Daniel Stillman, an executive coach, and facilitator, is an authority in the field of conversational leadership. With a wealth of experience as a conversation designer and an author, Daniel has dedicated his career to enhancing the way we communicate. His book, Good Talk: How to Design Conversations That Matter, is recognized for its impactful insights into communication dynamics and strategies. In this episode of the Unlearn Podcast, Daniel joins Barry O’Reilly to explore the importance of collaboration and how to create an environment conducive to productive dialogue, particularly in the context of leadership.

Conversational Leadership

Conversational leadership, as defined by Daniel, refers to an approach to leadership that emphasizes the importance of effective communication and dialogue. It relies on the power of conversation to inspire, motivate, and engage individuals or teams in a meaningful and productive manner. Conversational leadership also includes elements such as:

  • The “art of invitation” – leaders inspire others to participate in dialogues and actions, rather than dictating or forcing them.
  • Emphasis on playfulness as a form of intrinsic motivation.
  • Framing challenges effectively and inviting people into a collaborative space with a clear understanding of what needs to be achieved.
  • The creation of transformative conversations that lead to powerful outcomes.
  • A focus on listening, presence, and reframing questions to achieve real goals.

“You cannot have a divergent, emergent and convergent conversation truly all in one go,” Daniel quotes from Chris Ertel’s book, Moments of Impact. “Everybody wants to be in the conversation, and it’s not effective if everyone’s in the conversation, because everyone can’t talk all the time and there’s only so much time we can have together.” He explores the mechanics of designing productive meetings, especially in a remote work landscape. He explains that strategic collaboration, hinged on appropriate tools and methods, is integral to making meaningful progress. Barry comments, “This idea of opening, exploring, and closing – it gives people a framework [to have conversations with].” [Listen from 1:55]

The Nine P Model

Daniel introduces his holistic Nine P Model of Conversation Design. This includes:

  • Purpose (the reason or aim of the conversation),
  • Principles (the agreed norms and values to be adhered to),
  • Process (the methods or steps to be followed),
  • Place (the physical or virtual space where the conversation occurs),
  • Pitfalls (potential risks or problems),
  • Progress markers (indicators of progress),
  • Product or outcome desired (the tangible or intangible results expected from the conversation), and
  • People involved (the participants in the conversation), and Potential outcomes (the possible consequences of the conversation).

Link to learn more about the Model is here.

“In a leadership event [Nobody Studios] did a year ago, there was so much focus on getting the structure and flow right,” Barry shares, emphasizing the importance of intentional design in effective communication. “A friend even mentioned that the time when you can bring people together for complex collaboration [and] to solve problems is going to be really important.” [Listen from 9:45]

Asking vs Telling

Daniel examines the tension between ‘asking’ and ‘telling’ in the context of problem-solving and leadership. The ‘telling’ approach is directive, where the leader provides instructions or solutions directly. On the other hand, ‘asking’ is more participative, with the leader posing questions and inviting input from the team to collaboratively arrive at solutions. Daniel emphasizes that the ‘asking’ method, when used correctly, can be incredibly valuable. It creates a space for team members to contribute their ideas, fostering an environment of collaboration and mutual respect. Furthermore, this approach can lead to more innovative solutions, as it leverages the collective intelligence and creativity of the team. However, Daniel does not entirely dismiss the ‘telling’ approach. He acknowledges that in certain scenarios, it might be more effective for a leader to provide direct instructions or feedback. [Listen from 13:50]

Barry shares, “A simple question I’m going to ask myself before going into any meeting is, ‘What am I here to do? Is this something that I need to tell people to do that already has a defined solution?’ Is that even a meeting or is it an email?” Framing your intention this way helps you prioritize what to have meetings about. [Listen from 17:15]

B Prime

“My coaching mentor taught me the most fundamental change model: A to B. We’re at A and we want to be at B, and we just say, ‘What’s the gap?’” Daniel says. Real leadership in uncertainty, however, is not A to B leadership. “It’s what my coaching mentor calls B Prime.” Embracing the concept of B Prime, a future better than what we can currently imagine, requires leaders to let go of traditional paths. Creating B Prime involves framing challenges in a way that encourages expansive thinking and creativity. It pushes individuals and teams to transcend their current understandings and limitations, enabling conditions for dialogues and solutions that lead to more powerful and transformative outcomes. The hard part, Barry says, is letting go of the relative safety of the known. “The magic is the idea of going on the quest,” he adds. For startups, there’s often no path to taking the next best step, so you have to create it yourself. Navigating that uncertainty can be difficult, but with the right tools, it becomes not only possible, but also exciting. [Listen from 20:25]

Creating Transformative Conversations

Daniel warns of the danger of over-designing conversations to the point of stifling the magic. “Leadership is the ability to design the conditions for a transformative conversation,” he claims. Striking a balance between design and spontaneity is the key. You must be “willing to believe that something better is possible.” Additionally, he challenges leaders to be honest about their intentions when managing underperforming team members: either genuinely coach them towards improvement or make the tough decision to let them go if there’s no hope for growth. “It’s a process of experimentation,” Barry adds, “using tools to design great collaboration experiences. And it doesn’t happen overnight.” [Listen from 26:55]

Looking Ahead

Daniel is looking forward to the way collaboration, conversation and AI will intersect to foster more effective communication and goal achievement. He emphasizes the significance of adapting our thought processes, referencing the “Ask/Tell” two by two matrix (more on that here) and ‘triple loop learning’ (more on that here) as valuable tools for changing how we approach problem-solving and action. Daniel views AI as an assistive component that can enhance our conversations and relationships. [Listen from 28:35]