether an opportunity will close, when and for how much.

Poor forecasting is often rooted in the fact that sales and pipeline processes only look at milestones from one side of the story, and it isn’t the customer’s side. To be able to come up with a good forecast, you need a set of leading indicators that provide you with objective milestones for predicting the likelihood of revenue from a specific deal or collection of deals. This starts with a sales strategy that captures critical actions that the customer is taking at specific moments in the sales process. Both the sales and the pipeline processes need to incorporate the seller’s as well as the buyer’s point of view.

Pipeline management, forecasting accuracy and coaching are all interconnected. Sales leaders should use pipeline management to help their reps develop a more objective view of their opportunities and the steps that need to be taken to advance them. The forecast can also be a jumping-off point that leaders can leverage to be more strategic about how they coach their reps and what training they provide them.

Ensuring Sales Leaders Get Adequate Development

World-class sales organizations that are able to consistently achieve and exceed performance expectations recognize that coaching is a key strategic differentiator as well as a catalyst to long-term behavior change from sales training. Yet even though most sales leaders agree that coaching is critical to sales success, the vast majority either aren’t coaching effectively, aren’t doing it enough or aren’t even doing it at all.

Sales coaching data information

Why don’t sales leaders coach? While they may say they “don’t have time to coach”, the deeper truth is that they often don’t have clarity about what coaching is or a consistent definition that’s agreed upon across the organization, and many lack the appropriate skills to do it well. Together, these factors sap their motivation as well as their confidence in themselves to coach. New sales leaders, in particular, tend to be inadequately prepared and left to their own devices. To make coaching part of the culture, you have to develop both the mindset and the skillset to coach. Start by helping people uncover their “why” so they can tap into their own purpose and motivators for coaching their people. Make sure they understand what effective coaching looks like. Give them the skills to ask questions that will help their reps uncover answers for themselves and gain confidence, problem-solving ability and autonomy. Everyone, from brand new reps to star performers, benefits from and is looking for this kind of coaching.

Integrity Selling: Overcome Sales Challenges

Challenges such as longer buying cycles, well-informed and distracted customers, the availability of self-service or digital interactions, and artificial intelligence are just a few of the variables that make sales increasingly complex and competitive today.

In the face of these challenges, the Integrity Selling approach to selling reintroduces the human element into the sales conversation through a unique approach to improving sales performance. By viewing and defining sales as simply the process of finding solutions to customers’ problems that you can help solve and helping customers make buying decisions that are in their best interests, customer relationships are built on Integrity. The salesperson will be valued, respected, and sought out by customers. And these sales challenges above will be addressed much more effectively.

Salespeople that are confident and motivated to succeed get elevated to the status of trusted advisors. Integrity Selling empowers salespeople with a mindset rooted in values and ethics aimed at finding solutions to customer needs. Selling shouldn’t conflict with your values. It should, in fact, be rooted in them.

Integrity Selling’s unique approach to unlocking sales performance places the salesperson at the heart of any successful sales conversation. Let’s talk about changing the way you think about sales training and the way your customers think about you.


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