In this talk, Patrick Mosher explains how to start authentic, high‑impact conversations by using carefully crafted, empathy‑driven questions. He begins with the classic executive opener “What keeps you awake at night?” and illustrates why it works: it is other‑focused, shows empathy, gathers actionable insight, and gauges trust. Mosher then delves into the physics of voice, describing how sound waves create intimacy by literally rattling the listener’s ear bones and prompting the brain to evaluate the speaker. He stresses that a question is a gift and must be respected. He critiques superficial small‑talk (weather, family) as “intimacy‑avoiding” and introduces the concept of “true curiosity,” a mindset of asking without expectations, which deepens relationships and invites wisdom. Mosher outlines a framework of 4‑5 go‑to questions for distinct contexts—prospects, interviews, luminaries, icebreakers, and a universal question for anyone. He shares his own social‑gathering starter, “What is your superpower?” which he says consistently pulls people into focused, intense dialogue. The overall message is to prepare a small repertoire of thoughtful, expectation‑free questions, use voice intentionally, and treat each answer as a valuable exchange.
Chapters
What keeps you awake at night? As a newly minted consulting executive, they taught us to ask this go-to question when alone with a client executive. Why is this a great question? Well, it's other-focused, it demonstrates empathy, it gathers valuable and hopefully actionable information, and most importantly, the question gauges the level of confidence and trust you have with the client. I was asked this question and my answer blew up the intended discussion. My response: Oh, I sleep great at night, always have. In fact, when I was in kindergarten, my mom got a call from the teacher and I went on to tell a childhood story. The story of my lifetime sleep habits was probably not the discussion the other person wanted to have. Nonetheless, "What keeps you awake at night?" is still a great go-to question to initiate a conversation with an executive. How do you initiate a great conversation with an awesome question? Well, let's begin with voice. When you project your voice into the atmosphere, sound waves emanate from you. When they reach the other person, those sound waves rattle little bones in their ears Your voice initiates intimacy. As your question rattles the bones in their body, those bones translate the sound waves and their brain fires up to understand the question. It evaluates you. It accesses a database of stories, expectations, feelings, and facts. It compiles all that into a response. The response goes to their vocal box, and voilà, a response to your question travels on sound waves and rattles little bones in your body. I'm in awe of the complexity of our humaneness. And when you ask a question, remember you are requesting something from that person. Their response is a gift. Respect the gift. Yes, respect the intimacy of a question. We use questions to initiate conversations in cocktail parties, office gatherings, and holiday parties. And I'm terrible in these contexts and with these kinds of questions. How's the weather in Minnesota? How are you? How's the family? Do you really care about our subzero weather here in Minnesota? Do you wanna hear about my recent bout with a chest cold? And seriously, do you really wanna know about my latest family drama? I think not. The common response to this question is a horrible 4-letter word beginning with F. Fine. Intimacy avoided. Social courtesy box checked. Wasted breath and time, and that's not my cup of tea. If you want to engage in authentic discussion by asking a great initiating question, First, clear your mind of any expectation of how you want the person to respond. This provides fertile soil for their answer to take hold. I call this true curiosity. True curiosity carries no expectations. When you ask a question from a mindset of true curiosity, you exchange authentically. Your relationship deepens, and there's a great chance that wisdom is exchanged. There are different conversation initiating questions for different contexts. For example, prospects. What one question do you ask a prospect you really wanna land? Interview questions. What is your opening question to interview someone for a job on your team? Luminary. You have 30 seconds with a guru, expert, luminary, or thought leader. What one question would you ask? Icebreakers. What question do you ask as an icebreaker for your team or anyone? If you could ask every person in the world one question, what would you ask? So here's my challenge. Create a list of 4 to 5 go-to questions for different contexts. If you have them ready to go, you won't miss a beat and you'll get to the deeper intimacy faster. I have a few go-to questions at social gatherings. They aren't your typical cocktail party questions. My question usually results in the two of us or a small group of us locked into an intense conversation in the corner of the room. Now, that is my cup of tea. What's my go-to question for social gatherings? Well, imagine that we're standing with drinks in our hands. The room is loud as people all around us are engaged in light social conversations talking about the weather. We meet, we smile. You see me kind of blink long as I seem to transport to a different place. The noise in the room seems to subside. I open my eyes and peer into yours. You see my mouth move and hear the carefully crafted words in your ears. What is your superpower?