Unlocking Depth in Conversations: A Hack for Inspired Leadership

Rebecca Colwell

Rebecca Colwell

Rebecca is a leadership innovator, a thought leader in facilitative leadership and one of the world’s top two experts in Integral Facilitation. For the last decade, she’s been bringing her vision to life as the developer of the world’s premiere Integral facilitative leadership training, Integral Facilitator® and Next Stage Facilitation, with graduates in 5 continents.

Discovering the Power of Depth

In a world increasingly dominated by fleeting interactions, the art of facilitating depth in conversations is not only uncommon but immensely powerful. 

At a recent workshop, a leader asked me, “How can I have my group connect more deeply with what matters in our conversations?” It’s a sentiment many of us resonate with, particularly when desiring more authentic engagements.

The pursuit of depth is not merely about enhancing the quality of conversations. It’s about nurturing a trusting environment that champions growth, self-awareness, and transformative leadership.

The Problem with Surface Conversations

All too often, meetings and dialogues are lacking in depth.

 I have been part of conversations that feel superficial, and where members stay guarded and closed. Too little time has been spent in creating psychological safety. Topics themselves are abstracted and disconnected from the human experience of the leaders’ main concerns. People are held hostage by societal and group norms that emphasize conformity and comfort over authenticity and exploration. You can read more about this in my recent blog post on participation.  

And while there’s lots of room for light-hearted chats and socializing, the work of growth also demands a deeper connection, introspection, and the ability to take social risks and challenge the status quo.

Many of us share a similar motive “I want to go deeper because I made a commitment to stand for and encourage the growth and success of my members.” And, when facilitated correctly, deep conversations can unlock previously untapped potential in leaders, fostering adaptability and innovation.

The Transformational Journey of Depth

Take a moment now to reflect on the questions: 

What have I been up to in our conversations?
How has my facilitation (whether active or passive) influenced the quality of our conversations?

For example, ‘challenging our assumptions’ is a staple in many leadership circles.

Our logical and rational minds can enjoy sparring with ideas and unpacking the ways we think. You might be familiar with inquiries like: “Tell me why you believe that is so?”, “Is it true?”, “Can you see that that is limited?”. 

But too much of this kind of inquiry can feel like there is something ‘wrong’ or needs ‘fixing’. No one wants to feel interrogated.

The art of facilitating conversations with depth, with more flow and engagement – is more rare, and it promises more valuable outcomes. 

True depth in conversations blends challenging thoughts and ideas with empathy, balances advocacy with inquiry, facilitating a flow that enriches both individuals and groups. 

Why is this so? 

When we are in a conversation with a degree of depth, we spend time beneath the surface, challenging existing beliefs, assumptions, or perspectives, and this often evokes introspection, self-awareness, and a nuanced exploration of complex ideas or emotions.

Deeper conversations don’t just serve the participants in the conversation. When well-facilitated, they affect the individual and also the group.  These conversations generate new insights and enhanced self-awareness at the core of the leaders’ understanding of themselves.  

And, engaging with questions with depth can grow the relationships in the group, and spill over into the culture of the leaders’ organizations – encouraging reflection, learning, and personal growth.

The Hack: Crafting Meaningful Conversations

At the heart of meaningful conversations lies the ability to encourage introspection and be in the immediacy of the moment. So – here’s the “hack” that places you directly at the intricate nexus of where inner meets outer – the place where leaders’ internal landscapes meet the external challenges they face.

Here are the three key guiding principles:

  • Promote personal perspectives: Encourage the use of “I” language, allowing individuals to own their experiences and feelings.
  • Explore the unknown: Delve into areas outside the ‘grooves’ created by our expertise and certainty.
  • Use immediacy: Encourage participants to remain present, and actively engage with the topic in this very moment. “How do you feel about “quality x” here, right now?” 

This can be facilitated in a conversation between two people, as well as in group conversations. It is not necessary to always arrive at ‘an answer’ when these questions are posed, and sometimes the depths that are accessed and touched may not be visible to others until later. 

To encourage deeper self-awareness and self-knowledge amongst all the members of the group, invite the group to delve into the interplay between the unknown and your inner life as a leader in an “open conversation”. 

  • Start each conversation with a good orienting question that resonates with the group and draws people in. 
  • Prime the conversation with a brief anecdote about how this is relevant to you and what you’ve discovered or are moved by. 
  • You can close your deeper conversation with a go-round, completing the sentence ‘my (desired) future way of leading in uncertainty will be …’. And, of course, some words of appreciation. 


Here are some examples of questions that could be used to invite a 20-25 minute Open Conversation within a group. (We teach this conversational approach in our Next Stage Facilitation program). 

As you scroll through these examples, which ones do you like? What would you enjoy exploring with other leaders? Notice if any of the topics feel relevant and have some ‘life’ in them for you, and use that as a guide. 

Examples include:


Values amidst uncertainty: 

    • How do my values influence decisions during uncertain times?
    • How do my personal values align or clash with the collective values of the organization in uncertain times?

Vulnerability as Strength: 

    • How can I use moments of vulnerability as opportunities for deeper connection and trust-building with my team?
    • What do I feel the most vulnerable about right now?

Empathy & Connection: 

    • How does acknowledging my own internal struggles with the unknown help me empathize with my team’s challenges? 
    • How can I foster a culture where team members feel safe sharing their own internal journeys and uncertainties?
    • How do you feel connected to the members of this group right now? 

Intuition & The Unknown

    • How do I balance data-driven decisions with intuitive insights, especially when the way forward isn’t clear?
    • In what situations has my intuition served me well in the face of ambiguity, and how can I cultivate this inner sense? 
    • In what situations has my intuition been wrong?

Legacy in Flux:

    • How do I envision my leadership legacy in an ever-changing landscape?
    • How is my behavior threatening or undermining my potential legacy right now? 
    • What do I want to be remembered for, especially in how I led my team through the unknown?

Here are a few more questions from our friend Bob J. Anderson, founder of Leadership Circle® from his book, Mastering Leadership.

Authentic and Courageous Dialogue:  

    • How do I consistently speak the truth, especially when it requires courage? 
    • How do I have difficult conversations in a great way? 
    • How do I act out the vision I hold in every encounter? 
    • How do we create a collective and coherent field for dialogue that leads to breakthrough solutions to complex issues?

Encouraging Continual Growth

Concluding deeper dialogues is as crucial as initiating them. 

Encourage participants to reflect on what they are taking away from the conversation that reinforces their leadership mindset for uncertain times. Express appreciation for shared insights and collective growth.

When the conversation is closed, you have an opportunity to bring attention to the quality of the conversation itself, and notice what was satisfying about a deeper, more developmental conversation. In this way the group can mature its capacity to shape its own culture and be more deliberately developmental.

The Way Forward

More than ever before, leadership is becoming more relational and conversations are key.

Leadership growth demands connection, introspection, and a willingness to delve deep. 

The conversations that you facilitate can be part of the transformative process that leads to new levels of confidence and clarity, and to new mindsets that enable leaders to adapt, innovate, and navigate persistent and complex challenges with greater insight and flexibility.

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