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The Art of Conversation….Part II

A few years ago I wrote a blog post I audaciously called “The Art of Conversation”, which no doubt plagiarized the title of some book and in which I talked about my perception of how to have valuable conversations (in fact, after I wrote that sentence, I googled it, and indeed, there is a book!  Maybe I should read it…) Since then I’ve not only thought about conversations a lot, I’d like to think I’ve learned a little too, and since then it seems that we’ve had such a perpetual bombardment of social dismemberment that people still don’t seem to understand how to talk to one another.  Indeed, the famous question by Rodney King:  “Can we all get along?” seems pretty unrealistic these days.  Certainly that shitshow of a debate the other night was probably the worst verbal exchange in the History of The World.  But maybe we can indeed get along, if we can just have better conversations.    

In that earlier post I made a long case for the concept of simply asking questions of people as a way to engage with them, and not necessarily as a function of “I am asking this question about you because I want a new platform to tell you more about me!”  If indeed you are asking a question, you at least need to feign some potential enthusiasm in what may be the answer, if not actually be prepared to engage in the answer.  In other words, you need to be interested

Additionally, in order for a conversation to go both ways, being interesting will further the discussion; your conversation mate will be educated, influenced, or at least entertained (even a little!).   It’s very much possible to be interesting without being interested; I have met plenty of very engaging people who are full of knowledge, experience, introspection, anecdotes, and entertaining stories….but aren’t really that interested in other folks’ knowledge, experience, introspection, anecdotes, and entertaining stories.  Or there are (only a few whom I have seen) who are great at asking questions, but it can result in being a kind of social crutch, and the eternal questioning can be a bit overwhelming.  In an ideal conversational world, we are all equal parts interested and interesting, which makes conversation pretty fun.


I definitely need to work on this.   A coupla years ago we bumped into the venerable kayak couple Phil and Mary DeRiemer in the backwoods of Idaho.  Ashley and I hung out with them for an hour or two, drinking beer and – I thought – exchanging tales. But later that evening after we’d left them, Ash gently told me that she was a bit surprised that I had basically dominated the whole conversation and nobody else had barely gotten a word in edgewise.  This sort of horrified me; they are literally famous adventurers who do trips all over the world and are equally famously gracious, and instead of hearing more about them and their recent and notso-recent adventures and mutual friends, I just talked AT them about me and my adventures, which I of course thought were quite “interesting.”  But there’s probably a reason they haven’t reached out to me since to join them on their own future adventures; I yap too much, and am not that interested in them!

It takes work to be interested; as we all know, it’s quite easy to make snap judgments of people, and my own personal snobbery – that I like to think is borne from being able to spend a lot of time with a lot of very high quality people – sometimes makes me likely to be a bit dismissive of some folks, probably prematurely.  My wife Ashley has a few good mantras, and one of them is “I can learn something from everybody”, and by her influence I have become more willing to engage with a wider array of folks. 

But if you ask people questions, you gotta be prepared for the answers.  Thomas Friedman had a great column recently (regarding the politics of humiliation that pervades our political process, that was very much prescient to the debate), and in it he has a great quote:  “If you show people respect, if you affirm their dignity, it is amazing what they will let you say to them or ask of them.  Sometimes it takes not just listening to them, but deep listening  –not just waiting for them to stop talking (emphasis added).   Because listening is the ultimate sign of respect.  What you say when you listen speaks more than any words.”    Hear hear! (so to speak). 

Speaking of politics, it’s not news to anyone that we seem to be in a bi-polar universe, where you are either a Dem or a GOP, Conservative or Liberal, Trump hater or MAGA-yte, etc.  And there’s little effort at empathy; no one seems to be bothering to understand the perspectives of The Other Side (Friedman’s article referenced above provides one good rationale for doing so).  But it’s almost impossible to do because if/when we gave/give ourselves the opportunity to talk to someone from The Other Side, our questions tend to drip with disdain and are more bait for an argument than they are genuine desires to understand a different perspective.  Again, Ashley has come up with a great mantra to address that:  she tries to ask questions “out of curiosity, not judgment.”  Simple, and brilliant. 

For example, even though the answers to each theoretically should be the same, here are two questions that are completely different regarding Trump:  “How can you like that guy?” and “Tell me what aspects, policies, or characteristics about him you appreciate?” They are basically asking the same thing and should theoretically generate the same answer.  But the former comes across as quite judgey and will undoubtedly end in a zero sum game snarl-fest, while the latter is indeed curious and should form the basis of a civil discussion.  Yes, you can simply avoid these difficult subjects altogether, but then you risk perpetually defaulting into such boring topics as gasoline prices, traffic, gossip about famous people, or news about people I barely know/remember, etc.

Many of the smartest and best folks I know are lawyers, and one of the reasons why they seem so smart is because they need to understand the mind and motivation of their opponents, which they endeavor to do with questions.  There’s no doubt that in a legal situation questioning is literally a strategy and it may be used as a manipulative tactic, but it is still exercising the act of empathy.  Therefore, lawyers – and good managers – are always listening to people on two levels:  what is being said, and why it’s being said. What’s the motivation for that comment?  What’s the goal of the speaker?  What’s the emotion driving that?  What’s the backstory?  Pondering the why something is being said as well what is being said simultaneously can help all of us engender better conversations. 

Speaking of lawyers, when I think of a great conversationalist that I aspire to emulate, the first person I think of is my cousin Anne.  Anne Denecke is truly the warmest, friendliest, most genuine person I know, who truly exemplifies being both interested and interesting.  She lights up like a chandelier when she sees you, squeezes you harder than most in a greeting hug, asks somewhat surprising questions that are a step beyond “How are you?” indicating that she’s not just throwing out a trope but actually remembers important things about your life that she’s genuinely interested in, is acutely conscious of the engagement of everyone in the group, and Annie throws her head back with a huge – and genuine – laugh so often that it tends to make you think that you are actually funny. 

Annie with cousin Paul deep in the Grand Canyon

Notably, however, Anne is not all about asking questions:  she’s a gifted storyteller herself with a fun, varied life and community and is as entertaining as she is gracious, with impeccable timing.  But she’s no snowflake; as an employment lawyer she can and does ask hard questions in defense of her clients, articulates her own opinions well, and can take people to task for their transgressions.   But she does so with such respect and deftness that people simply are forced to agree by the sheer engaging power of her personality.

So even if you feel you are absolutely fascinating and interesting to other people, at least act interested as well, and if you find yourself running out of questions to ask, find some interesting things to add. Hopefully do both and do so as a function of understanding the perspective of your conversation-mate.

And if it’s indeed a bit audacious to think that I can rant a bit about the Art Of Conversation, I can find a bit of solace in that  – like all of “the arts”, there’s an infinite amount of improvement to make! 

Thanks to The Google for allowing me to poach a few cartoons (at least they say “cartoon stock”…)


  1. Dave Dave

    Should be required reading for current politicians. Well thought out and insightful.

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