15 of the Toughest Challenges Sales Leaders Face and How to Overcome Them

Hey, Enablers, Happy Friday. Mike Kunkle here. Welcome to this week’s edition of Sales Enablement Straight Talk!

Today, I want to share 15 of the toughest challenges that senior sales leaders face and how to address and resolve them.

Let's dig right in.

Introduction

Sales leaders and their teams face relentless challenges in today’s competitive market. This is not news. The pressures are constant -- delivering on aggressive targets, maintaining revenue growth, and staying ahead of competitors while managing internal and external complexities. Each obstacle carries its own weight, affecting not just performance metrics but also the morale and confidence of the team.

Below, I'll explore 15 of the most pressing challenges that senior sales leaders grapple with and provide actionable strategies to address each one.

1. Sellers Aren't Meeting Buyer's Higher Expectations

Challenge: B2B buyers today are more informed, discerning, and demanding than ever. They are also generally not pleased with what they get from sellers. They expect hyper-personalized interactions, rapid response times, solutions tailored to their exact needs, and what you see in the above chart (on which they are, in general, clearly disappointed). They don't want to be pitched -- they want to be helped. For sales leaders, it’s a moving target that can feel impossible to hit. And yet, missing the mark often leads to disengagement or outright rejection.

Solution: Achieving the right level of personalization begins with business relevance (not tailoring to personal details), which starts with what I call Buyer Acumen. Equip your team with a deep understanding of buyers’ roles, goals challenges, opportunities, and decision-making processes. I use the acronym COIN-OP for Challenges, Opportunities, Impacts, Needs, Outcomes, and Priorities. Develop comprehensive buyer personas and map their buying journey. Train reps to speak the buyer's language, aligning every interaction with what matters most to them. A culture of empathy and relevance turns those heightened expectations into opportunities to differentiate.

For a deeper dive into Buyer Acumen, you can refer to:

• This article: Buyer Acumen is the Best GTM Foundation
• This article: Two Enablement Shifts That Can Produce Huge ROI
• This video: What is Buyer Acumen & Why Does It Matter?

For a deeper dive into how to sell to modern buyers more effectively, explore:

• These articles: Blog Articles on Modern Sales Foundations
• These downloadable resources: Downloadable Resources for Modern Sales Foundations
• This sales methodology & course: Modern Sales Foundations Course

Statistics and Insights:

• Buyer Preference: According to Salesforce, 89% of buyers are more likely to buy from salespeople who understand their mission and goals.
• Buyer Concern: 71% of B2B buyers reported that most sales interactions felt transactional.
• Higher Conversion Rates: Companies that adopt a consultative approach see up to a 50% higher conversion rate compared to traditional selling methods.
• Enhanced Customer Trust: 81% of customers make purchasing decisions based on trust, which is a core component of consultative selling.
• Customer Retention and Loyalty: 79% of consumers stay loyal to brands that show genuine interest in helping them.
• Improved Cross-Selling Opportunities: Businesses using consultative selling methods saw a 30% rise in cross-sell and upsell potential.
• Results from our very own Modern Sales Foundations course:

2. Dealing with Unresponsive Prospects

Challenge: Few things are as demoralizing as pouring effort into outreach only to hear… nothing but crickets. Emails go unopened, calls unanswered, and LinkedIn messages ignored. Reps are left questioning their approach—or worse, their abilities.

Solution: Break through the silence with a refined outreach strategy. Start with relevance as discussed above, personalization by leveraging data and insights about the prospect’s industry, role, and priorities. Adopt a multi-channel cadence, balancing persistence with respect. Lead with clear, compelling value, and make outreach impossible to ignore by tying it to a trigger event or urgent need. And, take a problem-centric approach versus a product-centric approach.

For more on this topic, dig into these articles:

• Enable Your Sellers to GTM More Effectively
• Why Value Stories Trump Value Propositions
• How to Improve Your New Business Development Results

Examples and Strategies:

• Consistently share relevant updates and trends that align with the prospect’s needs.
• Offer a mini audit of the prospect's current strategies to position yourself as a valuable resource.
• Send personalized video messages and call on the phone to stand out in a sea of emails.

3. Difficulty Maintaining a Steady Flow of Leads

Challenge: A full sales pipeline is a lifeline. When lead flow slows, anxiety builds. Teams scramble to fill the void, often focusing on quantity over quality, leading to burnout and frustration (and the issue addressed above - unresponsive prospects who are unimpressed and likely feel more nagged than inspired).

Solution: Build a collaborative relationship with marketing (see challenge number 9) to generate leads that align with your ICP. Invest in inbound strategies like relevant content marketing, SEO, SEM, and webinars to attract prospects who are already searching for solutions. Balance this with targeted outbound efforts, using tools to refine your prospecting lists. As mentioned above, use a problem-based approach vs. a product-focused approach. Use an omnichannel approach and be professionally persistent without cutesy tactics (meaning, no messages asking if they've been abducted or appear on a milk carton; no requests for 27 seconds of their time). Nurture, nurture, nurture. Strive to deliver value first and consistently monitor lead flow metrics and adjust tactics when you spot downward trends.

PRO TIP: The same three resources from above (in #2) will help you here, as well. Develop relevant POSE Value Stories and enhance them with Ethos, Pathos, and Logos, as well as infusing outreach with insights (trends, data, client successes, and valuable collateral/assets/content).

Statistics and Insights:

• 61% of marketers struggle with lead generation.
• Companies that nurture leads get 50% more sales-ready leads than those that don’t.

4. Sellers Waste Time on Unqualified Opportunities

Challenge: Few things crush a rep’s motivation faster than realizing the "hot lead" they’ve been nurturing is nowhere near a good fit. It's also a nightmare for managers and sales leaders. Wasting time on unqualified leads leaves teams frustrated, stretches resources thin, and destroys sales productivity (revenue per rep). It also wreaks havoc on pipeline management and forecasting.

Solution: Sharpen your lead qualification process. Use lead scoring to prioritize prospects based on their fit and intent. Empower your team to ask incisive questions early to identify unqualified leads. By filtering out distractions, your team can focus their energy where it matters most—on high-potential opportunities. Incorporate your formal qualification methodology (you do have, right?) into your CRM and workflow. Use a rating system and have managers "trust but verify" to ensure the ratings make sense and are pressure-tested.

• PRO TIP: Obviously I am encouraging qualification, and it is important. At the same time, there is a balance needed. Don't rush to disqualify deals too quickly, unless the disqualification is abundantly clear. For example: If it doesn't seem there is funding, but you haven't included the right buying committee members, such as an executive decision maker who owns the problem you solve and the outcomes you deliver, you may not yet have engaged with the right person who has or can free up the necessary funding.

Examples and Strategies:

Implement a stringent lead qualification process to ensure leads match your ideal customer profile. We teach FACT + NASA (see the image above). If you first know you have Need And Solution Alignment (meaning, you know they have a problem you can solve and deliver the outcomes they want), you can explore:

• Funding: Can they pay for it? Is there a budget set aside and if not, can funding be sourced?
• Alternatives: What else are they considering, including competitors, DIY, and doing nothing (status quo or No Decision)?
• Committee: Are you speaking with all of the right influencers and decision makers? Especially the executive or Champion, who owns the problem you solve, and the Financial Decision Maker, who controls the budget or who can source the funding.
• Timing: Can you do it when they want (timeline) and is there a compelling event or reason for them to act (urgency)?

5. Getting Lost in a Crowded Market (Red Ocean)

Challenge: In hyper-competitive markets or Red Oceans, it’s exhausting to continuously explain why your solution is better. The pressure to differentiate feels like a constant uphill battle, with competitors eager to undercut or outshine you.

Solution: A strong Unique Selling Proposition (USP) is critical, but it must go beyond product features. Train your team to highlight the problems you solve and the outcomes you deliver for each of the personas you serve, and how you do it better. Build competitive intelligence into your sales process, enabling reps to anticipate and address customer concerns. Use customer testimonials and case studies focusing on problems solved, outcomes delivered, and customer satisfaction. Relationships matter, too—act with integrity and consistently demonstrate reliability to stand apart where it counts. Follow-up as you say you will. Deliver on your promises, no matter how small.

Statistics and Insights:

• 57% of sales leaders and managers say competition has increased since last year.
• According to a study by McKinsey, B2B companies that focus on brand differentiation are 2.5 times more likely to achieve above-average growth.

6. Slow Moving Sales Cycles

Challenge: Time can be the silent killer of deals. And maybe more than the time itself, because some solutions naturally have very long sales cycles, is the lack of momentum. The longer the cycle, the greater the risk of losing momentum, budget approval, champions (turnover), or stakeholder buy-in. Leaders feel the weight of stalled opportunities clogging the pipeline, creating pressure from all directions.

Solution: Einstein is quoted as saying, "Make things as simple as possible, but no simpler." That logic applied to this topic, might be:

"Close your opportunities as fast as you can, but no faster."

Break the cycle (aka the buyer's journey and your sales process) down into clear, manageable stages with well-defined exit criteria for each stage for each common persona (as in the diagram above). Focus on rigorous qualification at the start to ensure you’re spending time on deals worth pursuing. Equip reps with tools and insights that accelerate buyer decisions, such as collateral that answers the most common questions at each stage of the process, as well as business cases, ROI models, or success stories. Regularly analyze your pipeline to identify and assess slow-moving deals, to see if there are ways to accelerate them.

At the same time, consider the reasons for the slower motion and whether you are pushing selfishly, or for the sake of your buyer. For a balanced view on "the need for speed," see: The Misguided Need for Speed.

I won't say we should never nudge a buyer. We just shouldn't do it for our selfish reasons. If you have NASA and you could be saving your buyer time, reducing risk, or saving significant money and generally reducing negative impacts and delivering their desired outcomes -- and your buyer is stalling -- sometimes a nudge is in their best interest. But before nudging I would at least recommend trying to uncover the root cause reason for their stall.

Statistics and Insights:

• The average sales cycle length varies significantly by industry, with complex industries like pharmaceuticals averaging 153 days.
• More empowered buyers have resulted in longer sales cycles, with an average of 7 decision-makers involved in the B2B buying process.

7. Battling Pricing Pressures & Margin Erosion

Challenge: Discount demands are relentless. Reps face pushback on price, often feeling trapped between protecting margins and losing the deal altogether. Sales leaders feel the strain as profitability hangs in the balance. My employer, SPARXiQ, works primarily in the wholesale distribution sector, and this is a serious issue for distributors. Done well, strategic pricing can put 200-400 basic points back on the bottom line in 90 days, and it can go up from there, based on how disciplined the implementation is. But while distributor pricing is highly complex with literally thousands of SKUs, they are not alone -- other industries face pricing pressure, too.

Solution: Shift the conversation from cost to value. Arm your team with tools like ROI studies, documented cost saving, improved efficiencies, and case studies that showcase the impact of your solution. Train reps to negotiate confidently, positioning your offering as an investment, not an expense. Offer flexible options, such as bundling, to meet buyer needs without eroding value. Explore both tactical ("put your hand on your wallet") negotiation and collaborative (win-win) negotiation.

Statistics and Insights:

• Only 65% of companies worldwide possess true pricing power, meaning they can raise prices beyond the rate of cost increases.
• Data-driven negotiations can increase success rates by up to 30%.
• Companies that lack formal negotiation processes show a 63.3% decrease in net income.

8. Drowning in Overwhelming Data

Challenge: Many sales teams are drowning in data and coming up short on insights. Activity metrics, pipeline reports, account histories—it’s overwhelming and hard to know what truly matters. Decision-making slows, and focus suffers.

Getting a better handle on your organization's data can have several positive impacts:

• Improved Decision-Making: Organizations that leverage data effectively are three times more likely to report significant improvements in decision-making.
• Increased Efficiency: By optimizing data management, companies can streamline operations, reduce redundancies, and improve overall efficiency.
• Enhanced Customer Insights: Better data management allows for deeper insights into customer behavior and preferences, enabling more personalized and effective marketing strategies.
• Competitive Advantage: Companies that harness the power of data are better positioned to innovate and stay ahead of competitors.
• Employee Satisfaction: Reducing information overload and improving data access can enhance employee productivity and satisfaction, as they spend less time searching for information and more time on value-added tasks.

Solution: Centralize data with a robust CRM and provide reps with training to navigate it efficiently. Use BI and analytics tools (and learn AI) to surface actionable insights, such as which opportunities are at risk, or which behaviors drive success, or how the current enablement efforts are delivering results above an expected trendline. Streamline reporting to focus on the metrics that move the needle.

Here are some best-practice recommendations for effective data management:

• Define Clear Data Management Goals: Establish specific objectives for what you want to achieve with your data management efforts, such as improving customer insights or ensuring regulatory compliance.
• Create a Data Governance Framework: Implement policies and procedures to manage data quality, security, and privacy. This framework should outline roles and responsibilities for data management within your organization.
• Ensure Data Quality Assurance: Regularly monitor and clean your data to maintain its accuracy, completeness, and reliability. This includes removing duplicates and correcting errors.
• Ensure Data Security and Privacy: Protect your data from unauthorized access and breaches by implementing robust security measures, such as encryption and access controls.
• Streamline Data Integrations: Use tools and processes that facilitate seamless data integration from various sources, ensuring that data is easily accessible and usable across the organization.
• Enforce Proper Data Documentation and Metadata Management: Maintain detailed documentation and metadata for your data sets, including information about data sources, definitions, and usage guidelines.
• Implement Master Data Management: Establish a single, consistent view of critical business data across the organization to improve data accuracy and consistency.
• Leverage Data Analytics and Reporting: Utilize data analytics tools to gain insights and make informed decisions. Regularly generate reports to track performance and identify trends.
• Perform Regular Data Audits and Compliance Checks: Conduct periodic audits to ensure data management practices comply with relevant regulations and standards.
• Foster a Data-Driven Culture: Encourage a culture where data is valued and integrated into decision-making processes. Provide training and resources to help employees understand and use data effectively.

Implementing these best practices can help your organization harness the full potential of its data, leading to better decision-making, increased efficiency, and a competitive edge.

Statistics and Insights:

• Organizations that effectively manage their data can improve decision-making by up to 73%

9. Suffering from Sales and Marketing Misalignment

Misalignment between sales and marketing is like two people rowing a boat in opposite directions.

Challenge: Sales and marketing misalignment creates internal friction that negatively impacts organizational effectiveness, with the biggest loser being the customer. Leads often don’t fit the Ideal Customer Profile (ICP), messaging feels disconnected, and sales reps struggle to find collateral that answers common buyer questions. Meanwhile, marketing believes sales can't sell, and both teams end up pointing fingers. Can you believe this still happens in 2024?

Solution: Create alignment through shared goals, metrics, and feedback loops. Put the customer at the center of everything and align to support them. Regular joint meetings foster understanding and collaboration. Consider combined advisory boards and creating a Customer Advisory Board. Use shared tools to increase transparency and celebrate wins that result from teamwork.

Examples and Strategies:

• Advisory boards, as mentioned above. Rally around the customer, not silos.
• Regularly schedule joint meetings to discuss goals and tactics.
• Use shared dashboards to track progress and ensure both teams are aligned.

10. Ineffective Sales Coaching or a Lack of Sales Coaching

Challenge: Many sales managers are great sellers themselves but struggle to develop their team’s skills. Without proper coaching, reps stagnate, and results plateau. Sales leaders feel the pinch of underperformance but can’t always identify the root cause.

Solution: Build coaching into your culture with a structured framework. Train managers to coach effectively, using regular one-on-ones, performance reviews, and real-time feedback. Emphasize continuous improvement, making coaching a priority rather than an afterthought. Focus on developmental sales coaching and behavioral, skills coaching. This "raises the water level" across the organization, and what managers learn about developmental coaching can be applied to the other forms of coaching, such as strategic, tactical, and opportunistic coaching.

For more on sales coaching, see:

• Newsletter: The Mysteries of Sales Coaching Revealed!

• Course: Sales Coaching Excellence Course
• Video Overview of the Course: Sales Coaching Excellence - Training Program Trailer
• Video Overview of my Sales Coaching System: Walkthrough of The Sales Coaching System (Framework, Process, and Models)
• Video Overview of the 4 Types of Sales Coaching: Sales Coaching Excellence - The 4 Types of Coaching

Statistics and Insights:

• Companies with dynamic sales coaching programs (dynamic = adapted to individual rep's needs) achieve 28% higher win rates.
• Sales coaching leads to an 88% increase in productivity, compared to 23% from training alone.

11. Falling Behind in Technology Adoption

Challenge:

The pace of technological change is relentless. Falling behind can feel like losing the race, while constant upgrades risk overwhelming teams and budgets.

• High Costs: The initial investment for new technologies can be substantial, including costs for software, hardware, and training.
• Resistance to Change: Employees may resist new technologies due to fear of the unknown or concerns about job security.
• Complexity and Integration Issues: Integrating new technologies with existing systems often proves complex and time-consuming.
• Skill Gaps: There may be a lack of necessary skills within the team to effectively use new technologies, requiring additional training and development.
• Security Concerns: New technologies can introduce vulnerabilities if not properly managed, leading to potential data breaches.

Solution:

Stay informed by attending industry conferences and tracking tech trends. tools that align with your team’s needs, testing them thoroughly before rolling them out company wide. Ensure thorough onboarding and support to maximize adoption.

• Develop a Technology Roadmap: Create a strategic plan that outlines the technologies to be adopted, timelines, and expected outcomes. This helps in managing budgets and setting clear expectations.
• Invest in Training and Development: Provide continuous learning opportunities for employees to upskill and stay current with new technologies.
• Pilot Programs: Start with small-scale pilot programs to test new technologies and gather feedback before full-scale implementation
• Leverage External Expertise: Partner with technology consultants or vendors who can provide expertise and support during the adoption process.
• Encourage a Culture of Innovation: Foster an environment where employees feel encouraged to experiment with new technologies and share their insights.
• Monitor and Evaluate: Regularly assess the impact of new technologies on business processes and make adjustments as needed to ensure they are delivering the desired benefits.

Statistics and Insights:

• 77% of sales organizations harness digital tools to boost performance, with 66% employing AI tools for personalized coaching.
• Companies that adopt new technologies are 2.5 times more likely to achieve above-average growth.

12. Struggling to Hire and Retain Top Talent

Challenge: The churn of top performers is a blow to morale and momentum. And even average performers are expensive to replace, given the opportunity cost loss and the cost of recruiting, hiring, and training. Sales leaders grapple with the dual challenge of hiring the right talent and retaining them in a high-turnover profession.

Solution: Create a disciplined hiring approach and a compelling environment that attracts and retains top talent. During the hiring process, focus on candidates whose values align with your company’s and who possess the mindset and skill sets needed for success in the role. Recognize individual motivators, whether they’re driven by achievement, recognition, or growth opportunities. Offer competitive compensation, coaching and ongoing career development, and a culture of belonging to ensure long-term retention.

Ensure you have a talent management and development system to address all of the above.

Statistics and Insights:

• 60% of sales reps say they're more likely to leave their job if their manager is a poor coach.
• Companies with strong onboarding processes improve new hire retention by 82% and productivity by over 70%.

13. Wasting Time on Low-Value Tasks

Challenge: Administrative burdens weigh heavily on reps, taking precious time away from selling. Reps often lament, "I’m drowning in busywork," leaving leaders scrambling to solve the issue.

Solution: Automate repetitive tasks using CRM workflows and scheduling tools. Delegate administrative work to support roles. Freeing reps from these burdens allows them to focus on what they do best — selling. Remember that while the goal is always to increase the time spent engaging with prospects and customers, "time spent selling" may include activities such as sales call planning, because it improves the quality and effectiveness of buyer and customer interactions. Reduce or eliminate busywork wherever possible. Even planning should be just the right amount versus paralysis by analysis, but efficiency should never be prioritized over effectiveness.

"Strive to foster efficiency but never prioritize efficiency over effectiveness. Otherwise, your reps will just do more dumb stuff faster."

Mike Kunkle

Statistics and Insights:

• Sales reps spend only 34% of their time actually selling, with the rest consumed by administrative tasks.
• Automation can save up to 30% of a sales rep's time, allowing them to focus more on high-value activities.

14. Missing Opportunities Due to Inadequate Meeting Preparation

Challenge: Ill-prepared reps walk into meetings under-equipped, risking not just the opportunities but also their credibility. Leaders see the missed potential and wonder how much revenue is being left on the table.

Solution: Equip reps with pre-meeting checklists, sales playbooks, and access to relevant data. Encourage thorough preparation by role-playing key scenarios. Confidence stems from readiness -- and readiness wins deals.

• Clearly define objectives for both parties and establish a mutually beneficial agenda.
• Manage attendees (determine who is attending from both sides and plan internal roles)
• Research ahead of the meeting (company and people)
• Prepare presentation materials or sales collateral
• Send clear and concise pre-meeting communication

Examples and Strategies:

• Develop a standardized pre-meeting checklist to ensure reps cover all necessary preparation steps.
• Use role-playing exercises to simulate different meeting scenarios and improve reps' confidence and adaptability.

15. Disorganization Due to Inconsistent Sales Processes

Challenge: A lack of standardization causes inefficiencies, confusion, and lost opportunities. Leaders often feel like they’re herding cats, struggling to get everyone to follow the same playbook. Or worse, some don't care about consistency. There is a lot of "free-for-all" sales process, sales methodology, and sales management, in general. At the same time, the opportunities and rewards for getting it right, are significant. Given this, it's surprising how often formal process and methodology do not get the attention they deserve.

“Sales process and sales methodology adoption rates above 75 percent resulted in above average results for revenue plan attainment, quota attainment, and win rates.”

~ CSO Insights, 5th Annual Sales Enablement Study  

Solution: Develop clear, documented processes and the sales methodology that supports them. To maximize effectiveness, build both with how your buyers like to buy, or their buyer's journey (all part of Buyer Acumen, mentioned above in #1). Train your team on their importance and how to follow both. Use CRM and sales engagement and enablement tools to ensure easy access to resources. Embed your methodology into workflow. Regularly review processes to refine and optimize them, reinforcing accountability across the team. Train, coach, and provide feedback. Support the process and methodology with enablement and engagement systems. Coaching is especially important here, but you can only coach what is visible or knowable -- the things that you can see are or aren't happening. So, keep the old adages in mind:

What gets measured gets done.

What gets asked about gets attention and focus.

Statistics and Insights:

• Companies with well-defined sales processes see 33% more revenue growth than those without.
• Standardized processes can lead to a 28% increase in sales productivity.

Closing Thoughts

First, I want to recognize that while each of the above 15 challenges has something distinct about it, there is a lot of overlap. This is how systems thinking works -- there are interdependencies on so many things, and it requires getting each to an acceptable level (not always perfection, but at least GEFN or Good Enough For Now) to get the cumulative effect of improved performance. Please keep that in mind, as you tackle and address these issues.

With that said, the challenges of modern sales are real, daunting, and often unrelenting. Sales leaders carry the weight of expectations, balancing team performance, revenue goals, and strategic priorities. By addressing these challenges head-on with thoughtful, buyer-centric strategies and a commitment to continuous improvement, sales teams can not only survive but thrive. Success stems from focus, adaptability, and building a culture of excellence, a culture of coaching, and a cadence of continuous improvement that empowers everyone to reach their potential and the organization to perform at the highest level.

It is possible, it is worth it, and in end, it is very rewarding. Don't let anyone tell you otherwise.

Newsletter Pause for the Ho-Ho-Holidays!

This will be my last newsletter edition for 2024. I'm taking some time off for the holidays and taking a several-week break from writing. I want to thank you, my faithful subscribers and readers, for your support this year. I hope the newsletters have provided value for you and helped you in some way to become more effective and more successful. And, of course, #MakeAnImpact With #Enablement!

Sales Enablement Straight Talk will return on Friday, January 10, 2025.

Whatever you may celebrate, I wish you a Merry Christmas, Happy Hannukka, Joyous Kwanzaa, Peaceful Solstice, Happy Holidays, and a Partridge in a Pear Tree! And a Happy New Year!

Resources

There are a lot of links and resources embedded in this newsletter edition this week, in the 15 sections. Rather than copy/paste and repeat them here, please review them in the sections where they are provided. In addition, here are a few other related resources for you.

• PDF: Best-in-Class Sales Onboarding (ungated download)
• PDF: Sales Hiring System (ungated download)
• PDF: Sales Training System (ungated download)
• PDF: The Sales Management System (ungated download)
• Video: Improve Sales Results with a Sales Management Operating System

Well, that's it for this week, Enablers! Did you learn something new reading/watching this newsletter? If you did, or if it just made you think (and maybe chuckle from time to time - bonus points if you snorted), share it with your favorite enablement colleague, subscribe right here on LinkedIn, and check out The Building Blocks of Sales Enablement Learning Experience. For other courses and content from Mike, see: https://linktr.ee/mikekunkle

Until next time, stay the course, Enablers, and #MakeAnImpact With #Enablement!