The Conversations That Shape Leaders: Negotiation, Mindset, and the Power of Perspective
Summary
Many leaders think negotiation only happens in formal deals. How should we rethink negotiation as part of everyday leadership?
Ashli B. Carter explains that negotiation is not limited to boardrooms or formal deal-making — it’s something leaders engage in every single day. From aligning priorities and distributing responsibilities to navigating uncertainty and collaboration, negotiation is really about joint problem-solving. Ashli encourages leaders to move away from a “winning versus losing” mentality and instead approach conversations with curiosity, creativity, and flexibility. By broadening how we define negotiation, leaders can become more intentional communicators and more effective collaborators.
Your research explores “forest vs. trees” thinking. How does shifting between big-picture and detailed thinking change how leaders make decisions?
Ashli shares that effective leadership requires the ability to move fluidly between big-picture thinking and detailed execution. “Forest” thinking helps leaders focus on long-term goals, meaning, strategy, and vision, while “trees” thinking allows them to focus on process, implementation, and immediate next steps. She explains that leaders often default toward one mode more naturally, but strong decision-making comes from recognizing which perspective the moment requires. Ashli also highlights how self-awareness and collaboration are essential, especially when leaders need to balance visionary thinking with operational realities.
What’s one mindset or strategy that helps leaders handle difficult conversations more effectively?
One strategy Ashli returns to throughout the conversation is approaching difficult conversations like puzzles instead of battles. Rather than becoming fixated on “winning” or forcing a specific outcome, she encourages leaders to stay curious about the underlying needs driving the conversation. She explains that flexibility, reflection, and experimentation are critical communication muscles that strengthen over time. By asking better questions and remaining open to learning during conversations, leaders create more opportunities for meaningful problem-solving and connection.
How can leaders balance performance expectations with creating a culture where people feel supported and valued?
Ashli emphasizes that growth and learning require both accountability and psychological safety. She believes leaders play an important role in creating environments where people feel comfortable experimenting, practicing new behaviors, and reflecting on setbacks without fear of judgment. Rather than labeling people as fixed types of learners or communicators, she encourages leaders to focus on building self-awareness and agency. According to Ashli, when people feel supported enough to take risks while still remaining connected to clear goals and expectations, organizations create stronger cultures for long-term growth and performance.
How do you see AI changing the way people learn leadership and communication skills, or in how you teach?
Ashli sees AI as a powerful tool for helping people build communication and leadership skills through repetition, experimentation, and practice. She highlights how AI can create more opportunities for role play, idea generation, and skill-building in safe environments, helping leaders strengthen their communication muscles more quickly. At the same time, she cautions against outsourcing reflection, judgment, and self-awareness entirely to technology. Ashli believes the most effective use of AI happens when leaders first clarify their values, goals, and intentions — and then use AI to enhance, rather than replace, human thinking and connection.
Transcript
Rachel Cossar: Hello everyone and welcome to another episode of Conversations in the Future of Work. As always, I’m joined by really fascinating guests who have their hands in the honeypot in terms of their specific industry, role, profession, and perspective. And today I’m really excited to welcome a special guest, Ashli B. Carter. Welcome to the show, Ashli.
Ashli B. Carter: Thanks for having me, Rachel. I’m really excited to be here.
Rachel Cossar: Absolutely. Ashli, would you like to share a little bit with our audience about your background and what you’re most excited about these days?
Ashli B. Carter: Yeah, absolutely. Day to day, I’m an educator. I teach at a business school here in New York, and I teach on topics surrounding leadership, working in groups and teams. My focus is really looking at the mindsets we bring into different situations and helping people build more self-awareness so they can understand which mindsets are helping them and which are getting in the way. I’m really interested in bringing more intentionality and choice into how we show up. I do that through teaching, speaking at organizations, and coaching leaders as well.
Rachel Cossar: I know a lot of your work also touches on negotiation and difficult conversations. Many leaders think negotiation only happens in formal deals. How should we rethink negotiation as part of everyday leadership?
Ashli B. Carter: Yeah, I think that’s right. We often have this image that pops into our minds when we hear the word negotiation, and it feels very formal — like we’re trying to figure out deal terms or structure some major agreement. And that’s definitely negotiation, but I think we also have to recognize that we engage in joint problem solving almost every single day. We need one another. We’re constantly figuring out how to distribute responsibilities, share resources, and get our needs met together.
So I think broadening the scope of what counts as negotiation can actually free us up to be more creative and collaborative. Oftentimes, when we frame negotiation as “winning” or “losing,” it limits our creativity. But when we approach it as joint problem solving, it opens up many more possibilities.
Rachel Cossar: That’s interesting — thinking about collaboratively finding a solution rather than approaching it as something zero-sum where one person wins and the other loses. That definitely changes the energy of the interaction.
Ashli B. Carter: Exactly. And I think with negotiation, we want to free ourselves up a little bit. You need energy, creativity, and curiosity. When you go into a conversation too focused on one particular outcome, it can actually limit your ability to explore other possibilities. Sometimes situations are zero-sum, but often they’re not. Often there are different ways to meet people’s needs if we’re willing to ask questions and get curious about what’s really driving the conversation.
Rachel Cossar: What’s one mindset or strategy that helps leaders handle difficult conversations more effectively?
Ashli B. Carter: One thing I come back to a lot is approaching difficult conversations like puzzles instead of battles. When we become too attached to a specific outcome, we can lose flexibility and curiosity. But if we approach conversations with the mindset of learning and problem solving, it gives us permission to experiment, ask better questions, and try different strategies.
Difficult conversations often require multiple attempts and different approaches before we really understand what’s underneath the surface. So I think flexibility, curiosity, and reflection are really important communication muscles for leaders to build over time.
Rachel Cossar: I love that framing because so many leaders feel pressure to get it right immediately.
Ashli B. Carter: Totally. And I think difficult conversations are often less about perfection and more about willingness — willingness to stay engaged, stay curious, and continue learning through the interaction.
Rachel Cossar: Your research explores “forest versus trees” thinking. How does shifting between big-picture and detailed thinking change how leaders make decisions?
Ashli B. Carter: We can approach situations from very different mental perspectives. “Forest” thinking is more big picture — asking what the overarching goal is, what the long-term meaning is, or how something connects to our values and vision. “Trees” thinking is much more focused on the details, execution, and the step-by-step process of making something happen.
And the reality is we need both. Effective leaders are able to shift between those modes depending on the situation. Sometimes you need to zoom out and reconnect to strategy and purpose, and other times you need to zoom in and focus on implementation.
I’m also really interested in how organizations stereotype people as either strategic thinkers or detail-oriented thinkers, because that can shape opportunities and visibility within organizations as well.
Rachel Cossar: That’s such an important point. I think even in communication and marketing, it’s really easy to get stuck in the details and forget the larger context your audience actually cares about.
Ashli B. Carter: Exactly. There’s no single right approach. And even within one conversation or one project, you often need to move between both ways of thinking. A lot of leadership is really about awareness — understanding the context you’re in, understanding your goals, and then choosing the mindset or tool that best supports that moment.
Rachel Cossar: How can leaders balance performance expectations with creating a culture where people feel supported and valued?
Ashli B. Carter: I think real learning and growth require both accountability and support. So much of my work is about creating conditions where people feel safe enough to try, stumble, reflect, and improve. Learning can feel uncomfortable, especially when people are trying on new behaviors or communication styles that don’t immediately feel natural.
But if we focus too much on labels or fixed identities, we can limit growth. I’m much more interested in helping people build self-awareness and agency — helping them understand what mindsets are helping them, what mindsets are getting in the way, and how they want to intentionally show up in moments that matter.
Rachel Cossar: That’s such an important distinction because people often resist new behaviors by saying, “That’s just not me.”
Ashli B. Carter: All the time. And I think it’s important to recognize that discomfort doesn’t necessarily mean something is inauthentic. Sometimes discomfort simply means we’re growing or trying something unfamiliar. The goal isn’t to become someone else — it’s to expand your range and develop more intentionality around how you show up.
Rachel Cossar: How do you see AI changing the way people learn leadership and communication skills, or in how you teach?
Ashli B. Carter: I think AI can be incredibly helpful when it comes to practice and repetition. It gives people more opportunities to rehearse conversations, generate ideas, and build communication skills in safe environments. That’s really powerful because leadership and communication are muscles that strengthen through reps and reflection.
At the same time, I think humans still need to do the deeper work of clarifying their values, priorities, and goals. If we outsource too much of that reflection to AI, then I think we get into trouble. The most effective use of AI happens when we use it intentionally — as a tool to enhance our thinking and communication, rather than replace the human elements of discernment, self-awareness, and connection.
Rachel Cossar: I think that’s such a powerful reminder because AI can help us move faster, but it doesn’t necessarily create the space for reflection unless we intentionally make that space ourselves.
Ashli B. Carter: Exactly. And honestly, I think people are hungry for that space. They want opportunities to reflect, reconnect with themselves, and think more intentionally about how they’re showing up. AI can support that process, but it can’t replace the human work of self-awareness and meaning-making.
Rachel Cossar: Ashli, thank you so much for your time and for sharing your perspective with us. This conversation leaves us with so much to think about.
Ashli B. Carter: Thanks so much, Rachel. This was such a wonderful conversation.