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Daniel Stillman, Good Talk: How to design conversations that matter

The following excerpt is transcribed from the Zoom event that took place on 23 April.

Key points

  • There is opportunity to redesign many of the conversations we have whether it be in a professional context; conflict resolution; end of year reviews; check-ins; one-on-ones. To our personal lives; family meetings; workshops; culture etc. 
  • The mechanics of designing a conversation regardless of size we need to consider; having a strategy; remembering human connection through common ground; practising active listening. 
  • At its core, a conversation is made up of the people, the goals they have, the turns they take and the space it happens in.



Daniel Stillman, is the Founder & Director of The Conversation Factory. The Conversation Factory is Daniel’s Conversation Laboratory. Daniel recently published his new book Good Talk: How to Design Conversations that Matter. Daniel shares his philosophy for the mechanics and dynamics of building conversations that matter. As well as practical methods to design conversations. 


Deconstructing conversation

“Our lives are built one conversation at a time, and our lives are defined by the conversations we can and cannot have. Similarly, our organisations are defined by the conversations they can or can’t have.” – Daniel Stillman

When talking about designing a product, there are three clear identifiers; the design; the designer; the materials they’re working with. Even in the field of UX Design, we are able to break down the process of redesigning into touchpoints, customer journeys and flows, system maps and screens and
Fitts Law.

“To design is to devise courses of action aimed at changing existing situations into preferred ones.” – Herbert Simon

So, when posed with the question – how do you design conversations that matter? – we first need to turn our attention to what conversations are made of. We can deconstruct a conversation into elements such as emotions, questions, opinions, participants, pauses, even bias. However, emotions, unlike tangible materials, are incredibly difficult to design.


How do you design conversations that matter?

To answer this question attendees were broken into smaller groups and used a MURAL workspace to brainstorm new means to design conversations that matter. The key insights that came out of this brainstorm are as followed –  


Have a strategy

Many meetings and conversations occur without a definitive plan, causing them to be reactive and less productive. Defining objectives and identifying the stakeholders needed as a part of the conversation can help influence how conversations are held and what is being achieved during the allocated time.


Remember human connection through common ground

Communication isn’t limited to just words. Body language plays a large part when carrying conversations. This also means there is a need to find a comfortable common ground for everyone. Eye contact may be important to some, while others may not find it as comfortable and some may express themselves through physical touch or gestures. 

Embracing this diversity and being open-minded not only to the different voices and beliefs but also in the ways people choose to communicate with body language helps to establish common ground within a dialogue.


Practice active listening

Conversations go beyond hearing and exchanging words as they’re being spoken. Active listening goes through an arc that requires considered attention to what someone has said and asking relevant, intentional questions. By listening to hear and not to reply, we can have more meaningful exchanges.


Changing the interface of conversations

Space is one of the most powerful elements of designing a conversation, and creating the right interface comes down to what your goal is. Different conversations occur in their own physical ground. They can start in one space, and when there is a shift in the interface, the conversation changes.   

If we take a boardroom meeting that takes place in an office, it would be very different from a meeting that takes place in an open space, such as the beach. This shift in space would give a new energy and can dictate the conversations that start to form.

This also applies to digital spaces. Just as the dialogue and dynamic of the conversation shifted from Zoom in the main screen to Breakout Rooms, the energy, level of collaboration and input, and types of conversations changed along with the shift.


The 9 elements of conversation

Conversation OS, Daniel Stillman of The Conversation Factory

If we go back to the deconstruction of conversations, at its core, it is the people, the goals they have, the turns they take and the space it happens in. The conversation will change when there is an increase or decrease in the number of people involved, as does its complexity as more opinions are voiced. Other elements we can steer in a conversation are, but not limited to:

  • People
  • Invitation (to start a conversation/frames the dialogue)
  • Power
  • Turn-taking
  • Interface
  • Cadence
  • Threading (the narrative that holds a conversation together)
  • Goals
  • Error + Repair

Some elements are easier to see and shift, such as turn-taking and interface. Whereas changing power dynamics can be more difficult to achieve.

Design versus default

When talking about designing a conversation, we need to first look at the default, or the old, thoughtless design, of how conversations take place. As we understand these default behaviours, we can use the 9 elements to shift and design new conversations. Common defaults include – 

Default 1, first speaker  syndrome

The main concern with this default is that there is an anchoring bias where the first person to speak sets the terms of the conversation. This causes the rest of the dialogue to stem from the anchoring bias. The first speaker syndrome default can be shifted by designing a dialogue where there is a different cadence to the conversation. This enables people to take the time to think of their ideas first and then come back together to share with everyone.

Default 2, ping pong conversation

In this discussion, there may be a few people, going back and forth, exchanging opinions. This default is problematic because some people end up getting excluded from the conversation and are unable to find the right timing to jump in and contribute. Shift to designing a conversation where the turn-taking structure is used, the group gets a chance to hear from everyone before the conversation becomes a back and forth discussion.

Default 3, opening and closing at the same time

This type of conversation is problematic because someone may offer up an idea only to hear it immediately knocked down without consideration. This leaves no room for discussion around the proposed idea before it is entirely shut down. Shift the default behaviour so that there is an exploration of an idea before it is closed means that there is now a thread that creates a clear arc to the conversation.

Further reading

To see all our speaker Future Of Now book recommendations click here.


More about Daniel Stillman and The Conversation Factory


About the Future Of Now series

Our goal at More Space For Light with the Future of Now (FON) series is to build a community of like-minded passionate professionals. Initially, this series was created as a small in-person gathering to provide a knowledge share for our and our event sponsors community of clients and partners. However, by switching our operations to remote it has allowed us to raise the bar, and include our global network.

Our vision is the same, regardless of the potential scale of remote FON events. We intend to bring together like-minded professionals to share, inspire, and explore new opportunities for growth. So you can discover new ways of working to bring back into your organisation.

If you wish to connect with the broader community and join the ever-growing FON community on LinkedIn click here.


More about the organisations connected to this event

  • morespaceforlight.com.au – A strategy and innovation consultancy specialising in both in-person and/or remote workshops, design programs and Design Sprints.
  • MURAL.COheaps of new templates and tools. Sign up it is brilliant.
  • hacker.exchange – a global education company that is supercharging the next generation of startups & leaders.
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