君がその計画を実行するのを難しくしているのはなにでしたか。

English Translation

What made it difficult for you to carry out the plan?

Robotic word-for-word translation… なにでしたか is especially unnatural. My alternative translations are:

どうしてあなたの計画はなかなか進まないのですか?= (lit.) Why doesn’t your plan make progress as much as you expected?

あなたの計画を阻むものは何ですか?(あなたのけいかくをはばむものはなんですか?)= (lit.) What hinders your plan?

Although the English sentence is written in a past tense, I think a present tense sounds better in Japanese because I interpret the meaning as “you still have the problem”.