Why Pitching Perfect First Time is Bad Strategy

Most people think a good pitch means being perfect the first time. It doesn’t.

I write this from firsthand experience. I have a stubborn defect around over-preparing. For years, the one thing I tried to do, and was sometimes encouraged to do, was to hit the mark at any cost on the first attempt.

More often than not, this showed up as over-delivery.

Too many frameworks, too much material and too little space.

One example I can think of is when giving a short training session in Paris a couple of years ago was that I desperately wanted to cover all the frameworks because that's what I thought the client had paid for. Time was tight and I had anticipated too finish 5 minutes before but I hadn't anticpated the exchange with the attendees would take up so much time. That is what people were paying for ultimately, (not just the frameworks) and the feedback was lackluster. Trying to contol the flow of information too much in my experience rarely leads to a successful outcome. I believe the same can be said for any context. Especially a pitch.

This may resonate with you. You may well recognise the moment where you notice people’s attention drifting. Thier faces glaze slightly, questions start forming, but you stick to the plan anyway. Slide 18 is coming and you’re going to finish it, despite every instinct telling you to stop and open the room

This is a recipe for failure and a classic perfectionism trap.

What’s behind it is usually fear, fear of looking under-prepared, fear of being exposed which is often labelled as imposter syndrome. Ironically, imposter syndrome is usually a sign that you care about doing the work properly, not that you don’t belong.

The truth is simple. The only way to pitch well is to accept that every pitch is an iteration, a process. A chance to test, listen, adjust, and improve. Yet many founders and executives still approach pitching as a fixed performance. The intention is usually positive. Preparation. Professionalism. Respect for the audience. I understand it. But “perfect” pitches fail because they optimise for control, not for trust.

In real situations. Accelerators. Investor meetings. Informal rooms. Time-compressed conversations. This instinct backfires.

Pitching is not a static performance. It’s a live system.

The Hidden Cost of “Perfect First Time”

Many of us were trained in environments where authority meant being right immediately.

No iteration, no visible adjustment and no learning in public.

But what lands in a pitch is shaped by far more than content. It’s shaped by the audience in front of you, the time available, the energy in the room. The constraints you didn’t anticipate.

Trying to deliver a “complete” pitch in those conditions usually creates three predictable problems:

1. Too much information for the time available

2. Too many frameworks competing for attention

3. Too little space for the audience to process, react, or engage

   
   

Ironically, over-preparation often leads to under-connection.

What Actually Works

Effective pitches are not complete, they are precise and they prioritise relevance over coverage. They adapt to the moment instead of forcing a pre-built structure onto it. This is where sequencing matters. Sequencing is the discipline of deciding what to say first, what to say next, and what to deliberately hold back. Not because it isn’t valuable, but because it doesn’t fit the moment.

The goal is not to say everything.The goal is to move the audience one step forward, sometimes in a big way, sometimes incrementally.

The Reframe Most People Miss

Iteration is not a sign of weakness, it’s a sign of competence in complex systems.

Good software ships versions. Good products evolve in contact with users. Good pitches improve through real rooms, not rehearsals alone.

The mistake is judging live learning by standards designed for static performance.

A Simpler Rule Going Forward

To be clear. If you are preparing a tightly constrained, five-minute pitch with questions after, then yes. You should polish it, rehearse it, and pin it down properly.

But in most real pitching situations, a better internal rule is this:

Be precise, not complete. Prepared, not frozen.

Say what fits the moment. Create space for interaction. Let the next step do some of the work.

You are not lowering standards.

You are demonstrating authority under pressure.

For more information on how we can help you pitch better check out the Vortolo Pitch Method here: https://www.vortolocoaching.com/coaching-and-training-more