Choose the Boss over the Company


Having worked at 6 different companies now, ranging from an organization of 3 to 115,000, I was trying to figure out why I genuinely never really enjoyed working for any of them.

My first instinct was “Oh, I’m the type that needs to be my own boss. Blaze the trail. Screw companies.”

When I got my head out of my ass, I started taking a closer look at the different aspects of each job.

At first I thought it was the size of the company. Too big felt stuffy. Too small felt chaotic and unorganized. But even at the “right” size, something was wrong.

After going through a bucket list of reasons, and crossing myself as the issue, it’s then I realized that it’s not that I can’t work under someone else. I just haven’t enjoyed any of the people I’ve worked under. Their leadership style didn’t match how I wanted to be managed and didn’t optimize for my own learning.

So this got me thinking about how to be more critical about the people that I would eventually be working under.

Some red flags to look out for

1. First-time/inexperienced managers

Now, this isn’t to say all first-time managers are bad. But…you don’t have anyway of knowing if they’re good either. You can’t ask people how the person is as a manager. And that’s quite a risk to take on your own growth, development and advancement in the career ladder.

Your boss tends to be the one that removes an obstacle in your path, provides you with opportunities, makes sure you’re noticed and is your main advocate in a firm. That’s a lot of responsibility to give someone who themselves is figuring out office politics and has gone from managing their own career to managing the career of multiple people.

Just something to be aware of.

2. Orders rather than leads

If someone is just telling you what to do and then has no other interaction with you, then that’s not a boss who’s leading. That’s a boss who’s ordering.

You’re never going to learn from anyone who just tells you what to do.

The problem with orderers is they’re not actively engaged with the growth of their employees. They’re not teaching. They’re not providing solid feedback. They’re not motivating. Additionally, they may lack in showing the bigger picture and providing a sense of direction for the work they’re ordering their employees to do. I don’t see how you could become a better worker if someone like this is in charge of your progress.

3. More dedicated to their career at the expense of yours

Some would say that people should be more focused on their own careers than someone else’s. I argue the opposite for the case of managers.

There’s a saying in the working world that an employee’s job is “to make their boss look good.” Well, if your boss isn’t helping you to become a better worker, how on earth would you make them look good?Therefore, a boss who takes an active effort to progressing their employees directly impacts their own career as well. It’s a simple feedback loop.

Boss makes employee better →employee does better → boss looks better=everyone wins.

My “Boss” List

After evaluating all the different people I’ve worked under, I’ve figured out my working style and also how I want to be managed. I highly recommend anyone reading this to do the same for yourself. Because you may be working at your dream firm, but if your boss sucks, you’re going to leaveTherefore it’s important for yourself to know what you want and expect from your managers.

Again this is my personal list and doesn’t apply to everyone and shouldn’t apply to everyone. We’re all different and need different things. So I recommend taking the time to see what those things are.

1. Hands-on (but not micro managerial)

I want someone who is actively involved in my day-to-day interactions since I get bored quickly or lose interest in projects if it has a long tail and/or many iterations. Hands-off managers caused me to retreat into my little bubble and not be as forthcoming with my problems.

2. Motivational and positive

Some days at work just aren’t fun. The work isn’t interesting. And you’d rather be doing something else with your time. Having a boss that is able to motivate me and stay positive through the trenches would not only improve the working experience, but make me want to produce better work for them in return.

3. Direction, transparency and presents the bigger picture

Working blind is the easiest way to kill motivation and make your work lose meaning. Having a boss that presents the bigger picture gives me value and meaning to the work I’m doing. Additionally, having direction makes sure I’m not wasting my time with work that isn’t adding value to the team and isn’t adding to my knowledge base.

4. Mentor-like/invested in my progress

Simply put, I want someone who cares about me and my career. Someone who is able to teach me, guide me, and make sure I’m progressing at a good rate. Someone who is able to create opportunities for me if they believe I’m deserving of it and clear obstacles in front of me so I can produce the best work.

My mentor told me about one of her own bosses today and said that people would fight for one particular manager as you were pretty much guaranteed to be promoted if you worked under him. He was that dedicated to his employees. That’s the type of boss I’d want to work under. Also checkout her HBR article, “Four Lessons From the Best Bosses I Ever Had”. She’s pretty awesome hehe.

But it doesn’t stop at my boss

Relationships are a two-way street. The boss isn’t going to do everything and they definitely can’t read minds.

1. Be clear and transparent with my needs and expectations

It’s up to me to communicate with my boss what I need from them to grow. By setting out expectations early, my boss and I should be able to optimize my progress along my career path together because we’re both aware of how I need to be managed.

Additionally, I need to be an advocate for myself and escalate any issues I’m having with work. Otherwise, my boss can never help me.

2. Provide feedback to my boss

I value companies that do 360 feedbacks as a manager isn’t going to be perfect even if I set out all my needs and expectations. We all have room to grow and improve.

On a final note, I wanted to give a shout out to my mentor who pointed out what a privilege it is for me to be able to pick and choose a boss and be critical about it. Most people do jobs in order to just get by and pay the bills. So while I do push people to be more critical of their jobs as they enter the workforce, it’s always important to acknowledge the privilege we have and work towards helping those not in our position.

Hope anyone who is in the position to do so, really starts to become critical of not only the companies they work for, but the people they work under.