Six transformative techniques for collaborative conversation

Don’t pitch & sponge — turn your conversations into collaborations!
Tuesday, May 28, 2024

Creative professionals and consultants often feel misunderstood, and they often are. Even highly skilled professionals can struggle to engage in meaningful and balanced conversations. Experts of all kinds can undervalue soft skills such as the art of conversation. Here, we discuss six transformative conversation techniques.

For many, trouble surfaces when switching between two distinct modes: passive and active. I like to call this passive mode “sponge mode,” where the focus is spent on absorbing. Transversely, I call an active state “pitch mode,” wherein outbound communication happens in an attempt to convey ideas and opinions.

These two modes are foundational to communication. The trouble is simply toggling between them can feel like waiting for your turn to speak. It can feel transactional or, worse, oppositional. What’s more valuable: being correct right alone or achieving greatness together? We should strive to foster a shared understanding.

In a world where opinions frequently divide, the art of communication lies in our ability to listen, learn, and connect. That journey of curiosity and creativity starts not with our words, but with an openness to set aside egos and biases in pursuit of deeper insights. Good conversations drive interest, create understanding, and build trust.

At Territory, a remote-first organization rich in diversity and ideas, we’ve found that fostering trust and respect hinges on our approach to conversations — viewing them not as battlegrounds for our beliefs but as bridges to mutual understanding.

Embrace openness to make meaningful dialogue

The pathway to effective communication requires a commitment to continuous learning and adaptation, embracing each conversation as an opportunity to expand our perspectives. It challenges us to step outside our comfort zones, inviting us into a space where trust, authenticity, and respect for our exchanges are built without the goal of finding agreement.

In this digital era, where the nuances of face-to-face interaction are translated into pixels and text, the importance of genuine connection becomes ever more critical.

I’ve worked over the years to develop my own conversation skills in six key areas:

  1. Creating space, or practicing patience while stepping aside so that others can contribute
  2. Empathizing, a mindset that works to connect deeply with your conversation partners
  3. Listening, techniques that stretch beyond simply hearing and waiting for your turn to speak
  4. Reflecting, a formula that drives clarity and connection
  5. Visualizing, the simple art of turning complex words and ideas into concrete pictures to aid in understanding
  6. Asking, the rosetta stone for deep conversational understanding

This article offers a high-level overview of my approach in these areas. Individually, each technique can enhance your collaboration skills. When applied together and in sequence, they can sharpen your listening abilities, expand your perspectives, and strengthen relationships through the art of collaborative conversation.

Create space

You’ve been in those conversations or meetings—the ones dominated by the most aggressive, opinionated, or senior figures, leaving little room for anyone else. While it may not be an intentional act, it can feel suffocating and frustrating for all involved.

Whether you’re a passionate leader prone to monologues, or simply uncomfortable in silence, taking too much space in a conversation can kill critical moments of insight. If, like me, you’ve too often found yourself monopolizing the dialogue, you might try reminding yourself to literally wait. The W.A.I.T. technique (“Why Am I Talking?”) serves as a potent reminder not to overshadow your conversation partners.

My long-time collaborator, Jeremy Varo-Haub, introduced me to the W.A.I.T. technique. It prompts you to take a breath, allowing space for others to contribute or to gather your thoughts. For leaders, it’s a tool to encourage team contributions, steering participation towards more equitable and collaborative dialogues.

Admitting to frequent interruptions isn’t easy, but recognizing the urge to interject — whether from excitement or emotional reaction — is crucial. It’s hardly conducive to open, honest exchanges and may leave your partners hesitant. A Post-It with W.A.I.T. written in block lettering at my screen’s corner has been a helpful reminder to create space in conversations more often than I used to.

Distractions can diminish the depth of our conversations. Making sure you’re not one of them and taking W.A.I.T. to heart shifts the pace of our exchanges. This approach is crucial for fostering deeper understanding and meaningful insights, reminding us all why it’s often said we have two ears but only one mouth.

W.A.I.T. encourages us to consider whether our input is truly worthwhile or if we might gain more by listening. This practice fosters patience and makes room for quieter or hesitant voices to be heard. Sometimes, employing W.A.I.T. leads to longer or uncomfortable silences. Dive into those moments—great insights often emerge when space is granted.


Empathy is the ability to understand and share another person’s feelings. It’s an incredibly effective and valuable ability to master. Empathic communicators strive to understand their conversation partners’ motivations and emotions while also creating an inviting environment for sharing and collaboration. In this, exercising empathy is about tuning in to both yourself and others.

Paying attention to your non-verbal cues is key to practical empathy:

  • If you’re naturally expressive and tend to show a lot of emotion, you might need to tone down how much you let your face and body express. Change the vibe by staying collected and being the listener to whom you’d feel comfortable opening up. Jotting down what you catch and any thoughts popping up ensures you don’t miss out on anything good.
  • And, if you’re more of an inside thinker, remember that simple things like a nod, eye contact, or a smile can warm up and encourage the conversation.

When you pause and practice patience, especially if you’re entering a conversation that might get tense, it’s essential to lead with empathy.

Once mastered, employing empathy in every conversation will allow you to grow in understanding of the people you’re conversing with and become a more trusted and valued conversation partner—you may even be accused of being a mind reader!


There’s hearing, and then there’s listening. You can hear something without understanding it. Hearing is often a passive act, yet listening requires engagement because it’s an action to understand.

Collaborative conversationalists aspire to be exceptional listeners in an attempt to achieve deeper understanding and forge stronger connections. Effective listening goes beyond mere comprehension; it’s crucial for making your conversation partner feel genuinely heard. Although it might feel slow at first, this approach clears up misunderstandings and reduces the need for repetition or clarification.

Moving past quick, back-and-forth banter is also vital. While seemingly full of energy, such exchanges can inadvertently make you seem dismissive, irritated, or even arrogant, which might alienate your conversation partner.

Another tip I learned from Jeremy is the listen hard technique, also called active listening. Though it sounds simple, its impact is profound. Sometimes referred to as listening with your ears, eyes, and heart, it calls for undivided attention to the speaker, tuning into the subtleties of tone and body language beyond just their words. This level of focus ensures a deep understanding of the speaker’s message and intentions. Being fully present, especially in remote interactions, creates a chance for genuine connection across any distance.

“Listen hard” is not only a personal discipline tool; it can also encourage others to engage more deeply, making it invaluable for storytelling and leading groups. Trying this technique can greatly enhance communication effectiveness across various settings.


Following closely on the heels of active listening is the practice of reflective listening, also commonly referred to as empathetic reflection. This technique involves paraphrasing or summarizing the speaker’s words and asking for confirmation to ensure accurate understanding. It validates the speaker’s message and demonstrates that you’re not just hearing but comprehensively processing their words.

“What I’m hearing is _____.”

If your conversation is personal or becomes passionate, include how you perceive their feelings about it. It’s a potent formula to drive connection:

“What I’m hearing is _____, and it’s making you feel _____.“

This usually helps the communicator feel validated and relieved and de-escalates the tone of the conversation. It also allows your communication partner to clarify any potential misunderstandings.

A good formula to remember is Mirror/Validate/Empathize.

Mirror: “What I’m hearing is _____. “

Validate: “Am I hearing you correctly?”

Empathize: “I understand how you must feel ________.”

Conversations, inherently complex organisms, serve dual purposes: they facilitate both communication and connection.

Just as we can actively engage in reflective listening, we can also express the need for it in our interactions. I’ve been in countless conversations where I felt my contributions were misunderstood or, worse, dismissed. In these moments, rather than escalating the situation, I’ve found it effective to simply state, “I’m not feeling heard.” This expression can act as a catalyst for your conversation partner to employ reflective listening, thereby demonstrating their understanding. By reflecting back on what they’ve heard, they ensure clarity and reaffirm the connection, making it clear that the dialogue is a shared journey toward mutual understanding.


Don’t be intimidated by the idea of visualization. Do you take notes? If so, you’re halfway there. Writing is the most basic form of visualization—turning what you’re experiencing into language. The act of visualization is about showing your work to enhance communication.

Visualization is one of the most powerful skills you could develop in your communication arsenal. This technique employs rudimentary sketches alongside words and phrases to bring conversations to life, ensuring everyone involved feels acknowledged and understood.

The idea of shared note-taking or drawing in front of others can spark fear in even the boldest people. To reduce the very natural performance anxiety, I like to think of it as doodling. Doodling is an explorative low-stakes activity. After all, what you’re visualizing doesn’t need to be “right” to be effective. The only requirement for visualization is that it reflects what you’re interpreting. Indeed, some of the most effective visualizations I’ve made were wrong. A wrong visual can cue clarifying conversation.

Visualization facilitates a deeper comprehension among all participants by transforming abstract thoughts into concrete visuals. After all, a picture speaks a thousand words, establishing a shared reference point that can often be more easily agreed upon than spoken words alone.

The most basic sketches—dots and lines—are powerful communication tools. Building them into shapes like circles and squares can quickly create objects and people. It doesn’t have to be a fancy illustration—the most basic forms can move you miles down the road to understanding and connecting with your conversation partners.

Visualization requires only that you set aside any apprehension of judgment. It’s not about achieving perfection but enhancing dialogue, serving as a dynamic method to test and refine understanding. Incorporating simple visuals into your conversations clarifies ideas and reinforces the notion that visualization is a skill worth investing in. With practice, overcoming the fear of judgment becomes easier, allowing this iterative tool to flourish in facilitating mutual understanding.

We all began as fearless visualizers, wielding the powerful tool of expression and creativity with ease. However, this potent form of communication lies dormant for many of us. Perhaps harsh criticism of your drawings once dimmed your enthusiasm, or you were misled to believe that drawing is childish or wasteful. Regardless of the reasons, the moment has come to reclaim that pen and rediscover the magic of visualization.


Adopting an open mindset in our conversations is about being ready to delve deeper, showing we’re committed to uncovering new insights, and truly valuing and understanding the perspectives of others. This approach fosters a dialogue built on respect and trust—essential for nurturing meaningful connections.

Asking open-ended questions such as “What if … ?” and “How might we … ?” is a catalyst for understanding and innovation. It invites a level of inquiry that encourages comprehensive exploration of possibilities and fosters a culture of curiosity.

Another favorite ask is, “Can you say more?” or “Is there more?” Creating an opening and inviting your conversation partner can drive both understanding and personal connection.

The Five Whys technique was originally developed by Sakichi Toyoda at Toyota Motor Corporation as a systematic problem-solving tool to uncover root causes by repeatedly asking “Why?” until the fundamental issue was identified. I don’t work in manufacturing, but the same truth-finding technique can be employed to drive understanding of both business and personal issues within conversations, and often in far less than five steps.

Use The Five Whys technique to deepen your understanding of intentions and perspectives. Through the simple act of asking “why,” we can uncover the core of what your conversation partner is saying or feeling. This makes it especially useful for clarifying misunderstandings and discovering underlying reasons

To illustrate how it works, consider this hypothetical dialogue between Alex and Jordan, playing out using The 5 Whys in a personal conversation:

Alex: “Jordan, I’ve noticed you’ve been quite quiet in our team discussions lately. Can you share why that might be?”

Jordan: “I guess I feel like my ideas aren’t really being considered seriously.”

Alex: “Why do you feel your ideas aren’t being considered?”

Jordan: “Well, whenever I share something, there’s a brief acknowledgment, and then the conversation quickly moves on without much discussion.”

Alex could continue probing here, but a significant insight has already surfaced: Jordan doesn’t feel valued. This realization highlights the necessity of active listening and appreciating each other’s contributions to foster a genuinely open and engaging dialogue.

Employing The Five Whys in our personal conversations is an effective technique and a virtual gateway to richer, more meaningful interactions. They remind us of the power of curiosity and the value of empathy, guiding us to connections that resonate on a deeper level. In every question we ask, there lies an opportunity to learn and transform our conversations into bridges of deeper understanding and trust.

The path to open and effective communication

Opening up communication isn’t just about the words we exchange; it’s a broader journey toward understanding and connecting on a deeper level. Here are some closing reminders as you continue to evolve and grow as a conversation partner:

  • Embrace an open mindset. Approach every conversation with curiosity and an openness to learn. An open mindset invites us to consider diverse perspectives and to see dialogue as a rich opportunity for growth. Openness lays the groundwork for conversations that are heard and felt, creating a shared space for discovery and understanding.
  • Use them ordered, shuffled, or ad hoc. These six techniques offer a flexible framework for communication. Tailoring their use to fit the flow of your interactions serves as a dynamic method for deeper and more meaningful conversations. Their adaptability ensures you can navigate discussions with agility, making every exchange an opportunity for connection and growth.

Remember to contribute. Conversations are a dynamic exchange of give-and-take. Your active participation in sharing insights clearly and thoughtfully is crucial. It ensures the dialogue is balanced and enriching for everyone involved, akin to partners moving in sync in a dance. You can find some good techniques in Spiral-up your conversations.

Foster conversational growth

Adopting these practices and viewing each conversation as a chance to deepen connections can significantly enhance our communicative abilities. With dedication and patience, these principles evolve from mere concepts to integral parts of our conversational approach, enriching our interactions and fostering a culture of openness and empathy.

Matt Adams

A founding partner and Head of Creative Services at Territory, Matt is a master visual communicator and an acclaimed creator and director. He has a deep background in human-centered experience design, brand development, communication programs, and blended learning systems for Fortune 100 clients. He is a veteran co-pilot of the C-suite and seasoned expert in transforming great ideas into award-winning product.

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