While it may be construed as an important life lesson, continuing to ask questions is part of the process to fine-tune your message.
Even when filling out the brief, you’re trying to understand more and more about the audience and their real pains (and potential gains), so you can find their motivation and appropriate the message, and copy, and material to them.
Now, most founders would provide an answer that works for them, but it doesn’t necessarily work for their audience, for the decision-maker, or for the end-user. It will state specifically what it is they do but it won’t be clear why it is so valuable, making it a must-have (rather than just nice-to-have).
So keep digging even after they answer your question, cause it could provide more insights, look deeper into the problem, and help you answer the whys.
The simplest way is the ‘Five Whys’ used for problem-solving, which uncovers more and more information, without just accepting an answer at face value.
You get some information and ask ‘Why?’ which leads to its own answer and information. Based on that, rework the ‘next why?’ to dig deeper, and so on. You will learn new things and go into a direction you haven’t even considered in the beginning, and it will also shed some light for those founders who thought the original answer was sufficient. It will get them to look at a certain problem or difficulty in another light they may not have considered before.
But it isn’t just asking the Why, but constructing it, so to look into areas you’re unsure of, unaware of, and aren’t able to pin down. And there are always plenty of other questions that can paint a bigger picture.
Just keep asking questions…and more questions.