CEO - "We need a live streaming video platform"
Me - "What is the problem?"
CEO - "I want to do a webcast on our website"
Me - "Would embedding a YouTube video player work? It does x, y and z and it can be ready by tomorrow"
CEO - "Oh! I hadn't considered that"
You need to get back to first principles. Usually your boss wants to accomplish something and then they come up with a solution. Then they fall in love with the solution, not the problem.
You should be asking your boss what they're trying to accomplish instead of letting them propose the solution. If you help devise the solution/product you'll be much happier building it.