Some of you may not know that I write a bi-monthly email called the “Insider List,” and send it to everyone who has opted to receive it (you can do that here on the site, if you’re interested). Last time I wrote about the slipperiness of language—and how that slipperiness makes listening even more important. The example I used was the word/phrase “mayday” or “May Day,” which can either mean a happy spring holiday or a call for help.

In response, one of my “Insiders,” a friend and colleague named Todd Sattersten, sent me an email letting me know that there’s a word for words that have two opposite meanings: they’re called contronyms. Here are a few great examples (some of them from Todd):

sanction—‘a penalty’ or ‘official permission or approval’

fine—‘the state of being good’ or ‘a penalty for doing something bad’

shop—‘buy’ or ‘attempt to sell’

custom—‘special’ or ‘usual’

bolt—‘secure’ or ‘run away’

dust—‘add fine particles’ or ‘remove fine particles’

strike—‘hit’ or ‘miss (a ball)’

buckle—‘fasten together’ or ‘break under stress’

I love such quirky, illogical, counter-intuitive, imprecise aspects of language: I get a big kick out of the fact that such words exist, and that we’ve created a word for them.

And the fact that language is often like this is one of the main reasons listening well is so important. Contronyms are simply an extreme example of the potential for misunderstanding inherent in any conversation. It’s so easy to assume you understand what someone is saying…and miss what they’re actually saying.

If, instead, we were to approach every conversation assuming we really don’t know what the person is thinking or what they intend, and then get very curious about finding that out—I’m convinced about 90% of our misunderstandings, hurt feelings, and mis-matched expectations would simply evaporate.

Contronyms (and other slippery words) would lose their power to confuse—and speaking would become a bridge to understanding rather than a barrier.

What do you think?