I like the creative idea of a role play re domains
@thevictor - I think something that could provide insights, and I don't recall others using it on NPs. My answer would be....
I would start off by listening - how long has .com presence been established, has it met their expectations, how much they have invested, what concerns do they have about ngTLDs.
When the question is valid, e.g. some end users have never heard of many of the new extensions so isn't it risky, I would show them the ICANN surveys on it, but agree that yes it is a realistic concern. In a very minor way it is improving, but slowly.
However if some of their concerns are "urban truths" (often repeated even on NPs!) that are not based in fact I would show them the evidence. Like if they think Google discriminate against ngTLDs in search (most rank low but not because they are a ngTLD, but rather because they are not well placed in other ways like valued backlinks or quality of content, etc.). Or that all ngTLDs are spammy and abused, I would take them to Spamhaus data to show that is far too generalized a message. For spam some are worse, but many are better than .net and .com. Re phishing, would point out that the vast majority of that abuse comes from .com, and a very few mainly country code TLDs.
Primarily they probably wonder about marketing advantages and disadvantages. I would share with them the excellent Huffington Post article re domain name phrases and ngTLDs (see link).
https://www.huffingtonpost.com/entry/5947826be4b0d188d027fff9
Let me quote a couple of compelling examples quoted in that article.
"Bill McClure purchased coffee.club for $100,000 in November 2014 – within a week of the website’s launch, it ranked on page 1 of Google US for the term “coffee club." When I first learned that it super impressed me. Getting to first page of Google is not easy and it is valuable.
"
Wix recently ran an SEO competition with a prize of $50,000 to see who could rank best for a search term of their choosing. The winner & runner-up both used new-GTLD domain names that strongly matched the competition search term."
At this point I would probably share a snippet from the interview with the owner of home.loans. But maybe more impressive mention his previous enterprise,
https://www.multifamily.loans/. I was not familiar with the term, but he launched that with a .loans, and almost immediately got on first page of Google and had a successful business.
I would be honest with the potential purchaser, and tell them that ngTLDs have been slow to catch on, many in the branding and naming establishment are against them and feel that a .com is the only real choice most should consider.
I would probably suggest a strategy where the owner keep the .com, with all its advantages, fully operational and try out for a period of time a ngTLD and use it in a marketing campaign and use Google Analytics to track how effective it is.
I would share some of Names.of.London data re that particularly with mobile devices and social media clickable domain name expressions seem to work with consumers.
Anyway.... my answer... thanks for the opportunity to respond.