The Critical Importance of Coaching in Sales

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If you’ve ever played a sport or even supported a competitor from the sidelines, you’ve seen the positive impact (or perhaps the devastating results) of the work of coaching. If you haven’t, think of Ted Lasso, Friday Night Lights (the movie), Friday Night Lights (the show) or A League of Their Own (the movie or the show). Real coaching — good coaching — is not just about scoring points. It isn’t even about winning. It’s about creating organizational change by reinforcing new ideas and skill development, on and off the field.

So, while many sellers read “The Challenger Sale” and wonder “how can I bring this to my organization?” we’d posit that the real question is: “How do I create and sustain organization-wide change?” It begins with understanding the importance of Challenger sales coaching: asking questions, Tailoring conversations, and knowing how to focus a coach’s limited time and energy.

It goes beyond ensuring sellers remember what they learned during a keynote or a single workshop. Research from CEB (now Gartner) research shows that teams that receive high-quality coaching are far more likely to attain or exceed goals, and that combining seller training with coaching is four times more effective than training alone. These teams also report higher job satisfaction than teams getting low-quality coaching. There’s reason for individual sellers to buy into good coaching, as well: CEB research found that effective coaching can improve a seller’s gap to goal by up to 19%.

Yet, as any athlete can attest, not all coaching is created equal. When done poorly, coaching can hurt performance nearly twice as much as good coaching helps. The difference is so stark that it would be better to simply not coach at all than to do it in the wrong way. You can’t afford to get this wrong, so read on to learn more about how you can make the most of your training investments with stellar coaching that leads to real organizational change.

What is sales coaching?

Gartner defines sales coaching this way: “an ongoing and dynamic series of job-embedded interactions between a manager and a direct report, designed to evaluate, correct, or reinforce behaviors that are specific to an individual seller.”

Many organizations make the critical mistake of confusing sales coaching with performance evaluation. Yes, good management requires you to give employees an opportunity for performance evaluation. But coaching is something more.

Coaching is:

  • Developing and improving current skills
  • Setting mutually agreed-upon development goals
  • Frequent, ongoing interactions
  • Asking guiding questions for feedback and active listening
  • Leading sellers to discover the right solution to specific problems

Performance evaluation is:

  • Presenting a picture of the past
  • Evaluating past proficiency against formal performance criteria
  • A timeline set by the organization (annual/bi-annual)
  • Delivery led by the manager
  • Providing feedback directly through telling

It’s common for companies to adopt some sort of formalized performance evaluation process, but how many provide formalized coaching? For that matter, how many provide coaching to their coaches?

Coaching isn’t something that a great seller promoted to a sales management position will immediately do well. The Peter Principle, laid out by Canadian educational scholar and sociologies Dr. Laurence J. Peter, outlines this concept well: without continuous and intentional training, most employees will continue to rise through their organizations until they reach a level of incompetence. In short, coaches need training to deliver good coaching. That’s especially true for organizations who want to see positive outcomes from adopting a new sales methodology.

Why organizational change hinges on sales coaching

Teams might seek out sales training for a variety of reasons, but one big one looms large: they want higher win rates. While choosing a methodology and rolling out training is an essential first step, most companies need to think bigger by considering how to implement change management across their entire go-to-market organization. This means prioritizing reinforcement and coaching from frontline managers – a step many leaders fail to build into their change management plans. When we asked sales leaders about their approach to reinforcement, 66% told us they either offer no reinforcement (11%) or informal reinforcement (55%). Among the same group, 53% told us their organizations lacked a formal approach to coaching.

The reality is, without on-the-job manager coaching, sellers cannot effectively absorb and use what they learn from a book, a training, your sales kickoff, or any other point-in-time learning. To understand why, we can look to the Ebbinghaus Forgetting Curve. This model shows that without reinforcement, learners lose 67% of new information within one day. Within a month, that number jumps to 87%. The best way to combat that trend among newly trained sellers is to empower your frontline managers to coach and reinforce new skills.

chart graphic of the Ebbinghaus Forgetting Curve

Recall the last time you learned a new game. Let’s say it was pickleball. Your neighbor invited you to the court, and over the course of a few hours you learned the rules, hit a few balls, and maybe even won a match. In scenario one, after that initial, intense training session, you went home – and never met up with your neighbors again. Next time someone invites you to play, will you remember the rules? In a second scenario, you parley that initial training session into a weekly court meetup. You grow under Neighbor Janet’s careful tutelage, and soon you have a new favorite activity. Why? You received personalized coaching, got a chance to test your new skills, and benefited from the accountability of a weekly meeting (you really owe Janet dinner).

That’s a lot like training for your sellers. They may learn in the classroom, but they struggle to bring those new skills to life if there isn’t someone there to provide accountability and on-the-job reinforcement.

Coaching provides the essential basis for reinforcement because it:

  • Is experiential and closer to the actual performance (while training is disjointed from everyday activities).
  • Can be personalized to the individual seller development areas and learning preferences, compared to training’s more standard, less customizable approach.
  • Enables seller self-discovery, whereas training tends to be one-way information delivery.

Permanent changes to seller performance hinge on successful Challenger sales coaching. Just look at the work of John Kotter, author of the organizational leadership book Change. In coaching more than 100 organizations through successful (and more often unsuccessful) changes, Kotter began to identify trends and eventually distilled them into eight reasons why change fails.

      1. Not establishing a great enough sense of urgency
      2. Not creating a powerful enough guiding coalition
      3. Lacking a vision
      4. Deciding to move on from the program too soon
      5. Under communicating the vision
      6. Not removing obstacles\
      7. Failing to recognize and share short-term wins
      8. Not anchoring in the organization’s structure and culture

Effective sales coaching can help diagnose, treat, or prevent almost all these issues, either directly or by surfacing issues up the ladder to leaders with the power to manage an effective rollout. Leaders who invest in training without investing in coaching and reinforcement set their sellers up to fail. A coach can turn a generic lesson into a personalized development opportunity by tailoring the conversation to the individual’s performance, leading to bigger performance gains and higher employee engagement.

How good sales coaching stands apart

We so often associate coaching with sports that it’s easy to imagine a sales coach sliding into the shoes of, say, Coach Taylor from Friday Night Lights: calling plays, pulling players in and out, and yes, helping nurture their untapped talents. But even organizations that acknowledge the importance of coaching worry that there may not be “enough” time for coaches to make a difference. This is especially pressing as deals increase in complexity. Even the most well-meaning coaches may find themselves tempted to parachute in to break up the gridlock or “save” the deal, at the expense of coaching opportunities. The ineffective nature of this approach aside, time is not as much of a barrier as you might expect because it turns out, coaching is not a question of quantity.

Challenger research shows that coaching’s benefits plateau around five hours per month. The sweet spot appears to be between three and five hours per person per month — roughly the amount of time a manager might spend with a seller over the course of four one-on-ones set at a weekly cadence.

Good sales coaching is a matter of quality. Gartner, back in the CEB days, surveyed nearly 6,000 frontline reps, finding that bad coaching was twice as detrimental to performance as good coaching was beneficial. That means that it would be better to provide no coaching at all than to provide bad coaching.

Sales leaders should focus not just on coaching, but on adding good coaching. That doesn’t mean empowering managers to call plays as much as it means empowering and training them to ask questions. One hallmark of truly great coaches is the tendency to ask their sellers what would solve a problem, how they should approach a buyer, why a deal is stalled, and on and on. It’s also important to recognize the difference and strike a balance between questions focused on moving the deal forward and questions focused on building a skill. Coaches who spend lots of time talking about deals and little time building skills are essentially playing a game every night without ever attending practice. Coaching skills improves performance over the long term, something that’s particularly important when sellers learn a new methodology.

Relative impact of coaching on performance chart

Moving the middle by coaching average performers

While more coaching isn’t always better – and, in fact, can yield diminishing returns – many sales coaches still face the reality that the sweet spot of three to five hours per seller per week isn’t even possible. Faced with the decision of where (or, more accurately, on whom) to spend their time, many coaches will choose to spend their time trying to coach underperformers up to their standards. Or they might take the more comfortable route, electing to sit more with star performers who make them look good. Both are logical approaches, but neither yields the biggest performance gains.

Instead, our research suggests that the biggest gains come from “moving the middle” by coaching average performers. The reason is surprisingly logical: with help and coaching, these individuals can move from okay to excellent. Because the largest number of performers fall into this category, it’s a shift with the potential to greatly impact overall team performance.

As for the other sellers, the truth might be hard to hear. Coaching low performers provides only marginal changes in performance. Similarly, high performers don’t benefit from coaching guidance in the same way that core performers would. Coaches should spend time with these performers because it improves their job satisfaction and ensures they sit tight on their teams.

Distribution of Relative Sales Rep Performance by Coaching Effectiveness chart

Now, let’s get to the heart of good Challenger sales coaching. Here, the core Challenger skill of Tailoring comes into play. Great coaches know they need to Tailor their coaching approach to each seller across a few specific traits.


How coaches approach conversations with their sellers should vary by individual performance. We already know that coaches should focus on moving the middle by dedicating the most time to core performers, but that doesn’t mean ignoring the other sellers under their purview. For instance, spending time with high performers is enjoyable and helps with retention. Spending time with low performers can afford coaches the opportunity to help them find roles that may be a better fit.

Here’s how effective coaches Tailor conversations across performance levels.

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High performers:

Coaching conversations should focus on job satisfaction, engagement, retention, seller’s value, development and career goals, and Challenger skill opportunities and activities

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Core performers:

Coaching conversations focus on identifying which Challenger skill opportunities will have the greatest impact, setting defined and achievable goals, creating accountability, identifying specific activities for skill development, and motivating and identifying opportunities for long-term growth

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Low performers:

Coaching conversations focus on highlighting each win and identifying short-term goals, embedding training opportunities, and discussing career path and development goals to determine if sales is the right fit

Communication Styles

Good coaches Tailor their communications as well. The SOCIAL STYLE Model lays out four different “styles” with unique approaches to time management, interacting, and making decisions. Understanding where coaches and their sellers fall on this scale can improve communication and lead to more effective coaching relationships.

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The Analytic:

Organized, thorough, logical, accurate, and systematic. They tend to say, “Let me think about this.”

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The Driver:

Candid, results-oriented, strong-willed, decisive and independent. They tend to say, “Let’s take action on this.”

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The Amiable:

Diplomatic, loyal

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The Expressive:

Enthusiastic, ambitious, spontaneous, outgoing, persuasive. They tend to say, “Let me tell you my ideas about this.”

Building Challengers through effective Challenger sales coaching

Of course, this discussion isn’t about coaching broadly (the extended pickleball metaphor notwithstanding) or even about sales coaching. It’s about Challenger sales coaching. Organizations hoping to create effective change by adopting a Challenger sales methodology across their workforce need to foster and reinforce a very particular set of skills.

As a refresher, “The Challenger Sale” began with research from CEB (now Gartner) that revealed that the sales experience was the biggest driver of customer loyalty. This revelation pushed Matt Dixon and Brent Adamson to ask: What makes a good seller? They asked thousands of sales managers to identify the top 20% of their sales force as measured by performance against goal and used the results to sort reps into five profiles. Core performers came from every category, but star performers came from one dominant category: the Challenger. Of all the high performers in the study, nearly 40% were Challengers. Meanwhile, Relationship Builders generated the fewest star performers.

Challengers achieve their success, even under difficult circumstances, by convincing reluctant customers to think differently about their problems. When the authors of “The Challenger Sale,” zeroed in on Challenger behavior, they found that this type of seller excels at four interwoven skills: Teaching, Tailoring, Taking Control and creating Constructive Tension across the sale.

In addition to the four skills, Challengers typically engage in the following behaviors:

  • Maintain a unique view of the world
  • Understand their customer’s business
  • Are comfortable and prepared to discuss new ideas
  • Proactively manage the buying process
  • Generate momentum and urgency toward desired outcomes

We know that most Challengers aren’t born — they’re made. And that’s what makes the work of Challenger sales coaching so powerful. Effective training and coaching can help sellers who identify as a Relationship Builder, Problem Solver, Hard Worker, or even a Lone Wolf, begin selling with Challenger skills. Here’s how that might look across a typical coach’s schedule.

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  • Open a discussion on how Challenger selling positively impacts customers to drive better results
  • Share how customers react to the Challenger approach
  • Have sellers describe how they applied Challenger skills to a recent sales interaction
  • Review Challenger skills and concepts
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Team and leadership

  • Ask peers about their team’s Challenger successes
  • Share valuable internal and external resources that provide customers with a unique perspective (Also part of developing your Commercial Insight)
  • Identify any resources you need to build Challengers on your team
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Ask your team
how you can help

  • “How could I better support your shift to a Challenger approach?”
  • “Where are our team’s biggest strengths? How can I reinforce them?”
  • “What Challenger skills should we practice in our next team meeting?”

Coaching is critical to your sales team’s success

Most sales leaders with an imperative to turn around failing teams seek some sort of organizational change. But, while training might be on their minds, the coaching and reinforcement necessary to making change stick can fall by the wayside. Investing in good sales coaching is an essential, unskippable step along the path to transformation. By understanding that managers should focus on moving the middle and developing Challenger skills through ongoing, personalized interactions, organizations can move beyond short-term streaks to build a winning team of capable Challenger sellers.

If you’re taking the first step toward building that team, know that we view sales as part of the ongoing customer experience, rather than a goal to be achieved or a single transactional moment in time. We’re pushing the vision of “The Challenger Sale” forward by exploring the latest developments in sales and marketing through expert interviews in our webinar series in our Winning The Challenger Sale webinar series and on our podcast.

Join us there to take the next step in your Challenger coaching journey.

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