Pitching Is Storytelling With a Deadline
By Joel Asante · Career & Business
Sit through enough pitches and the same shape recurs. Company slide, product slide, features, some numbers, a request. Competent, complete, and it does not move anyone.
The information was all there. The order was wrong, and order is most of the game.
Delivery counts more than investors say
Before the shape, one piece of evidence about why the spoken pitch matters at all. In 2008, Colin Clark had business angels rate live entrepreneur pitches on 32 separate aspects and asked them how interested they were in investing.1 The aspects of presentation, how the pitch was delivered, weighed most on that interest. Yet when the investors explained their decisions, the reasons they gave were about the business.
That is one study of one group of investors, so it is not a law. But it suggests a pitch is judged partly on things the judges do not report, and that a well-organised, well-delivered case is not decoration on top of the business. The full write-up is here.
The problem with leading on the solution
Starting with what you built asks the audience to do the hardest possible work: hold an unfamiliar solution in mind while working backwards to the problem it addresses, and at the same time decide whether they have that problem.
Most people will not do this. They will form a rough impression early and spend the rest of the pitch confirming it.
Lead with the problem, and the work disappears. If they recognise it, they are now invested in how you solved it. The solution slide, arriving second, gets a completely different reception. The room is looking for it rather than evaluating it cold.
A shape that holds up
1. The situation. Neutral, factual, agreed. No claims yet, just the world as it is.
2. The complication. What breaks. Specific, ideally with one number that is hard to dismiss and that you can source.
3. The stakes. What that costs. If you cannot say what it costs, you may not have a business, and that is worth knowing before the room finds out.
4. The solution. Now you get to talk about what you built. Two sentences before any detail.
5. The proof. Why you, why this works, why now. Evidence, with the adjectives left out.
6. The ask. One specific thing. Amount, meeting, pilot, decision.
Steps one to three are the story and should take about a third of your time. Many pitches spend nearly all of it on step four.
A worked example
Say you are pitching an onboarding tool to the head of people at a mid-size firm. Here is the shape filled in, with invented figures standing in for the ones you would bring:
Situation. "Most firms your size run onboarding through email and a shared spreadsheet."
Complication. "When we surveyed new hires at our pilot companies, a large share could not answer a basic question about their own benefits at day thirty." (In the real pitch, this is your actual survey and your actual number.)
Stakes. "Each of those questions becomes a ticket for your team, and some of those people are already wondering if they joined the right company."
Solution. "We replace the spreadsheet with a checklist each new hire works through, with answers they can find themselves."
Proof. "Three firms use it. Benefits questions to HR fell in each of them in the first quarter."
Ask. "We would like to run a four-week pilot with your next intake."
Only the last three lines are about the product. By the time they arrive, the room has a reason to want them.
The ask is not optional
A surprising number of pitches end without one. They trail into "so, yeah, that is what we are working on" and stop.
The ask is a single clear sentence: "We are raising X to do Y, and we are looking for a decision by the end of the month." Or: "We would like to run a four-week pilot with one of your teams."
Then, as with a salary number, stop talking. If your ask includes a figure, the first number said out loud tends to set the range for everything after it, which is why it should be chosen on purpose. Anchoring explains how.
Handling the interrupt
Pitches get interrupted. Someone jumps to slide nine on slide two. This is usually good news; it means they are engaged. It is also where prepared speakers come apart, because they have rehearsed a linear path.
Two rules:
Answer the question, briefly, then return deliberately. "Yes, twelve months, and the reason is X. I will come back to that properly in a moment, because the next bit explains it." You have answered without abandoning your structure.
Know which parts are load-bearing. If you have twenty minutes and get eight, which three things must be said? Decide before you walk in. A compressed pitch is a different, shorter set of points. The full pitch delivered faster will not survive.
Common mistakes
A complication nobody in the room feels. If the problem belongs to someone else, the rest of the pitch has no grip.
A number you cannot defend. One unsourced figure early on makes the room doubt the ones that follow.
Features as proof. "It has twelve integrations" is a feature. Proof is evidence that it works for someone like them.
Asking for three things. A pilot, an introduction and feedback, all at once, is no ask at all.
Rehearse the first ninety seconds relentlessly
Steps one to three are where the pitch is won or lost, and they are the part people rehearse least because they feel like preamble.
They are the reason anyone listens to step four. If the problem does not land, nothing after it can.
A ten-minute drill
Write your pitch as six sentences, one per step. Say them out loud in under a minute. Then hand the sheet to a friend, have them interrupt you at any point with a question, and practise answering in one sentence before returning to the next step. Do it three times, with the interruption in a different place each time.
References
- Clark, C. (2008). The impact of entrepreneurs’ oral “pitch” presentation skills on business angels’ initial screening investment decisions. Venture Capital, 10(3), 257–279. https://doi.org/10.1080/13691060802151945