Initial Version
Trying a sentence structure to help the user.
Our first approach was to have each prompt help the user craft a sentence. For example: "The winner will have the highest 'objective', while playing as 'champion name', over the course of the next 'timeframe', including the players 'game limit'.

We pursued this approach for quite a while, and went through many, many versions. We created something of the vast complexity that every designer knows and fears:

Research and Testing
Room for improvement.
Luckily, we had access to a solid group of beta testers in the form of college gaming clubs. The go-to-market team at Rainmaker had identified these clubs as a great way to find and locate the type of gamers we were looking for.
We were able to run a series of beta tests in which we would have the gaming club leader create their own challenge, speaking along the way to any confusion or complexity.
Our takeaways were fairly simple and classic UX revelations: make it simpler, make it quicker, keep the optionality.

Final Version
Reduced upfront complexity & gimmicky sentence structure.
Ultimately, our findings not only convinced us to change the flow, but also to reduce the complexity of our entire product. We realized that we were creating a spaceship without our users actually asking for it.