“What ho!” I said. “What ho!” said Motty. “What ho! What ho!” “What ho! What ho! What ho!” “After that, it seemed rather difficult to go on with the conversation.”

–P.G. Wodehouse from My Man Jeeves

Have you ever noticed how many recommendations come flooding your way each week—most without you even asking for them? Yet come they do and in such torrents that you ask yourself “Is it me?” “Is it something I did or said?”

Giving recommendations is a high art and is one of the reasons why I admire skilled conversationalists. Their gift of talking with you and not at you is always a rarity and while we can’t always exactly say why we enjoyed chatting with certain people so much, we know it was pleasant and rewarding—especially if they slipped in a recommendation or two.

On the other hand, we all know the misery of getting stuck with a true bore—a particularly acute dilemma when we can’t find an escape. For me the worst were those times in the cramped confines of an airliner cockpit—experiences that made me wonder if there are indeed fates worse than death. This is why pilots insist that the most important portion of an airline interview is determining if the candidate has the personality you can stand for a four day trip.

The most dangerous bores, conversationally speaking, are recent converts to a cause—any cause. They feel duty bound to convince us to sail with them under their new flag. It might be a health or exercise regimen, a certain political view, or any of a number of other topics that you were hoping to avoid. Maybe they are simply looking for a validation of their choices in life, but for whatever reason they are a furious force of nature.

Yet good info is worth its weight in gold and we value those who tell us something new and worthy. One colleague with whom I regularly flew was an inexhaustible storehouse of good tips (Hacks or Pro-tips in today’s vernacular) and I knew a gem was forthcoming when he would suddenly ask “Dude, did you know…?” 1980s Sean Penn style aside, whatever followed was sure to be noteworthy.

Yet where is the dividing line between the person who just likes to hear himself speak when parceling out these bon mots of wisdom (in his mind of course) and the person who is actually giving beneficial suggestions? We know from experience it is devilishly hard to find.

I am sorry to admit that too often I have prematurely chimed in with an opinion or advice when I was, albeit unknowingly, speaking with a subject matter expert in the topic at hand. Whether I was on land, sea, or in the air, I opened my mouth too soon. In hindsight these occurrences are all the more embarrassing for the warning signs were there and it all could have been avoided if I had simply asked a question or two.

My past missteps include giving medical advice to a man who was a surgeon, thoughts on how to structure our national trade policy to a Commerce Department official who was riding next to me as I was deadheading as a passenger on a flight, and running tips to a former elite triathlete. Not stopping there, I have even given automotive repair tips to a mechanic and insight into China to someone who had, I was about to learn, lived there for twenty years. As you can see my mistakes were deep and wide.

Fortunately all these conversational partners were gracious sports about it and took my ramblings in stride. To their credit they let me down softly with their, shall we say, more precise views on whatever we were discussing.

After one too many of these miscues I decided enough was enough and I started to finally (!!!) pay attention to how the real conversational pros avoid this pitfall. Surprising of course to no one but myself, they do it with well-placed, well-meaning, and very unobtrusive questions. They get to know the lay of the conversational land and it pays the dividend (among many) of not putting their foot in their mouth.

These masters of the chat never come across as if they are conducting an interrogation. Certainly you know the opposite—the discomfort when someone poses question after question to you while not revealing anything about themselves.

It is quickly obvious as to what they are doing and you realize they are taking Dale Carnegie’s How to Win Friends and Influence People to an insane level. Even if they are just trying to be nice, it comes across as seriously creepy.

Worse, since there are some odd and dangerous people roaming this earth, we are justified in raising our personal safety antenna. One can never be too careful with those who probe too deeply.

Congenial conversationalists avoid such unpleasantness. They salt their chats with sincere questions and deftly fold them into the start of any new topic. They can subtly determine your experience and expertise before they decide to weigh in. We never even notice this seamless transition to another topic and the result is a most satisfactory chin wag.

As an average gent I wish I could be as good as they are—for they are often also witty and funny. A con-fab with them refreshes and reinvigorates you and turns bad days into good ones. Yet even if I can never be as good as they are, I can definitely enjoy the consolation prize of listening to them ply their gifts.

Thank you good reader for allowing me to wedge one more idea into your ever-full suggestion box. Be assured that I am beavering away to take my own advice. At the very least it should save me from more embarrassment!

…and to think, I don’t even need to start off with “Dude, did you know?”

What ho what ho!