Until just a few weeks ago, I spent my Friday evenings and entire Saturdays bumping fists and sporting a comically large pink mustache on my SUV. Why? I was moonlighting as a driver on the popular ridesharing platform known as Lyft. It wasn’t a full time gig, but rather a way to supplement my income as my cofounder and I bootstrapped our budding startup Whttl.

Like many other Lyft drivers out there, I wanted the task to be about more than just the greenbacks. (Read Uber vs. Lyft, A Driver’s Perspective.) Feel-goodery aside, there was some real world utility up for grabs when driving. When behind the wheel, I organically promoted my startup and received early stage feedback. Strangers became friends, which proved particularly valuable in a new locale. I racked up 10,000 miles within San Francisco, a city that measures only 49 square miles. Suffice it to say, I’ve seen a ton of this beautiful city by the bay.

While my proverbial resume can now include wheelman duties, there is so much more that I got out of the task than simply cash and knuckles.

Very early on, I adopted the philosophy that it would be a wasted opportunity to carry on with shallow, one-dimensional conversation about such trivial topics as weather and traffic. Instead, I used this drive time to learn something from my passenger, and reciprocally share some insight that I hoped would be equally as valuable.

To do this, I pretended I was Conan O’Brien. Tailored suit, goofy hair, and television cameras aside, I considered it my job to keep the conversation flowing, interesting, and comfortable, just like Conan. For the sake of myself, and also for my passengers, this proved to be a mutually beneficial tactic.

Here’s what I learned about the art of conversational navigation.

Ask For Stories, Not Answers

One way to get beyond small talk is to ask open-ended questions. Aim for questions that invite people to tell stories, rather than give them permission to respond with bland, one-word answers.

Avoid light weight questions like “How are you?”, “How was your day?”, “Where are you from?”, and “How long have you been living here?”

Instead, dive a bit deeper. Try asking “What’s your story?”, “How’d you end up in your line of work?”, and “What’s the strangest thing about where you grew up?”

My personal favorite is “If you could teleport by blinking your eyes, where would you go right now?”

I was often amazed at the extent of personal stories that my passengers would tell me. Interestingly, the people that started off particularly stone-walled often spilled the beans more than most. The key was to ask unique and intriguing questions, instead of merely going through the motions of polite conversational small talk.

Two Ears and One Mouth

The thought leaders from decidedly different disciplines, including management, sales, leadership, and relationship building, have a few bits of knowledge that overlap. One such commonality is the importance of listening, and that a ratio of two parts talking to one part hearing is optimal.

Actively listening has a two pronged positive effect. First, it’s difficult, if not impossible, to learn anything by talking. You’ve got to listen to acquire knowledge. It is simple to learn tremendous amounts with the mere act of shutting up and tuning in. Second, your conversational counterpart will feel much more engaged with the discussion. Interestingly, they’ll actually think more highly of you if they are afforded the opportunity to do the bulk of the talking.

Incorporate All The Guests

With the introduction of Lyft Line over the summer, I could pick up 2–4 people that were complete strangers. (Think of it as a well orchestrated carpool.) This could prove awkward, as the passengers that were picked up later in the ride felt like oration outsiders. To combat this, I worked the newbies into the conversation, just as Conan does with his guests that have been relegated to the couch from the spotlit chair. I’d say, “Hey Tom, welcome to our Lyft. Susan & I were just talking about her trip to Italy last August. Have you done any traveling yourself?”

Time Awareness

Live TV shows run with incredible precision. Schedules don’t deviate by more than a few seconds, and commercial breaks, talking points, and segments are all compiled to produce one delicious cocktail of content. Alcohol references aside, such was the case with driving. I’ve got anywhere between 5–15 minutes to elevate the conversation to a level that carries substance. The time clock is ticking, but it need not be rushed. It’s an elusive balance to achieve.

On a related but tangential note, I’ve noticed a pattern after watching dozens of podcasts and fireside chats. Quite often, the conversation starts off pretty immaterial. It takes up to twenty minutes for the dialogue to get meaningful and really build up some steam. I’ve found myself close to abandoning an episode, only to hold on and find myself saying “What a great chat!” only twenty minutes later. The sooner such a threshold is broken through, the more skilled the host.

Multitasking

I can’t vouch with entire certainty, but I suspect Conan has never received pre-show instructions saying, “Go out there and just talk. We’ll take care of the rest.” No way. Conan has to carry on a dialogue, all the while mandating the pace, direction, and ultimate destination of the conversation. Producers are directing him via his ear piece. Stage hands are signaling to him. To nearly all viewers, this goes unnoticed, because he is good, really good. He lets all this noise happen on a different mental frequency. He operates in parallel tandem; the internal processes are taking place independently from the external.

The Lyft analogy applies here, too. Lest we forget that I’m doing that whole, errr…driving thing. Driving duties had to revert to the subconscious, all while remaining safe, abiding by the laws of the road, and getting to the destination via the fastest and most efficient route. That way, I can allocate mental energy to foster meaningful conversation.