Boss’s Day, reconsidered: what managers actually need from their teams and their companies.
Every October 16, offices across the United States mark Boss’s Day with cards, cupcakes and a group-signed gift. The day has a sweet origin. In 1958, Patricia Bays Haroski, a secretary at State Farm Insurance in Deerfield, Illinois, registered “National Boss’ Day” with the U.S. Chamber of Commerce. She chose October 16 because it was her father’s birthday, and her father was also her boss. Illinois Governor Otto Kerner made it official in 1962, and today the day is also observed in countries such as the UK, Australia and South Africa. When the 16th falls on a weekend, it moves to the nearest working day. This year it lands on a Friday.
Almost seventy years later, the day deserves a second look. Appreciation is not out of date. The job of “boss” has changed, and the people doing it are under more strain than the greeting cards suggest.
Managers are the most squeezed people at work
Gallup’s State of the Global Workplace 2025 report found that global employee engagement fell from 23% to 21% in 2024. The drop did not come evenly. Engagement among individual contributors held flat at 18%, while manager engagement fell from 30% to 27%. Managers under 35 lost five points. Female managers lost seven.
That matters because of a second Gallup finding: about 70% of the variance in team engagement is attributable to the manager. When managers struggle, teams feel it first.
Middle managers translate strategy into Monday morning. They absorb pressure from above, carry the needs of their people, and in hybrid and cross-border teams, they translate across time zones and cultures as well. They are expected to coach, and rarely get coached themselves.
What a better Boss’s Day looks like
Workplace etiquette has long held that gifts should flow down, not up, and a collection for the boss can feel awkward for junior team members. The good news is that the appreciation managers value most costs nothing. Three gifts to try:
- Specific thanks. Skip “best boss ever.” Name one thing your manager did this year that made your work easier, and say what changed because of it. Specific recognition tells people their effort was seen.
- One honest question. Ask: “What’s one thing I could take off your plate this week?” Then follow through. It turns appreciation into practical support.
- Good news, early. Managers hear about problems all day. Tell them what is working, before anyone has to ask.
For leadership: the real gift is investment
Gallup’s own recommendations point in the same direction: train every manager, and take manager well-being seriously. In practice, that can look like this:
- Onboard new managers into the role itself, not just the title. The first year sets habits that last.
- Make room for managers to be coached, not only to coach.
- Ask managers what slows them down, and remove one thing this quarter.
- Recognize managers for the people they grow, not only the numbers they hit.
This connects to Mattering at Work, one of the five essentials for workplace well-being in the U.S. Surgeon General’s framework. People need to feel that they matter at work. Managers are people too.
If you are a manager reading this
Use the day to turn appreciation around. Thank one person on your team, specifically, for something they did this month. It takes two minutes, and it shows the kind of culture you want to build.
Building the support managers need
At Happy Work Studio, we help organizations build happy, high-performing and human workplace cultures. Our leadership programs, from the New Manager Leadership Program to Being a Resilient Leader in the New Era and Effective Feedback, are designed for the person in the middle.
Happy Boss’s Day. This year, give your managers something that lasts longer than cake. Learn more at happywork.studio.
Sources: Gallup, State of the Global Workplace 2025; Hallmark, National Boss Day history.
HWS Team