Why It’s Hard to Coach for Challenger Skills

The ability to teach, tailor, and take control is what distinguishes sellers in the Insight Selling era. But these skills are difficult to develop and even more difficult to coach.

The difficulty lies in two separate but related issues:

Tacit Skills—Unlike the ability to know products’ features and benefits, Challenging requires judging the unstated needs and signals of the buyer. This can be difficult to develop as it’s often situation-specific and the ways that reps’ internalize requirements can vary widely.


Inter-Related Skills—Teach, tailor, and take control are distinct skills, but the combination is what creates the powerful impact. Breaking the skills into component parts in order to coach each separately can be difficult for managers who don’t know what to look for.

SEC recommends three things that can combat the unique difficulties of coaching to Challenger:

Planned Coaching Interactions: In many instances managers parachute in to save deals, or give retrospective coaching. Using a framework like PAUSE helps managers prepare for coaching interactions and is particularly helpful for skill development. It focuses the interaction on the particular skill to be developed and gives both manager and rep a goal at which to aim.


Hypothesis-Based Coaching: It is also helpful if reps and managers understand what an ineffective behavior looks like. Instead of focusing on what is not happening but should be, it is much easier to identify what is happening that should not be. Arming managers with a list of behaviors seen as ineffective can help them understand which skills require attention.


Create a Challenger Training Eco-System: Even if reps are able to demonstrate early mastery of a skill in training or coaching interactions, the long-term application requires something more from your organization. Strategically positioning resources and opportunities around developing the three skills has a large impact on the longevity of Challenging within your organization.

To support you in this effort, we have created an Ineffective Challenger Behaviors Heat Map that will help managers hypothesize which skills need development based on the current behavior and point in the buying cycle. Listen to the upcoming webinar where we will preview the heat map and explain how it can be used.

SEC Members, register for the upcoming webinar Coaching the Challenger Rep. Also, review our resources to support managers’ coaching efforts and see The Challenger Starter Kit for more ideas on how to promote Challenger in your organization.