Becoming great at listening

A concise guide on going from good to great at listening. Plus, an audio deep-dive that reveals what world-class listening looks like, how you can get there, and why it matters.

Listening and thinking actually don’t go well together.

Your job as a listener is to consume in a few seconds or minutes what the speaker might have experienced over weeks, months, even decades.¹

So, as a listener, odds are stacked heavily against you.

What can you do about this?

Partition listening and thinking.

View them as phases or modes, not concurrent activities.

When you are in listening mode, just be in listening mode. Just absorb. Don’t judge, don’t filter, don’t be overcome by emotions. This is not easy, but I have found it to be very powerful.

Then, once listening mode is over, get into thinking mode. At this point, I ask the speaker if I can think for a few seconds or a minute.

I am now in pure thinking mode. This is when I evaluate, synthesize with my experience and viewpoints. And I mentally frame my response.

Then, I speak.

This is sometimes awkward, especially when I am speaking with someone for the first time.

But this awkwardness usually dissipates once they see
a) the degree to which I have absorbed their message
b) the quality of my response

As with all my writing, this is not for everyone, but it will be useful for some and transformative for a few.²

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Want a deep-dive on listening?

Do you want to go much more in-depth into the art of listening?

Do you want to understand what the absolute pinnacle of listening skills looks like and ways to get there yourself?

Do you want to learn why gaining mastery in listening isn’t a feel-good, altruistic act, rather, it is the most practical thing you can do towards becoming a world-class leader?

If yes, here’s a unique, 15 minute bonus deep-dive for you:

Note: I’ve generated this deep-dive using NotebookLM, using not just the post above but also some of my other advanced, private writing on the topic of listening. This is based on content you won’t find anywhere else, which also means that this podcast, while AI-generated, has depth and insights you won’t find anywhere else in the world. It is not for everyone, but will be mind-blowing for a few who are able to engage without ego and… actually listen³

1. For those who really care about the art of listening, I’d ask you to read that sentence again. It is not a small point, it is a very big point. It is only through genuinely understanding this point that someone has any hope of creating the internal conditions necessary to become great at listening.

2. Since I have only just begun posting to Substack, and since most people are used to long form posts on Substack, I want to remind you that my writing style is very concise (after years of being the opposite). While it may not always look that way, I pack extreme density into a short post like the one above.

What this means for readers:

a) it is advisable to read my posts much slower than your typical pace of reading

b) the density and depth of each post will begin to become apparent as you genuinely think about the message of the post

c) if a given idea in my writing resonates with you, the nice thing is that you will be able to apply it to your specific situation by augmenting the idea with your thinking - in that sense, my writing is different from frameworks, playbooks, tactics, which can make you average (if you’re below average) and above average (if you’re average), but those things will never make you extraordinary or world-class

d) a few people (but not a majority) report that because my writing is concise, they are able to retain the core idea(s) better and at some point it becomes a part of how they naturally think and operate i.e. it is no longer a separate entity, separate content, it is now within you, indistinguishable from the rest of what makes you you

I will repeat the above message occasionally as new subscribers join this Substack, because, as I’ve said before, my writing is useful for some, transformational for a few, but it is definitely not for everyone. I do not write for broad appeal. I write for myself, because it is fun for me. If it benefits some people, wonderful. But that isn’t the chief reason why I do it.

3. Some of you (not all, but a majority) might get turned off by this podcast because “it’s AI”, “it isn’t in your voice”, “it lacks personality” (it doesn’t), etc. Any smart person can always cite reasons to dislike something. I get it.

What I want you to know is that I think it is really great. And as someone who knows more about this specific topic than anyone else in the world (sort of by definition, since I wrote this stuff), I will say that if you can get over your bias against AI-generated podcasts, you will discover that there is so much gold in this particular podcast that you will not find anywhere else in the world.

And remember that this was generated with a ton of unique content of mine on listening i.e. it wasn’t just a lazy one-shot “please create a podcast on listening, make it sound good, thank you”. A ton of effort, thinking, and unique context went into creating this.

You are of course welcome to think whatever you want.

All I am saying is that (a) if you truly care about this topic and (b) if you care about gaining an advantage for yourself in work/life more than you care about signaling to yourself or others that “all AI is slop”, then there is nothing else anywhere in the world that will illuminate the very advanced ideas on listening than this deep-dive.

Lastly, if you don’t like audio as a format, that’s fine. People have different preferences (some love it - some use it to augment what they’ve read - etc.) Remember that this audio content is a pure bonus.