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Pajamas or Office: Should Your Small Business Force Them Back?

Updated: Sep 21, 2023

It's a post-covid question that's as divisive as pineapple on pizza: "Should your small business force employees into the office?" It has become a perplexing problem for many small business owners. There are many clear "business" benefits to having your team in the office, but what's a definitive "business" decision is not always the same as what is right for your small business.

woman working on her laptop while sitting on top of a mountain with an expansive view behind her

Buckle up because we're about to unpack what we mean there with the charm, quirkiness, and dad jokes you've come to love from Out of the Box Advisors, the small business coaching wizards who know how to turn a challenge into an opportunity!


The Traditional Office: Where Water Cooler Chatter Flows Freely (and So Does the Coffee)

Let's set the stage for the traditional office experience. It's like entering a parallel universe where Sharon from accounting passionately discusses last night's reality show drama while you politely nod and smile... Ah, the good old office – a place where your daily grind includes both coffee and camaraderie!

group of coworkers forming a train with a series of office chairs
If every day were like this, office life would be great!

For some small businesses, there's no place like the office. It's where teamwork blooms, spontaneous brainstorming sessions happen, and epic birthday cake surprises are planned. A team full of socialites working together, who thrive with that quick chat in the cubicle next door can absolutely thrive in the office.

However, this positivity isn't always the case. Productivity can be swapped with gossip or other interpersonal conflicts. Dreary eyes abounds from the early morning required to beat the traffic into the city to clock in on time. "Mondays" become more of a disease infecting your small business week after week, with dread rising upon each successive experience.

Small business owners typically lean to being the type that needs to have their hands in everything. That's a nice way of saying that you likely have control issues. In fact, we often tackle this very behavior early on when helping our clients. We mention it here, because you need to be aware of your inherent bias when deciding to be in office or remote.

But is having your employees in office the secret sauce to success? Or just an extra dash of chaos in your coffee?

Remote Work: Pajamas and Productivity – An Unlikely Duo

Fast forward to the era of post-covid, and remote work is all the rage. Who needs a fancy office when you can conquer the world from your cozy couch in pajamas, right? Well, maybe that's an exaggeration, but remote work does have its perks!

woman working in a makeshift office in the back of her van out in the wilderness
How "remote" is up for debate!

When employees work remotely, they have fewer commutes, more flexibility in their schedules, and the freedom to prove that yes, they can be trusted to work while wearing bunny slippers.

But, can employees stay home and still produce at the same level as in-office? Unfortunately, that comes down more to your business' structure and the composition of your team. However, since lockdowns etc., we have a plethora of data across just about every industry and size business that shows that most businesses can keep on ticking with little to no decrease in productivity with an all remote staff.

This is where it gets a bit sticky. Is that maintained productivity a product of having too much waste to begin with or is it because being in the office has no effect on your small business? For example, maybe your staff's individual productivity tanked when they went remote, but you simply didn't "feel" it because the employees who dropped off weren't really producing anyways? It can be very difficult to discern which is precisely why every small business owner out there is struggling with this very problem.

a young orange cat laying in front of a laptop where it appears as though it is working
The BEST Co-worker!

Either way, on the personal level, most employees of small businesses are happier working remote. Taking out the commute being one of the largest factors. But, we believe that one of the best reasons to work remote is that it increases your employee's time with family.

This is what we were alluding to when we began this article. Even if your business could benefit more from in office work, sometimes choosing to stay remote is the better overall decision for the people that work for your small business. Which will ultimately create more loyalty and a stronger workforce.

But... if you must have them in office, perhaps you can have your cake and eat it too.

The Hybrid Approach: Broker Peace Between the Office Valkyries and Pajamas Warriors

We know you originally came here for the answer on if you should force your small business' employees into the office or not, but perhaps there is another way. Imagine the hybrid approach as the truce between those who thrive in office and those who prefer wearing pajamas in remote work.

a young professional business owner leaning over to pet her dog she brought to the office
Hybrid could mean bringing home to the office!

Picture this: Mondays and Fridays at home, with your furry loved one cuddled at your feet, and midweek at the office for that much-needed face-to-face time. It's like dating the office without the commitment. And let's face it; commitment issues are a thing, even in the world of business.

This approach works best for those types of small businesses that absolutely have to have that in office time, but still wants to tap into those remote benefits. If meetings tend to be less effective on Monday's and Fridays, for example, why would you want to continue pushing your employees to come in to no effect? Instead, you could focus on scheduling your in office meetings or functions in the mid-week and allow for flexibility near the weekend.

Be careful however, if you try to also create a strict, traditional business atmosphere when people are in the office, this can directly contrast with the pajama lifestyle. Knowing your company culture is critical to success in a hybrid setup.

Pros, Cons, and a Dash of Humor: Which Style is Right for Your Small Business?

Now let's explore the pros and cons of each work style. Just like choosing between your favorite ice cream flavors, deciding on the right work setup for your small business involves weighing the delicious upsides and the potential for a brain freeze. Whether you're a die-hard traditional office enthusiast, a pajama-clad remote warrior, or somewhere in between, we're about to dive into the sweet and not-so-sweet aspects of each approach.

Traditional Office:

In the traditional office, employees gather like a well-rehearsed orchestra, fostering camaraderie and spontaneous brainstorming sessions amidst the aroma of freshly brewed coffee.

Guy holding a tablet in his hand while dancing on top of an office conference table
This dude LOVES work I guess...

While it offers a bustling hub of teamwork and a break from household distractions, it also comes with the daily commute, office politics, and the occasional microwave fish incident in the break room. For some, it's the heart of productivity and social interaction; for others, it's a dash of chaos in their daily coffee cup.


Face to face communication, increased culture creation, more control over employees, coffee on tap, water cooler gossip, and the occasional desk dance party.


Less time spent with family, fall victim to traditional business tropes, less freedom and flexibility, commute-induced hair frizz, office chair rivalries, and the dreaded fluorescent lighting.

Remote Work:

In the realm of working from home, employees relish the comfort of their own spaces and the liberty to set their own schedules. Pajamas become the new dress code, and snacks are just a kitchen trip away.

lady wearing a jumper and straw hat sitting on a beach working on her laptop
Maximizing "remote" work!

With the added perk of pants being entirely optional, it's a world of unparalleled freedom and individuality. However, amidst this flexibility lies the challenge of combating feelings of isolation, battling the fatigue of countless virtual meetings, and resisting the temptation to swap work for Netflix marathons. It's a realm where cozy comfort meets unique distractions, and where self-discipline plays a crucial role in productivity.


Pajama freedom, pants are optional, much happier employees, more furry cuddles, endless snack choices, and no judgment for talking to your houseplants.


Virtual meeting madness, less employee accountability, unknown payroll waste, the great sock hunt, and the risk of falling into the "Netflix at noon" abyss.

Hybrid Approach:

In the realm of the hybrid work style, employees experience the best of both worlds, with a harmonious balance between office dynamics and remote freedom. It's a work style where Mondays and Fridays are spent at home, often surrounded by your furry co-workers (pets), while midweek, you return to the office for invaluable face-to-face interactions.

stadium style conference room where the small business owner is on a monitor working remote
Meshing in-office with remote work!

This approach combines the flexibility of remote work with the collaborative benefits of the office. However, it does come with the challenge of navigating scheduling complexities, potential communication gaps, and the ongoing quest to find the perfect balance between comfort and formality. It's a work style that offers a taste of both worlds, allowing you to enjoy the benefits of each.


Potential to have the best of both worlds, maintain moderate control over staff, perform critical in-person tasks, build more cohesion, still have happier employees.


Scheduling Sudoku, communication gaps, increased drudgery, the battle of home vs. office coffee, and the eternal quest for the comfiest desk chair.


Remember, that while we're having some fun here, the pros and cons are all part of the decision-making process. It's essential to find the right balance for your small business and your team's unique needs. Not every solution works for every business.


Out of the Box Advice: Flexibility Is the Key to Success

So, should your small business force employees into the office? Well, there's no one-size-fits-all answer. We would say it's all about balance and flexibility. It's about creating a work environment that aligns with your unique small business, your team, and your goals.

Remember, small business growth is about maximizing the sometimes limited advantages you'll have along the way. Being adaptable to work styles for your small business can both enhance growth and attract better talent. So, get innovative, embrace change, and don't forget to have fun along the way!

In conclusion, whether you're team office, team remote, or somewhere in between, Out of the Box Advisors is your trusty companion on the journey to small business success. So, take our advice with a pinch of humor, a dash of creativity, and a sprinkle of quirkiness, and you'll be on your way to building the business of your dreams!

Keep it quirky and jump start those creative juices by scheduling your first session! It's on us!

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