What do you think a question like that achieves? He's never going to answer it to your satisfaction and it's only going to make him spew bullshirt, get defensive, and not answer better questions. Asking that is like asking Loomis, "why do You blow so bad?"
There are ways to ask for the same information without making it an accusation of incompetence. Again, reporters aren't there to be the voice of the fans.
The questions you ask are things like "what are you doing different this time to ensure that you are going to hire the right guy for the HC position?" "What is the organization doing different to make sure this is an impactful draft like the 2017 draft?"