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6 Ways to Customize Training for the Individual

May 14th, 2021

As true as there are differences between the generations, there are also differences within a generation. For example, not every millennial prioritizes working for an ethical business. And not every boomer has been left behind by the digital revolution. The most important thing is to treat your team as a set of individuals and be willing to provide diverse options based on the person. In coaching, one size doesn’t fit all. You need to understand your workforce and their values to offer flexibility that fits the way they work and learn. By providing options that fit their unique personality and outlook, you can help improve individual results, creating a more significant impact on the organization.

In doing this, sales enablement leaders can cater to all generations and personalities, from 30-year sales vets to newer reps with just a few years under their belt.

Some reps strongly prefer a less formal, just-in-time training structure they can consume in “snackable,” bite-sized amounts. At the same time, others prefer more traditional formal curriculum-based training. The preferred learning methods may differ from rep to rep, but what stays the same is the need to engage in impactful conversations with buyers every time.

Fortunately, sales readiness platforms enable organizations to cater to a healthy mix of informal and formal learning to help all sales reps prepare for buyer interactions.

Let’s look at how you can alter your coaching strategy to appeal to your reps using sales coaching technology.

1. Digital Coaching Across Digital Channels

Employees are increasingly digital natives. Not only are they comfortable with things like video and mobile technology, but they also often prefer it. Sales enablement for these individuals is about making your content and resources accessible to reps digitally where and when they need it. While the basics of selling haven’t changed, what has changed is how you can deliver training and coaching.

Ensuring your sales coaching technology can be accessed and utilized from wherever your reps need it maximizes engagement.

2. How Video Coaching Technology Works

Unlike other corporate employees, salespeople can’t just complete their training and move on; they must understand the skills and knowledge necessary to sell effectively. Sellers need to feel confident and prepared as revenue goals rise. Sales leaders need confidence that every rep has mastered critical messaging, processes, systems, and more. It is just as important for sales managers to validate that reps have learned essential messaging, strategies, techniques, and more. Video coaching technology can help in both areas while creating a culture of coaching ingrained in the DNA of your sales organization.

Video coaching starts with a request. For example, a sales manager may request his or her team to share their best elevator pitch on a new software feature that the company is offering. Reps can submit their video responses to this challenge via their phone or laptop. After managers assess each video using scoring and performance ratings, they can then provide constructive feedback and identify which team members need practice. Helping to save time and simplify the coaching process, you can introduce automating coaching and AI-powered insights to your assessment program.

The best submissions quickly become on-demand learning content allowing others to see real examples of compelling pitches.

Informal Learning

Peer and just-in-time learning primarily make up the informal coaching. Without structure or scoring criteria, reps will feel less pressure and have more fun with them.

3. Peer Learning

Peer learning drives reps’ performance by capturing and sharing knowledge throughout your sales team. This knowledge can be passed down from veteran reps to newbies or from A players to B players through video coaching. One example of a peer learning challenge would be to have your reps explain their most innovative prospecting technique. Reps can share their best-selling tips while picking up new ideas from colleagues to add to their repertoires.

Peer learning challenges should happen frequently – weekly or bi-weekly – and submissions should be under five minutes long. This type of learning should be subject matter expert-created, sales enablement refined.

It is important to remember how your veteran reps bring with them years and years of selling experience to share with their more inexperienced colleagues. Peer learning is a great way to help bridge that gap and initiate knowledge sharing.

4. Just-in-time Learning

Just-in-time learning is one-on-one coaching and initiated by either the sales manager or the rep. Suppose a rep wanted to practice how they would handle a significant closing call. In that case, they could practice via video and send the recording to their manager. Or a sales manager may initiate a just-in-time coaching session for a rep that is struggling with their negotiation tactics.

This type of learning can be thought of as “in the moment” coaching and should happen regularly – at least once per week.

Just-in-time learning allows for in-the-field coaching opportunities for reps to hone their skills allowing for personal development opportunities.

Formal Learning

Individual and organizational mastery make up formal coaching. These learning opportunities are highly structured and involve the content sales reps need to master to produce impactful conversations with buyers.

5. Organizational Mastery

Organizational mastery consists of the core competencies that the entire sales force must master. For this type of training, measurements of success should be clearly defined upfront. The rep must be fully aware of the criteria used to assess them. Examples requiring organizational mastery include new hire onboarding, new product launches, a new sales methodology.

Remember to let your reps know who will be reviewing their submissions upfront and keep the number of reviewers to less than five. Full transparency is critical to the success of organizational mastery.

6. Individual Mastery

Individual mastery includes continuous coaching and assessment focused on the ongoing development of individual reps. These activities could consist of leadership development or even onboarding if a rep joined the company after group onboarding already occurred.

Rather than immediately giving a star rating, ease into feedback. Ask reps what they thought they could’ve done better, as well as helping them understand what they did well and what needs improvement.

To allow reps to receive different points of view, consider switching up the reviewer every so often. Doing this also takes some of the pressure off having to present to their direct manager.


The way individuals learn is unique no matter a seller’s generation. The key is to offer diverse options using technology-based programs to resonate best with their individual needs. Features such as video-based coaching and automated coaching with machine analysis are critical to implementing the best coaching strategy.