Simon Sinek's "Start with Why" enabled many companies to rethink their purpose and approach to a number of business activities. Answering the simple question of "why do we do what we do?"
Asking why, of course, leads to a better understanding of any topic. But asking "why" once doesn't lead to the in-depth level of understanding businesses and teams often need to formulate good strategy and make sound decisions. This is especially true when I facilitate meetings.
Let's take an example: you learn a client believes the project schedule is important. You ask "why?"
The response you get is "well, some projects previously didn't meet the schedule, so we need to make sure we show that we can this time." Great! Right? You've got intel to act on to create a value proposition.
But hold up - that's not enough. Let's go a level deeper and ask "why" prior projects didn't meet schedules before? The response you get is "there were quality issues that came up and had to be resolved; that took a lot of extra time and rework." Ah-ha! Ok, now we're getting somewhere. Let's keep going...
You ask a third "why" pertaining to why there were quality issues. The response: "our last vendor didn't have the right quality procedures in place - and that is something that will be critical when we choose our next vendor." Got it! We can now more confidently understand the real issue - and that allows you to develop your plan to be the preferred vendor of choice.
Had we stopped at the first ask of "why" the value proposition would have likely revolved around just the schedule - how to accelerate perhaps; whereas the real concern is quality so that it doesn't impact the schedule.
Could you go even deeper by asking "why" again and again? Sure, but I've found that three is typically the threshold that gets you the understanding you need, but without becoming annoying to the person you're asking. In the case above, asking another "why" wouldn't make sense because only the vendor (your competition) would be able to answer. And, well, they don't need to...you'll take it from here!
Best of luck as you ask more "why" questions to gain a better understanding!