Kill happy-ear forecasts

The most important question to answer during discovery calls: “Why will this deal fail?”

Kill optimism before it kills you.

Why?

Founders love fat pipelines; investors love them fatter.

The problem: Too many perfect looking pipelines hide silent vetoes - security reviews, political turf wars, budget cliffs - that detonate at quarter‑end.

You hire based on an overly optimistic pipeline, only to lay them off three months later when “commit” turned into air.

Instead, flip the script: hunt the loss, not the win.

Before the demo, surface the risk that will kill the deal.

Pricing mismatch? Legal land mines? Competing pet project?

Drag it into daylight now.

Founders / reps who surface objections first turn forecasts from fiction into fact.

The pipeline shrinks, but accuracy spikes.

You stop wasting time on deals that will never close and can spend more on those you can win.

To do so, surface: Why will this deal fail? Who loses power if we win this opportunity? Which budget line dies to fund us? How can legal kill this? What happens to the buyer’s KPI if rollout flops? etc

If you can’t answer these, the opportunity isn’t real - yet.

Ask upfront.

Teams that expose objections early close cleaner, faster, and cheaper.

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Enjoyed reading this?

Then check out my conversation on the focal podcast with Basile Senesi, founding CRO of Arc (>$180M raised in debt and equity from YC, Bain, NFX, and Left Lane)

Youtube | Apple Podcast | Spotify

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