The Best Pitches Devolve into Dialog

If you are pitching a VC, you aren’t succeeding because you are sailing through your slides perfectly. You are succeeding if the meeting transforms into a dialogue driven by the investor asking the right questions.

When an investor asks questions that follow logically from an understanding of what you’ve just said, or when they push deeper on ideas you’ve shared, you are succeeding. Even when they challenge your assumptions, it is a sign of engagement. A good VC will quickly ask questions that get right to the heart of the risks inherent in your venture—provided you communicated clearly enough in the first ten minutes to allow them to see those risks.

(For completeness, let me point out the inverse: If they are asking questions that reveal a lack of understanding of the basics you just covered, you are failing. The onus is yours to be perfectly understandable.)

From Monologue to Dialog

When your pitch devolves into dialog you are on the pathway towards the destination you’re hoping to reach. You advance on that pathway if the VC is asking smart questions and you keep answering them intelligently and concisely.

Why is this better than keeping tight control on the narrative? Because every VC will bring their own prism to your pitch meeting. Every VC has different aspects of a business that they are going to perceive as the most important. VCs are pattern matchers. But you don’t know which pattern any particular VC will be looking for. It might be scalability or customer acquisition cost or technical moats.

When you get them engaged they are signalling what they think is important. That allows you to spend the time speaking to them about exactly what they think is critical.

Dialog is also the terrain where you can signal confidence and intellect that does not cross into arrogance. For example, it’s where you can acknowledge certain risks or unknowns if the VC finds their way to them. Sober acknowledgement that there are of course some unknowns and real risks in your venture shows intellect in a way that zealous defence of every opinion you have does not.

Tactics

There are practical tactics that follow from this philosophy: Your entire pitch strategy should be based on the goal of getting to the Q&A quickly. This demands the ability to communicate the essentials of your business in 10 minutes flat.

How do you do that? You treat your 10 slide pitch not as a continuous essay, but as 10 separate elevator pitches, each no more than 90 seconds in length. Your product slide is accompanied by an elevator pitch about your product. Your traction slide is accompanied by an elevator pitch about traction. Etc.

If you have the discipline to not explain everything and ability to be concise then you will drive the meeting towards the dialog you want it to be. In fact, when you get really good at this, you will learn to put hooks in your pitch that lead the listener directly to the questions you want.

Furthermore, embrace digression. Digression in the direction the listener’s questions take you is what you want. If a VC interrupts you on slide 3, just go with it. Don’t be in a rush to get back on the rails of your script. The script is merely a backstop to use if their line of questioning ends.

The icing on the cake here is when you have prepared enough so that you even have tight answers to whatever questions come at you. Nothing signals expertise like clear concise answers to difficult questions.

Two things enable this:

1. Pattern Recognition: VCs use similar prisms. You will get certain questions again and again.
2. The “Never Twice” Rule: If you are ever asked a question that you don’t answer superbly, you must do the work necessary so that the next time you get that question, you crush it.

The practical takeaways:

1. 90 seconds per slide max; 10 minutes total.
2. Each slide is an elevator pitch that can stand on its own.
3. Your pitch never goes deep; go deep when a question takes you there.