Every year Boss Day falls on October 16th.
Since 1958, this tradition has offered grateful employees the chance to show appreciation for their boss. Bosses get a lot of stick in the movies and are often presented as mean, corrupt, and sometimes even bordering on psychopathic!
Yet in reality, they can be generous, inspiring individuals and deserve more credit than Hollywood suggests. Bosses can offer invaluable support and guidance for employees, particularly during those first few weeks on the job.
So how to express your good wishes on Boss Day?
It can be extremely tricky to find the right tone. A message too plain or generic could appear cold and ungrateful. On the other hand, you do not want to cross any professional boundaries by taking a joke too far.
To help you on your way we have created a number of useful categories of Happy Boss’s day messages, to make sure you get on the right side of your boss today!
Happy Boss Day Messages
For those wanting to show gratitude to a great boss, these messages will make your manager smile.
From the day I started here, you have made work a positive and inspiring place to be. Thank you for being a great leader.
Thank you for making work something I look forward to on a Monday, not something I dread!
To the leader of our fierce wolf pack, have an amazing Boss Day. Thank you for always keeping us going, even when the going gets tough.
Sending my best wishes to an extremely talented manager. I consider you one of the finest role models I have ever had the pleasure to know personally.
You made me feel so welcome when I first joined. It has been amazing to feel part of something so special. Thank you!
Boss, I wanted to say thank you and express how grateful I am for all the support and guidance you have given me over the years.
Happy Boss’s Day to an awesome manager. Your hard work and dedication is totally inspiring.
To a Boss who always has our backs (even when we totally muck-up!), have an awesome day celebrating!
Thank you for making early mornings feel more like a pleasure than a chore.
It has been a fantastic opportunity to join this company. Thank you for taking a chance on employing me. I look forward to proving you made the right choice!
Happy Boss Day to the person who keeps the team together. If you were a soccer captain, you would be world class.
You sure put the super in supervisor. So, when is the Marvel film coming out?
To a manager who always keeps me motivated and enthusiastic: It is a pleasure working for you. Have a great day!
Thank you for always having the solution to my many problems. Raising a glass to you today!
Boss, you are one-of-a-kind. You have taken this team from strength to strength, and we could not be more grateful to have such an inspiring powerhouse behind us.
To a manager who gave me the chance to better myself: thank you for having more faith in me than I did.
Happy Boss’s Day. Thank you for always listening to my questions, and nearly always coming up with the answer.
Your hard work and dedication is inspiring. Thank you for putting so much energy into this business because it is infectious.
You have been a guiding compass for me when all seems lost. Thank you for keeping me on track to succeed. I am enjoying every minute of the journey. Happy Boss Day.
When the workload piles up and tensions are high, it is fantastic to have such a positive leader to keep the team optimistic that we will succeed. Raising a glass to a great leader.
Funny Boss Day Messages
For those on particularly good terms with their boss, the following funny messages are sure to make them chuckle.
My boss is like a red, red rose. She always blooms in spring. But when I ask her for a rise, she never says a thing.
A good manager brings out the best in his team. In that case, you must be pretty good because we are all outstanding.
My boss is kind and patient, my boss is fair and wise, but when it comes to pay day, he/she never gives a rise.
Happy Boss Day to a manager who nearly makes me want the weekend to go faster (nearly, not quite!).
You sure put the ‘y’ in ‘bossy’. Only joking! Have a great day (and please do not fire me for this).
You get better wages, a nicer office, people to bring you coffee…surely you do not need a whole day as well? Ah well, I wish you the best Boss Day!
My boss is a piece of work. A piece of work because he was kind enough to offer me the job! Thank you for this opportunity.
Hey Boss, thank you for keeping this business running (because without you, it would be more of a slow walk).
Have you heard about the film Horrible Bosses? No? Wow, I thought they might have rung you up during the casting!
I do not know what Dolly was talking about…working 9 to 5 in an office like this really is a way to make a living!
If you were not my boss, every day I would be at a loss. Thank you for your untiring support.
Little did you know that when you were interviewing me, I was interviewing you. Now, after over a decade of trial period, I am pleased to announce that you have got the job.
Why do we have Boss Day? I have a sneaky feeling it was invented by Bosses as an excuse to eat cake! Enjoy the treats today, Boss.
To my best manager ever, have an amazing Boss Day. (I will try to be kind enough not to remind you that you are my only manager.)
Your favorite employee would like to wish you a very Happy Boss’s Day. Since she/he remembered, would you consider giving her/him a promotion?
Working under you means I never eat Kit-Kats. Who needs Kit-Kats when you do not want a break?
A gentle reminder that the retirement age is 67.
If this business was a country, we would win all the gold medals at the Olympics. Here’s wishing a champion Boss, a great day.
This business is running so well because you always go the extra mile. Happy Boss’s Day to a manager whose energy is catching.
Thank you for getting me on the ladder of success and for not letting go! Have a fabulous day.
Boss, if you were a playing card you would be the Ace. I am sorry that I tend to be the joker! Happy Boss Day.
Boss Day Quotes
Use the words of another inspiring individual to emphasize your gratitude.
“I suppose leadership at one time meant muscles; but today it means getting along with people.” – Mahatma Gandhi
“A great person attracts great people and knows how to hold them together.” – Johann Wolfgang Von Goethe
“If the highest aim of a captain were to preserve his ship, he would keep it in port forever.” – St. Thomas Aquinas
“If your actions inspire others to dream more, learn more, do more and become more, you are a leader.”– John Quincy Adams
“Every leader is a boss but every boss is not a leader.” ― Amit Kalantri
“I would have sold my soul to the devil, but my boss had a better offer.” ― Ljupka Cvetanova
“Rule # 1: Your boss is always right. Rule # 2: Whenever you feel otherwise, refer to rule # 1.” ― Nipun Varma
“I prefer to sail in a bad ship with a good captain rather than sail in a good ship with a bad captain.” ― Mehmet Murat ildan
“Beware of the boss; they are like the Bermuda Triangle, you have to die clueless.” ― Dr. P.S. Jagadeesh Kumar
“A good leader inspires people to have confidence in the leader, a great leader inspires people to have confidence in themselves.” – Eleanor Roosevelt
“People ask the difference between a leader and a boss. The leader works in the open, and the boss in covert. The leader leads, and the boss drives.” – Theodore Roosevelt Jr.
“Hers was a tone and manner that assured the listener they had only two choices; obedience or death.” ― Loretta Chase
“Management is efficiency in climbing the ladder of success; leadership determines whether the ladder is leaning against the right wall.” – Stephen Covey
“Example is the greatest of all seducers.” – French Proverbs
“A leader is someone who creates infectious enthusiasm.” – Ted Turner
“The best executive is the one who has sense enough to pick good men to do what he wants done, and self-restraint to keep from meddling with them while they do it.” – Theodore Roosevelt
“The conventional definition of management is getting work done through people, but real management is developing people through work.” – Agha Hasan Abedi
“Good management is the art of making problems so interesting and their solutions so constructive that everyone wants to get to work and deal with them.” – Paul Hawken
“One measure of leadership is the caliber of people who follow you.” – Dennis A. Peer
“A good manager is a man who isn’t worried about his/her own career, but rather the careers of those that work for him.” – H.S.M. Burns
“Someone is sitting in the shade today because someone planted a tree a long time ago.” – Warren Buffett
“Profitability is coming from productivity, efficiency, management, austerity, and the way to manage the business.” – Carlos Slim
“Family, Religion, Friendship. These are the three demons you must slay if you wish to succeed in business.” – Mr. Burns (The Simpsons)
“Those who want respect give respect.” – Tony Soprano (The Sopranos)
“You are like a captain navigating a ship… You must give the right orders, thoughts and images to your subconscious which controls and governs all your experiences.” – Joseph Murphy
“The strength of the group is the strength of the leaders.” – Vince Lombardi
“Earn your leadership every day.” – Michael Jordan
Formal and Professional Happy Boss’s Day Messages
The following messages will help you keep things work-place appropriate this Boss Day.
This Boss Day I would like to express my thanks to you for the opportunity to be part of this exciting journey.
Today, I want to express my sincerest appreciation for all the support you have given me throughout my career so far. Thank you!
Happy Boss’s Day. Thank you for your mentorship over all these years. I feel very lucky to have grown as an individual under your leadership.
I have a huge amount of respect for the amount of hard-work and dedication you put into this business. Thank you for inspiring me to always strive to be better.
Thank you for bringing great insight and creativity to the daily running of this business. It has a brighter future because of your work.
It has been a brilliant opportunity to join this team and watch it go from strength to strength under your leadership. I look forward to what the future holds.
Today, I want to reflect on all the fantastic achievements this company has made under your leadership, and also to look forward to all those yet to come.
It has been such a pleasure to learn under your guidance. Thank you for all the support you have given me and Happy Boss Day.
I was very nervous upon joining such a large corporation but am extremely grateful for the warm welcome I received from you. Thank you for immediately making me feel part of this fantastic community. Wishing you the best day!
It is such a pleasure to work under your exceptional leadership. Thank you for inspiring this team to reach for higher things and enjoy reflecting on all your achievements this beautiful day.
I have a huge amount of respect for the way you have transformed a group of individuals into a well-oiled machine of success. Sending best wishes to a terrific leader.
I hope you take some time to reflect on what you have created today. This is an inspiring place to work and I, for one, am very proud to be part of it.
Congratulations on all that you have achieved this past year. The company goes from strength to strength thanks to your untiring pursuit of improvement. Have a very happy and proud Boss Day, reflecting on all that you have made possible.
We have some amazing individuals in this office, but we have become an amazing team thanks to your inspiring leadership. We want to wish you a happy Boss’s Day and thank you for bringing so much passion to our work.
Messages For A Boss Who Is A Friend
If you are lucky enough to be employed by a friend, these personal messages will fit the bill perfectly.
On the business end of things, I would like to wish you a Happy Boss’s Day and express my sincerest gratitude for all your guidance. On the other end, when is our next pint?
As a boss you are always generous with your time and support, and as a friend you are even more so.
Happy Boss’s Day Friendo! I feel so lucky to get the best of both worlds when it comes to you. Like a good meal I get the main and the dessert!
If you were a haircut you would be a mullet: business in the front, party in the back!
Happy Boss Day to the best Boss ever! The greatest in the world! The most successful in history! (Not that I am biased or anything….)
Happiest Boss Day wishes to a friend who thinks he is super hard core (but I know deep down he has a super squishy center!).
As a manager you always perform under pressure but as a person you boss life even more. Sending a big hug to a manager and, more importantly, an amazing friend.
I know you think you are something of a big deal at work, but just remember who wins tennis at the weekend! All the best!
Sending the happiest Boss’s Day wishes to a sensational woman. She gets totally merry at the weekend but always feels better by Monday…now that is good management.
Sending lots of love and luck to a man/woman who runs this office like it is heading for war (do not worry, I will not tell everyone at work that by the weekend you turn into a big softie).
To a great manager and amazing friend, you are doing a fabulous job. As your number one supporter, I could not be prouder.
To a great friend and fellow dreamer: When you first told me about your vision I was sold, and now that we have turned it into a reality, it sells itself.
Happy Boss’s Day to a man/woman whose mind is filled with the logic and talent of a great leader, but whose heart is filled with the kindness and thoughtfulness of an amazing friend.
Happy Boss Day to my business partner at work, and compadre at the weekend. It is a real treat to work with you.
It is not every day that one is lucky enough to have a friend for a boss. In fact, I must be one of the few people in the world who genuinely wishes their manager a Happy Boss’s Day.
Bosses get a lot of stick, but I can vouch for this one. He/She is a good egg. Have a cracking Boss Day, I hope you it is really egg-cellent.
Good friends make amazing bosses because they always give their friends a raise….so I am looking forward to mine!
- Happy work anniversary: Do you know a special colleague, friend or family member celebrating a work anniversary? Look no further, because we have the perfect message for them!
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