Lydia Sullivan- You Gotta Play to Win

The Power of Humor in Leadership: Insights from Lydia Sullivan 


About the Guest(s): 

Lydia Sullivan Lydia Sullivan is the Vice President of Operations at the Society for Information Management (SIM). With over 15 years of experience in nonprofit management, she has dedicated 10 of those years to association management. Lydia has been a certified association executive for five years and has played pivotal roles in supporting boards, philanthropic organizations, and chapters from various industries. Outside of her professional life, Lydia is passionate about house projects, local breweries, the Houston Astros, and taking part in game shows and giveaways. 

Episode Summary: 

Join us in this episode of “Humor in the C-Suite” as Kate Davis sits down with Lydia Sullivan, the VP of Operations at the Society for Information Management (SIM). Lydia shares her journey from working with youth in mental and behavioral health to leading a major nonprofit association for technology leaders. She emphasizes the importance of authenticity, humor, and empathy in leadership, especially when serving an organization that relies heavily on volunteer efforts. 

In this engaging episode, Lydia discusses her strategies for incorporating humor and levity into the workplace, even in remote settings. She shares anecdotes about her early mishaps, how a sense of humor helped her team navigate the challenges of the COVID pandemic, and the role of fun interactions like Haiku Fridays and personalized out-of-office messages in building a connected, vibrant team culture. Listen in for insights on how to keep things light while fostering strong team collaboration. 

Key Takeaways: 

  • Balancing Professionalism and Humor: Lydia Sullivan highlights the balance needed between maintaining professionalism and incorporating humor to create a positive working environment. 
  • Authentic Leadership: Emphasizing the importance of being an authentic leader, Lydia discusses how being your true self encourages your team to do the same. 
  • Humor in Communication: From witty out-of-office messages to Haiku Fridays, Lydia offers various ways to incorporate humor in written communication to build rapport and lighten the atmosphere. 
  • Resilience Through Levity: Past experiences in challenging roles taught Lydia the importance of resilience and humor in overcoming organizational and personal hurdles. 
  • Empathy with Volunteers: Lydia emphasizes the critical role of empathy in managing volunteer-led organizations, ensuring volunteers feel valued and connected. 

Notable Quotes: 

  • “Empathy and humor are critical when leading a volunteer-run organization. You have to create a positive experience for them.” 
  • “Being an authentic leader means being your whole self and understanding the humans that are working with you.” 
  • “The best way to feel connected is through shared experience, empathy, and humor.” 
  • “Everything is solvable; nothing is life and death in this organization. It’s important to have fun while we work.” 
  • “Be so completely yourself that everyone else feels safe to be themselves too.” 


  • Society for Information Management (SIM) Website 


From the Woods to the C-Suite: Lydia Sullivan on Humor and Resilience 


The Role of Empathy and Humor in Leadership 

In the fast-paced and often stressful world of technology leadership, maintaining a lighthearted approach can be transformative. Lydia Sullivan, VP of Operations at the Society for Information Management (SIM), personifies this approach. With her deep-rooted belief in the power of empathy and humor, Sullivan manages a network of 40 chapters and 5,000 members, ensuring that each interaction is infused with genuine connection and warmth. 

“Empathy and humor are critical when you’re leading organizations volunteer-led,” Sullivan explains. She emphasizes the importance of understanding volunteers’ unique challenges and creating a positive atmosphere where their efforts are appreciated. Sullivan’s approach is a testament to the principle that when volunteers—who juggle full-time jobs and family responsibilities—feel valued and enjoy their contributions, their engagement and productivity soar. 

Moreover, Sullivan’s collaboration with CEO Mark Taylor showcases how humor can reinforce professional relationships. “I publicly take jabs at him on almost every call,” Sullivan confesses, highlighting the playful dynamic that makes their partnership strong and relatable. This openness not only strengthens their bond but also sets a precedent for a culture where humor is a valued part of the organizational ethos. 

Balancing Professionalism with Authentic Leadership 

A prevailing theme in the episode is the concept of authentic leadership. Lydia Sullivan underscores the necessity of being one’s true self in a leadership role. “An authentic leader is being your whole self and understanding the humans that are working with you and what their experience is,” she notes. This philosophy is deeply embedded in SIM’s approach to training technology leaders, emphasizing the significance of authenticity over traditional managerial skills. 

Incorporating humor into daily routines is one way Sullivan practices authentic leadership. She mentions, “Before in every meeting, we try to have a little bit of time… the first five minutes, we’re laughing.” These moments create an environment where team members feel comfortable and connected, fostering collaboration and innovation. Humor, as interwoven into Sullivan’s leadership style, serves as a mechanism for easing tensions and building camaraderie. 

However, humor in leadership also requires a delicate balance. Sullivan recounts the occasional challenge of humor not landing as intended, particularly in written communication. She advises, “Sometimes when things get mucky, and you try to bring humor into it, it just makes it muckier.” The solution, she suggests, is a straightforward apology and a willingness to try again, underscoring the importance of intent and clarity in communication. 

Personal Growth Through Humor and Resilience 

Lydia Sullivan’s narrative reveals how her personal experiences have shaped her approach to leadership. Her time working in a wilderness camp with teenage boys was particularly transformative. “I spent time with them all day, every day for 365 days of my life,” she recalls. This period taught her the value of humor in building resilience and coping with challenges. 

These experiences have profound implications for her professional life. Sullivan states, “If you can’t laugh about it, then what can you do? You can’t get mad about it. They’re just being human.” This perspective encourages a forgiving and light-hearted outlook, which can help navigate the complexities of managing a large, volunteer-driven organization.  

Moreover, her attempts at securing a spot on game shows and her success in random giveaways, like winning free chicken for a year, symbolize her zest for life and willingness to seize opportunities. “I’ve not been on any game shows to date, but I applied to be on Wheel of Fortune a hundred times in that single year,” she shares, embodying the ethos of persistence and a playful attitude towards life’s uncertainties. 

Reflecting on Key Insights 

From this conversation with Lydia Sullivan, it is evident that humor and empathy form the bedrock of her leadership style. These traits enable her to connect deeply with both her volunteers and her team, creating a work environment that is as supportive as it is productive. Through her stories, Sullivan illustrates that maintaining a sense of humor can help navigate even the most challenging situations—like the infamous Zoom bombing incident during the early days of the pandemic. 

Empathy and understanding, as Sullivan exemplifies, are facets of leadership that cannot be understated. Her commitment to being “completely yourself” so that others feel safe to do the same is a powerful statement about the role of authenticity in leadership. This approach not only humanizes the workplace but also drives engagement and loyalty. 

Sullivan’s emphasis on personal growth through humor and resilience offers a compelling lesson for emerging leaders. Her narrative proves that humor can be a powerful tool for overcoming adversity, building strong teams, and ultimately, finding enjoyment in one’s work. Leaders at all levels can learn from Sullivan’s example to create a more positive, inclusive, and effective workplace culture. 

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