Productive Communication Begins With Genuine Conversation: An Interview With Sayre Darling

[Click here to watch/listen to the podcast interview]

In today's fast-paced business world, leaders often prioritize automation and efficiency. However, as communications expert Sayre Darling highlights in her recent interview with Bill Storm, meaningful conversations—not mere exchanges of information—are crucial to building trust, connection, and ultimately, a successful business. Darling, a seasoned corporate communications professional, shared her insights on how authentic conversation transcends basic business communication and serves as a powerful tool for middle managers, CEOs, and teams alike.

Here’s a deep dive into the key takeaways from their discussion, along with actionable steps for leaders who want to foster a culture of open, effective communication within their organizations.

1. Conversation vs. Communication

One of the most important distinctions Darling makes is between business communication and true conversation. In business communication, there's often a back-and-forth exchange of information—like a tennis match. Questions are asked, answers are given, and objectives are met. However, while functional, these interactions?rarely build a personal connection or inspire deeper understanding.

In contrast, a conversation is more than just a transaction; it is about connection. Darling argues that real conversations allow people to show their authentic selves, understand each other’s values, and?build a relationship based on trust. Leaders who prioritize conversation over communication create a work environment where employees feel understood, valued, and motivated to engage fully.

Action Step: When engaging in dialogue, aim to go beyond answering questions. Ask follow-up questions that help uncover motivations, feelings, and concerns. This builds a more holistic understanding and encourages people to share more freely.

2. Middle Managers as the “Head and Heart” of the Organization

Darling describes middle managers as the “head and heart” of an organization because they must effectively communicate both up and down the hierarchy. Middle managers play a vital role by interpreting the strategic vision of senior leaders for their teams, while also conveying the aspirations and needs of their team members to upper management. This balancing act is crucial for a cohesive, high-functioning organization.

However, Darling notes that middle managers are often promoted without being adequately prepared for this dual role. Many times, high-performing individual contributors are promoted into managerial positions without sufficient training in communication, leading to misunderstandings and missed opportunities. Middle managers, she says, need skills in leading with influence, building trust, and fostering open communication across levels.

Action Step: Provide targeted training to middle managers that focuses on both interpersonal and communication skills. This can include training on managing up, handling difficult conversations, and understanding team dynamics.

3. Asking the Right Questions to Expand Conversations

A key theme of the interview was the importance of asking questions that expand the conversation. Too often, leaders stick to a script, asking surface-level questions that yield only surface-level answers. However, if leaders approach conversations with genuine curiosity, they open up the possibility for deeper connections and insights.

This approach also benefits future interactions. As Darling points out, if a salesperson or a manager doesn’t ask expansive questions, they won’t have touchpoints to build upon in future conversations. By asking open-ended questions, leaders can uncover valuable information that provides a clearer understanding of an individual’s goals and challenges.

Action Step: Make a habit of asking follow-up questions and checking for understanding. Encourage curiosity and explore answers with a “tell me more” mindset. This can lead to richer discussions and better outcomes.

4. Transforming the Role of Middle Managers

Darling believes middle managers should shift their focus from “me” to “we.” Instead of only seeing their roles in terms of individual achievements, middle managers need to see themselves as facilitators of team success. This means building trust within the team and ensuring that every member feels empowered to contribute their best work.

However, middle managers often feel caught between senior leaders’ strategic demands and the concerns of their teams. When a team member feels they’re being “interrogated” rather than engaged in a conversation, it can create a barrier to honest communication. Instead, Darling suggests that leaders create a culture where employees feel comfortable expressing their thoughts and ideas openly.

Action Step: Middle managers should focus on developing empathy and trust with their team members. Establish regular check-ins with open-ended questions about team needs and how they’re feeling in their roles. This can foster a supportive environment and encourage transparency.

5. Becoming the “Host” of Conversations

One of Darling’s practical tips for fostering better conversations is to approach each interaction as though you are the host. Just as a host makes their guests feel welcome, introduces them to others, and ensures they’re comfortable, leaders should do the same in conversations. Acting as the “host” keeps the focus on the other person’s comfort and well-being rather than on one’s own agenda. This builds rapport, encourages open dialogue, and allows people to feel genuinely valued.

Action Step: In your next conversation, focus on creating a welcoming environment. Take time to listen, validate the other person’s perspective, and show interest in their well-being. This approach can help build rapport and strengthen professional relationships.

6. The CEO’s Role: Listening as a Core Skill

The higher a leader’s position in an organization, the lonelier it can feel. CEOs, in particular, often face immense pressure, with little room to discuss their challenges openly. Darling highlights that having a confidant—a trusted individual who can offer honest feedback and help process complex decisions—is invaluable for leaders.

Leaders need an outlet where they can think through challenges and receive feedback without feeling judged or pressured. For many CEOs, having someone with whom they can discuss their thoughts candidly helps them make better decisions, manage stress, and ultimately lead more effectively.

Action Step: Leaders should prioritize finding a trusted confidant—whether within or outside the organization—with whom they can have open conversations. This can be a mentor, executive coach, or trusted peer.

Final Thoughts

Effective communication in leadership goes beyond information exchange—it’s about building genuine connections. By prioritizing conversation over transactional communication, leaders can create a culture of trust and empathy that drives lasting success. For middle managers and executives alike, taking the time to ask expansive questions, acting as hosts in conversations, and understanding the unique needs of each team member can create a more unified and effective organization.

If you’d like to contact Sayre Darling, click here to connect with her on LinkedIn. ?

Bill Storm

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About Sayre Darling

I have been advising and supporting C-Suite leaders and Middle Managers working at the forefront of change throughout my career working with more than 200 individuals and companies in multiple industries – associations, technology, financial services, insurance, higher education and professional services. I also have a breadth and depth of experience in health care with more than 25 years of experience working with industry associations, providers, payers, national associations, medical device, and insurance organizations.

Through that experience, I have seen the need and value in strengthening organizational leadership in two areas:?

Balancing the C-Suite's strategic leadership with Middle Managers' people leadership

Refining the Middle Manager's role and strengthening their leadership skills

For executives,?this means challenging existing assumptions, and requires rescoping the traditional leadership roles and responsibilities, raising the expectations and accountabilities of middle managers, and bridging the gap of understanding between senior executives and middle managers.

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Bill Storm is a seasoned advisor and consultant renowned for his expertise in driving peak performance and fostering effective leadership within Fortune 500 companies. With a multifaceted skill set spanning organizational systems, the psychology of achievement, team building, and sales, Bill serves as a trusted resource for executives, managers, and team leaders seeking to maximize their potential. Bill's career trajectory is marked by a commitment to innovation and excellence in team dynamics. Drawing from his extensive experience as a Peak Performance Strategist with the Tony Robbins organization and as a Team Building Specialist with the John Maxwell Leadership Team, he has developed a unique set of frameworks tailored to the needs of industry leaders. These frameworks provide a foundation for building winning teams and achieving sustainable success in today's competitive landscape. Driven by a passion for continuous improvement and a deep understanding of human behavior, Bill Storm empowers organizations to reach new heights of performance and effectiveness. His strategic guidance and hands-on approach have earned him a reputation as a go-to advisor for companies seeking transformative solutions. With Bill's guidance, businesses can unlock their full potential and achieve lasting success in the ever-evolving marketplace.