top of page


This article was based on episode 012 of The Modern Manager podcast. To hear this episode, and many more like it, you can subscribe to The Modern Manager Podcast on iTunes, Google Play, Spotify, and Stitcher.

We have conversations every day. We have them with our family and friends, our colleagues at work, and strangers at the grocery store. We have them online. We have them in our heads. They are often organic which can sometimes leave us feeling unresolved. Is it possible that something as routine as a conversation can be intentionally designed and facilitated to actually deepen connections and produce specific outcomes?

Daniel Stillman says yes. As a “conversation designer,” he applies the same tools from his work as an experience designer - which focuses on the quality of the experience for the end user of a product or service - to facilitate constructive conversations about product innovation, culture and collaboration

In episode 012 of The Modern Manager podcast, I speak with Daniel - conversation designer, coach, consultant, author, and podcast host - about his work and how teams and organizations of all sizes, and even us as individuals, can benefit from it.


Conversation design is the art of designing an interaction between two or more people, such as a meeting, workshop, or an off-site, to “create an experience that shifts a group of people to a new trajectory, to transform teams and companies long after we work together,” says Daniel. As a conversation designer, he explains, “I do it by co-creating a powerful and engaging conversation with my clients using the tools of experience design applied to conversations.” He continues: “Meetings are experiences in the same way a digital product or service is an experience. And experiences have a clear architecture, that, once you see, it’s impossible to unsee. And once you see the components of an experience, you can shape them!”

There are five stages to the process of conversation design which are borrowed from the five Es of experience, or human-centered design. They are enticing, entering, engaging, exiting, and extending.

Enticing, Entering, and Engaging: Opening and Exploring the Conversation

These are the beginning and middle stages of conversation design. It’s important to begin with enticing, or inviting people into the conversation. “If you push something on people, it gets rejected. If you find a way to pull them in, that's a great way to get people to actually accept it,” says Daniel. Give people the big picture or a sense of what will be discussed. There’s no need for the content or topic to remain a mystery and cause unnecessary anxiety in meeting participants. (Note that this is why getting a text message or email from someone that just says, “We have to talk” can induce so much anxiety; people have no idea of the content or significance and are left to ruminate in their own minds.) It’s also unlikely people will want to come to a conversation when they have little or no idea what’s to be discussed. Instead, entice people by sharing your intentions. Then, they will willingly enter into a space that you are creating and be ready to engage with the topic.

Exiting and Extending: Closing the Conversation

These are the final two pieces of conversation design. Without an intentional ending, even the best conversation can feel awkward or somehow diminished. To skillfully manage an exit to the experience, consider what emotional state you want to close on, make sure you reiterate any positive outcomes, and review what the next steps are going to be. Clarifying the next steps will help to extend the experience beyond the meeting room for a lasting impact.


Managers, meeting leaders, and product innovators are looking for honest feedback, especially honest critical feedback. But this is often the most difficult feedback to get, because participants may feel unsafe being vulnerable and offering their unvarnished thoughts. To get around this psychological dilemma, Daniel uses a critique format called Rose, Thorn, Bud developed by one of his work partners.

The key to the effectiveness of Rose, Thorn, Bud in eliciting honest feedback is that everyone is asked to identify all three - roses, thorns and buds. It starts with identifying the positive, or what is working. These are the roses, and they provide confidence that some things are going well. Then the process moves to the thorns, or what is not working. The sting of this section is lessened by coming after the positive. Finally, it’s time to consider the bud, which is “some potential little seed of goodness in the idea or concept that with some thought or development could be transformed into a rose,” says Daniel. In other words, buds are new ideas, improvements or enhancements to the ideas on the table.

To ensure thoughtful and democratic participation, Daniels begins by handing out sticky notes in three different colors. He allocates silent time for every person to write down two roses, two thorns, and two buds, and then puts the sticky notes on the wall for everyone to see. “Creating that space to do all three is going to give you a balanced critique of whatever it is you're trying to do,” Daniel explains. “And it's going to make it easier for people, some of whom are not comfortable with negativity and some of whom are not comfortable with positivity, to give you both.”

Drawings elicit new and different thinking

Daniel says that physical drawings can help spark conversations and elicit new information. He often warms up his clients by asking them to sketch a picture of their job or ideal customer. The act of drawing often relaxes people by reminding them of their childhoods and giving them a simple experience of fun. Daniel hangs the pictures on the wall and the group discusses them. The pictures provide “an amazing wall of data to work through over time,” bringing out information that may not have emerged if the conversation was only vocal.


In his conversations with community leaders for his podcast, Daniel discovered that the leaders all share a self-care practice like meditation in which they “cultivate and sustain their internal conversation.” He identifies this kind of conversation as one of the nine conversations that comprise whole leaders, and this has attuned him to the kinds of conversations he was and wasn’t having with himself.“Conversations feel human to me and [conversation design is] a way of taking all of these technical aspects of meetings and organizational change and just grounding it into human behavior,” says Daniel.

Whether it’s internal or external or both, how can you more deliberately manage the conversations in your work and life to deepen relationships, elicit honest thinking and achieve your desired outcomes?

This article was based on episode 012 of The Modern Manager podcast. To hear this episode, and many more like it, you can subscribe to The Modern Manager Podcast on iTunes, Google Play, Spotify and Stitcher. Never miss a worksheet, episode or article: subscribe to Mamie’s newsletter. Join the Modern Manager community on Patreon and get additional exclusive resources and services.


twitter: @dastillman

linkedin: Daniel Stillman

Optimize your time. Cultivate your team. Achieve your goals.

Leave a comment below or tweet at me @mamieks.

Love this post? Share it!



Commenting has been turned off.


When you subscribe to my email list, you'll be notified when new blog posts are released.

bottom of page