The basic idea behind five times why is that you can always find the root cause of any problem by just asking why five times. When people first get started on five times why they tend to fire off five quick why's. This can be fun at first, but will get boring soon and will unfortunately not help you to get at root causes.
"By asking and answering ‘why’ five times, we can get to the real cause of the problem, which is often hidden behind more obvious symptoms." — Eric Ries, The Lean Startup
So here are some tips to give your five times why the attention and results it deserves:
When you start asking questions the first answers will tend to be very obvious, but not really specific to the situation or very focused on something incidental. By asking five times why you will get at different root causes for most of the causes first mentioned like in the image below.
This way you can go from non-specific ("I can't send information on time") to something that you can measure and check ("Schedule keeps changing"). As you can see in the image above not all root causes have been found yet, more why questions need to be asked. When analyzing root causes you may find you need to go back and measure some more data to check your root causes and earlier assumptions. This is perfectly normal. Once you have all your root causes you can check them with the team (if they have not all been working on it with you) and go to the solution phase.