Kindness At The Helm: 30+ Examples Of Compassionate Bosses

By Jana I November 26, 2023

Working means showing up at the workplace on the days you are expected to and always being on time. It also means dealing with colleagues and your boss. The latter is easier said than done because not all managers are a pleasure to work with. Some are slave drivers who delight in being a nightmare to their employees. We’re happy to tell you that the prevalence of poor bosses is relatively low. Plenty of wonderful people are admirable leaders, concerned with their employee’s welfare and always going above and beyond to ensure their staff feels valued and appreciated. Scroll below to explore some remarkable instances of exceptional bosses, as recounted by contented employees from various corners of the internet. These stories highlight the bright side of leadership and show that there’s no need for unkindness to run a successful company.

Bouquet For a Better Day

In a touching display of empathy, a compassionate manager presented an employee with a beautiful bouquet of flowers to lift their spirits. This thoughtful gesture offered comfort and support during a challenging time. Actions like this remind you that you’re not alone, whether it be a breakup, divorce, or death in the family.

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The bouquet brightened the recipient’s day and underscored the caring and supportive atmosphere cultivated by the manager. It emphasized the importance of well-being, leaving a lasting impact that goes beyond the physical flowers. The florals may wilt, but the thought will stay on their mind forever.

Relatable Boss

This employee, usually early and on time, arrived at work late due to unexpected traffic. To their surprise, their boss was also running behind schedule. After explaining the tardiness, the boss empathized, recognizing that everyone experiences occasional delays. Sometimes, things are out of our control, and there’s nothing we can do.

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This understanding response alleviated the colleague’s stress and reinforced a sense of camaraderie in the workplace. Instead of getting angry, the boss demonstrated that he is human too and subject to traffic laws. It was a valuable reminder that even superiors can face the same challenges.

That is One Hell Of a Boss!

One delightful story features a boss who embarked on a month-long adventure abroad. What makes this tale even more heartwarming is that they granted paid leave to their diligent employees during their journey, ensuring they enjoyed a well-deserved break. After all, the staff also do their best for the company.

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To top it off, the boss returned with thoughtful gifts, surprising everyone with a collection of makeup goodies. It’s a testament to their generosity, thoughtfulness, and the positive, relaxing atmosphere they fostered in the workplace, making it a tale that warms the heart.

Christmas Thank-You Card

In the spirit of the holiday season, a boss spreads warmth and gratitude by purchasing a stunning Christmas thank-you card for their dedicated employees. The card, adorned with festive designs and heartfelt words, conveyed the boss’s appreciation for their hard work.

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It served as a touching reminder of each team member’s value to the company, fostering a sense of camaraderie and goodwill. Such thoughtful gestures go a long way in creating a positive, uplifting work environment. This makes the office a place people look forward to spending time in.

Boss That Understands Boundaries

A truly exceptional boss goes the extra mile to ensure their employees’ well-being by encouraging relaxation over the weekend instead of asking them to toil at work. This compassionate leader, recognizing the importance of work-life balance, suggests that the team spends quality time unwinding on the beach.

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Their thoughtful gesture promotes a healthier work environment and underscores the value they place on their employees’ happiness and mental rejuvenation. It’s a testament to their leadership style, fostering a sense of trust and appreciation that resonates with their workforce.

Early Birthday Cake Surprise

A thoughtful boss surprised their employee with an early birthday cake in a heartwarming display of appreciation and camaraderie. This sweet gesture, filled with delightful flavors and adorned with candles, reflected the boss’s caring nature. It was more than a cake.

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It symbolizes the strong bond between employer and employee, creating a positive and enjoyable work atmosphere. The early celebration not only made the staff feel cherished but also underscored the boss’s commitment to celebrating the personal milestones of their team members.

A Boss That Likes Fish For Some Reason

In a gesture that welcomed a new team member with warmth and enthusiasm, a considerate boss presented them with a bouquet of vibrant balloons. These colorful symbols of celebration brightened the workplace and conveyed a sense of belonging and support.

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The thoughtful act helped the new employee feel instantly embraced by the team, creating a positive and inclusive environment. Such gestures remind everyone that they are valued and appreciated, setting the tone for a harmonious and inviting workplace.

A Super Reasonable Boss

In a shining example of understanding and empathy, a boss demonstrated their commitment to work-life balance by wholeheartedly supporting an employee’s request for time off to celebrate their daughter’s birthday. We’re sure they were elated to be able to celebrate such a milestone with their loved ones.

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This approach not only underscores the boss’s appreciation for their team’s lives but also fosters a sense of trust and loyalty. By prioritizing family occasions, the boss creates a workplace where employees feel valued as individuals, leading to a happier and more motivated team.

A Very Open Approach

An inspiring poster gracing the office walls celebrates the employees while also serving as a protective emblem of their well-being. The poster, adorned with an uplifting message, recognizes the hard work and dedication of the team. Surely, the staff feels great knowing the company has their back.

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It’s a visual reminder of the company’s commitment to its employees, promoting a safe and nurturing environment. This motivates and boosts morale and also signifies that the workplace prioritizes the welfare and success of its staff. Customers deserve respect, but so do the staff. If you think you can do better, you’re welcome to apply.

Boss That Appreciates Hard Work, and Actually Rewards It!

In a gesture of immense gratitude and recognition, a generous boss awarded an employee with a bonus for their commitment to working during Christmas. This act of appreciation not only acknowledged the sacrifices made but also celebrated the employee’s dedication. A thank you is always welcome, but cash goes a long way for folks who earn only the minimum.

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The bonus was a tangible expression of the company’s commitment to valuing and rewarding its hardworking team members. We’re sure this made the staff’s holidays brighter. A simple thank you warms the heart, but monetary rewards go a long way, especially for workers who earn only the minimum.

What an Unexpected Pep Talk!

In a touching display of support and appreciation, a thoughtful boss delivered an uplifting pep talk to their employee through a heartfelt text message, expressing gratitude and highlighting the employee’s exceptional efforts and contributions. We would surely feel valued if we received such a message.

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The encouraging words served as a reminder of the boss’s belief in the employee’s capabilities, motivating them to excel further. This simple yet powerful gesture boosted morale, and we won’t be surprised if the employee exerts more effort to ensure he does his work right.

Wednesdays are For Breakfast With the Boss

Every Wednesday, a boss goes the extra mile by preparing breakfast for their employees. This act of kindness ensures that no team member is hungry before starting their day. The boss’s culinary efforts create a warm atmosphere, promoting a positive start to the workday and boosting team morale.

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This regular breakfast ritual underscores the boss’s commitment to their employee’s well-being and happiness, making it more than a meal; it symbolizes their appreciation and dedication to fostering a harmonious and enjoyable workplace. You’d be surprised how many workers start their day without having eaten.

The Doggo Gets a Bonus Too

In a heartwarming gesture, a boss extended the spirit of giving during the holiday season by awarding a Christmas bonus to a furry friend that regularly accompanies its owner to work. This act symbolizes the boss’s recognition of the dog’s impact and companionship in the workplace.

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It added an extra dose of holiday cheer and reinforced the sense of unity and inclusivity within the team. How wonderful it is to work in a place that values its employees and their loyal four-legged companions. We’re sure the employees are proud to be connected to such a company.

Manager Of the Year!

Emergency sweets! This should be a requirement in all offices. Heaven knows this won’t go to waste because we can think of many occasions when a packet of sweets can do so much to uplift a staff’s mood and make them feel better. Bless the heart of the considerate manager who came up with these.

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An office should not be a place where people get stressed about deadlines and perform tasks. It should also be a place where everyone looks out for one another and ensures their peers are doing fine. Even something as small as chocolate or candy can make a person smile and feel better.

Boss That Leaves Notes on Paychecks

And not any notes, no, no. Cute notes. These heartfelt messages go beyond financial compensation, showing appreciation for their employees’ hard work and dedication. The notes inspire and uplift, fostering a positive and motivating atmosphere in the workplace.

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This small yet meaningful gesture means this office is a place where employees are nurtured, and their contributions are valued. Wouldn’t you want to do better if you received such notes? It makes you look forward to being in the office and doing your work.

A Boss That Shows Kindness and Appreciation

Receiving positive feedback from a boss serves as a validating moment, affirming years of dedicated hard work and commitment. It’s a powerful reminder that kindness and appreciation can be the catalyst for achieving even more.

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Such gestures of recognition boost an employee’s spirits and inspire individuals to push their limits and contribute more to their teams and organizations. When leaders express gratitude and acknowledge efforts, it creates a cycle where pursuing excellence becomes a shared goal.


We all know Japanese restaurants can be expensive so it was heartwarming for this boss to give their student employee a New Year’s card that offered the delightful experience of dining at a sushi restaurant. This thoughtful act went beyond mere words, symbolizing the boss’s appreciation and care.

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This reminds everyone to share their blessings. We are sure this employee was happy to be given a chance to enjoy dinner at a fancy place. The card represented a token of recognition for the student’s hard work and dedication, ushering in the new year with a special treat.

A Boss That Understands

A truly exceptional boss recognizes the importance of downtime and celebrates their employees’ free days and long weekends. We are sure millions of employees worldwide wish they had a boss who understands the significance of work-life balance and encourages their team to enjoy well-deserved breaks.

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The boss reinforces their commitment to employee well-being and happiness by valuing personal time and relaxation. Such celebrations of free days and long weekends will give the staff the time they need to recharge so they can return to work energized and motivated! They’ll be able to achieve more when they’re well-rested.

Have a Good Trip! Here is a Tip!

In a remarkable display of thoughtfulness, a boss wished their employee a fantastic trip and added an extra touch of generosity with a $100 bonus. Whoa! Wouldn’t you love to work for such a wonderful person? Only a few bosses would go the extra mile and give you pocket money for your trip.

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This person clearly has a big heart for his workers, sees all their efforts, and appreciates everything they do for the company. He understands that when you take care of your employees, your employees will take care of the company.

Care Packages All the Way!

It’s not every day that a boss demonstrates genuine care for their team by crafting personalized care packages for employees during a period of closure. The employees must have been surprised and touched by such a gesture. The boss understands the challenges that lay ahead and does everything he can to help them, even in a small way.

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The care packages provided practical essentials and also conveyed emotional support. This boss’s commitment to the team’s welfare extends beyond professional duties. We are sad about their closure, but hopefully, everyone was able to find a new place to work in.

New Monitor Check!

Exhibiting exceptional consideration, a boss went above and beyond by purchasing a large monitor for an employee with sight issues, ensuring a more comfortable and accommodating work environment. Now, he can see better and do his work better.

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Wouldn’t it be wonderful to have a boss who understands that although some employees have problems, they can still do their work well when given the necessary tools to perform their tasks easily? This is a workplace where people would be happy to belong.

When Your Boss is a Trooper

It’s always a relief to know your boss recognizes and understands that employees can be anxious about many things, demonstrating a profound commitment to mental well-being. A person becomes an excellent boss by respecting boundaries and knowing that not everyone is comfortable in a particular setting.

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Instead of forcing the employee to work at another store and telling them they have no say in the matter, this manager asked first and didn’t get angry or disappointed when the answer wasn’t in the affirmative. It reflects a leadership style that values the individual, acknowledging the importance of mental health.

Delivery Driver Fueling Station

When you think all hope is lost, someone with a heart changes your view of the world. This boss understands how hard it is to work as a delivery driver, out in the sun and rain and ensuring packages reach recipients intact. He leaves snacks and drinks for his drivers to recognize their hard work.

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He understands that his crew plays a crucial role in the day-to-day operations, and without them, the business will be crippled, and customers won’t be able to get their orders on time. It creates a positive ripple effect, spreading smiles on the drivers’ faces.

Heartfelt Message

When you work hard, it warms your heart if your boss recognizes all your efforts. Even something as small as a heartfelt message appreciating your hard work and dedication greatly affects your mood and well-being. We wish more bosses see their employees as more than someone who gets paid to do things.

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Whether employees are paid by the hour or not, they are people, too. They must be acknowledged if they did something excellent and went above and beyond their duties. Let’s do away with the culture of only calling the employee’s attention when they did something unacceptable or aren’t performing well.

First Game Certificate

This person had never attended a baseball game and had to make do with watching her favorite team on the television, so you can imagine her happiness when her boss gifted her with the opportunity to experience her first baseball game. She even got a certificate to prove it!

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We understand that some companies are on a tight budget, so we’re even more appreciative of managers who reward their hardworking and deserving employees. This lady must have had the time of her life. You can tell from her smile that she is very happy.

What a Great Day to Be an Intern

Although some interns get paid a small amount, most of them do the work for free or in exchange for academic credit toward graduation. So, you can imagine that not all interns have the money to spend on beauty products, fashionable clothes, or designer footwear. Knowing such a thing, this incredible boss gifted their intern a bag of lipstick samples.

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Lipstick samples may not amount to much, but as they say, it’s the thought that counts. The boss understands that interns are often pressed for cash and may not have the money to spend on something they badly need to look presentable in the workplace. We need more bosses like this.

This Boss Chose World Peace That Day

Multitasking becomes much easier when you have the right equipment. Ask anyone, and they will tell you so. This person’s boss noticed him struggling with his 17-inch monitors and replaced them with two larger, 24-inch monitors. How cool is it to have a person who ensures that work challenges are minimized, if not totally eliminated?

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The boss did not need to spend company money to replace the monitors because there was nothing wrong with them, but he saw his employee’s difficulty, and he wasn’t about to let one of his team members struggle while working. What a great boss to have!

A Heartwarming Goodbye Note

It is always heartbreaking to let an excellent employee go, whether it be to retirement or another company. After two years of dedicated service, a boss penned a beautiful, simple message expressing gratitude and appreciation. This heartfelt gesture marked the milestone and reflected the boss’s recognition of the individual’s contributions.

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We are sure that the staff was also sad to leave behind such a wonderful boss and workplace, but there are times when you need to move forward and do greater things. On another note, we can’t help but chuckle at Photopoop. Is it supposed to be Photoshop?


Most bosses consider staff to be people who do the work they’re told to do when they are told to do it and how they are told to do it. This boss, however, is cut from another cloth. He displays a remarkable understanding of his employees and knows what they like and doesn’t like.

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This person’s favorite time of the year is the spooky season, so they were elated to receive such a cool and quirky Halloween card. Halloween might still be two and a half months away, but their boss never forgot it by sending an advance greeting card.

DIY Last Minute Gift

Instead of generic and bland birthday cards, this boss outdid himself with his choice of last-minute birthday gift. The staff appreciated the gesture and was psyched to receive something he liked for his birthday. You can tell that this boss knows his employees well.

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He might not have the correct balloons, but we can look past that. We all know bosses are also up to their neck with work and are responsible for many things. The fact that they carve time from their busy schedules makes a person feel seen and valued.

New Coffee Mug To Drink A Lot of Work Coffee Out Off

What could be a better present for a caffeine addict than a cute and quirky mug from which to drink their favorite beverage? This person surely agrees with us and appreciates their boss for a new coffee mug adorned with cute stickers.

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The creative touch not only adds a touch of joy to the employee’s daily routine but also underscores a positive and appreciative workplace culture. Such gestures enhance the bond between employer and employee and present opportunities for delicious coffee-drinking sessions.

Hummingbird, An Office Pet

Bosses should look after their employee’s welfare and ensure they are sensitive to the needs of their staff. This boss, however, does more than that. He looks out for the little guys, including little animals who can’t help themselves. Demonstrating compassion beyond the workplace, he rescued an injured hummingbird, bringing it to the office.

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Now, the tiny, feathered guest has become a cherished part of the team, with employees taking breaks to spend time with the delicate creature, feeding it, and looking after it. A hummingbird may not be the first to come to mind when discussing office pets, but it can make the office better.

A Thank You Card is Never a Bad Idea

Working in a place where the littlest mistakes get pointed out and where you are ridiculed instead of corrected can easily zap your energy, desire, and motivation. Luckily for these people, they work somewhere, achievements are commended, and efforts are seen and appreciated.

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They received a postcard from their boss, who had nothing but great things to say. After reading such a heartfelt message, the staff must have had a huge smile on their face the whole day and went out of their way to ensure customers had an excellent experience.

Gift Card For Chick-fil-A

Yes, we’re back with another gift card story. This may not be the first on this list, but we can assure you that this will warm your heart and make you smile. This person is a big fan of Chick-fil-A, so you can only imagine their happiness upon receiving the gift card.

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Some may say that $20 is not a big amount, but that can already buy you a filling meal, and some people are struggling to afford such a thing. This definitely made the employee’s day, and they were so happy, they just had to let everyone know.

So Admirable

There are times when even though you love your work very much, you must choose between it and your mental well-being. Such was the case here. The staff had many personal stuff to deal with that they often had to be away from work and were considering leaving.

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Instead of getting angry at the staff for being away often, this exceptional manager goes beyond professional responsibilities, demonstrating genuine concern and empathy during tough times. They clearly cared about their staff and wanted to let her know that if she ever came back, she would be welcomed with open arms.

A Management That Stands By Its Staff

A protective and compassionate boss takes a stand for their employees, encouraging an environment of kindness and peace. In a rare display of advocacy, they might ask customers to leave if their behavior is disruptive or disrespectful, and we should say that more places need to be like this.

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Servers may serve you, but they are not your servant. You might pay for food, goods, or services but that doesn’t mean you can treat staff disrespectfully. We’ve seen too many folks shout and sometimes physically harm staff, and it’s about time employees feel safe, protected, and valued.

When Staying Late Pays Off

It’s not unusual for staff to stay late at work in a bid to finish work in time for their deadline. What’s not common is a boss who sees such sacrifices and goes out of his way to buy presents for exemplary employees who deserve treats.

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If more bosses were like this, there would be happier employees who would willingly stay late instead of complaining about being asked to stay in the office when others are already leaving. Being appreciative of the people who work for you goes a long way.

Thoughtful When You Need It Most

Most bosses think of themselves as people who hand out instructions and people who tell others what to do. This person doesn’t think that way. Knowing that one of their team is facing some challenges, they even offered to call the hotel for them.

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They went above and beyond to support an employee amid a family crisis. Undoubtedly, this person felt cared for beyond professional boundaries. We are thankful for employers who value the well-being of their team members, especially during difficult times. The world is a better place with them.

Special Helmet For a Special Boy

Anyone with a boss who is thoughtful, supportive, and appreciative is very lucky, but having a boss who is all those things and with a sense of humor? It’s like hitting the employment jackpot! This person is indeed very lucky. Look at what his boss gave him!

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In a lighthearted and playful gesture, his boos gave him a helmet as a humorous souvenir for his time spent in Egypt. While not intended for work, the souvenir reflects a leader who values the individuality of their team members and seeks to create an enjoyable and positive work environment.

Looking Forward To Tea Time

Doesn’t it warm your heart to know that someone remembers you and remembers the things you like? This person just had to share how appreciative they were when their boss went the extra mile by purchasing their favorite tea as a heartfelt gift.

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The gift made them look forward to afternoon breaks at work when they get to savor their favorite tea with their colleagues. Gifts don’t have to be expensive, and gestures don’t have to be over-the-top, sometimes it’s the littlest things that matter.

Christmas Hamper Full of Goods

Being asked to work during Christmas can be a bummer. No one likes slaving away in the office or store when most folks are out and about shopping and enjoying the holidays with their loved ones. This boss understood that and wanted to let the staff know that they were thankful for their presence.

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This is more than a hamper with treats and goodies, it’s an appreciation for employees who work on holidays when they could be relaxing at home or enjoying ‘me’ time. Having such an appreciative boss makes the Christmas season even better.

You’re Loved, Buttercup!

If you have hardworking and exemplary employees, you can be assured that the future is bright for your company. That’s why it’s important for companies and managers to take care of such people, and that’s exactly what’s happening here. This manager let their staff know that they would be footing the bill.

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The employee was expectedly grateful for the offer and was teary-eyed. We would be too if we had a boss who values our loyalty and our work, and who thinks we’re a great person. This person is a lifesaver and may there be others more like them.

Adulted Today!

Being an adult is difficult, to say the least. You have taxes, bills, and rent to pay, and you need to put food on the table. Sometimes, we just want to go back to our childhood days when all we cared about was what our mothers were going to prepare for dinner.

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This boss understands how overwhelming life can get sometimes and in a bid to encourage his team and make them smile, he wanted to remind them that even the smallest of achievements is still an achievement. We’d be more than happy to wear this pin all day.

Fully Understanding Leader

Life is tough, but it’s even tougher for some people, and that’s why we should always be kind to others. You never know what a person is going through. This person needed to work more hours because she was going through a tough time.

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Their boss liked their work and was more than happy to help them during a rough patch, telling them that they would be given as much work as they wanted. We’re teary-eyed reading the message. Hopefully, they were able to pull through.

What a Beautiful Expression of Gratitude

While working, it’s not uncommon to have weeks when hardly anyone can afford lunch and each minute is spent working towards a deadline that can make or break a valuable deal. The workers in this office have just been through such a hell week.

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Their boss recognized their dedication, leaving a kind note on a book for employees who worked late on Patch Tuesday. Aside from expressing his gratitude and appreciation, the boss also told the employees to take an extra hour for lunch.