The article hits the nail on the head .. somewhat. I've found that asking a slightly deeper level question more helpful personally. In the article's example :

The article hits the nail on the head .. somewhat. I've found that asking a slightly deeper level question more helpful personally. In the article's example : What are we trying to do ? Show a diagram. While it is tempting to ask "What tool should I use", perhaps it is worthwhile thinking "What is the deeper need here"? If it is communicating with stakeholders (duh), can I get away with a pencil sketch and digitise them? This way, I have shaved a bunch of time learning ASCII tools or Adobe Illustrator. Kind of fits in with my (borrowed) mindset of "Doing things that don't scale" [0] Of course, if I find myself doing pencil sketches all the time , it is worthwhile investigating better ways. [0] https://www.inc.com/business-insider/paul-grahams-counter-intuitive-startup-advice-do-things-that-dont-scale.html#:~:text=Paul%20Graham%3A%20%27Do%20Things%20That%20Don%27t%20Scale%27%201,single%20user.%206%20Don%27t%20have%20a%20big%20launch https://www.inc.com/business-insider/paul-grahams-counter-in....