A Comprehensive Guide to Sales Coaching

For many sales organizations, coaching is a tricky subject. As an ongoing activity, it is sandwiched between more exciting events, like onboarding and sales training. But sales coaching also suffers from a secondary malady. Though everyone agrees it is necessary, few do it right.

As sales coaching and training experts, let us dispense with one persistent myth. There is no “one-size-fits-all” way to coach. The best sales coaching is dependent on the manager/rep relationship. What is right for one sales rep may not work for another. Rather than fit your coaching into a preconceived box, it is more productive to consider today’s best practices. This way, effective coaches can tailor their coaching to their individual sales reps.

What is Sales Coaching 

Sales coaching is the process of evaluating and supporting sales professionals to improve performance and achieve desired results. The key word here is desired. For coaching to be effective, there must be specific goals. Otherwise, there is no way to measure the effectiveness of the coaching.

Three results to consider are:

• Sales goals and outcomes
• Performance metrics, such as KPIs
• Personal objectives

However, while there is a desired result, how we achieve the result varies. Sales reps are not automatons or a homogonous mix of familiar stereotypes from popular movies. They are an eclectic blend of personalities with two related goals. These are to help customers and achieve their own personal and professional rewards.

In the same way, while the metrics remain consistent, managers should tailor coaching to the rep. They must target the outcomes but alter the approach. This includes purposeful coaching that addresses the skills and behaviors to hit their marks.

In addition, as the sales environment changes, coaching must adapt. Managers can no longer gather their team in the conference room for an impromptu quota meeting. Today’s teams are too dispersed. What once worked in person might not be best for remote sales professionals.

Plus, whereas a number-centric coaching style once thrived, today’s sales representatives want more. It is no longer productive to simply set a quota and expect reps to reach it. Modern workforces thrive on terms like culture, transparency, social awareness, and life/work balance. They might not respond well to hard numbers unrelated to values. To be effective, sales coaching must be relatable and speak the language sales representatives understand.

What Sales Coaches Do

To start, sales coaches must understand the duel and sometimes competing needs of coaching. On the one hand, you have the organization’s collective goals and objectives, the “desired” results. On the other hand, you have the sales professionals’ personal motivations and rewards. These may be monetary, but they can also include other considerations, such as life/work balance.

In addition, to be effective, sales coaches must provide the following:

• Team meetings
• One-on-ones
• Monitored and joined sales calls
• Role play and other exercises

Team meetings can be considered an overview or macro coaching. This means communicating management directives all reps must know and ensuring an even playing field. It can also build teamwork and bounce ideas from top performers to new or struggling sales reps.

One-on-one coaching can then target the specific behavior and activities of these individual sellers. If Maddy excels at building rapport but falters in product differentiation, coaching should target this skill. The same goes for Max, who struggles with closing.

One of the most effective coaching techniques is monitoring sales calls. This lets coaches view reps in real time. Here, they can praise what works and why along with what can improve and how.

This is sales coaching at the micro level. It is when coaches use their expertise and experience to address the specific needs of their team members. In addition to a rep’s needs, however, coaches must consider personalities. This ensures they convey the right message.

In this, coaches should be less prescriptive—like “Do this!” Instead, a descriptive or illustrative approach can help. For example, consider delivery, such as, “When the customer paused on price, you addressed features. Next time, consider adding value first.” In addition, storytelling can foster relationships and turn critique into counsel. Of course, this depends on the type of coaching and the rep’s coachability.

Role play and other exercises are also effective coaching methods. This helps reps prepare for situations they will encounter and develop strategies to succeed. Plus, good coaching can then take this back from the individual or micro level to the collective team. Let your team create specific scenarios from their own experience. They can in turn act out and discuss their approaches.

The Goals of Sales Coaching

As salespeople transitioned from product-centered “order takers” to trusted advisors, the role of coach has shifted. With the cost of hiring, onboarding, and retaining talent, sales coaches must balance the needs of organizations and individuals. Of course, shifting roles require shifting goals.               

Today, effective sales coaching should provide the following:

• Ongoing communication
• Resources
• Emphasize solutions
• Improve performance
• Build strengths
• Limit weakness

For coaching to succeed, it cannot be irregular, haphazard, or disorganized. Instead, it must be regular, ongoing, and formalized. Of course, how often coaching occurs will vary by organization. Once a quarter may be too infrequent. Once a week may be too often. Instead, coaching intervals should provide reps with flexibility and opportunity while considering the bandwidth of the sales coach.

Communication is central. However, this does not mean sales managers speak more. In fact, like effective sales reps, coaches should listen more than they speak. Before telling reps what to do, ask how they felt about an engagement. Let them describe what worked and what might improve.

At the same time, however, coaches should supply continuous resources, and they must be relevant. This includes impromptu advice, books and videos, and relevant thought leadership. Today, there is a wide array of material online, including sales blogs and webinars. Good coaches should target these to specific reps.

In sales, it can be easy to overemphasize numbers. This does not mean metrics and analytics are not important. However, good coaches know that, like clients, reps want solutions. It is one thing to know the target. It is another to hit it.

In addition, today, meeting quota is the average. It is expected if not required. Top coaches know this is not good enough for the organization or the sales rep. Rather, coaches must continuously move the bar to increase performance.

The key is knowing each rep’s strengths and weaknesses. All reps do not start at the same place. However, the coach must increase performance across the board, from the highest achievers to the lowest. Generic sales lessons will not reach all reps. They also will not help those who already excel. Coach to the individual rep at their respective level.

The Benefits of Sales Coaching

• Relationships
• Culture
• Retention
• Performance

As with sales reps and clients, in coaching, relationships are key. Sales leaders who lack positive and productive relationships with reps cannot coach successfully. At the heart of coaching is honesty, compassion, and a shared desire for results. Without these, messages can be misunderstood, intent can be misconstrued, and reps will be unmotivated.

Central to successful sales coaching is culture. This is not limited to a happy and pleasant environment. As necessary as these are for productivity, organizations must build a culture of coaching. This is where coaching is emphasized from the top down. The entire organization, from the suites to the cubicles, values the means and goals of sales coaching.

For sales reps, a coaching culture is a prime motivator to succeed. It shows that leaders share their commitment. This is more than motivational phrases on coffee mugs. It is an active and persistent enablement. Further, sales coaching builds a sales rep’s investment in your organization. Rather than seeking new opportunities elsewhere, reps will learn and grow with yours.

More than anything, however, effective sales coaching boosts performance. In addition to relationships, culture, and retention, this affects an organization’s bottom line. If happy sellers meet quota, motivated and enabled sellers exceed it. They will not only do what they must for a paycheck. They will do more to ensure their own and their organization’s success.

As sales organizations and sellers are unique, the best sales coaching is specific to your team. Of course, this is not to say sales coaching must be groundbreaking. Like your products and services, even the greatest are often variations of what works. Therefore, know the best practices for sales organizations and professionals and implement what makes sense in your environment. In the same way, selling is creative, coaching should be dynamic. It is not rote, tedious, or static. Instead, sales coaches should customize coaching to what drives and motivates their reps.

Establishing the Coaching Culture

As one might assume, the concept of an open dialogue within an organization is only effective when everyone agrees to check their egos at the door. There is a tendency for reps to get defensive when attempting to be coached by a manager, and the same tendency when a rep attempts to give feedback to a manager – no matter how constructive in nature it may be.

How can this be avoided?

Although communication is encouraged in every direction, coaching and therefore a culture of coaching, is something that must be mandated from the top down.

The first step in implementing a coaching culture is to achieve complete buy-in from company executives. Executives need to send a clear message to the organization, outlining the manner in which they would like internal communication to be handled. From there the concept needs to be endorsed and embraced at every level.

How Sales Coaching Differs From Sales Training

The other half of the coin, sales coaching isn’t about new knowledge and skills acquisition. Rather, it’s about helping employees apply learned material and theory to their daily job, and to use those skills and information sets to the highest possible level. The objective here is mastery of skills and knowledge, and coaching is arguably the single greatest factor in whether or not sales training is ultimately successful. Far too often, we see sales leadership think the solution to failed sales training is to provide more training. But the reality is, the employees already understand the knowledge, skills, and theoretical foundation for what they’ve been taught. The problem is, they don’t know how to implement what they’ve learned into their jobs. And that’s where properly executed sales coaching can correct the issue.

In practice, sales coaching involves refinement, adjustment, and tweaking of an employee’s currently possessed skillset and knowledge. Furthermore, unlike sales training, which is static (the information and skills are learned and practiced or refreshed, and the training event ends), sales coaching is a dynamic, constantly reoccurring process – happening much more frequently than sales training.

Sales Coaching in Action

Coaching at its best means investing in individual contributors over the long term. As the legendary football coach Vince Lombardi once said, “The difference between a successful person and others is not a lack of strength, nor a lack of knowledge, but a lack of will.” Give your reps that will. And make it clear that they have a stake in the game. Only then will they have a chance of scoring winning goals.

Updated 4/10/2025

Nick Kane

As Managing Partner of Top 20 Sales Training and Consulting company Janek Performance Group, Nick Kane works with corporate clients to develop sales strategies and implement sales training programs that focus on cultivating a more client-focused environment that drive results in today’s marketplace. During his career, Nick has trained more than fifteen thousand sales professionals worldwide, and he is passionate about helping sales leaders and sales professionals improve their careers and, as a result, their lives. He is coauthor of the book Critical Selling and a regular contributor for Training Industry and Selling Power.

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