“If you want to collect all the hearts, you should lead with a high-numbered heart.”
“When making a speech, you should lead with a joke.”
“Lead with” comes from card games, where the first person to play a card must decide which card to play first, or lead with. We can use this phrase in any situation where someone has to make a decision what to do in order to begin something.
「ハートをすべて集めるつもりなら、まず大きい数字のハートを出さなきゃ。」
「スピーチをするときは、最初にジョークを言いましょう。」
Lead with は、トランプで最初の人がどのカードを出すか決めないといけない時のフレーズです。トランプ以外でも、どのような行動で物事を始めるかを決めるときに使えます。