Judging
It is tricky how to teach or impart someone whether older or younger if one does not have a wide array of knowledge on how generosity can be exemplified and not only limited to the financial aspect. "I'm generous in my time"2 a pastor for more than 30 years once preached.
One could easily be influenced by the people that surround him and bend his conviction in a subtle way. His conviction would be reignited if someone influential and scholarly spoke directly and boldly on the pulpit.
If we assess someone who is not being generous don't ask the person explicitly rather evaluate how you define generosity.
Footnotes:
1 Biblehub. https://biblehub.com/matthew/6-3.htm (Accessed Sept 14, 2023')
2 Cunanan, Fer. Seedtime & Harvest: Blessed to be a blessing. Sermon at ENCM/S, Mississauga, ON, July 23, 2023'

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