Podcast episode
Why Your Discovery Call Isn’t Finding Real Problems | Bite-Sized Tactics
30 Minutes to President's Club19 May 20258 min
Description
Max Licht (Enterprise AE @ MaestroQA) breaks down his shadow-based discovery process. This technique goes beyond typical discovery calls, allowing you to witness firsthand where inefficiencies and bottlenecks are happening. 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. RESOURCES DISCUSSED: Join our weekly newsletter Things you can steal Save $50 on any 30MPC course with code “PODCAST” 30MPC Training: 30mpc.com/training
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So as you're going into the shadow process, you're constantly sounding like, oh, the shadow is gonna be great for that. Because we're gonna be able to articulate how much time this takes you in the current state. I'm gonna take some screenshots, and when we go up to your boss, we're gonna be able to really articulate the painful aspect of XYZ thing that we're replacing. So I think for one, like, really, at the end of the day, you are watching them click through their workflow. You're kind of watching the pain of what they do every day. “But you're selling how it aligns to the business case.” You're selling how it's de-risking implementation. They're really gonna be encouraged to do that, and they're gonna understand where it's going. So I think another big aspect of this, like, champion building is such a massive aspect of the shadowing piece. Because by the time we're going into these shadows, if they're willing to do it, if they're kind of gung-ho about it, it means we're forming champions who trust that we're going to solve a problem.
then how that filters into reporting, and then how you go from that reporting, and then you go communicate to your executive. So usually it's about five to six things that we want to shadow. Let me know if you have any questions, but guessing that's something that's kind of central to you. So you're really defining what that shadow process looks like. By the time they hop on, they should be very aware about what aspects of the workflow they're shadowing. “You should be very innately aware of where your specific differentiators apply to each part of that process.” If I'm shadowing this selection process, what are the two to three things that my technology does in that selection process that are really going to differentiate it? And then I'm looking for that, and I'm calling it out. Can you show me that field again? Oh, that field's going to be really important. If your competitor is not talking about extracting that field, let's make sure to button that away for later and make sure we talk about those really tactical things.
this is what you wanna share with them is like, look, share your experience, kind of a pointed observation, open ended question. A lot of the time I do all this great business discovery with my business stakeholders. And then we get to the Snowflake owner after three months of hard work, and he takes it all over it. What I would like to do is work with you to unlock a shadow with that technical stakeholder. So we can actually align “on your use case with the person who's gonna be making that integration. So long winded way of” saying you wanna do those business shadows, but then those are gonna unlock the systems underpinning that because there's huge gatekeepers underneath those processes that are going to kill you in the last mile of the deal. And you wanna use these technical shadows to get in front of them and not just yourself, like bring the superstars on your team. I'm bringing my CTO, MIT grad, engineer extraordinaire to go nerd out with them.
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