Humor in the Heart of Leadership
- Jennifer Laurence
- 6 days ago
- 11 min read
How Levity Shapes Stronger Teams
I arrived in Big Sur with the simple intention of walking among redwoods, listening to Pacific surf, and letting the pace of nature slow my pulse. A favorite escape of mine, I go on this sacred excursion about 4-6 times per year. One afternoon, I wandered deep into a fern-draped glade, past mossy trunks and quiet understories. I discovered a small forest pub hidden in the shade amongst a row of roadside eateries and trinket shops. Between two towering redwoods, strung as if by intention or serendipity, was a banner that read:
✨ “Laugh Like Jen” ✨
Totally organic and unexpected, I had to take a selfie to memorialize the tribute in the trees to my namesake! It felt like a beckoning, a signal, from wood and wind, to pause, to soften, and to remember that even among weight and solitude, laughter is both a tether and a signpost.
If you know me, you know I don’t take myself too seriously. I’ve always prided myself on balancing poise with professional humor when the moment calls for it. In truth, humor, when used with intention, is one of the most underrated leadership tools we possess. It disarms tension, puts people at ease, and reminds us that beneath titles, pressures, and performance metrics, we are all profoundly human.
In high-stakes environments, where precision and polish are non-negotiable, knowing when to turn up the charm or turn on the “posh polish” can transform a moment. But humor is not performance…it is presence. It reflects a leader’s ability to read the room, meet others where they are, and bring warmth into spaces that might otherwise feel cold or hierarchical.
Leadership, like laughter, is contagious, and humor can beat the heart of it. The more authentically we show up, imperfections, humor, and all, the more we create environments where others can thrive, too. Sometimes the greatest leadership skill isn’t strategy; it’s the ability to stay lighthearted when things get heavy. To pause, breathe, and find joy even when the path feels uncertain.
Leadership begins in presence; the courage to be both real and radiant.
Whether consulting in a luxury estate or guiding leaders through complex change, my mission remains the same: to bring humanity, humor, and heart into every environment I enter. Because service should feel joyful, and leadership should, too!
Yet as much as I treasure that forest encounter, the real task is not to romanticize that moment, but to translate its lesson into the language of leadership and organizations. Because the question I now carry into every boardroom, estate kitchen, renovation site, client meeting, or leadership retreat is this:
How can we instill leadership with levity without undermining rigor?
The Strategic Logic of Humor in Leadership: Reconceptualizing Humor as a Leadership Tool
Traditionally, humor has been seen as a social or recreational add-on — enjoyable, but peripheral to “serious work.” Yet in the last decade, scholars have begun to frame humor not as frivolity, but as a strategic leadership lever. In their recent toolkit article, Wijewardena, Samaratunge, and Härtel (2024) argue that humor can be intentionally deployed to shape emotions, promote trust, and facilitate influence (Wijewardena et al., 2024).
Their work outlines a "humor-event" framework: a leader senses the context (emotional tension, task fatigue, relational distance), evaluates relational quality, and then decides whether and how to introduce a humor event — slipping in a joke, a self-deprecating turn, or a whimsical metaphor — that softens or resets emotional climate (Wijewardena et al., 2024).
Critically, they caution that humor is not universally benign. When used injudiciously — at a moment of crisis, in a relationship of low trust, or across cultural differences — humor may misfire, alienate, or even exacerbate stress. Thus, part of the leader’s skill is knowing when to withhold humor (Wijewardena et al., 2024).
Benefits and Risks: The Double-Edged Sword
A growing body of empirical literature supports the upside of humor in leadership. In a meta-analytic review, Rosenberg et al. (2024) found that leader humor broadly correlates with beneficial follower outcomes, including increased job satisfaction, psychological well-being, and stronger interpersonal bonds, but with nontrivial variance depending on the humor style and context (Kong et al., in Rosenberg et al., 2024).
Another recent study examines how leader humor can enhance employee creativity by reducing perceived workload and promoting psychological flexibility (Hu et al., 2023).
Meanwhile, a more recent global survey (cited in a 2025 article) estimated that 84.5% of leaders say they use humor to connect with employees — signaling that leaders increasingly view humor not as optional, but as a relational centrality (Bennett, 2022, in the 2025 article).
Yet humor is not wholly safe. In “The Double-Edged Sword Effect of Leader Humor on Employee Thriving,” the authors show that beyond the positive effect it generates, humor may inadvertently cause information loss (i.e., employees discount key messages) and may intensify surface emotional labor, especially in hierarchical or culturally distant settings (Apps et al., 2024).
One more caution: a recent field and lab study published in the Academy of Management Journal (Peterson, Hu, Parke, & Simon, 2024) found that excessive humor from managers can pressure subordinates into “surface acting” — faking amused expressions — which, over time, leads to emotional exhaustion and lower job satisfaction. The study’s finding: “fewer, higher-reward attempts” at meaningful humor are preferable to frequent joking.
Thus, humor operates as a double-edged instrument — capable of elevating trust, creativity, and relational bandwidth, but also capable of overreaching, distracting, or depleting resources if misapplied.
Theoretical Anchors: Emotional Intelligence, Authentic Leadership, and Psychological Safety
To wield humor credibly, a leader must anchor it in deeper capacities. Three theoretical streams offer foundations for integrating humor thoughtfully.
Emotional Intelligence (EI) as a Foundation
At its core, humor is an emotional act. Leaders who can sense, regulate, and respond to emotional undercurrents are best positioned to use humor without misstep. Mayer, Salovey, and Caruso’s EI model (1999) describes four major domains: perceiving emotions, using them to facilitate thought, understanding emotional nuance, and managing emotions. Leaders with high EI are more adept at calibrating tone, timing, and intensity of humor in relation to group mood.
Modern research links emotional competence to a lower incidence of humor gone wrong. A leader who misreads the emotional tenor of the room — when stress is high or a team is in conflict — risks humor coming across as tone-deaf. Thus, in practice, humor should flow from emotional attunement, not as a performative cover.
Authentic Leadership and Humor
Authentic leadership theory (Avolio & Gardner, 2005) emphasizes self-awareness, relational transparency, balanced processing, and internal moral perspective. Humor, when drawn from authentic self-expression rather than contrivance, reinforces authenticity. When a leader laughs at or with their own imperfections (rather than mocking others), team members perceive the leader as courageous and trustworthy.
Wijewardena et al. (2024) emphasize this: pseudo-humor — forced jokes or manipulative humor — can break trust more than no humor at all. Authentic humor becomes a mirror: it says, “I belong with you in this human experience.”
Psychological Safety and Humor’s Social Terrain
Edmondson’s (1999) construct of psychological safety — the shared belief that a team is safe for interpersonal risk-taking — provides the relational infrastructure in which humor can thrive. In high-safety environments, a quip or ironic aside is less likely to be misinterpreted.
Humor contributes to psychological safety by normalizing vulnerability. When a leader cracks a light, imperfect remark, it signals that mistakes and humanity are part of the work. Conversely, in low-trust or punitive cultures, humor may be parsed as minimizing or dismissive, eroding safety rather than reinforcing it.
Recent research on leader humor and organizational identification (2024) suggests that humor can strengthen employees’ sense of belonging, mediated by positive affect and perceived fairness, thereby deepening their identification with the organization (Zhang et al., 2024). But this effect is contingent on a backdrop of trust and justice.
Humor in Practice: Applying It in Estate & Luxury Service Contexts
Working in estate management, luxury hospitality, or highly curated service environments brings specific relational and emotional textures. The stakes are high, margins are tight, and clients expect flawless competence — yet behind every gilded curtain and gourmet dinner lies a web of human coordination. How can humor be woven in without undermining professionalism?
1. Know your relational substrata
In luxury estates, teams often cross cultural, generational, and hierarchical divides — including property managers, groundskeepers, butlers, horticulturists, artisans, security personnel, and hospitality staff. A humorous gesture that lands with one group may misfire with another. Use humor that resonates across roles: absurd observations about weather, shared constraints, or the absurdity of over-engineered systems can unite rather than divide.
As Wijewardena et al. note, leaders must adapt their use of humor to the relational quality. When trust is shallow, use safer forms (affiliative humor, light banter). As relationships strengthen, riskier self-ironies become more acceptable.
2. Embed humor around operational rituals
Luxury environments depend on rituals — evening briefings, staff huddles, shift changeovers. In those spaces, a well-timed light tease or a humorous framing of a challenge (e.g., “Let’s treat this glitch like a guest — make it comfortable, then show it the door”) can reset the tension. Because these moments are anticipated, a leader’s humor is less disruptive and more skillfully integrated.
3. Use humor to guide, not distract
When introducing change — a new workflow, a technology upgrade, a safety protocol — leaders may cushion resistance with a humorous metaphor or story. But the humor must clarify rather than obscure. The concept is to use levity as a bridge, not a veil.
4. Practice calibration and restraint
Recall the warnings: too frequent jokes, especially from high-status leaders, can pressure team members into emotional labor (surface acting). In high-power-distance settings, team members may feel obligated to laugh even when they don’t (Peterson et al., 2024).
Therefore, leaders in luxury service should treat humor as a high-currency move — sparingly, meaningfully, and in moments where relational payoff exceeds risk.
5. Train and workshop humor fluency
If humor is to be strategic, it must be cultivated. Wijewardena et al. recommend incorporating role-play, simulation, and feedback cycles into a “humor toolkit” training for leaders. In an estate-level leadership development program, you might include micro-case drills: how to pivot a tense client meeting with a light remark, how to intervene in staff conflict with a bit of ironic distance, how to close a rigorous walkthrough with a playful metaphor. Over time, humorous moments become part of your leadership vocabulary.
From Insight to Influence: Actionable Leader Guide
Below is a structured approach to bringing humor into high-level leadership with consistency and integrity.
Phase | Objective | Method & Example | Caution Checklist |
Scan & Sense | Assess emotional tension or relational fatigue | Pause: breathe; sense the mood; notice micro-tension | Not a crisis moment; team isn’t overwhelmed |
Decide Mode & Style | Choose the right tone (affiliative, self-enhancing, wit) | “That email chain is starting to feel like a Russian novel — let’s shorten the chapter” | Avoid humor that mocks, alienates, or belittles |
Deliver with Ownership | Frame with humility or vulnerability | “We’ve all tripped over these systems — I lost count by week two.” | Nonverbal cues consistent, voice steady |
Observe & Adjust | Watch reactions; shift if silence or discomfort arises | Shift tone, circle back later privately | Don’t double down on joke if it fails |
Debrief & Reflect | Solicit feedback, iterate | “Did that land okay? Too much? Too light?” | Avoid defensiveness; remain curious |
Institutionalize | Embed humor into rituals, culture, and training | Humor prompt at briefings, laughter check-ins | Ensure humor is inclusive, safe, and culturally aware |
Additional Considerations
Match humor to energy cycles: early morning, midday, or late-shift moods differ.
Layer humor, don’t force it: a series of micro-jokes over time is safer than a sudden “comedy shift.”
Consider congruence: Research on leader–employee humor congruence (e.g., Yuan, 2021) suggests that innovation is maximized when humor styles are complementary rather than identical. In some cases, incongruity (e.g., employees being more playful than leaders) spurred higher creative behavior.
Guard against information loss: in complex communications, don’t let a witty aside divert attention from key instructions (the double-edge effect).
Be culturally attuned: humor styles vary across cultures, generations, and languages. What triggers warmth in one group might feel condescending in another.
Conclusion: Leading with Lightness and Gravity
Leadership is often framed as a balance between control and freedom, vision and structure, authority and empathy. Humor, properly wielded, joins that balance. For those who lead others, the ability to show up with presence, authenticity, and levity is not ornamental — it is foundational. These qualities form the foundation of actual influence, enabling leaders to connect, inspire, and create environments where people feel both safe and valued.
In the domains of estate management and luxury service, where expectations are high and margin for error is slim, humor must be both elegant and precise. It is a relational tone-setter — but never a substitute for clarity or accountability. Embedded in emotional intelligence, rooted in authentic leadership, and scaffolded by psychological safety, humor becomes a kind of relational glue. It humanizes hierarchies, refreshes tethered teams, and signals that behind impeccable operations is a human heart.
If you, as a leader of teams in high-touch, image-sensitive contexts, can pause to breathe, sense the emotional field, and then introduce calibrated levity, you begin to shift the space around you. You let your team know that performance and presence can coexist. You model that service — especially in luxury settings — is not only about precision, but also about joy.
Dwight D. Eisenhower once remarked that “A sense of humor is part of the art of leadership, of getting along with people, of getting things done.” His insight remains timeless: humor is not a distraction from leadership — it is part of its artistry. It reveals discernment, empathy, and grace under pressure.
So yes: laugh with intention. Make it thoughtful, make it sparse, make it authentic. Because leadership done well need not be austere — it can glow, and sometimes, giggle.
📩 To collaborate, train your team, or book a speaking engagement:
© Luxury Lifestyle Logistics 2025
References
Avolio, B. J., & Gardner, W. L. (2005). Authentic leadership development: Getting to the root of positive forms of leadership. The Leadership Quarterly, 16(3), 315–338. https://doi.org/10.1016/j.leaqua.2005.03.001
Apps, M. A. J., Hirst, R. J., & Wyer, N. A. (2024). The double-edged sword effect of leader humor on employee thriving: When humor helps and when it harms. Applied Psychology: An International Review, 73(2), 428–456. https://doi.org/10.1111/apps.12593
Bennett, L. (2025). When laughing becomes labor: How forced humor drains emotional energy at work. Harvard Business Review. https://hbr.org/2025/03/research-when-laughing-becomes-labor
Business Insider. (2024, March). Laughing at your boss’s dumb jokes can lower job satisfaction, study finds. Business Insider. https://www.businessinsider.com/laughing-at-your-boss-dumb-jokes-can-lower-job-satisfaction-study-2024-3
Edmondson, A. C. (1999). Psychological safety and learning behavior in work teams. Administrative Science Quarterly, 44(2), 350–383. https://doi.org/10.2307/2666999
Goleman, D. (1995). Emotional intelligence: Why it can matter more than IQ. Bantam Books.
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Mayer, J. D., Salovey, P., & Caruso, D. R. (1999). Emotional intelligence meets traditional standards for an intelligence. Intelligence, 27(4), 267–298. https://doi.org/10.1016/S0160-2896(99)00016-1
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Yuan, Y., Lyu, Y., & Zhang, Y. (2021). Leader–employee congruence in humor and innovative behavior: The moderating role of dynamic tenure. Frontiers in Psychology, 12, 640139. https://doi.org/10.3389/fpsyg.2021.640139
Zhang, H., Li, X., & Zhao, X. (2024). Enhancing organizational identification through leader humor: The roles of positive affect and organizational justice. Frontiers in Psychology, 15, 1158791. https://doi.org/10.3389/fpsyg.2024.1158791
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Jennifer Laurence is the founder and president of Luxury Lifestyle Logistics, a leading estate management consulting firm renowned for elevating service standards in ultra-high-net-worth (UHNW) luxury residential estates. With over 25 years of distinguished experience in hospitality and private service, she is a trusted authority in estate operations, specializing in optimizing household workflows, developing bespoke service protocols, and cultivating high-performing teams. Jennifer advises estate owners, family offices, and private service professionals on staff training, leadership development, conflict resolution, and guiding estates and luxury hospitality environments through organizational change and service culture creation. As a Doctoral Candidate in Organizational Leadership, she blends academic research with hands-on estate hospitality expertise, uniquely positioning her to drive operational excellence and foster collaborative, results-oriented estate teams. As Principal Liaison Director for the Private Service Alliance, she actively contributes to industry advocacy, thought leadership, and best practices. Her insight ensures that every facet of estate management—from daily service delivery to long-term operational strategy—meets the highest standards of precision, discretion, and sophistication for the families she serves.
📍 Website: Luxury Lifestyle Logistics
📍 LinkedIn: Jennifer Laurence