Before you start pitching to sell something, it’s useful to prepare. This means knowing the content of what you’re pitching and practicing the delivery to increase the probability that it evokes a positive response in the recipient.
However, no matter how much preparation you do in advance of the actual pitches, you will face unexpected questions when the pitches begin. Game time always creates surprises that you didn’t anticipate in practice.
The good news is that, after a few pitches (usually less than 5), you’ll have been hit with nearly all of the different questions that could be asked during your pitch. After this point, the same questions that surprised you in previous pitches will no longer surprise you in future ones.
While you may have felt ready by preparing well in advance of your first actual pitch, you’ll only be truly ready after giving a few actual pitches. As a result, you should schedule a few initial pitches where the stakes are low (in other words, being turned down isn’t that important) so that you’re truly ready when the stakes are high.