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Essential Qualities of Highly Successful Online Sales Training

By Chris Evans on September 2, 2020

The level of disruption to the sales environment today is immense, with sales practices that would have been industry leading 10-15 years ago quickly becoming irrelevant. The digital revolution has empowered buyers to expect a level of personalization, insight, and accommodation to their buying process that would have been unimaginable at this scale 20 years ago. Customers expect companies to accommodate simple transactions and digitally empower them to execute transactional sales efficiently and at their leisure. When they interact with sales teams they expect them to depart from old sales techniques and adopt a customer-centric approach that adds real solution value that they couldn’t have done themselves with a Google search and 20 minutes. In fact, in one study, 61 percent of salespeople said selling is harder or much harder today than it was five years ago. 

Also, given that sales teams are increasingly dispersed, particularly as a result of COVID-19, making online sales training available to your team is a critical aspect of any competitive strategy. To help ensure your ROI is as high as possible, here are 5 essential principles of highly successful online sales training initiatives are built on.


Start with the sales leaders

Aligning, and where necessary upskilling, sales leaders makes them more engaged and more capable of leading others to success. Highly effective sales leaders not only show sales reps what successful selling looks like, but they also guide and coach individuals on their teams to follow sales strategies and tactics that are proven to work in their industry and with their clients. Engaged sales leaders also drive accountability to participate in and apply the learnings. In fact, one study found that 69 percent of salespeople who exceeded their annual quota rated their sales manager as being excellent or above average.


Development for sales leaders should include areas such as change management, empowerment, strategy development and execution, coaching, and performance management. These should be prioritized based on feedback from the sales team and the leaders themselves.


Communicate why training is happening and the benefits regularly 

It’s hard to care about something you don’t understand, and yet, sales teams often find themselves pulled into an online sales training session with little to no explanation of its purpose or how it will help them drive greater sales. Employees today crave a deeper understanding so they can identify the purpose of training and see how it impacts their overall success at work. Without this, especially in sales, they will see the time spent in training a waste of time and will be distracted by trying to make sales while passively attending the online sales training.


In light of this reality, it is important to ensure your online sales training has a communication strategy that builds excitement before the training begins, reminds participants of the rationale during the training, and reinforces the importance of what was taught post-training. Doing so will make it infinitely easier to engage your sales teams in the training process and improve your odds of seeing it applied.

Learn practical steps to building a world-class sales team in this helpful  guide.

Take a high engagement approach

In the case of sales teams, how you deliver training will be almost as important as what you deliver. Salespeople live in a distraction-rich environment with many demands that can make focusing fully on training a challenge. To actively engage salespeople with the training content, you can do so with experiential learning and a world-class facilitator to keep their attention in training, where it should be. 


When experiential learning is used in online sales training individuals learn by participating in interactive learning scenarios that mimic the workplace. The key differentiator of this delivery method is that it builds conviction within salespeople to do things differently or think about the customer in a new way. Learner engagement significantly increases when this methodology is deployed compared to passive, self-guided learning.


Go beyond knowledge transfer, build conviction and provide clarity on how to apply content

All sales training is not created equal, and simply offering static online sales training is no guarantee that the behavior of your salespeople will change. In my experience less than 20% of participants are likely to do anything different as a result of that kind of knowledge dump. To ensure you deliver sales training that makes a measurable impact, it’s important that your training shows participants the gap in their behaviors and how to close it. 


Virtual Live Online sales training that has participants personally and actively involved in their own learning in psychologically safe approaches, facilitates understanding of the new behaviors and allows participants to internalize them quickly. Once this conviction has been built participants must then begin to build competence through application. By providing time in the safety of the online sales training classroom to practice the new skills and tools, ask questions, and work with colleagues, sales professionals will emerge more competent and confident.


Reinforce, coach, and share application back on the job

Training can reach its full potential only if it is not seen as a fad or “one off.” Regular retention and reinforcement activities ensure a strong return on training investment and keep individuals focused and engaged long enough to form new habits. Research shows that regular reinforcement of training content also improves overall sales rep effectiveness. One study found that organizations that use post-training reinforcement realize 34 percent more first-year sales reps achieving quota than do organizations that skip reinforcement. Training retention and reinforcement activities can include: 

    • Reinforcement and Coaching by Leaders: Sales leaders coach reps as they apply and begin to master new sales behaviors. They can also reinforce newly learned behaviors by recognizing progress and successes in a timely manner and proactively engaging individuals and their team as a whole in conversations about how to apply.
    • Best Practice Sharing: In my experience the most credible application content comes from other sales team members sharing what is working in the field. By capturing, curating and celebrating participation in growing together sales teams can self generate the most useful and relevant application.
    • Mobile and gamified reinforcement: Learning content, questions, and feedback from training can be delivered to employees using a range of micro-learning technologies that keep the learning top of mind, prioritize focus at the individual level and create a learning community beyond the class event.

Self-Assessment and Personal Learning Plans: Facilitating growth focused self assessments, culture pulse check surveys periodically gauge employee focus and attitudes towards growth. Engaging with those realities with empathy and creating an environment that supports “owning your own development” with the full-support of the sales enablement or training team creates the right framework to grow together.



While sales training always seems like a “good idea” no senior team wants to pay for training that doesn’t impact results. Translating good training content into tangible results takes more than logging into an online classroom and hoping employees know how to apply the knowledge. You must change their behavior and improve results. With the right strategy that includes training for sales leaders and representatives combined with the right content, delivery and reinforcement, you can deliver impactful online sales training that helps your sales organization build the needed skills to improve sales effectiveness.

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Chris holds an MBA from Cornell-Queens Executive MBA Program. From 2006-2014, he was the Executive Director and COO of Muskoka Woods Sports Resort. He is now the Executive Vice President Marketing and Business Development at Eagle’s Flight. His diverse executive background managing portfolios include operations, sales and marketing, finance, fundraising and Human Resources. Eagle’s Flight benefits from Chris’ experience and expertise in leading, facilitating and consulting for client executive teams, specifically in the development of their strategic vision and plan.

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Founded in 1988, Eagle's Flight has earned its reputation as a global leader in the development and delivery of business-relevant, experiential learning programs that achieve specific training objectives and lasting behavior changes.

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