As you may know, the Sales Executive Council's research with 600 companies showed a 14% lift in goal attainment when the Challenger style was used vs. when it was not used. The methodology itself makes sense primarily because it is so closely aligned with what buyers are telling us they want and need from sellers.
Buyers are more empowered than ever before & have more options + less need to work with a seller. Challenger selling keeps sellers relevant and equips them for creating value. This level of differentiation and buyer engagement is essential.
Like any new approach, it does take training, practice, reinforcement and self-discipline to master Challenger selling. My experience with similar sales force transformations is that you have to give rigorous focus to this for a minimum of 6 months before you can realize the full benefits and ROI. As you measure the ROI, I'd also suggest that you keep the following in mind:
1) Your measurement of activity should have a qualitative component. Sellers who are new to this will not be able to do it well the first many times they practice. Putting only a quantitative measurement in place may actually have two adverse effects -- it may inadvertently reinforce the wrong behaviors (rushing through, not quite getting it right) and the domino effect is a conclusion that it doesn't work (if not done well, of course it won't work as well).
2) Customer reactions are helpful to measure. Conducting post-meeting interviews with prospects and customers will give you insights about what worked and what didn't work as well. A best practice is for sales managers to conduct interviews when there is a purchasing stall -- this is a great supplement to coaching for reinforcement.
Of the clients I work with who have adopted a Challenger approach, there is a high degree of satisfaction. Initially, there is some skepticism (especially from Relationship sellers). But those who genuinely work with Challenger principles quickly see their merits. Anecdotally, I have heard several stories about prospects who wouldn't budge before but then did become customers after the Challenger approach was employed. The "Teaching" aspect is what these customers report has made the difference for them.
If you are interested in learning more about WHY this is so important at this time, take a look at this white paper that describes the gap between buyer and seller perceptions about what matters to buyers. This explains the need for Challenger selling. http://peoplefirstps.com/sales-evolution-from-the-perspective-of-selling-professionals/