Ep. 89, Listen, Listen, Listen: How to Build Deep Connections | Summary and Q&A

May 9, 2023
Stanford GSB Podcasts
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Ep. 89, Listen, Listen, Listen: How to Build Deep Connections

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In this podcast episode, Matt Abrahams interviews Rachel Greenwald, an executive fellow at Harvard Business School and a professional matchmaker and dating coach. They discuss the challenging aspects of relationship building, specifically focusing on small talk in both professional and personal contexts. Rachel emphasizes the importance of asking better questions and giving more interesting answers to make small talk more engaging and enjoyable. She also provides advice on initiating and ending small talk, as well as the use of light banter and humor in conversations. Throughout the interview, Rachel highlights the significance of making others feel good and creating a deeper connection through effective communication.

Questions & Answers

Q: What is one of the most challenging aspects of relationship building that applies to both the business world and dating world?

One challenging aspect is small talk, which often becomes boring and predictable. Many people default to asking typical data collection questions, leading to unengaging conversations. The key to successful small talk is to be intriguing and ask better questions that spark curiosity and interest in the other person.

Q: How can you make small talk more comfortable when meeting someone at work or on a date?

Instead of being a data collector and asking mundane questions like "What do you do?" or "Where are you from?", aim to be intriguing by giving unexpected answers. For example, on a date, when asked about your profession, you can turn it into a guessing game by providing clues and making it more enjoyable and memorable. The goal is to move beyond predictable conversations and create a better connection with the other person.

Q: How can you initiate and end small talk effectively?

Initiating small talk can be made easier by making observations about the environment or situation rather than using typical questions. By sharing an observation, you create a bid for connection and establish a sense of familiarity and engagement. Ending small talk on a positive note is important, and one technique is using the "white flag" approach. This involves asking one last question related to the conversation and giving a sincere compliment before parting ways. Ending with positivity enhances the overall experience and impression.

Q: How do you coach people on effective communication in dating and seeking romantic partners?

The advice for effective communication is the same in both romantic and professional contexts. The focus should be on how you make someone feel rather than the words you say. Show genuine interest in the other person's stories and experiences, making them feel smart, funny, or accepted. Avoid being self-centered or using humor excessively, as this can create a barrier and make the other person feel exhausted or unsatisfied.

Q: How can light banter be used in conversations to create connection and lighten the mood?

Light banter, which is a less daunting alternative to humor, can be used to create a playful and relaxed atmosphere. It involves making unexpected observations about the environment or situation, facilitating a sense of camaraderie and shared experience. The goal is to enhance the conversation by adding lightness and making it more enjoyable without the pressure to be funny.

Q: What are some bad conversation habits that can negatively impact communication?

One common bad habit is the tendency to mirror the other person's conversation, constantly mirroring their own experiences without adding depth or genuine engagement. This can make the conversation feel superficial and choppy. Other bad habits include being an interrupter or trying to impress the other person by being the comedian. These habits hinder meaningful connection and leave the conversation partner feeling unheard or exhausted.

Q: Who is a communicator that you admire?

Rachel Greenwald admires Priya Parker, author of "The Art of Gathering." Priya focuses on reimagining how people spend time together to create more meaningful connections. She emphasizes the importance of setting the tone before an interaction or gathering to prime participants for a positive and engaging experience. By considering the context and environment, communicators can create a more receptive atmosphere for effective communication.

Q: What are the first three ingredients of a successful communication recipe?

The first ingredient is active listening, which involves genuinely paying attention to the other person and asking follow-up questions to show interest. Second, it is essential to prioritize making the other person feel good and accepted during the conversation. Finally, being aware of and managing one's communication blind spots is crucial for effective communication, as everyone has blind spots that others can see but they are unaware of.


Forming relationships requires effective communication skills, particularly in the realm of small talk. To make small talk more engaging, avoid being a data collector and ask better questions that generate intrigue. Initiate conversations by making observations about the environment and end them on a positive note using the "white flag" technique. Light banter can be used to add playfulness to conversations, while excessive humor can create a barrier. Avoid bad conversation habits such as mirroring, interrupting, or relying too much on humor. Actively listen, prioritize making the other person feel good, and seek feedback to improve communication blind spots. Setting the tone and context before interactions can enhance the overall communication experience.

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