Become a better listener by asking what words mean

David Dikman
4 min readFeb 27, 2022
When you say “an Apple” is that the edible kind or the really expensive kind?

I think words are important. I have always liked how stringing together the right ones makes poetry. Switching a single word in a sentence can change the sentiment completely.

Words have power. They inspire emotion and can bring us together, or apart. If I ask you to think of Spring, something Sweet or simply say Warm, some image will come to your mind. But it might not be the same image as would come to me.

This is what I want to touch on in this post. How we have to agree on what words mean in order to communicate well.

What do you mean?

The other week I was discussing with a colleague. We were trying to agree on some details about a system integration we were about to build.

We got stuck on this one point arguing about the pros and cons of having a “dynamic schema”. We went back and forth, I proposed my arguments and my colleague theirs. However, these arguments did not contradict each other yet somehow, we seemed to be on separate sides of the argument. After a good ten minutes, I stopped to ask, “what do you mean with dynamic schema”?

Abstract words have lots of room for misunderstanding

When I was told what this colleague of mine meant when they said “dynamic schema” I realized we had been talking about completely different things these past ten minutes.

In both cases the words were applicable but “dynamic schema” is so abstract it could be used for a lot of different things.

Once we understood that we were talking bout different things we proceeded to show in actual text (JSON code in our case) what we meant with a “dynamic” versus a “fixed” schema and also clarified where we meant that this schema would be applied.

All said and done, we were actually on the same side all along. We had been arguing for or against the same thing, in different places.

Listening to understand

As much as I like well-chosen words, I must admit this is not something I am very good at. I often speak too soon and frequently make mistakes, saying one thing when I actually mean another. This is something I am trying to work on.

However, I think speaking clearly is only half of the problem. There are always two sides to a conversation and we play both the talker and the listener and we can improve in both of these.

If we think that our only job as a listener is to hear what the other party is saying, we are wrong. Communication is successful only if it is both received and understood and this is a team effort.

How to listen better

In the past few years, I have found several newsletters and podcasts which have stressed the importance of listening better.

I believe these made an impact on me because I have followed them for a long time and came across certain stories at just the right time. However, I hope that you check them out and that perhaps at some point they will be as helpful to you as they have been to me.

First and foremost, although there is no one single episode specifically, time and time again the Your are not so smart podcast comes back to listening. David McRaney has researched and written a lot about changing opinions and from what I understand it comes down much more to listening than speaking.

From the Farnham Street newsletter, I found this article on Becoming a better listener which has a lot of useful practical tips. Also, their Knowledge Project podcast episode with Todd Simkin on making better decisions has a part in it that exemplifies reflective listening really well.

In the Heartbeat podcast from Know your Team, one episode with Will Larson from Stripe talks about listening as a core part of leadership. In another episode, Jerry Colonna from RebootHQ proposes using the WAIT acronym (Why am I talking).

Other practical tips

To wrap up I would like to share a few practical things of my own that I have got either from the above sources or elsewhere and that I try to keep in mind when I am discussing with others.

  • Assume your counterpart has good intentions, if they argue for something, they probably have some point (from James Clear’s newsletter, author of Atomic Habits)
  • Clarify what values you have, why are you arguing for your opinion, is it cost, reputation, willingness etc (from Developer Tea podcast)
  • Don’t listen waiting to speak, listen to really understand, by asking you might in fact be able to get your opinion across anyway
  • If you are like me and quick to speak, keep in mind how much you talk, try to listen more than you talk
  • Ask open questions, rather than “do you agree?” ask “how do you feel about this?”
  • Ask what thinking led to the conclusion, were any alternatives considered?
  • If you are unsure about abbreviations, ask straight away. Don’t feel ashamed (write up the answer so you don’t need to ask again). Many times others in the room might not know what the abbreviations mean either
  • Ask what your counterpart means with words (phrases, concepts etc), ask them to define them. Clarify your own definition as well. It may seem silly sometimes but really simple words can have widely different meanings to different people
  • Use and ask for practical examples, say “show me”, ask to get a picture drawn or to get an actual example shown, this is the best way to get on the same page

I hope this helps and I’d love to hear your thoughts on this, do you have any tips or tools you use yourself to have better dialogues? Let me know in the comments!



David Dikman

Full-stack developer and founder. Writing here and at Currently open for contract work.