Why Training Salespeople Is Often Difficult

Training salespeople is critical to building a successful sales team but often presents many challenges. Despite the best efforts of trainers and managers, many sales effectiveness training programs fail to produce the desired results. Understanding the complexities of sales training can help organizations devise more effective strategies and overcome these obstacles.

Key Challenges in Training Salespeople

1. Diverse Skill Levels and Backgrounds

Sales teams often comprise individuals with varying degrees of experience and diverse backgrounds. This diversity can make it challenging to design a one-size-fits-all training program. Some salespeople may already possess advanced skills, while others may be new to the field and require basic training.

That is why the first step we take when engaging with a sales team is having the entire team take a sales effectiveness assessment. We look at 21 competencies that make top-performing salespeople. We receive a team report and a report by person. We offer team training in the biggest sales skills gaps common among sales team members and individualized coaching.

2. Resistance to Change

Many salespeople have established methods and routines that they are comfortable with. Introducing new techniques or changing existing processes can be met with resistance. Overcoming this resistance requires careful planning and communication to demonstrate the benefits of the latest methods.

For example, most salespeople have fallen into the trap of being busy, often too busy to sell. In our training, we provide training to remove or reduce nonsales activities. Salespeople have grown comfortable doing that, which other team members would better handle. This is a big change for some salespeople. They will now be doing more sales activities, and their sales activities will be measured.

One team, for example, found that their salespeople were having sales conversations only 15% of their sellable time. Working with the sales leaders and managers, we increased their time selling to 40% of their sellable time. We established leading sales indicators and tracked them closely. Salespeople who drifted back to their old ways of sales time management were quickly coached.

3. Keeping Training Relevant

The sales landscape constantly evolves due to market conditions, customer preferences, and technological advancements. Keeping training programs up-to-date and relevant to the current market is a continual challenge. Outdated training can lead to a gap between what salespeople are taught and what they need to succeed.

Again, we assess the salespeople, compare their skills to those of over 2.5 million other salespeople globally, and suggest training and coaching to fill skills gaps and address motivation issues and any limiting beliefs we discover.

We also add voice-of-customer interviews to capture what is essential to their customers today. How do their customer decision-makers want to buy today, and what can salespeople do to help their customers? What are customer challenges and constraints today? We build the insights from these interviews into the training to ensure we deliver skills and insights valuable to customers to drive sales growth.

4. Measuring Effectiveness

Evaluating the Effectiveness of sales training can be complex. Traditional metrics such as test scores or completion rates do not always correlate with improved sales performance. Measuring the real-world impact of training on sales outcomes requires sophisticated tracking and analysis.

In each live instructor-led training, we have role-playing scenarios for salespeople to apply the new skills. Here, we see the level of mastery each salesperson has attained and gather insights into additional training and coaching required. We also train sales managers how to observe the skills with customers and debrief sales calls with coaching.

5. Engaging Training Methods

Traditional training methods, such as lectures and slide presentations, often fail to engage salespeople effectively. We refer to this as death by PowerPoint, and rarely does this alone provide the lasting skill improvement a leader desires. Interactive and experiential learning methods, which are more effective, can be more difficult and costly to implement. Keeping salespeople engaged and motivated during training sessions is crucial for retaining and applying new skills.

We deliver a blended stacked learning approach. We use virtual sessions, individualized coaching, live sessions, and support materials like videos and often books based on our training skills. These sessions are delivered in less than one day for 6 hours because as high as 90% of that training will not be retained 48 hours after the training session. We deliver sales skills training virtually in small bite-sized chunks over time with review and refresh in each session. Each virtual session has application exercises we review as a team. The live training becomes a quick review, and then we jump into real sales scenarios and ask the salespeople to apply the skills.

In the live session, we facilitate peer-to-peer learning. Senior salespeople share techniques they have used to win sales, while other salespeople share struggles, and the entire team works to help each other.

6. Application in Real-World Scenarios

Training environments and real-world sales situations often need to be connected. Salespeople may understand the theory behind a technique but need help to apply it in practice. We refer to this as the figure-it-out factor. They know about a skill but have yet to connect the dots to how to use it in their daily work. Ensuring that training includes practical, hands-on components that mimic real sales scenarios is essential for effective learning. We have salespeople develop discovery and qualifying questions in their language to ensure they feel authentic. We practice various scenarios, such as handling common objections and negotiating and closing techniques.

7. Time Constraints

Salespeople are often under pressure to meet targets and may view training as a time-consuming distraction from their primary goal of selling. Balancing the need for continuous training with the demands of day-to-day sales activities requires careful scheduling and prioritization. This is why we have short virtual trainings each month and then live ½ day sessions. Salespeople are already under tremendous pressure to spend more time selling to customers. Our training is designed not to interrupt that objective but to help them have more skill when they sell.

We also need to talk about sales manager concerns. Often, sales managers struggle to commit to the time required to train their salespeople. This is usually because they have participated in poorly designed training that had little impact on sales performance. We must engage sales managers early in the training process to ensure they coach their salespeople to attend and apply the skills they are learning.

8. Personalization

Personalizing training to address individual salespeople’s specific strengths and weaknesses is challenging but necessary for effective development. Generic training programs may not address each salesperson’s unique needs, leading to suboptimal results.

The sales effectiveness assessment tells us what skills the team and each salesperson need to develop. Once the team has improved its foundational sales skills gaps, we can prescribe specific skills training for each salesperson.

9. Reinforcement and Follow-Up

Training should not be a one-time event but a continuous process that includes reinforcement and follow-up. Ensuring that salespeople apply what they have learned and continue to develop their skills over time requires ongoing support and coaching.

As discussed, one-and-done sales training is often forgotten in 48 hours if the salespeople do not have application exercises and reinforcement. We record the sessions for salespeople to view again, deliver handouts of key learning objectives, have homework application exercises after each session, and share the results with the team.

10. Salespeople and or Sales Managers not Coachable

In some cases, we discover salespeople and some sales managers who are not coachable based on how they answered the questions in the sales effectiveness assessment. If they score below 50% out of 100%, we need to discuss a different strategy to improve their sales effectiveness because they will not be engaged in training and often need a figure-it-out factor. The figure-it-out factor is also something we learn from the assessment and helps us understand if they can quickly apply the new skill, process, or tools or if they need more help.

As trainers, we often experience that 60% of a team wants and is eager to learn to improve their careers and make more income. However, 10% of the cohort feels the training is too fast or slow, and 10% are disengaged because they are not trainable or coachable.

I have helped sales teams with some team members who were not trainable or coachable, but how I help them is much different from sales skills training.

The sales effectiveness assessment helps me and the teams I serve quickly identify the sales team members who need and are open to training and those who are not coachable.

Strategies to Overcome Training Challenges

1. Tailored Training Programs

Develop training programs that cater to your sales team’s different skill levels and backgrounds. This could include offering basic training for new hires and advanced courses for experienced salespeople. It could also include market-specific applications and industry training.

2. Change Management

Implement change management strategies to address resistance. Communicate the benefits of new techniques clearly and provide ample support during the transition. Several sales trainers fail to discuss what’s in it for the training participants. Top-performing salespeople have a high utilitarian trait. In other words, they feel that if they invest time in something, they must see a desired return.

The assessment shares where they are today regarding sales skills and where they could be with training and coaching over time. We often take this one step further and share how the salesperson will feel the training in additional income, improved customer relationships, and less drama daily.

3. Continuous Updates

Update training materials regularly to reflect current market conditions, customer needs, and technological advancements. This ensures that the training remains relevant and valuable.

Here, we leverage the voice of customer insights and tackle real challenges and constraints their customers are experiencing.

4. Measure Real-World Impact

Develop metrics that link training to sales performance. This could include tracking sales growth, customer satisfaction, and other key performance indicators.

A byproduct of training is often new KPIs and customer satisfaction surveys six to twelve months after training to see the impact.

We often run a net profit by customer report before training and then six months after to see the impact of training on customer profit.

5. Interactive Training Methods

Incorporate interactive and experiential learning methods such as role-playing, simulations, and hands-on exercises. These more engaging methods help salespeople retain and apply what they have learned.

6. Real-World Application

Design training programs that include real-world scenarios and practical exercises. This helps salespeople bridge the gap between theory and practice.

Today, we asked salespeople to share their most difficult scenarios, and we added skills training and practice sessions in these areas.

7. Efficient Scheduling

You can integrate training into the regular workflow without overwhelming salespeople. This could involve shorter, more frequent training sessions or on-the-job training.

Our most popular design includes two to three monthly virtual sessions with application exercises that the salespeople review with their sales managers and the trainer. We prescribe live instructor-led training so that the salespeople apply the new skills in live scenarios in the safety of their team ( not with customers) until they are comfortable using them.

The live instructor-led sessions are designed for salespeople to apply their learned skills and receive coaching. They are booked months in advance and often are scheduled as part of a sales kickoff event or sales meeting or, in some cases, held before a large trade association event the entire sales team attends.

Some clients use the best examples of application exercises to create sales playbooks, battle cards, and talk tracks available in online learning libraries.

8. Personalized Learning

Use assessments and feedback to personalize training programs. Focus on each salesperson’s specific needs and areas for improvement.

We train sales managers to use the coaching dashboard for each salesperson to prescribe personalized training. Often, sales managers prescribe salespeople to revisit and refresh past training and discuss the sessions when the sales manager observes the salespeople struggling with a skill.

9. Ongoing Support

Provide continuous support and coaching to reinforce training. Regular follow-up sessions and refresher courses can help ensure that salespeople continue to develop their skills.

We train sales managers and other sales leaders on how to add sales skills reviews to their quarterly performance reviews and weekly coaching sessions.

Often, we suggest one of the three learning library platforms, and the sales managers can prescribe short training modules based on each person’s learning path.

We also suggest books for sales teams to read, YouTube videos to watch, and articles to refresh and reinforce sales training.

Some teams want team coaching sessions monthly, and we refresh and then role-play common scenarios.

10. Sales Manager Training and Ongoing Support

We ask sales managers to participate in each sales training session and review the homework assignments. We then train them in skills like coaching, time management, and recruiting and coach them through the pipeline. Finally, we equip them with skills and tools to keep the training and coaching alive.

One of the most scalable parts of training sales teams is training managers.

Often, we provide one-on-one coaching for sales managers once or twice per month after their training.

Training salespeople is inherently challenging due to their diverse skill levels, resistance to change, and the need for ongoing relevance and engagement. We often ask sales managers or top-performing salespeople to deliver training, and they have little knowledge of sales training best practices and methodologies. As a result, we often see easy training for the trainer to deliver but fails to deliver the results the team desires.

However, by understanding these challenges and implementing targeted strategies, organizations can develop more effective training programs that drive real sales performance improvements. Investing in tailored, engaging, and continuous training ensures that sales teams have the skills and knowledge they need to succeed in a competitive market.

Download my white paper, Sales Training Reimagined, for more of my advice on improving your team’s sales skills.

How effective is your sales team today?

How much more effective could they be?

What impact would improving sales effectiveness have on your bottom line?

Do your salespeople know how to ask great questions in discovery and qualifying, or is your pipeline full of sales forecasts that will never become revenue?

Do your salespeople know how to ask for the order, or are they like 67% of salespeople struggling with sales closing skills?

Are your salespeople leaving money on the table because they do not know how to negotiate?

The good news is that you do not have to guess anymore.

As the above image illustrates, we can assess your team’s skills and prescribe training and coaching to help your team improve sales skills and drive explosive growth in revenue, market share, and gross margins.

We work together to design sales training, processes, and coaching programs to improve sales effectiveness and fix any problems we discover.

Let’s schedule a call if you want to improve and transform your sales team’s skills and results.