The question of what to say to your boss on Boss’s Day is on many employees’ minds as workplaces across the United States prepare to celebrate this year’s holiday on Thursday, October 16, 2025. From heartfelt messages to team notes and digital shoutouts, American workers are finding new ways to express gratitude to their leaders in meaningful ways.
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When Is Boss’s Day 2025 and Why It Matters
Boss’s Day is celebrated every year on October 16 in the United States. If it falls on a weekend, the holiday is observed on the nearest business day. In 2025, it happens midweek, giving teams a perfect opportunity to acknowledge their bosses’ contributions.
The holiday originated in 1958, when Patricia Bays Haroski, an Illinois insurance company employee, registered it with the U.S. Chamber of Commerce. Her goal was to strengthen relationships between supervisors and employees and to recognize leadership efforts in the workplace.
Today, Boss’s Day is marked in offices large and small. Many teams plan group cards, lunches, small tokens of appreciation, or simple but sincere words. The message itself often carries the greatest impact.
Why Words Matter More Than Gifts
In recent years, managers have consistently said they value authentic words of appreciation more than material gifts. A thoughtful message can create a stronger, lasting impression than a mug, flowers, or a gift card.
The rise of remote and hybrid work has also shifted how people celebrate. Digital notes, virtual cards, video calls, and emails have become just as common as handwritten messages. The key is choosing the right words that reflect genuine appreciation.
Trending Message Styles for 2025
As Boss’s Day approaches, certain message styles are standing out in workplaces across the country:
- Authentic and personal: Employees are using specific examples instead of generic praise.
- Team-focused: Group cards or collaborative notes show collective appreciation.
- Short but heartfelt: Concise, sincere messages often make the biggest impact.
- Digital expressions: LinkedIn posts, team chats, and shared documents are popular ways to celebrate leadership publicly.
Examples of What to Say to Your Boss on Boss’s Day
Here are practical, ready-to-use examples of what to say to your boss on Boss’s Day in 2025. These reflect current communication trends across U.S. workplaces.
Formal and Professional
Ideal for traditional office environments or newer working relationships:
- “Thank you for your guidance and leadership. Your support sets the tone for our success.”
- “We appreciate your integrity, professionalism, and dedication to excellence.”
- “Your leadership inspires confidence and teamwork every day. Thank you for all you do.”
Friendly and Appreciative
Perfect for teams with a relaxed atmosphere:
- “Happy Boss’s Day! Working with you makes every day motivating. Thank you for being such a supportive leader.”
- “Your positivity and encouragement make a real difference. We appreciate you.”
- “Thanks for leading with heart and making work enjoyable.”
Team Messages
Best for group cards or collective notes:
- “Happy Boss’s Day from the whole team! Thank you for your leadership and constant support.”
- “Your vision and dedication keep us moving forward. We’re grateful for everything you do.”
- “Our team thrives under your guidance. Thank you for being a strong and inspiring leader.”
Remote Work Messages
For hybrid or fully remote teams:
- “Even from afar, your leadership brings us together. Happy Boss’s Day!”
- “Thank you for leading our team with clarity and care, no matter where we work.”
- “Your communication keeps us connected and motivated every day.”
Tips for Crafting the Perfect Message
Writing a message doesn’t have to be complicated. These quick tips can help you make it stand out:
- Be specific: Reference a moment when your boss supported or inspired the team.
- Match the tone: Align the message with your workplace culture—formal, casual, or creative.
- Keep it short and sincere: A few heartfelt sentences often carry more weight than long, generic notes.
- Avoid clichés: Personalizing your message makes it more memorable.
- Deliver thoughtfully: If possible, say your message in person or at least personalize it digitally.
How Workplaces Are Celebrating Boss’s Day in 2025
Across the United States, companies are preparing for Boss’s Day with a variety of gestures. Recent workplace trends show:
- 58% plan to sign group cards or digital notes.
- 41% will host small lunches or coffee breaks to honor their leaders.
- 25% are using professional social media platforms for public appreciation.
- 18% are giving small personalized gifts, such as plants or team-signed tokens.
Many workplaces are also shifting to inclusive celebrations, recognizing multiple leaders rather than focusing on a single individual. This reflects the growing emphasis on collaborative leadership in modern organizations.
Common Mistakes to Avoid
Even with good intentions, some Boss’s Day messages can miss the mark. Here’s what to avoid:
- Generic messages: Overused phrases like “best boss ever” can feel impersonal.
- Forced humor: Jokes that don’t fit the workplace culture can backfire.
- Overly personal remarks: Keep the message professional and appropriate.
- Poor timing: Deliver your message early in the day so it’s received thoughtfully, not rushed.
Why the Right Words Strengthen Workplace Culture
Taking a moment to craft a thoughtful message does more than celebrate a single day. It contributes to a stronger, more respectful workplace culture. Expressing appreciation improves morale, builds trust, and reinforces positive leadership practices.
Even a short, genuine message can remind leaders that their efforts are valued and recognized.
Final Thoughts
Knowing what to say to your boss on Boss’s Day can turn a simple holiday into a meaningful moment. Whether through a handwritten card, a team note, or a quick message, sincerity is what truly counts. Share how your workplace plans to celebrate or your favorite message ideas in the comments below.