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I worked at a company that had our team in a monthlong rolling crisis born of bad management.

They wanted updates for the director who didn’t even understand the technical issues at least twice daily. Frequently, it was done over a teams channel so it was a rolling half hour text conversation/distraction trying to explain technical issues to someone who was bad at listening. By the end of it I was ready to sabotage the project just to end it.

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explaining fairly complex stuff to non technical people and using diagrams (we called them crayon diagrams) can be an art form. Its a balancing act of showing something too complex vs too simple ie,showing one box and saying its broken(I've seen that happen).

imho, The best way to start is by asking the stakeholder what they know about the system and asking them stuff. this is good in different ways,

1) you can assess their level of technical abilities

2) assess how interested they really are

3)engage with them and create a personal relationship

and take it from there, using analogies can be extremely useful

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