If there’s one thing that keeps me up at night, it’s how to bring enablement sessions closer to reality.

Why does it keep me up at night? Because the more realistic enablement initiatives are, the better equipped reps are to do real-world selling. Their confidence goes up, their pitches get better, they qualify (in and out) more effectively, and they maximize their productivity. As I’ve written before, rep productivity is perhaps the strongest (and most important) metric for quantifying the success of your revenue organization.

The less realistic they are, the more all of those elements suffer. They may be able to parrot a generic marketing message, but if they’re not equipped to handle tough objections and audibles, their productivity and your revenue generation suffers.

So how do you connect enablement with reality? It centers on scenario-based work, grounded in solid proof points.

The overarching goal of enablements is to model an ideal pitch: Get everyone aligned on positioning, messaging, common objections, and pitch specs.

Each of those elements needs defining. You need to partner with Product Marketing to get clear on positioning, identify the ideal words to use in messaging, list objections (and the best responses), and develop the unifying pitch.

Your leaders will have instinctive ideas of how to complete each of these steps. But the best way to get buy-in from your reps is to ground each in proof points: objective data from actual deals that substantiates training content. Capturing and synthesizing as much customer data as possible is the foundation of developing and modeling a gold standard. (Gong automates much of this process, maximizing data capture and synthesis, and illuminating a clear path toward the ideal.)

Once you have a clear sense of what you want your reps to say, the best thing to do is to put them in role-playing scenarios that are as close to reality as possible. It’s one thing to internalize a marketing message; it’s another thing entirely to practice saying it in real time.

How can you make role-playing as realistic as possible? Again, I’d point back to proof points. Have your role-players look at the most common use cases customers in various segments are interested in. Familiarize them with which competitors come up in these conversations, and how you differentiate against them. List out common objections and identify which responses tend to play best in live conversations.

Another way to drive rep buy-in is to have leadership take part in these sessions. This is partly because leadership presence substantiates the connection between the specifics of enablement sessions and overarching strategic goals. It’s also because leaders have more domain experience, and can more credibly play various roles in scenario-based work.

With modern tooling, so much less of this process has to be speculative. The better your data capture, the more you can turn theory into reality—and get everyone aligned on a singular vision.

First, you train your reps on a gold standard pitch. Then, you role-play the pitch as realistically as possible—and with the presence of leadership to validate the exercise. Last, you test your training against reality: actual customer calls, snippets of which you incorporate into reinforcement and future enablement programs.

Real customer responses are the most valuable data points for how your messaging is landing. You can validate, iterate, and/or rehash based on how customers respond, and socialize common responses among your entire sales team.

Get great data → model an ideal → conduct realistic role-playing sessions with leaders involved. And, of course, let there never be one-offs. Ideals aren’t mastered overnight; the more frequently you conduct targeted, high-quality sessions, the better your reps will retain the information and represent it well during real conversations.

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