Key Takeaways
- Discovery calls often produce polite nods instead of real commercial interest because founders pitch products without verifying an unavoidable blocked project.
- One startup trying to sell an applicant tracking system to municipal governments completely pivoted after a buyer dismissed the software but admitted they would pay immediately to fix job descriptions.
- Founders trapped in what Rob Snyder calls the pain cave of zero to one need to recognize when systematic discovery has stalled and take radical action.
- When systematic outreach across multiple cohorts fails, Snyder recommends entering goblin mode: flying to an uninvited European conference tomorrow or knocking on doors to force quick customer feedback.
- Teams facing lukewarm sales calls can find real buyer demand by applying The Hail Mary Question Rule.
The Hail Mary Question Rule
- The Trigger: Use when an outreach or sales discovery call reveals lukewarm enthusiasm and no pull for your original hypothesis.
- The Question Prompt: Ask verbatim: “Is there anything on your to-do list that you would pay me to do right now, like that you would pay somebody to take off your plate?”
- The Follow-up: If the prospect mentions an urgent blocker, immediately treat it as a new candidate pull hypothesis and test if other similar profiles share that identical priority.
When This Works (and When It Doesn't)
Rob Snyder points out that founders use this question at the end of unproductive discovery calls to uncover real buyer priorities instead of leaving the conversation empty-handed. The tactic works because enterprise buyers rarely volunteer their dirtiest, most urgent operational problems when listening to a polished software pitch. When you drop the presentation and invite them to offload something painful, they stop evaluating your pitch and start thinking about their immediate workload.
This method breaks down if you treat every stray answer as an immediate company pivot. If a government bureaucrat asks you to format their spreadsheets, you have not discovered a venture-scale business until you verify that twenty other buyers share that identical blocker. The Hail Mary question generates hypotheses; it does not replace testing them. Use it to escape dead ends, but run the candidate problem through the same validation rigor you gave the original idea.
When systematic discovery fails repeatedly, Snyder advises shifting into goblin mode. As Snyder explains, “If you're in this pain cave of zero to one, it's the worst time of your life and you just don't want to prolong that. So just get on a plane, go to the office, go in person, do whatever it takes to find something.” Snyder calls it a break-glass measure where you go all out, book a flight to a European industry conference tomorrow morning without an invite, and corner operators in hotel lobbies to discover who will pay for something today.
What to Do With This
Run this on your next sales call that flatlines. If you are demoing your workflow tool to an engineering manager and notice their responses dwindling to polite nods, stop your screen share ten minutes early.
Say: “It seems like this tool might not solve an immediate issue for your team today. Is there anything on your to-do list that you would pay me to do right now, like that you would pay somebody to take off your plate?” Write down the exact project they name. Before you build a single feature, send cold messages to ten other engineering managers asking if that specific blocker is stalling their week.