Effective Conversation is a Skill and Here’s How You Can Improve It

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Show Notes:

If you think you’re good at making conversations, think twice. There are always multiple conversations happening within one conversation so you should always try to understand the other person’s perspective. Today, we get to hear from a conversation expert, Daniel Stillman.

Daniel is an executive leadership coach, a keynote speaker, and a conversation expert. Or as he likes to put it, he designs conversations for a living. Daniel has quite an impressive portfolio. He works with organizations like Google, Nike, and Visa to help them sustain productive dialog, and coach them through the innovation process. He’s also the author of Good Talk: How to Design Conversations that Matter and a host of The Conversation Factory podcast.

Daniel believes that we are all defined by the conversations we can and can’t have. There’s an entire spectrum of conversations happening among us and we should try our best to be better at them.

In this episode of the Think Business With Tyler podcast, we talk about ways to improve your conversation skills, the importance of adopting an error and repair mindset. We also discuss the critical elements of a productive conversation and why you need a coach to help you work on yourself.

If you want to make sure your message comes across effectively every single time, this is the perfect episode for you. Tune in to hear what Daniel has to say about conversation designing.



💡 Name: Daniel Stillman

💡 What he does: Daniel Stillman designs conversations for a living, and insists that you do, too. He works with organizations like Google, Nike, and Visa to help them frame and sustain productive dialog, deepen their facilitation skills, and coach them through the innovation process.

💡 Noteworthy: Daniel’s the author of Good Talk: How to Design Conversations that Matter and a host of The Conversation Factory podcast.

💡 Key Quote: “It’s really important for people to realize that in one-on-one conversations, there’s patterns and structures, but the inner conversation the self-talk is what drives all of it.:

💡 Where to find Daniel: LinkedIn

Key Insights


There are always multiple conversations within one conversation. According to Daniel, the first step to having better conversations is realizing you’re always having multiple conversations when speaking to someone one-on-one. That’s because each and every one of us is always having an inner dialogue, so-called self-talk. Self-talk is the driver of all conversations, so we need to improve how we talk to ourselves first and foremost. Daniel explains, “There’s a lot of ways we can take this, but the first is just to realize that they’re having a lot of conversations and to realize that they have a choice about how they can steer them or not steer them. […] I was just interviewing a wonderful guy who talks about spheres of conversation and so inside of this one-on-one conversation that you and I are having is your thinking, your self-talk, your inner dialogue, and mine. This is the classic: what I meant to say, what you heard, what I think you heard, and what you think I meant to say, So what we ask for, what we what we’re willing to respond to is all based on the inner conversation. And so it’s really important for people to realize that in one-on-one conversations, there’s patterns and structures but the inner conversation, the self-talk is what drives all of it.”

We should adopt an error and repair mindset. Because conversations are so complex, there will always be errors. The trick is to recognize them and figure out how to deal with them. Instead of solely criticizing, try to get to the bottom of each error and ask why it happened. Was there an underlying issue that you need to tackle? Is there a need to include an additional step in your process? According to Daniel, we should adopt an error and repair mindset. “Having an error and repair mindset of let Me seek first to understand before J’accuse, let me first slow down and say what made this possible and accept some responsibility for the system, which I helped create before we go to the cutting room or the killing floor. […] I’d like to find out what their view of this is. And that’s a great conversation. There’s two sides to the coin. And there’s a universe in that interaction.”

Context, clarity, and curiosity are the three key elements of an effective conversation. There is no productive conversation without context, clarity, and curiosity. By providing context to each conversation, you provide the background story. This is particularly important in leadership. If you want your employees to see the bigger picture, you need to put things in context and explain your goals. Another critical element is clarity. You need to be able to explain the context with clarity. And finally, curiosity is the willingness to sit down with your team, work on your conversations, and ultimately be curious about other people’s perspectives. “People talk about having a purpose and agenda for every meeting conversation. But the ability to communicate that purpose, and also to realize that someone else might have their own purpose and their own context. It just means that you got to suss that out in the beginning and say, here’s what I want to get out of this conversation. This was important for me, what’s important for you?”

Get a professional coach. Daniel believes that everyone can benefit from having a personal coach. Whether you have an important meeting coming up or you want to improve your conversations altogether, you will achieve those goals much faster with the help of a professional coach. “I had a coaching coach when I started a couple of years ago wanting to make coaching a bigger part of my business, I got a coach for my coaching. How meta is that? I have a men’s group that helps me, we’re emotional coaches for each other. Everybody needs, I think you need more than one coach. It said this, but if there’s something you really want to get good at and you want to improve, you have to invest time and money, either your own on yourself and we all know how hard that is. Or you can buy time with you or me to guarantee that you’re going to focus on these super important questions.”

Top Quotes


“Most of us are conversation designers in our work and our home lives and some of us are just doing it more artfully or on purpose. But the conversations I tend to design, I’m an executive leadership coach so those are conversations I design. I sit in deep dialogue with leaders to help them work through all sorts of conversations that they need to design, like the conversation with themselves, building change in their organizations. And other conversations I design include the podcast that I host and a community of folks that I support, who’ve come through public workshops that I run on facilitation and conversational leadership.”

“When I talk to a business leader that’s struggling, it’s usually because one of the main conversational sizes is missing. So they’re not taking enough time for themselves. Classic, right? They’re just not taking reflective time. They don’t have a coach. Or they do but they’re not doing any work between sessions to reflect. They’re not doing some sort of reflective practice like meditating or journaling or exercise. The self-care and your self-talk is core.”

“One of the elements of the conversation operating system is the interface for the conversation. […] Text messaging, phone calls, video calls, say different things. And this is really, really key to make sure that the interface we pick sends the right message.”

“Helping people understand the big picture, the purpose, the goal, the overarching story, will help make the next piece clearer, because it’s in that context, and I think that’s something that leaders and business owners have to do all the time, which is put things in context of purpose and goals.”

“You can coach yourself. Sit down as my negotiation coach, my teacher at Harvard told me, sit down in your chair, and then put a chair next to yours. Say your problem then go sit in the next chair over and look over at yourself and say, ‘Okay, from my perspective over here, this is what I would do’. It’s so hard to take that time to think which is why paying someone to be with you is sometimes the only way to guarantee that you take that time to think.”


Personal Website

The Conversation Factory

The Conversation Factory Podcast

Good Talk: How to Design Conversations that Matter

Online Facilitation Master Class

Akata Witch (the Nigerian Harry Potter)

A Culture of Excellence

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