Talking About Conversation Coaching

How I help students build social skills & conversational fluency.


Hi, how’s it going? Good? Yeah, me too. Nice weather we’re having! Well, why don’t you pull up a chair, & we’ll chat about how I go about helping people become more adept and at ease in conversation. Go ahead, put your feet up—we’re relaxed around here. 🙂

Cutesy introduction aside, this is an interesting article for me to write. See, when I started doing this job, I didn’t expect to coach conversation. It’s not Public Speaking per se, and the dynamics are very different from the professional communication settings that are my bread & butter. But when students regularly cited ordinary conversation as a pain point & asked for help, I did my best to oblige. & after a few years of pondering & teaching the subject, I am proud to announce that I have Cracked the Conversational Code! With my simple 3-step process, you, like me, will go from Committed Wallflower to the Life of Every Party, all without changing your personality or communication style!! So hurry & buy my book, now out in hardcover!!! 

Three graduates of my Extroversion NOW program.
We even show you how to do wacky & potentially dangerous group photo stunts like leaping on icy sidewalks.
👀

... no, sorry—in case the frenzy of exclamation points didn’t tip you off, that was satire. 😬 Conversation is too nuanced for simple success formulas, and I’m really still a student myself—battling normal challenges in my daily interactions, & not always coming off as a paragon of suavity to say the least. But! By paying close attention to what makes conversations flow or stall, & watching what helps students build their own skills, I believe I’ve developed a useful framework for improvement. See what you think: 

  1. Tackling speaking anxiety

 Usually, this sort of student suffers from some underlying communication-related nervousness that makes conversing with others—especially new or unfamiliar people—very uncomfortable. So much so that they may avoid socializing, and keep quiet when in company. In fact, one of the biggest challenges I encounter with these folks is encouraging them to take what they’re learning out into the world, hang out with people, and get into conversations. The great exchanges we’re having in-session may be fun, but they’re supposed to be preparation for real-life interactions, not a substitute. So we likely need to explore your speaking fears, & look for some mindset shifts that can turn those nerves to confidence.  

Of course, mindset shifts work best when joined with Actual Skills, so we also spend a lot of time on ... 

2. Thinking on your feet 

 For the less proficient, conversation can seem to move very quickly. When it’s your turn to talk, coming up with something to say Suddenly, With People Looking At You, may feel a herculean task—and unfortunately, taking a couple moments to formulate a reply just produces the dreaded Awkward Pause! 

This means that improving your mental processing speed is key to conversing comfortably—& happily I have a lot of exercises for that, many of them improv-inspired. 

3. Brainstorming content 

 I often hear these students say that they just lead boring lives—“all I do is work, plus eating & sleeping”—so that’s why they have nothing to say in society. But then it frequently turns out, after I get to know them a bit, that they do have some intriguing interests, perspectives or experiences—they just didn’t think them worthy of bringing up, and/or felt sheepish about opening up to others.

“Who wants to hear about my skydiving anyway?”

Good news: You don’t have to be the Most Interesting Man in the World to hold up your end of an exchange. Usually just a couple of introductory tidbits plus some quick thinking is enough to get a good conversation up & running.

So! Since certain topics & questions come up regularly in social settings, it can help to workshop little spiels to have ready on demand. Then you can use those to lay the groundwork for a broader back & forth, going in who knows what directions! So we’ll work on drafting some basic, frequently relevant conversational content. 

4. Elaboration 

Another common problem I notice in the conversation-challenged among us is that they seldom expound much at all on their stories & comments. This is usually partly due to lack of skill, & partly to insecurity about others’ finding them dull. While the instinct is understandable (if your content is blah, it may be best to keep it short), unfortunately heavy abridgement can be a self-fulfilling prophecy: Once devoid of lively detail, what could have been a compelling contribution is now rather yawn-worthy. What a pity! So fleshing out ideas is an area we’d work on for sure. 

5. Appearing interested in your own material

 Many subpar conversationalists speak a very flat, quiet, hesitant style. This, unfortunately, exacerbates their troubles: If you don’t sound interested in what you’re saying, how can you expect your audience to be interested?* If your communication style signals “I’m falling asleep just listening to myself, ho hum,” your listeners might actually believe you. To remedy this, we’d work on improving your body language and vocal delivery to be more engaging, & signal that you think you’re worth paying attention to.** 

 & of course you’d want to return the favor to your conversation partners, expressing interest in what they have to say via both your facial expressions and your verbal responses. 

Timmy shows how it’s done.

6. Asking questions 

Conversation isn’t just about being able to talk to others—it’s about helping others feel comfortable talking to you, and inviting them to share more about themselves. This means identifying opportunities to delve deeper into others’ remarks, & asking good questions: initial and follow-up, closed and open-ended, informational and exploratory, all kinds! In addition to being rather flattering—most people like it when someone shows curiosity about them—questions give you more time to think and more potential things to react to! A win-win! “Interviewing,” as I call it, usually plays a central role in conversation training. 

 ... & that’s how I go about it! As with my standard public speaking students, all the session material is customized to your unique conversation goals & needs, so we’d emphasize the various skills above to whatever extent you need each. Hopefully after a while, you’ll feel much more equipped to start conversations, sustain them, and feel comfortable in them. For some initial practice, you could set up a free conversation/consultation with me! 🙂


*Exception: The dry, understated speaker whose deadpan style knowingly sets off/contrasts with fascinating or humorous remarks.

**This is how some people can make seemingly mundane events/topics feel fun & exciting.

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In Praise of Plan-As-We-Go Speech Coaching

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Public Speaking Coaching & the Practice Paradox