While our recent research on the state of sales training and continuous learning highlighted the clear benefits of highly effective sales training, it also revealed that many organizations struggle to achieve these results. As part of our survey of 242 sales professionals across various industries and regions, we asked respondents to identify the biggest challenges their organizations face in providing effective sales training and development for people in sales roles.
The responses paint a picture of the complex landscape sales leaders navigate when implementing training initiatives. From time constraints to measuring ROI, organizations encounter a range of obstacles that can hinder the success of their sales training programs.
Our analysis revealed several common hurdles that repeatedly surfaced in respondents' comments. These challenges shed light on why, despite widespread recognition of its importance, many companies struggle to excel in sales training implementation.
Understanding these challenges is crucial for sales leaders and L&D professionals looking to enhance their training initiatives. By identifying these common pitfalls, organizations can proactively address them and improve the effectiveness of their sales training programs.
In this article, we explore six prevalent challenges uncovered by our research and provide insights on how to mitigate their impact. We've included direct quotes from our research, in which sales and enablement leaders weigh in on challenges facing their organizations.
Whether you're just starting to build a sales training program or looking to optimize an existing one, these insights will help you navigate the challenging terrain of sales training implementation.
6 Common Sales Training Challenges
1. Time Constraints
Balancing training with daily sales activities; finding time to implement new learnings
Direct quote from research:
“Time commitment—our sales teams are under significant pressure to generate new clients AND account manage existing clients... These things make it hard for sellers to dedicate time (and at specific times) to learning.”
How to Address:
A modular, multi-modal approach to training delivery can help on both counts. For example, using a flipped classroom model with microlearning, video, and exercises happening in advance of classroom sessions allows participants to learn key concepts before coming together in interactive and collaborative sessions where they focus on practice, application, and feedback.
Beyond the time constraints for actual training, sellers and sales managers also express frustration around finding time to implement their daily sales-related actions. This is one of the reasons we emphasize the importance of addressing productivity as part of sales training.
Our research shows that Top-Performing Sellers are 62% more likely to maximize time spent on high-value sales activities. By combining skill development with productivity coaching, organizations can help sellers find the time for training and implementation of new skills, ultimately leading to better results.
2. Organizational Issues
Lack of alignment between departments; frequent leadership changes
“Constant change in sales leadership. Lack of clarity around the value of sales enablement. Poor communication & collaboration between business units.”
How to Address:
It’s important to gain executive sponsorship and stakeholder engagement from the outset. The Craft-Deliver-Enable framework we recommend—what we call Execution Assurance—includes developing a change strategy and aligning key stakeholders to overcome organizational barriers.
This involves:
- Assessing the current organizational culture and its impact on sales enablement initiatives
- Identifying and engaging influential leaders across sales, marketing, and product teams to build strategic alliances
- Clearly communicating the vision and expected outcomes of the sales training initiative to all levels of the organization
- Developing a communication plan that keeps all stakeholders informed and involved throughout the process
- Creating cross-functional teams to break down silos and promote collaboration in support of the sales enablement initiative
- Establishing a community of practice comprising sales professionals and top performers who can champion the change and help support continuity during leadership transitions
- Aligning the sales training initiative with broader organizational goals and values to increase buy-in and resilience to leadership changes
By taking these steps, you begin to create a more stable foundation for sales training and enablement initiatives, improving your ability to weather organizational changes and maintain momentum towards sales performance goals.
3. Accountability and Engagement
Ensuring consistent follow-through; motivating reps to take training seriously
Direct quotes from research:
“Getting sales reps to believe that training will help them. Getting sales leaders to coach (not just opportunity review).”
“Getting our agents to understand how important daily training and activity is and they won't see results until they do.”
How to Address:
You can ensure accountability and engagement are baked into your sales training initiative from the start (see Craft-Deliver-Enable above).
Encourage accountability partners in the learning process to boost both accountability and engagement. You can do this by pairing sellers or creating small accountability groups to foster peer-to-peer learning, motivation, and support.
These partnerships encourage consistent application of new skills, provide opportunities for collaborative problem-solving, and create a sense of shared responsibility for growth. We also know from our research that the most effective onboarding programs emphasize teamwork and collaboration (61%), which is something you gain with accountability relationships.
Include structured assignments and peer reviews, which use these accountability relationships to reinforce learning and drive behavior change. This peer accountability, combined with manager coaching and organizational support, creates a multi-layered system to ensure consistent follow-through and maintain engagement with the training.
Implement a 90-Day Sales Achievement Challenge post-training along with ongoing Application Coaching. These challenges are led by your managers and coaches to drive adoption, accountability, and engagement among sellers. After all, organizations with the most effective sales training are 5.2x more likely to offer resources that prepare sales managers to motivate and coach their teams.
4. Budget and Resources
Limited funding; lack of dedicated training staff
Direct quote from research:
“Training budget cuts, training is seen as an expenditure rather than an investment.”
How to Address:
We recommend that clients focus on ROI rather than cost per person when budgeting for sales training. One option is to start with a smaller group if resources are limited, then expand based on demonstrated success (e.g., pilot and rollout).
There are also ways to address the lack of dedicated training staff by tapping into external resources while leveraging internal resources to get the biggest bang for the buck.
For example, RAIN Group clients can take advantage of Total Access, which provides comprehensive access to our suite of instructor-led sales training programs, online learning, performance support tools, learning journeys, and resources for the entire sales team.
5. Customization and Relevance
Tailoring content to diverse sales roles and real-world scenarios
Direct quotes from research:
“Customization, the trainings are not that much tailored, our environment is a bit challenging to apply all the sales principles.”
“Training often serves us one size fits all and not role-based training.”
How to Address:
Yes, tailoring program curriculum, content, and cohorts to the organization's specific world can be resource intensive. But it’s critical for ensuring that the sales team can effectively apply their training to daily work. Here's how you can address this challenge:
- Use a sales competency model for each role, clearly defining what great performance looks like
- Conduct a thorough assessment to identify specific skills gaps and learning objectives for different sales roles
- Create custom cases, job aids, and playbooks that directly apply to sellers' daily work and reflect real-world scenarios they encounter
- Develop role-specific learning paths that address the unique challenges and opportunities of different sales positions
- Incorporate industry-specific examples, language, and best practices into the training content
- Use a modular approach to training design, allowing for mix-and-match content that can be tailored to different roles or experience levels
- Leverage technology to create personalized learning experiences, such as adaptive learning paths based on individual performance and needs
- Involve top performers and sales leaders in the content development process to ensure relevance and credibility
- Regularly update and refine content based on feedback and changing market conditions
- Share best practices and examples of sellers using new skills and tools
If your in-house team is overwhelmed by the customization process, consider tapping into a license option like RAIN Group's Total Access. This provides a comprehensive foundation of high-quality content and tools, allowing your internal resources to focus on customization and implementation rather than starting from scratch. By using pre-built content and then tailoring it to your specific needs, you can achieve a high level of customization and relevance without overtaxing your internal resources.
6. Measuring Effectiveness
Quantifying ROI and linking training to performance improvements
Direct quote from research:
“Establishing the causal link between sales training and development and business results.”
How to Address:
Linking training to performance improvements is crucial for justifying investment in sales training and ensuring continuous improvement. Take a data-driven approach to measuring the effectiveness of your sales training initiatives. Here's how:
- Start by defining clear business metrics at the outset of any sales training initiative. This includes both lead (early indicator) and lag (outcome) metrics
- Establish a baseline for these metrics before training begins to enable accurate measurement of improvements
- Implement ongoing measurement and reporting processes to track progress and demonstrate ROI over time
- Use a mix of quantitative and qualitative data to provide a comprehensive view of training effectiveness (e.g., performance metrics, participant and facilitator feedback, employee retention, assessments)
- Use technology and analytics tools to streamline data collection and analysis
- Regularly review metrics with key stakeholders to drive accountability and identify areas for improvement
- Connect training outcomes to broader business results to demonstrate strategic value
- Conduct periodic in-depth evaluations to assess long-term impact and ROI
By implementing a robust measurement strategy, organizations not only demonstrate the value of their sales training investments, but also continuously refine their approach to maximize effectiveness.
Why to Rethink Your Implementation
Implementing effective sales training is a complex endeavor, but understanding these common challenges is the first step toward overcoming them. By addressing time constraints, organizational alignment, accountability, budget limitations, customization needs, and measurement difficulties, sales leaders can significantly enhance the impact of their training initiatives.
Ultimately, the effort invested in overcoming these hurdles can lead to a more skilled, engaged, and productive sales force, driving better results for your organization.
