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Working For A Small Business: The Good, The Bad, And The Ugly

Working For A Small Business: The Good, The Bad, And The Ugly

I went looking for unbiased opinions of what working at a small company is like, and boy did I find them!

I broke down what working at a small business is like into separate categories, such as the impact your work has on the company, the ‘family’ culture, and salary – just to name a few. Read on to find out more.

Working For A Small Business: The Good, The Bad, And The Ugly - Your Work

Your work

The Good: Your contributions are valued
The Bad: But it’s easier to notice if you ‘don’t work as hard’ as others
The Ugly: You might be micromanaged to heck

If you’re working for a small business, your boss might be the owner of the company. In those cases, everything you do is funneled directly to them, so they know exactly what/how you are doing.

On one hand, having a direct line to the owner of the company is a magnificent thing. It’s easy to share your ideas and a lot easier to get them implemented since they don’t have to follow a chain of different people for approval. In addition, the good work you do gets noticed immediately – and if your boss is any good, it gets praised.

On the other hand, it can sometimes feel like you’re being micromanaged. An over-involved boss can quickly make your working environment uncomfortable. Being so involved can make employees feel like they’re not trusted, not good at their job, and constantly watched – none of which are a good feeling.

The Good:

“I prefer working with smaller organizations. Bigger companies have some extra perks and better views, but in my experience the cons outweigh the pros. It takes a long time for change to take effect, innovation is stifled in favor of sticking to the way things have always been, and you feel like another cog in the system. With smaller orgs, you miss out on the top floor office and the company car, but (ideally) you’re encouraged to innovate, change takes effect quickly due to constant collaboration with leadership, and you get to feel the impact of your work.” -Matt V., Full Stack Talent

The Bad:

“At the small company, it is noticed much more if you are not working as ‘hard’ as your coworkers, even if those coworkers are giving their personal time to do that work. It can be seen as not giving as much of your attention to your job, even if you give 110% for the 50 hours you are actually on the clock. Small companies can foster a lot of micromanaging. As great as our CEO is, sometimes they gets way too involved in the day-to-day processes of the office and end up making it harder to get things done. It’s great to have a CEO that wants to be involved in even the small parts of their business, but sometimes it’s better to just let your employees do what they do best.” -Anonymous

“I am a junior dev working directly under the CTO. Micromanagement is definitely an issue. We can’t build a page without him okaying the UI design, the front-end architecture (which he really doesn’t know that much about), etc. But he wears so many hats that we bottleneck on his approval every day. I’ve had entire weeks where I can’t do anything but sit at my desk, meanwhile, the customer is breathing down our necks, but he’s in meetings all day or out of town and can’t sit down for an hour to have us walk him through our proposed implementation. Really it boils down to a trust thing. He can’t pass the ball to anyone. He doesn’t trust them.” -Anonymous

The Ugly:

“My first dev job was at a small family-run company and it was a hot mess. All upper management were relatives, and they also micromanaged a lot. I worked directly with the owner. We had to clock in and clock out despite being salaried, we had to provide verbal updates of what we were going to do that morning, and then had to email what we actually did at the end of the day. If we were talking for more than 5 minutes, they would be like ‘time to get back to work.’ I think part of it is they did have some hourly employees and wanted to keep everyone on the same page, but as a developer, I grew to resent their lack of trust.” -Anonymous

Working For A Small Business: The Good, The Bad, And The Ugly - Wheelhouse

Doing tasks not in your wheelhouse

The Good: You will wear many hats
The Bad: You will wear many hats
The Ugly: You might even have to learn these tasks by yourself…

When working at a small business, you may have to wear many hats. It’s common to have some job responsibilities that don’t fit with your title. In addition, other departments may ask for your assistance on their projects because they simply don’t have the resources. Currently, I’m the Marketing Director here, but I also run payroll for us and do other accounting work, since I have the prior experience to assist with that. In my books, anything I can do to take pressure off the boss is a good thing.

Taking on additional tasks can definitely be great for your career. Not if you’re the IT Project Manager / oil change person (I’m not bitter…) of course, but if the secondary tasks you’re performing are relevant to your chosen field, it can be great experience to add to your résumé for later. Additionally, you’ll be less likely to be pigeonholed into a small box for future roles, as you’ll have a broader range of skills.

The Good:

“Coming in as a junior dev, I was able to touch a lot of pieces that a jr wouldn’t have access to in larger corporations – and some stuff that would have been outside of my job description regardless of experience level. I was able to take part in design and high-level architecture of the application, and I actually got to be part of building an application from the ground up, which is a rare lifecycle to see end-to-end in a larger company. I learned a lot more from all of this than I could have in a larger company with a more rigid application of job descriptions and authority isolation, and while I made a lot more mistakes than I might have been enabled to in a more constrained environment, I think it forced me onto a more rapid understanding of some common blunders and really ingrained in me the importance of proper CI/CD integration and source control.” -Anonymous

The Bad:

This is my own experience, unfortunately. At a prior small company, I was an IT Project Manager, but also the owner’s assistant. One day I could be working on infrastructure planning for a brand new building, and the next I’d get an oil change for my boss. It can mess with you to be both a high-performance PM and the oil change girl.

The Ugly:

“I had very few people to look to for guidance. The company was just beginning its foray into some new platforms, and the only experienced dev we had on the team was pretty fresh to the newer tooling. I had to figure out a lot of stuff on my own, as he was bad at leadership, even when he could help with something. This led to a lot of hacky solutions to try to keep up with a deadline, and at this point, we have some major technical debt on the table to go back and re-architect. Additionally, while the shallow management tiers allowed me a lot of freedom in my role and visibility to a lot of extraneous aspects of the business, it also means that we have no diversity of authority, and when one king rules a company, there is little chance to course-correct when he sets his sights on something. Dictatorships are not healthy for governments, and the same goes for organizations, because no one person can be infallibly correct every time, and it’s especially dangerous when that person actually believes they can.” -Anonymous

Working For A Small Business: The Good, The Bad, And The Ugly - Work-Life

Work-life balance

The Good: Generally, it’s much better
The Bad: But not if everything is on fire
The Ugly: “Oh God why am I working 80 hour weeks?!?”

This may depend on which phase the business is in. If the business is in the startup phase where everything is on fire, work-life balance may be on the backburner for a bit. But if the business has been established for a while and is on cruise control, your work-life balance will most likely be much better than it would be at a larger company. Small business owners generally understand how important it is to maintain a healthy work-life balance and spend adequate amounts of time with family, friends, or pets – or all three.

The Good:

“Small companies tends to care more about making sure you have time with your family because, chances are, your boss and coworkers all know your family. The company I worked for before this was a huge multi-billion dollar corporation and they could not give a flying fart about making sure you spend time with your family. I personally would pick a small business over a large corporation any day.” -Anonymous

The Bad:

“At a prior job, I was expected to work over 40 hours. I wouldn’t say work-life balance was non-existent, but sometimes my home life definitely suffered for the good of the company.” -Anonymous

The Ugly:

My own experience. I worked at a 6-person IT company in the past. Lunches were spent at your desk, working. If you did actually take your hour lunch, it was a huge deal. Overtime was expected, but you didn’t get paid for it, because you were salaried. The techs were on-call 24/7. When someone got fired, they were not replaced, so the techs got busier and busier. Work-life balance was not a thing at this company. PTO was rarely approved. Mental health days, which were a huge boast for them, were incredibly hard to get approved. Not a good place to work. 0/10, would not recommend.

Working For A Small Business: The Good, The Bad, And The Ugly - Benefits

Benefits can go either ways – some companies have great benefits, others are abysmal

The Good: Some companies do it right and take care of their employees
The Bad: Others cover the bare minimum
The Ugly: Others cover… well, nothing.

Smaller companies can lack in the benefits department – there often simply aren’t enough funds. We’re pretty lucky at Full Stack Talent. Our boss covers 50% of our health insurance, we have vision and dental, $50k of life insurance, a 401(k) with 4% match, etc – the list goes on. Our boss was smart: he covered all these benefits right from the start to get a clear financial picture.

I say this not to brag, but because it’s a big problem amongst smaller companies: they don’t cover health insurance from the start, they decide to offer it a year down the road, are shocked at the costs, and end up not offering it. Taking these costs into account from step zero is the smarter option.

The Good:

“The company I’m at now actually has very good benefits, and I would like to think that it’s because we have so few employees that they can afford the better insurance. I pay about $11 per paycheck for the highest tier of coverage. The large company I worked for before this had terrible insurance and for almost no coverage I was paying about $80 per paycheck. Keep in mind, I am not married and have no kids so that’s just for me. I felt like the bigger corporation was just doing their due diligence by having an option for healthcare, but not actually caring about how accessible it was, whereas the small company knows that if we have good coverage, we are better able to take care of ourselves when the need arises.

As for what they can offer or not offer due to funds, to be totally transparent, our CEO is pretty incredible and treats us to outings, team building events in and out of the office, and office perks such as lunch or swag (jackets, umbrellas, clothing, trinkets, etc.) almost weekly. Even though our company is small, we do a lot of big business transactions all over the world and our CEO rewards the teams for accomplishments as much as he can. I feel like maybe he’s not the best example of not being able to offer as much [because of being small], but I have noticed that in our day-to-day duties, anything regarding money going in or out of the company is looked at very closely by every manager that is on the chain of command between the salesperson and the CEO. Discounts are given to customers sparingly, and we really only take fault of an issue when we are truly at fault.” -Anonymous

The Bad:

“I worked at a smaller company that didn’t offer much in terms of benefits. We got health insurance plans, dentals, and vision, but the company didn’t cover any of it. We had good PTO (2 weeks right off the bat) and flex time. However, we didn’t get any retirement options: no 401(k), no IRA, no stock options, etc. Covering the bare minimum of benefits is ok, but I don’t like working at companies that won’t offer me long-term benefits.” -Anonymous

The Ugly:

I’m going to use my experience at that small IT company again. The only thing we really got, as far as benefits, was 50% of our health insurance covered. No dental, no vision, no life insurance, no 401(k) or IRA, no tuition reimbursement. Technically you got 14 days of PTO, but again, incredibly hard to get approved.

Working For A Small Business: The Good, The Bad, And The Ugly - Family

Everyone is family

The Good: They care about you
The Bad: If you don’t like them, you’re screwed
The Ugly: They will sometimes track your every move

At smaller companies, everyone knows everyone – and that means everyone knows everyone’s business. But, this also generally means that everyone’s birthday is celebrated, parties are thrown for retirements and baby showers, and when someone is going through something, those people all care and want to be there for you. It really sets the ‘family’ culture of the company in stone.

On the negative side, since everyone works so closely together, if you don’t like your team, you’re a little screwed – especially if you’re the kind of worker that takes pride in your output and the rest of your team does not.

The Good:

“Our CEO tries to make sure we all feel important by buying us lunch, randomly handing out company swag, and arranging company events frequently, which he/she can do because there are only 30 of us.” -Anonymous

“I worked at a small business in the past. It was a great experience. Everyone knew each other, everyone cared about each other, and everyone succeeded or failed as a group, and the learning opportunities were tremendous.” -Anonymous

The Bad:

“I currently work at a small company. I work remotely, which is great since I get to see my kids every day. The rest of my team works remotely as well. However, there is a lack of team communication, and lack of leadership. It’s leaving this void in me, because I want to work towards something big. This team is ‘clock in, clock out.’ No talking, no questions, no thoughts. But despite the negatives, I still find myself being incredibly motivated, and there’s zero micromanagement – so overall, it’s still a decent place to work.” -Anonymous

The Ugly:

“When I first relocated from NJ to Tampa, I was unemployed for the first 3 months and collecting a nice unemployment check (NJ pays 60% of your weekly salary in unemployment, unlike Florida). I took the first job I was offered because I couldn’t take staying at home doing nothing, even though I was making more money from unemployment.

It was at a small marketing agency on RT54 – your run-of-the-mill sweatshop. I worked there for a year. What made me quit was, one day, I took the day off to deal with some personal matters with my daughter. Since I was new to Tampa, I used to go to a lot of meetups after work to network and meet people. I happened to go to a meetup the evening of my day off and tweeted about it. The next day when I arrived at work, I was asked to go to the manager’s office.

I go in thinking they were going to ask me about how my daughter was doing. Instead, they ask me why I took a day off to go to a meetup. I lost it. I confronted my manager and told him, first of all, the meetup was after working hours, and what I do in my free time is my business. What was worse is, the HR manager was monitoring our social media. So I went to her office and gave her a piece of my mind as well. I quit the next day.” -Anonymous

Working For A Small Business: The Good, The Bad, And The Ugly - Salary


The Good: “We got funding and can pay you what you’re worth!”
The Bad: “You’ll be a little bit under market for a bit, we’re sorry :(”
The Ugly: “We’ll pay as little as we can to get you”

Money is a little self-explanatory, right? Some small businesses do great and can pay you an adequate salary, and other can’t, or refuse to. If it’s the latter, you should probably flee while you still can.

The Good:

“I feel like my salary is very competitive given my experience and I’ve gotten great bonuses and significant raises just in the 1.5 years I’ve been with the company. The benefits are stellar and would make leaving hard to consider. Some benefits are 100% 401(k) matching (yes, dollar-for-dollar), full health for me and family, dental, stock options, very generous PTO, and flex-time on top of that. I realize that at some point I will probably need to change companies to get a raise that reflects my skills/contributions, but I can’t see that being necessary for some time.” -Anonymous

The Bad:

“My experience overall at a small company was great. My only complaint was money. I received a few raises over my tenure, but not enough to bring it in-spec. During my last year there, I specifically stated what my target was, and was told that the company couldn’t afford it. At that point, I told them I would be looking for a new job. I worked there until I got a new offer.” -Anonymous

“I got bought low when I started. I had a wife that was due in a month with our first born, so I was candid and told my boss exactly what I needed to be on budget – and I got exactly that. I’m not salty about it because I kinda saw it coming, but I didn’t have the leisure of being picky or playing my cards close. That said, I’ve been there for 11 months now, and I got a $10k increase in January (per my request, had to bring it up myself), and another $7,500 two months ago because one of our three devs (and longtime employee) left. You don’t normally go from $40k to almost $60k in a year at a larger company – not without a major position change, at least.” -Anonymous

The Ugly:

Enter my experience at the IT company again! My salary was at least $20,000 below what I was worth. Felt great to quit.

Overall, working for a small business truly is a mixed bag – it’s all about finding the particular company that’s right for you. But, out of all the people I spoke to, the majority – by far – enjoyed working at a smaller company more than a big corporation, and most stated that the downsides of working for a small company can also be found at bigger companies too.

Do with this what you will.

I, however, will pick a small business over a large corporation every single time.

Roxanne Williams is the Marketing Director at Full Stack Talent, a technology staffing agency in Tampa, FL. Find her LinkedIn here.