Designing better workplace conversations with Daniel Stillman

You use the analogy “your life is a conversation.” Can you elaborate on what that means for how we show up at work? 

Daniel Stillman: My parents used to say, when my brother and I fought, that it takes two to tango. In difficult situations, it’s easy to push the blame onto someone else.  

If I believe it’s all the other person’s fault, then there’s nothing I can do to change things. However, if I see the situation as a system—this conversation includes both of us—how I respond can change the whole dynamic, even just by shifting my own intention.  

We have conversations with others and ourselves all day, and the energy we bring shapes those interactions. Some people light up a room and create great interactions around them. I’m not always that person, but I believe we can choose what kind of conversations we want to have more of in our lives. And we have the power to create them.

 

You also describe organizations as conversations, with their own products and dynamics. How can leaders design better conversations, especially when it comes to addressing conflict and moving things forward? 

Daniel Stillman: Hard conversations don’t get easier over time; they often become more difficult. In my work, I help people describe their challenges as clearly as possible: here’s the situation, the behavior, the impact, the facts, the feelings, and the opportunity. There are many ways to frame things, but the key is to acknowledge what’s going on—without accusation or condemnation—and start with the facts.  

That’s one way leaders can approach tough conversations: by being real and vulnerable, and by being aware of the impact we have on each other and our own humanity and preferences. 

Leaders can use data, better forms and structures, and separate facts from feelings to clarify things. Taking a moment before each day to review their meetings and ask, 'What’s my purpose here? What are the pitfalls? What do I want to contribute? What do I need to get out of these meetings?' is challenging, but it’s essential design work—even if time is limited. 

 

You often use playfulness in your approach, even in formal or serious workplace settings. Can you share your thoughts on the role of playfulness at work and why you choose to bring it into your conversations? 

Daniel Stillman: One way to think about conversation design is through the idea of range.  

For example, I sing in a gospel choir in Harlem—even though I’m a Jewish kid, it’s great music and a lot of fun. I’m a tenor, so I have a certain vocal range; I can’t go where baritones go, but I can sometimes reach countertenor or alto parts.  

Humor is also an aspect of range; some people just don’t have it in their repertoire. But humor is an incredibly powerful leadership tool. My friend Naomi Bagdonas wrote a book called Humor, Seriously about how humor can create levity and cohesion, or you can use seriousness and intentional eye contact to connect.  

Most people only use a small part of their vocal instrument, but having a bigger range, whether in voice or in how you show up, lets you bring more variety and interest to meetings and conversations.  

 

Research shows most people feel conversations often go on longer than they'd like (Harvard Gazette), and some end up feeling stuck while others keep engaging. What advice do you have for people in these situations? 

Daniel Stillman: The simplest approach is to take ownership: if you can't delegate or ignore something, you have to make it excellent. I use the fun acronym DIE—Delegate, Ignore, or make Excellent.  

With small talk or conversations that drag on, remember it's a collaborative game and you can change the dynamic. Like any skill, small talk can be practiced and improved.  

Everyone is a fan of something, so it's interesting to discover what excites the other person. Whether you're introverted or extroverted, it's about finding what works for you and making the experience excellent, even if it means stretching yourself and building that muscle over time. 

 

What does it take for leaders to overcome conversation roadblocks and avoidance, especially when people would rather text or use TEAMS than have real conversations? How can we build trust and keep people engaged? 

Daniel Stillman: The key is to make conversations worthwhile and even enjoyable, rather than a struggle. Many meetings drag on because people feel they're not solving the real problem.  

I often ask groups, "Have you ever been in a meeting that wasn't addressing the real issue?"—and almost everyone raises their hand. It's important to ask, "Are we having the right conversation? What problem should we be solving?" This helps get everyone aligned and invested in the process.  

Ultimately, good conversation design means structuring interactions so people know why they're there and feel empowered to participate or move on. 

 

Given the rise of social isolation and less face-to-face connection, especially with the impact of social media and AI, what do you see as the future of conversations?  

Daniel Stillman: I believe we should let computers do what they're great at, and leave what humans do best to us.  

AI can generate content based on past data and patterns, but it's really just guessing what's likely. It's useful for poking holes in ideas, but ultimately, people make decisions and take action, not AI.  

The real act of humanity is deciding what kind of future we want to co-create or participate in: to dream, envision, plan, create, collaborate, and connect. That's what leadership is—inviting others to join you in building something great. 

 

Many leaders struggle to create meaningful conversations in hybrid meetings. What are your top tips for designing excellent hybrid conversations that help everyone feel connected? 

Daniel Stillman: Every conversation has an interface—a space and a place where it happens—and that affects what’s possible. In-person interactions are fast and dynamic because we’ve evolved to communicate that way, but hybrid meetings present real challenges. Often, remote participants are at a disadvantage due to audio issues and lack of engagement.  

My best advice is: if you’re going hybrid, consider making everyone remote for true equity. If that’s not possible, have everyone in the room on their own laptop and use a shared digital space, like a Google Doc or digital whiteboard, so everyone can participate equally.  

As a facilitator, your job is to ensure equal participation and keep everyone engaged. Make the problem or topic important and interesting, create a cadence that demands 100% participation, and use techniques like “jazz fingers” to check engagement. 

 

How can leaders overcome the initial difficulty and inertia of making meetings and conversations more intentional and impactful? What practical steps can help teams focus on what matters most? 

Daniel Stillman: It’s easy to get caught up in the urgency of everything, but as Eisenhower said, “The urgent are never important and the important are never urgent.” Leaders should focus on what’s truly important, even if it’s not urgent, and rearrange their schedules accordingly.  

Start by looking at your team’s “conversation diet”—are you talking too much or not enough? Get everyone’s input, and don’t be afraid to delete unnecessary meetings from the calendar.  

Design the most important conversations well, and begin every meeting with a moment of human connection, like asking, “Are you in the red, green, or yellow zone today?” This helps everyone feel present and connected, setting the stage for meaningful and effective collaboration.