Humor as a Leadership Tool
Use self-deprecating humor and cartoons to build trust, break tension, and unlock creative conversation
The Humor as a Leadership Tool framework uses self-deprecating humor — particularly cartoons and visual humor — to create psychological safety, surface uncomfortable truths, and strengthen connections within organizations. Tom Fishburne discovered that a weekly cartoon poking fun at his own industry became the most effective communication tool he had ever used. Humor works because it gives people permission to acknowledge what everyone is already thinking but nobody is willing to say out loud. When a leader laughs at their own industry's absurdities, it signals that honesty is safe and that the culture values truth over image management.
- Humor gives permission to acknowledge uncomfortable truths that formal communication cannot surface
- Self-deprecating humor builds more trust than self-promoting content because it signals honesty and humility
- Cartoons and visual humor create a safe container for difficult conversations about industry dysfunction
- Everyone has an innate sense of humor that can be tapped as a leadership and communication skill
- Identify the elephants in the roomLook for the patterns, absurdities, and uncomfortable truths in your organization or industry that everyone recognizes but nobody talks about openly. These are the richest sources of humor because they validate what people are already feeling.Pro tipThe topics that make people laugh hardest are the ones they are most relieved to hear acknowledged. If a joke gets a big laugh, it has revealed an important truth.WarningThere is a difference between laughing at yourself and your industry versus laughing at specific individuals — the former builds trust, the latter destroys it.
- Use humor to open difficult conversationsWhen you need to discuss a sensitive topic — a failed campaign, a dysfunctional process, an industry trend that threatens your business — lead with humor rather than data. A cartoon, a self-deprecating story, or a well-timed joke about the situation disarms defensiveness and opens people up to honest dialogue.Pro tipShare the humor first and let people laugh before transitioning to the serious discussion. The laughter creates enough psychological safety for the hard conversation that follows.WarningHumor should open the conversation, not replace it. If you only joke about problems without addressing them, humor becomes a coping mechanism rather than a leadership tool.
- Make humor a regular practiceLike any skill, humor in leadership improves with practice. Create regular opportunities to use humor — a weekly team email with a relevant cartoon, a lighthearted opening to serious meetings, or a running tradition of self-deprecating stories about industry challenges.Pro tipConsistency matters more than brilliance — a weekly practice builds a culture of openness over time, even if not every joke lands perfectly.WarningForced humor is worse than no humor. If a joke does not come naturally, do not force it — let the practice develop organically.
- Channel humor into strategic communicationUse humor deliberately in marketing, presentations, and external communication to differentiate your brand and build authentic connections with audiences. Humor is one of the few communication tools that audiences actively seek out and share voluntarily.Pro tipThe most shareable content in business is humorous content that makes people feel understood. Create humor that says 'I see what you are going through' rather than 'look how funny I am.'WarningHumor in external communication requires careful judgment about audience and context — what works internally may not translate externally.
Tom Fishburne started drawing weekly cartoons about the absurdities of his marketing job at General Mills as a creative outlet. The cartoons resonated so strongly with colleagues and eventually a global audience that after eight years, he turned it into a full-time business. Companies now hire Marketoonist to use cartoons as strategic communication tools — saying through humor what memos and presentations cannot.
Tom Fishburne started drawing a weekly cartoon strip poking fun at his day job at General Mills over 22 years ago as a creative hobby. After eight years, his audience had grown large enough that he and his wife started Marketoonist as a full-time business. He discovered that cartoons had a unique power: they could say things that would be threatening in a memo or email but were completely safe — even welcomed — in cartoon form.