What is the Real Question? How To Be An Exceptional Listener


Summary

The episode opens by highlighting the ubiquity of questions in our professional lives, from job interviews to everyday workplace conversations in tools like Slack. The host notes that while questions are critical, most people don’t recognize their importance or the skill required to answer them effectively. The initial instinct is to focus on crafting our own answer, interpreting the question through our personal context, history, and feelings.

This self-focused approach is contrasted with the practice of good listening. A decent listener understands the words and their job-related context, but an excellent listener strives to understand why the person is asking the question and how they are feeling. The host emphasizes that listening is about understanding what people mean beyond their words, interpreting the full spectrum of communication including body language, tone, timing, and the signals in asynchronous messages.

The core challenge presented is to shift from being an automatic “query engine” to asking, “What is the real question?” or “What is the real intent?” This is framed not as a suspicious sleuthing activity but as an exercise in empathy—understanding where the other person is coming from and what they truly need. An important mental model is introduced: when someone asks you a question, they are putting their trust in you. Each question is a vote of confidence, an opportunity to help, rather than mere cognitive load being dumped on your plate.

The episode concludes by encouraging listeners to view questions as the natural, human way to initiate deeper conversations. By focusing on understanding the questions better—their intent and the trust they represent—we can become far better listeners. The host then promotes the Developer Tea Discord community as a space for thoughtful, slower communication and asks listeners to support the show through reviews and sharing.


Recommendations

Actions

  • Leave a review in iTunes — Suggested as one of the best ways to help support and grow the podcast organically.
  • Share the show with someone — Suggested alongside leaving a review as a key action to help the show grow through word of mouth.

Communities

  • Developer Tea Discord Community — Promoted as a free, thoughtful, and deliberative community for asking questions and discussion, characterized by longer, more thoughtful messages and a slower pace of communication than typical workplace chats.

Topic Timeline

  • 00:00:00The prevalence of questions in professional life — The episode begins by asking what it means to be a good listener, framing the discussion around the professional context of interviews, layoffs, and daily work. It points out that a huge part of our jobs involves listening to and answering questions, noting that most workplace conversations, especially in tools like Slack, start with a question. The host establishes that questions are a critical, yet often unnoticed, component of our work.
  • 00:02:00The common mistake: focusing on your answer — The host explores the common gut instinct when hearing a question: to immediately focus on formulating your own answer. This means interpreting the question through your own personal lens—what it sounds like, what it reminds you of, and your own history. The problem is that this self-contextualization often happens when the question was asked for the other person’s benefit, not yours, unless it’s a coaching question from a manager or mentor.
  • 00:03:14Defining good, decent, and excellent listening — The host distinguishes between levels of listening. Good listening is understanding what people mean beyond their words. A decent listener understands the words and can contextualize them to the person’s job or recent events. An excellent listener goes further, trying to understand why the person is asking the question and interpreting how they are feeling. The full bandwidth of communication—body language, tone, timing—is discussed, along with the lower fidelity but still present signals in async communication.
  • 00:04:49The challenge: Ask “What is the real question?” — A simple challenge is presented: when you hear a question, ask yourself, “What is the real need here?” or “What is the real intent?” The host cautions that this is not about assuming bad intent or sleuthing for nefarious motives. Instead, it’s framed as an empathy activity—an effort to understand where the person is coming from and why they are asking you, specifically, at this moment.
  • 00:05:49Questions as a vote of confidence and trust — A key mental model is introduced: when someone asks you a question, they are putting their trust in you. People generally ask questions of those they believe can provide an answer or help. Therefore, each question received is a vote of confidence and an opportunity. The host advises against viewing questions purely as cognitive load being shoved onto your plate. Instead, reframe them as a sign that this person believes you can help them.
  • 00:07:08Questions as natural conversation starters — The host reflects on how human nature leads us to communicate through questions. It often feels more natural to ask “What was the last time you worked on topic X?” than to directly state “I’d like to talk to you about topic X.” Questions serve as effective introductions to deeper conversations. The episode concludes by encouraging listeners to become better listeners by focusing on understanding questions better.

Episode Info

  • Podcast: Developer Tea
  • Author: Jonathan Cutrell
  • Category: Technology Business Careers Society & Culture
  • Published: 2023-10-21T07:00:00Z
  • Duration: 00:09:11

References


Podcast Info


Transcript

[00:00:00] What does it mean to be a good listener?

[00:00:15] There’s many of you who are interviewing right now.

[00:00:19] You’re interviewing for a new role.

[00:00:22] Perhaps you are one of the many people who was impacted by layoffs this year.

[00:00:28] Or maybe you are the one doing the interviewing.

[00:00:32] Or maybe you’re just going about your normal, everyday job.

[00:00:37] A huge part of our lives and our jobs is composed of us listening to questions and coming up

[00:00:48] with answers.

[00:00:50] Think about it.

[00:00:51] How many conversations in your workplace, certainly almost every interview,

[00:00:58] that you take part in, is composed almost entirely of questions.

[00:01:03] But if you were to go back and look at your most recent conversations in Slack, how many

[00:01:09] of them start with a question?

[00:01:13] Sure, sometimes somebody comes in and makes a statement to start a thread.

[00:01:21] But in most cases, our conversations begin with a question.

[00:01:30] Maybe they’re looking for a specific answer, or maybe it’s broader, more general.

[00:01:36] Maybe they’re looking for a yes-no answer, maybe it’s an open question.

[00:01:40] In any case, questions are a critical part of our jobs.

[00:01:47] And yet, this has probably gone unnoticed.

[00:01:50] Most people don’t recognize the importance and the prevalence of questions and being

[00:01:57] able to answer them.

[00:02:00] But what does it take to be able to answer a question?

[00:02:03] Most people, most people listening to this podcast right now, your first gut instinct

[00:02:09] is to focus on your answer.

[00:02:13] Think about this for a moment.

[00:02:15] Focusing on your answer means that you’re going to interpret the question for what it

[00:02:22] means to you.

[00:02:26] What does this question sound like?

[00:02:27] What does it feel like?

[00:02:29] What is it about?

[00:02:32] What thoughts does it trigger?

[00:02:33] What history does it remind me of?

[00:02:38] And all of this, all of this context is brought up in your mind when another person is asking

[00:02:43] a question that is likely for their benefit.

[00:02:50] This isn’t always the case.

[00:02:51] Sometimes your manager will ask you questions that are intentionally trying to coach you.

[00:02:55] Maybe a mentor would do that.

[00:02:58] Trying to coach you, trying to trigger some of those thoughts and feelings and context.

[00:03:05] But in almost every other case, the question that you are hearing is not the only message

[00:03:14] behind the question.

[00:03:17] Good listening is about understanding what people mean.

[00:03:22] It’s about listening beyond the words they’re saying.

[00:03:27] A decent listener will understand the person’s words completely and they’ll even contextualize

[00:03:34] it as it relates to that person’s job or maybe recent events.

[00:03:39] An excellent listener understands why that person is asking that question and they try

[00:03:47] to interpret how that person is feeling in order to ask that question in the first place.

[00:03:55] The question comes along with all kinds of communication.

[00:03:58] If you’re face to face, this communication is very high bandwidth.

[00:04:02] You can read body language, tone of voice, all kinds of subtle signals, even the choice

[00:04:08] of when and where to ask the question.

[00:04:11] Asynchronous communication doesn’t have as much fidelity, but there are still signals

[00:04:15] that we send through our asynchronous communication.

[00:04:18] Of course, in all of these situations, there’s also the potential for you to misunderstand

[00:04:23] or miscalculate those signals.

[00:04:28] But the truth is, it doesn’t take much to be head and shoulders above the average person

[00:04:33] when it comes to listening.

[00:04:36] Most people are on automatic, they read a question as if it was a query that was given

[00:04:41] to them and they are the query engine.

[00:04:44] They’ll read the question and immediately turn it into something for me.

[00:04:49] I have a simple challenge for you today.

[00:04:52] I want you to ask, when you hear a question, when a conversation starts with a question,

[00:04:58] I want you to ask, what is the real need here?

[00:05:03] What is the real question?

[00:05:05] What is the real intent behind this question?

[00:05:10] I want to caution you to avoid thinking that everyone has bad intent.

[00:05:17] In almost every scenario that you face, questions are not going to be posed with bad intent.

[00:05:23] What is the real question is not a sleuthing activity.

[00:05:28] It’s not you trying to figure out people’s underlying motivations in a nefarious manner.

[00:05:33] Instead, it is an empathy activity.

[00:05:37] It’s you understanding where are they coming from and why are they asking me right now

[00:05:43] for this?

[00:05:45] One other important mental model to put in your back pocket.

[00:05:49] When someone asks you a question, they are putting their trust in you.

[00:05:57] Think about it.

[00:05:58] When you think of someone that you can ask a question of, are you going to ask someone

[00:06:04] that you don’t think could give you an answer?

[00:06:09] In most cases, the answer is no.

[00:06:12] Of course, if you’re going out of your way to go and connect with someone and ask them

[00:06:17] a question, you probably expect them to be able to help you.

[00:06:22] When other people come to you with questions, that’s a vote of confidence.

[00:06:26] Each question that you receive is an opportunity.

[00:06:32] My word of caution here is to avoid filtering or interpreting questions as purely cognitive

[00:06:42] load that people are shoving onto your plate.

[00:06:45] Instead, view questions as a vote of confidence.

[00:06:49] This person believes that I can help them.

[00:06:53] Now the challenge is, can I?

[00:06:56] Am I capable of answering this person’s question or getting them what they need?

[00:07:02] Perhaps the question is not actually the real question, as we already mentioned.

[00:07:08] Perhaps the question is only leading to a conversation, and that’s as good of an intro

[00:07:13] as any.

[00:07:15] Think about it.

[00:07:16] What seems more common and natural to you?

[00:07:19] For someone to say, I’d like to talk to you about topic X, or for them to say, what was

[00:07:25] the last time you worked on topic X?

[00:07:29] It’s human nature to communicate through questions, and I’d encourage you to become a better listener

[00:07:36] by focusing on understanding questions better.

[00:07:41] Thanks so much for listening to today’s episode.

[00:07:43] If you enjoyed this discussion, I’d encourage you to join the DeveloperT Discord community.

[00:07:48] Head over to developert.com slash Discord to join that community totally free today.

[00:07:54] You can ask questions, you can discuss.

[00:07:57] It is not an overwhelming number of notifications.

[00:08:01] The community tends to send longer, more thoughtful messages, so if you’re interested in that

[00:08:06] kind of slower communication than you may be used to with messages firing off all the

[00:08:12] time at maybe your worst workplace or something, then this community might be the right one

[00:08:17] for you.

[00:08:18] It’s a thoughtful, deliberative community.

[00:08:20] Head over to developert.com slash Discord.

[00:08:22] It’s totally free and it always will be.

[00:08:25] If you enjoyed this episode and you don’t want this show to disappear, there’s no chance

[00:08:29] that that’s happening anytime soon, by the way, but if you want us to keep on going,

[00:08:33] one of the best ways to help kind of add gas to the engine, so to speak, is to leave a

[00:08:38] review in iTunes and then to turn around and share the show with somebody you expect might

[00:08:44] enjoy it.

[00:08:45] These two simple actions allow the show to grow organically, and honestly, that’s the

[00:08:50] only way the show has ever operated, by spreading through word of mouth and people sharing it

[00:08:55] with each other.

[00:08:56] So thank you so much for doing that already, and if you would like to invest again in the

[00:09:00] community, that is the best way to invest.

[00:09:03] Thanks so much for listening, and until next time, enjoy your tea.