Planning Your Sales Training: A Step-by-Step Guide

There's no room for improvisation when it comes to sales training.

In a recent study from the RAIN Group Center for Sales Research, only 33% of respondents rated their sales training as extremely or very effective, indicating a significant gap for most organizations.¹

However, some organizations still get training right. These organizations build training to address specific needs and plan their logistics from start to finish.

You can do the same by following a proven process and focusing on the key characteristics that lead to impactful training.

This guide outlines a step-by-step approach you can take to ensure your sales training delivers measurable results.

Plus, we’ve included links to our sales training guide, packed with templates and tools you can use starting today.

Step 1: Define the business results you want to achieve.

The first step in planning your sales training is identifying the specific business outcomes you want to impact. Common results include:

• Increasing win rates
• Improving margins
• Growing account size
• Filling the sales pipeline
• Increasing sales productivity
• Shortening sales cycles

Once you define your goals, align them with lead (e.g., pipeline growth, sales activity) and lag measures (e.g., revenue growth, win rates) to track progress.

Get a list of sales training and enablement metrics here. >>

The most successful organizations measure performance against clear metrics. Unfortunately, organizations that rate their training as moderately, slightly, or not at all effective—the majority at 67%—are 13.6x(!) more likely not to measure.

By setting measurable targets from the outset, you can better assess the effectiveness of your training and ensure it drives real business results.

Step 2: Assess where your sales team is now.

Assessing your sales team’s current capabilities is a critical step. Our research reveals that proactive use of assessments is one of the three key drivers of effective sales training and development.

Why is this so important? Because it allows you to identify the specific skill gaps within your team and align your training to close those gaps.

With an assessment in hand, you can confidently secure leadership buy-in and target the skill development areas that will move the needle. The results of these assessments will vary by role, so it’s important to consider the differences between your BDRs, sales reps, account managers, sales managers, etc.

Assessment tools are invaluable because they pinpoint which skills are most critical to develop, helping you design a curriculum that addresses the unique needs of each role in your organization.

Here’s an example from our sales manager assessment, which is part of our Sales Capability and Execution Assessment process.

Skill Ratings Across the Top-Performing Sales Manager Model

Step 3: Create a development plan.

When we examine the most effective sales training programs, three characteristics stand out:

1. Regular mentoring or coaching is encouraged and supported.
2. Managers are prepared with resources to coach and motivate their teams.
3. Continuous learning is a key part of the culture, supported by leadership.

Sales Training and Development Characteristics
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Including sales managers in your development plan is crucial. Managers work directly with sellers and, when trained alongside their teams, are better prepared to reinforce learning, coach effectively, and drive results. Our work with clients consistently shows that integrating manager-specific training yields stronger, longer-lasting outcomes.

The third point—continuous learning—highlights the importance of a long-term approach to sales training. Unfortunately, many training programs are short-sighted, focusing only on immediate needs, such as improving a single skill (e.g., needs discovery, objection handling, account growth, filling the pipeline, negotiation, etc.). A program is built and delivered to address that skill, and sellers gain and use the skill for a while. However, when enthusiasm wanes, new sellers are hired, or skills are not reinforced or supported over time, initial adoption and success fades.

By building a continuous learning culture where managers regularly coach their teams and support is provided over time, your organization can bridge the gap from onboarding to ongoing skill development.

Effective training isn’t a one-time discrete event—it’s an ongoing process.

Step 4: Build or tailor training.

To maximize the impact of your sales training, it’s critical that the content resonates with your team and addresses the specific needs identified through your assessments. Tailoring training to align with your business goals and the unique challenges of your sales organization ensures it’s relevant and actionable.

Key factors to consider when building or tailoring your training:

• Relevance to roles: Different roles within the sales team will have different needs. Account managers, sales reps, and sales managers all require role-specific training. Generic training may miss the mark, leading to disengagement or ineffective skill-building.
• Customization: Incorporate examples, case studies, and scenarios that mirror real challenges your team faces. When training reflects the day-to-day experiences of your sellers, it becomes more meaningful and easier to apply.
• Practicality: Ensure the training provides hands-on, practical tools that can be immediately applied. Whether it’s using new discovery techniques, refining negotiation strategies, or improving pipeline management, actionable content increases engagement and knowledge retention.
• Flexibility: Every team is different, and so are their learning preferences. Offering a blend of self-paced modules, live sessions, and hands-on workshops allows learners to engage with the material in ways that suit them best.

Developing a program that fits your organization is essential. Whether you’re partnering with an external provider or building it in-house, your content should address both immediate skills gaps and long-term strategic goals.

Step 5: Plan for effective training delivery.

The modality, structure, and pacing of the program all influence how well the training sticks. Let’s explore the various modes of delivery.

Delivery Methods for Highly Effective Training
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• In-Person Workshops: Despite the shift toward virtual learning, 93% of organizations with the most effective training still rely on in-person instruction. There’s something irreplaceable about face-to-face interaction, group activities, and the energy that a live event can bring. In-person workshops are excellent for deep dives, collaboration, and building camaraderie.
• Virtual Instructor-Led Training (VILT): This option has become popular due to its flexibility and convenience. While it lacks the same level of personal connection as in-person training, VILT can still foster engagement through interactive elements such as breakout rooms, live facilitated discussion, and group exercises.
• Virtual Self-Study: Asynchronous modules allow learners to go through material at their own pace. This method is ideal for reinforcing knowledge, enabling individuals to revisit content and focus on areas where they need extra practice.
• Blended Learning: The most effective training strategies often combine multiple delivery modes. Hybrid training that blends self-paced learning with live instruction offer the best of both worlds, enabling teams to absorb material independently, then apply it in a collaborative setting.
• Reinforcement and Coaching: Don’t stop once the initial training is over. Continuous learning through coaching, quizzes, and refreshers helps maintain momentum and ensures that new skills are truly embedded. Regular reinforcement sessions will strengthen retention and lead to long-term behavior change.

Carefully selecting the right mix of these delivery methods based on your team’s preferences, learning culture, and geographical spread will optimize engagement and learning outcomes.

Step 6: Measure and iterate.

No training program is complete without proper evaluation and iteration. Organizations with effective training programs continuously measure their results and refine their approach based on data.

Training Effectiveness Measures Used by Organizations with Highly Effective Sales Training
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Here’s how to ensure you’re tracking the right metrics:

• Sales Performance Metrics: As we mentioned earlier, start by determining which business outcomes you want to impact (e.g., win rates, sales cycle length, average deal size). By regularly measuring these, you’ll be able to assess whether your training is producing the desired results.
• Feedback from Facilitators, Employees, and Managers: Surveys and feedback forms are invaluable tools for gathering insights from all participants. Facilitators may provide observations on areas where learners excelled or struggled, while employees and managers can give real-time feedback on the relevance and effectiveness of the material.
• Knowledge Retention: Post-training assessments and quizzes can help measure whether participants have retained and understood key concepts. Tracking how knowledge evolves over time through follow-up assessments will also show whether your reinforcement efforts are working.
• Skill Application: Observing how effectively sellers apply newly acquired skills on the job is crucial. Managers should monitor performance through role-playing, call reviews, simulations, or ride-a longs to see if the training is translating into real-world behaviors.

Use your findings to tweak and refine the training content, delivery methods, or reinforcement. Continuous improvement is key to ensuring that your sales training stays relevant, impactful, and aligned with both short-term needs and long-term strategic goals.

By measuring and iterating, you’ll ensure that your training not only addresses current gaps but also evolves to meet future needs. In this way, your organization can consistently deliver high-impact, ROI-driven training programs that empower your sales team to perform at their best.

By following this step-by-step guide, you’ll be better positioned to plan and implement an effective sales training program. Each step, from defining your goals to continuously refining your approach, is crucial to ensuring long-lasting improvements in sales performance. Be sure to leverage the resources in the CSO Planning Essentials Compendium for even more practical resources and set your team up for success this year.

1. RAIN Group Center for Sales Research and Allego, Continuous Learning in Sales.