May Is More Than a Month — It’s a Mirror for Leaders

May bursts onto the calendar like a season finally keeping its promise. The air warms, flowers bloom, and something else quietly unfolds: a parade of holidays that, if leaders pay attention, can reveal a great deal about the people they serve.

May’s Lineup of Celebrations 🎉

Before we dive in, let’s appreciate just how packed this month really is:

•       May 1 – May Day / International Workers’ Day — A global tribute to labor and workers’ rights

•       May 5 – Cinco de Mayo — Commemorating Mexican heritage and the Battle of Puebla

•       May 10 – Mother’s Day — Honoring mothers and maternal figures everywhere

•       May 16 – Armed Forces Day — Recognizing the men and women currently serving in the U.S. military

•       May 19 – Malcolm X Day (observed in some cities/states) — Honoring the civil rights leader’s legacy

•       May 20–22 – Shavuot — A Jewish harvest festival and celebration of the Torah

•       May 25 – Memorial Day — A federal holiday honoring U.S. military personnel who have died in service

•       May – Asian American & Pacific Islander Heritage Month — A monthlong recognition of AAPI contributions to American culture and history

•       May – Jewish American Heritage Month — Celebrating Jewish contributions to American life

•       May – Mental Health Awareness Month — Spotlighting mental wellness and reducing stigma

What Holidays Tell Leaders

Here’s a truth that doesn’t get said enough: the calendar is a culture map.

Every holiday on that list represents something someone on your team holds meaningful — a heritage, a sacrifice, a belief, a loved one. When leaders take time to acknowledge these moments, even briefly, they send a powerful signal: I see you. You belong here.

For example: I had just started with a new client several years ago and was doing an office visit. I learned that morning that it was National Chocolate Cookie Day, so I brought in a batch of cookies. To say they were a hit is an understatement, and learning that no one had ever celebrated any holiday there told me a LOT about the culture the owners never acknowledged.

Inclusive leadership isn’t about grand gestures. It’s often the small ones that land hardest. A team message recognizing Memorial Day for those who’ve served. A note of acknowledgment during AAPI Heritage Month. A flexible afternoon for a team member observing Shavuot. These moments cost very little and mean everything.

The reverse is also true. When leaders bulldoze through May without a nod to its meaning, employees notice the silence — especially those whose identities are tied to the month’s observances.

Leading with a Wider Lens

The leaders who build the most loyal, energized teams aren’t necessarily the ones with the best strategies. They’re the ones who make people feel known. Holidays give you a ready-made, low-pressure entry point to do exactly that.

This May, challenge yourself: learn one thing about a holiday you’ve never observed. Ask a team member what a celebration means to them. Let the calendar teach you something about the people around you.

Great leadership, after all, begins with attention — and May is full of things worth paying attention to.

A bonus: Take the time to join conversations where you can share what you appreciate about that person and ask where they would like to grow next.

Growth is not a one-way highway. When you choose to learn, you have the opportunity to see where others want to grow, too. If anyone in your workplace, including your direct reports or your team, is ready for more leadership growth, I’m finalizing my list for my next Lead Strong Mastermind, and I would love to chat with them to see if they are a great fit.

They are a great fit if they show strong signs of wanting to grow and take on more responsibility, yet lack some people skills and awareness you find important.  To explore more, click here and share the link for a complimentary leadership quiz.

Frequently Asked Questions

Q: Why should leaders pay attention to holidays and cultural observances?

A: Holidays are a window into what your employees value — their heritage, beliefs, sacrifices, and loved ones. Acknowledging them signals that you see your people as whole human beings, not just workers.

Q: Do I need to celebrate every holiday to be an inclusive leader?

A: Not at all. Awareness goes a long way. Even a brief team message, a moment of acknowledgment, or simply knowing what a holiday means to someone on your team can make a meaningful difference.

Q: What are some simple ways leaders can recognize May observances?

A: A few low-effort, high-impact ideas: send a team note on Memorial Day, share a resource during Mental Health Awareness Month, offer flexibility for employees observing Shavuot, or open a conversation about AAPI Heritage Month.

Q: Isn’t this the job of HR, not individual leaders?

A: HR sets the foundation, but culture is built day to day by the people leading teams. Inclusive habits at the manager level are what employees actually feel.

Q: What if I get something wrong or don’t know enough about a holiday?

A: Curiosity beats perfection every time. Ask a team member what a celebration means to them, do a little research, and lead with genuine interest. People appreciate the effort far more than they expect expertise.

Q: How does recognizing holidays connect to employee retention and engagement?

A: Employees who feel seen and valued are more loyal and engaged. Small, consistent acts of recognition build the kind of trust that keeps great people around.