I’ll address the quote from the title in a second.  First I’d like mention a story from a few years ago.

Granted I did come across a scene in Mea Shearim like this, but generally this is not the preferred method for communicating Jewish ideas.

When I was living in Burbank walking around the shopping center one day, I saw a Christian pastor reading aloud.  I had just started the path I’m on now and may have been looking for a bible battle.  The pastor noticed me watching him and after a few minutes came over.  We actually had a coffee and talked for hours.  But the reason I mention this exchange is that when I said that standing on a soap box telling people they’re going to hell isn’t the way to influence people, he replied, “As long as I get though to one person, then it’s all worth it.” 

I replied, “but what about all the dozens of people who you just made your religion look abhorrent or that you offended?”  And since then, I’ve come to learn Judaism has a very similar perspective.

For one thing,  Jews ARE commanded to reproach people who are doing things wrong.  “It is a mitzvah for a person who sees that his fellow… has sinned or is following an improper path [to attempt] to correct his behavior… (Mishneh Torah, Hilchot De’ot) and the Rambam continues, “one is obligated to rebuke a colleague who does wrong until the latter strikes him and tells him: ‘I will not listen.’ ” Huh… so we are supposed to get into people’s faces until they threaten to punch us in the face?

Yes and no.  Now I’ll bring up the quote from the title.  It’s from Gemara Yevamos (65a). “Just as it is a Mitzvah… so too is it to not say something that won’t be heard.”  What this means is that though we are commanded to admonish someone, if they will not hear it from us, then it is forbidden.

If they won’t hear it.

What does that even mean?  What does it take for someone to hear what we’re saying?  People give us criticism all the time and we shrug it off with the likes of, “What do they know?” or “If they saw what I was dealing with they wouldn’t be talking.”  Why do we listen to criticism from some and not others?

When trying to influence people, giving unsolicited advice is always going to be tricky if not impossible.  The only time it ever effectively comes across is if it is from a place of authority (the recipient has to believe it’s coming from an authority, don’t decide you are an authority) and when it comes from a place of love.  It is tempting to give advice.  It’s an ego boost to have someone listen to you and feel like that authority.  But it is infinitely less effective.

So what should that pastor be doing?

I don’t know.  He comes from a faith different than mine with a different set of responsibilities.  Also Jews aren’t supposed to actively convert.  But in terms of affecting people with regard to a belief system?  Inspire.  In Hebrew we call it being a Kiddish Hashem.  Gandhi put it, “Be the change that you wish to see in the world.” (Though the Vilna Goan said something very similar a couple hundred years before.)

To drive home the point and finish off, I’ll tell over a story of The Chazon Ish.  The Chazon Ish was a Torah giant among the rabbis in Israel in the early-mid 20th century.

The Chazon Ish was walking with a student one Shabbat in Bnei Brak.  There was a sharp divide in the city.  On one side was a community who was completely shomer shabbos. On the other side, the city hardly kept shabbos at all.  The Chazon Ish asked his student, “Do you know why this side doesn’t keep shabbos?”
The student thought for a second then responded, “Perhaps cultural differences or they’ve never tried it?”
The Chazon Ish responded, “No. It’s because that side (pointing to the observant community) doesn’t keep it like they should.”

If case you don’t quite get the Chazon Ish’s meaning,  if the observant Jews were keeping Shabbos they way they should, it would inspire the Jews on the other side to do the same.

Lead by example. Live well.  Love.  Inspire.