1. Identify the Painful Process

- Research the customer's current workflow and tools (e.g., Excel, Salesforce) to understand the manual, time-consuming steps involved.

- This reveals where inefficiencies exist, giving you a clear picture of the pain your solution can alleviate. It also helps you identify the "drag them through the glass" moments where the pain is most acute, which is critical for building urgency.

2. Set Up the Shadowing Session

- Frame the shadow as a collaborative step to fully understand their process. Instead of just making claims, say something like, *“Before I make any promises, I want to fully understand your current reporting process to see where we can add the most value.”*

- This approach shifts the focus from selling to problem-solving, making you a trusted partner rather than just a vendor. It also sets the stage for a more meaningful business case.

3. Conduct the Shadow

- Watch the prospect use their current tools and processes. Take notes, capture screenshots, and pay attention to friction points, inefficiencies, and workarounds they rely on.

- Seeing the workflow in action often reveals unspoken pain points and limitations that even the prospect might not articulate in a standard discovery call. This firsthand observation helps you tailor your pitch to the reality of their day-to-day work.

4. Use Shadows to Build a Business Case

- Use the insights gathered to frame your solution as a direct response to the pain points you observed. For example, highlight how your tool eliminates specific inefficiencies, reduces manual steps, or streamlines complex reporting.

- This concrete evidence makes your pitch more credible and aligns your solution directly with their business goals, increasing the likelihood of internal buy-in.

5. Follow Up Strategically

- After the shadow, summarize your findings in a follow-up email or meeting, highlighting specific pain points you observed and how your solution can address them. Use this to drive urgency and move the deal forward.

- This reinforces your credibility as a problem-solver and keeps the conversation anchored in real, observed issues, rather than hypothetical value propositions.

6. Use the Shadow as a Catalyst for Future Conversations

- Reference specific pain points in later stages of the sales cycle, using them to frame your solution as a clear, tangible fix for their current frustrations.

- This approach keeps the focus on solving their problems, reducing friction in the decision-making process and increasing the likelihood of a successful close.