After 10,000 Hours of Challenging Customers, Are Your Sales Reps EXPERTS?


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By 2016 the first generation of Challenger Sales Reps had been Challenging customers for over 10,000 hours. That seems like a lot of Challenging!

This post is a retrospective look back to attempt to answer the question “Is Challenger working as planned, and if not, what mid-course corrections should be made?”

The Gladwell Equation: 10,000 Hours of Practice = EXPERT Fluency Level

How long is 10,000 hours you ask? Well, in the Monday through Friday working life of a B2B Sales Rep, 10,000 hours equals 5 years.  So it was 5 years ago this year that the first batch of newly-minted Challenger Sales Reps were released into the customer jungle, with the explicit instruction to “go forth and challenge the heck out of as many customers as you can”.  So what is the verdict, is it working or not?

If you’re a reader of books like me, does “10,000 hours” sound familiar?  Well, as it turns out, 10,000 hours also happens to be the amount of “Practice Time” that is required for a novice in any field to become a fluent EXPERT.  This is the provocative conclusion offered by Malcolm Gladwell in his best-selling book titled “Outliers”.

10,000 hours; what a coincidence!  If we apply The Gladwell Equation to the first generation of Challenger Sales Reps (at least those still practicing the Challenger craft after 10,000 hours), we can deduce that these Challenger Sales Reps should be EXPERTS.

So if your company has embraced Challenger, the question is “Are your sales reps EXPERT Challengers?

Challenger: A Selling Methodology Designed with a CUSTOMER-FIRST Mindset

For the record, having come from the “buy-side” as a Fortune 500 CFO, I resonated with the CUSTOMER-FIRST mindset promoted by the Challenger Sales Model when it was launched over 5 years ago.

Never before in the history of B2B Marketing had a CUSTOMER-FIRST sales methodology been more needed.  The advent of the internet and advances in other forms of technology had converged to completely change the customer’s world forever.   5 years ago it was abundantly clear to customers that B2B Marketers were losing their influence over the investment decision process.

Challenger Held Out Hope to Both Sides

The B2B Marketing profession was at a crossroad: either they would re-establish their relevance with customers or they would die a slow death.  The Challenger Sale held out hope to B2B Marketers that they wouldn’t die the death of irrelevance.

But here we are in 2016 and B2B Marketers continue to struggle gaining relevance with customers.  Customers don’t trust sales reps, even though they continue to search (because of the constant PRESSURE to improve performance) for customized business advice from people outside of their organization.

Customers desperately want trusted Business Advisors (who just happen to be B2B Marketers) because Business Advisors don’t “sell” or “market”.  Instead, they offer CUSTOMIZED business insights on their company.  In 2016, Business Advisors are more RELEVANT to customers than B2B Marketers.

So it was that the Challenger Sales Model held out hope, not only to B2B Marketers, but also to customers, that B2B Marketers would one day be transformed into trusted Business Advisors.  The CUSTOMER-FIRST theme in the Challenger Sale was refreshing.

But customers are smart. They knew the key would be whether Challenger would get properly implemented in the field by B2B Marketers.  They wondered if it would deliver on its promise and favorably impact their actual CUSTOMER EXPERIENCE working with sales reps.

I Confess I Had Concerns about Implementation

Over the last 5 years I began to have concerns about whether Challenger would actually get “properly implemented” and CHANGE THE BEHAVIORS of B2B Marketers in the field.   B2B Marketers are slow to change behaviors unless they see immediate value in the change.  I knew (as did the authors of the Challenger Sale) that Challenging was a learned and practiced behavior.  Challenger would take patience and persistence to successfully implement across a diverse sales force.

I also had concerns about the multitudes of B2B sales reps that weren’t naturally born to CHALLENGE, and whether they would survive a Challenger implementation.  I wondered about the sales enablement and learning & development organizations and whether they would run into implementation issues and cultural resistance.

And finally, I wondered about whether the marketing organizations of Challenger client companies were really up to the task of implementing Challenger.  I knew the importance of marketing support in the critical path of a Challenger implementation, and there was no room for error.  Here’s an example of my concern in this area: The Challenger Conundrum: What If Marketing Isn’t Up to the Challenge?

What Is the Verdict? Are Your Sales Reps EXPERT Challengers?

So on this quinquennial anniversary of arguably the most highly-marketed B2B selling methodologies in decades, I have 3 questions for Challenger-client companies:

  1. What is the verdict?  Are your sales reps EXPERT Challengers?
  2. If not, why not?
  3. What mid-course corrections can be done to begin producing Challenger EXPERTS?

Personal Observations on Question #1

I can attempt to answer the 1st question (What is the verdict?) by sharing my personal observations working with Challenger sales reps in training workshops. Many of my clients have embraced elements of the Challenger Sales model, so I have the unique opportunity to work with Challenger reps in my Business Advisor Training (BAT) and CRED Training workshops.  Unfortunately, I haven’t seen many EXPERTS so far.

Here are a few observations from participating in role play with them.

Conversational skills are below-average.  Skills gaps are obvious in two critically-important competencies: (1) being able to conduct rapid customer due diligence and quickly uncover UNIQUE CUSTOMER INSIGHTS, and (2) being able to leverage that customer-specific insight in the natural flow of a customer conversation in order to demonstrate credible-levels of customer-specific business and financial acumen.  In role-plays, sales reps seem overly stilted, as if they are reading from a script.

Listening skills are below-average.  It’s almost like their natural conversational curiosity and in-the-moment instincts have been taken away from them.  Many reps seem to be listening with the intent to RESPOND, rather than with the intent to UNDERSTAND.  It’s as if they can’t wait to get back on their “commercial teaching” script.

A Brief Historical Digression: The Challenger Profile Emerges from the Survey

To attempt to answer the 2nd question (Why aren’t Challenger Sales Rep EXPERTS yet appearing?), let’s briefly look back to the birth of Challenger to find some possible insights.

The profile persona of a Challenger Rep was born out of a provocative data-intensive study designed to identify the “abilities” of top-performing sales reps. To promote its findings, the authors (The Corporate Executive Board’s (CEB) Sales Executive Council (SEC)) published a book titled “The Challenger Sale … Taking Control of the Customer Conversation”.  The book was purposely provocative and full of commercial teaching insights, and it created an instant buzz in the B2B Marketing world.

Prior to the study, conventional wisdom suggested that the DNA archetype of a “high performer” was that of a RELATIONSHIP BUILDER.  For decades sales leaders had preached (and reinforced through formal sales skills training) the virtues of methodically building deeper customer relationships.

However, as you might expect, CEB/SEC challenged this conventional thinking with its provocative interpretation of the study data.  They controlled and teased the survey data, and in the process created a new seller profile cohort provocatively labeled “The Challenger”.

Details of the study caught my attention.  Only 39% of the “high performers” surveyed fell into the new Challenger profile cohort, but it turned out to contain the most “high performers”; it was 1.5 times the next largest cohort identified.   So, unexpectedly, the Challenger profile became the marketing headline challenging conventional wisdom.  It certainly caught the attention of B2B Sales Leaders.

CEB/SEC’s study also gave birth to 4 seller profiles in addition to The Challenger.  They were: The Lone Wolf, The Hard Worker, The Reactive Problem Solver, and The Relationship Builder.  Interestingly, The Lone Wolf profile came in a close 2nd to The Challenger at 25% of the “high performers”.

Perhaps the most provocative study finding, however, was that The Relationship Builder (the profile preferred by Sales Leaders) came in last, at only 7% of the “high performers”.  The frenzy had been ignited; conventional thinking had been turned on its head!

Primer: “Abilities” of a Challenger Sales Rep

According to CEB/SEC, Challenger Reps posses 3 distinguishing “abilities”:

  1. Challenger Reps are able to teach for differentiation given their unique perspective on the customer’s business and ability to engage in robust customer conversations.
  2. Challenger Reps are able to use their superior sense of a customer’s economic and value drivers to tailor the message for resonance to the right person in the customer’s organization.
  3. Challenger Reps are comfortable discussing money, and when needed, can press the customer and take control of the sale.

You will know you are in the presence of a Challenger Rep EXPERT when you see these “abilities” on display during a customer conversation.

“39% of High Performers” is a Small Cohort When You Look at the Entire Sales Force

Here’s a TRUE/FALSE question.  According to The Corporate Executive Board’s (CEB) Sales Executive Council (SEC), authors of The Challenger Sale, the majority of “high performing” sales reps are Challenger Reps.  True or false?  The answer is FALSE.  Of the 2,000 “high performing” reps originally studied, only 39% fell into the Challenger profile.

Stop and think about what you just read; 39% is not a very big number when you consider the broad mix of seller profiles in a typical sales force, even just looking at the “high performing” cohort.  In fact, 39% is a minority of sellers, whereas a majority 61% of “high performers” is non-Challenger reps.

Let’s extend the math one more step.  If we were to assume that a company’s “high performers” constituted 20% of the total sales force, then the percentage of sales reps naturally characterized as a Challenger is only 7.8% (20% times 39%).  Of course, there may be Challenger reps in the “low performers” cohort that aren’t being counted, but that’s not likely according to CEB/SEC.

So 7.8% is a probably a good estimate of the concentration of natural Challengers found in a sales force.  What are the implications of that when you are considering a Challenger implementation?

If we apply this 7.8% estimate to a company with 100 sellers, the result is 8 Challenger reps, leaving a whopping 92 reps who are not Challengers.  This Challenger/non-Challenger mix of 8/92 demonstrates the point: the overwhelming majority of sales reps in a sales force are not, by nature, Challenger Reps.  This makes sense to me as I don’t think many sales reps are naturally born to be Challenger Reps.  So they have to be “nurtured” (re-wired) to mold them into Challenger Reps.  And the “nurturing” is probably left to their Sales Leaders during the implementation phase.  Unfortunately, the odds are that most of these Sales Leaders are also not Challengers!  This presents yet another implementation hurdle.

A Challenger Implementation Is a MASSIVE Change Management/Skills Training Journey

If 8/92 is an accurate estimate of the Challenger/non-Challenger mix in a typical sales force, then we can understand the size and complexity of a Challenger implementation.

But what if Sales Leaders RUSHED the implementation of Challenger, purposely or not?  Critical Success Factors (CSFs) may have been overlooked, such as sales rep “buy-in”, sales manager alignment, skills assessment, gap identification, skills training curriculum development and delivery, marketing support and collateral, sales enablement support, measurement systems, and ongoing field coaching and support resources.  There was a lot that could have fallen through the cracks.

So why would Sales Leaders RUSH the implementation of Challenger?  What would motivate them to rush so much?  Well remember that CEB/SEC borrowed a page right out of their Challenger Rep playbook with their provocative marketing campaign.  They challenged conventional wisdom that a Relationship Builder was the best seller profile by providing solid data-driven evidence.  They even showed how the favored Relationship Builder profile came in last.  This convincing evidence persuaded many Sales & Marketing VPs to act immediately on its recommendations.  It also didn’t hurt that many of these same Sales Leaders were members of the CEB/SEC organization at the time of the launch.

CEB/SEC’s Warning Label: Challenger is a “Multi-Year Journey”

There was real project execution risks here given the magnitude of change needed (given the existence of an 8/92 mix of Challenger/non-Challenger sales reps) and the possibility of a rushed implementation that manifested itself in unaddressed CSFs.

So if your company is struggling with implementation, perhaps this answers the 2nd question I posed above: Why aren’t Challenger EXPERTS appearing in large numbers after 10,000 hours?

Hindsight is now 20/20, but if we were to roll back the clock 10,000 hours, this is likely where Challenger implementation issues started to develop, if they did.  The size and scope of organizational change (not to mention the behavioral change needed) was under-estimated and the implementation timeline was rushed.

Ironically, and to its credit, CEB/SEC went out of their way to warn that the Challenger Sales Model was a “multi-year journey”.  In several blog posts in 2011, CEB/SEC warned Sales Leaders, “If this transformation (and there is no question about it, it is exactly that) is successful, it will be a multi-year journey for your sales team”.


If your company has already embraced Challenger and is experiencing “execution issues” and a dearth of Challenger Rep EXPERTS, here are some suggestions to get back on track.

    1. Go Slow to Go Fast (GS2GF) – I borrowed this execution strategy from Honeywell CEO David Cote. GS2GF provides excellent (albeit counter-intuitive) advice for implementing Challenger.  Sales Leaders are naturally hard-wired (and incented) for speed, but this is a time to take an assessment.  Sales Leaders should develop a list of implementation CSFs (whether put in place or not) and make an unbiased assessment of progress.  Measurements should be made and analyzed.  Interviews of sales reps and marketing associates should be conducted and summarized.  If any Challenger Rep EXPERTS do exist, extra attention should be given to interviewing them.  Customer feedback should be solicited.  And most importantly, a detailed ROI analysis of the Challenger implementation project should be prepared (by people not in the sales and marketing function) and future anticipated investments should be conservatively identified and evaluated.

      2. Assess Sales Rep Competencies and Identify Skills Gaps I believe there are 4 foundational competencies for a Challenger Rep that must be assessed, rep by rep and for the sales force as a whole. They are:

        > General business and financial acumen selling skills The ability to understand the economic drivers of a company’s business initiatives, key performance metrics, and critical success factors.

        > Customer-specific business acumen and ability to identify unique insights – The ability to quickly research and understanding of the target customer’s business drivers and financial performance.

        > Message development skills –The ability to create relevant and “sticky” (memorable and action-promoting) conversational messaging and agendas.

        > Message delivery fluency –The ability to assure controlled, yet naturally-flowing highly-engaging, two-way customer conversations.

        3. Target Training and Coaching in High-Growth Regions (HGR) – HGR is another execution strategy borrowed from Honeywell CEO Cote.  Honeywell’s internal Strategy Setters prioritize new investments in geographic areas of the world that demonstrate high-growth characteristics.  Similarly, a HGR prioritization framework can be a useful tool to help B2B Sales/Marketing Leaders prioritize who within the sales force should receive skills training and increased coaching support.  Rather than continuing to “boil the ocean” across the entire sales force, sales leaders should leverage the assessment in #2 above as a data point to tier the high-potential cohort and the low-potential cohort.

        4. Develop a “License to Challenge” Certification and Apprentice Strategy – Other professions require certifications so why shouldn’t the B2B Sales & Marketing profession?  I believe each of the four foundational Challenger competencies listed in #2 above can be trained and certified.  I also believe there should be an apprentice period where newly-certified Challenger Reps would be assigned to shadow Challenger Rep EXPERTS in the field.  A “License to Challenge” credentialing process, as well as on-the-job-training, would go a long way in helping to produce more Challenger Rep EXPERTS.


        1. Do you agree with my point of view?
        2. Have you seen a lot of Challenger Rep EXPERTS?
        3. If not, why not? What would you prescribe?

        Republished with author's permission from original post.

        Jack Dean
        As co-founder of FASTpartners LLC, Jack brings extensive technology buying experience as a Fortune500 Chief Financial Officer to the B2B technology sales training industry.He has facilitated client-sponsored business acumen training for 15,000 B2B technology sellers representing 150 global technology companies.Participants in Jack’s business acumen training have produced directly-attributed revenue of over $1 billion (in the 3 months after training) and training engagement ROIs averaging 500%.


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