Most reps ask “When do you plan to buy?” and stop there. The best ones go further “Why then?” They uncover the real reason behind the buyer’s timeline and use it to guide every conversation. This post breaks down how to find the why now in every deal and how managers can coach reps to create urgency that actually closes business.

Most managers think they’re coaching when they’re really firefighting or mentoring. In this article, Colum Lundt explains the four levels of sales coaching—no real coaching, general talk, deal coaching, and developmental coaching—and shows how moving up the levels transforms reps and results.

Too many frontline managers are promoted for hitting quota, then left to figure out leadership …
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CROs face a math problem: managers are spending only 5% of their time coaching, while reps are losing 87% of what they learn in training within a month. AI-powered role-play solves the “practice gap” by giving reps instant, objective feedback in a safe environment, while managers use that data to drive targeted, accountable one-on-ones. The result? Faster skill adoption, stronger pipeline, and consistent quota attainment.

Ask any sales enablement leader what they need right now, and you’ll hear one word on repeat: data. Not dashboards. Not vanity metrics. They want proof. Because right now, Sales Enablement is under pressure to show how their work translates into revenue. And for many teams, the signal-to-noise ratio is terrible.

Sales enablement isn’t just a support function anymore; it’s a measurable, strategic driver of revenue …
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In this episode of Coach to Scale, sales trainer and former Olympic trials athlete Neil …
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Tom Young, VP of Sales at BMC Software, joins Matt Benelli to challenge outdated assumptions …
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