Oh Hey, Boss… Two Kinds of Bosses. What are the Odds?

By October 9, 2018 Food for thought

When you have to report to someone else, have someone else dictate their work life and goals, let you know if you’re allowed to leave…you know, another rung up the ladder – you’ve got a boss.

It’s ok to have a boss. I have a boss. Even if you become your own boss you still have all the people who are paying for what you do as your boss. I read that once.

Anyway, You know working up is exactly that. You’re working up. Working up the chain to either learn everything you can or make a lot of money or both and get better perks. Then either start your own, leave and move up again or retire early. (Well most of us do anyway) So, for now let’s say you have to have a person to report to. You’re going to end up with two, maybe 2.5, gambles on what type of boss you’ll have and why.

  1. “Hey, Boss…”

You ended up having a manager who is a manager because they’ve been there for so long it just happened or they know someone another rung up that helped them out. Not sure how, but anyway, they’re more of a middle person that just knows all the rules or finds them out for you. They’re a resource for you because it’s like having a punch clock, employee manual, company historian…like an Alexa who may (hopefully!) or may not be a good person.

“Hey, Boss… quit being a dick”: Here’s where the “maybe three” gamble comes. If they’re a “Hey, Boss…” and have an underlying insecurity problem, a comfortable routine problem or worst of all –  an ego problem –  it could shorten your longevity with the company even sooner if they didn’t and were just a mere tour guide in this thing called a job.

What do you mean I’ll be leaving? Yep. I bet. Eventually. If you have the “3” ringers, more than seven years would be a stretch working there, but possible it could be possible if 1. You like your team 2. You get a decent earning plus one more thing like commute time, flexible schedule, benefits – then you could live a personal life balance that makes it fit your current lifestyle. Eventually you’ll hit an age where it’s now or never because you’re well, bored.  Take any of the perks away, then you’ll be more bored and gone for sure within 2-4 years.

Why?  If you’re someone who is hard wired with determination, ethics and a desire to make things better than you find them –  the ones who give your all at your job regardless of what it is or what it pays, you know what I’m saying. You are a walking, talking, driven son of a gun making your family proud – then you can’t stay monotonous. You. Just Can’t. You want enough time to look like you mattered to the company and have resume cred but you know if you stayed even a little longer then maybe they’re more open to thinking you’ll bring your rockstar moxie with you as you woo them in the interview to move on. Cause you’ll be more likely to get the opportunity to even interview this way.

Side bar – if you aren’t someone hard wired that way and believe employment is a right and not an opportunity to challenge yourself, they’ll want to get rid of you but take forever since they aren’t really ready to make decisions that aren’t already printed somewhere.

OK, back to why working for a “Hey Boss” that can also be an asshole at times due to the above underlying problems. These behaviors are a result of their personal blind spots (more like blackouts) that make your day stressful and it’s hard to like them when you already struggle to respect them for their lack of leading already. It’s easier to find reasons to respect someone for at least being a nice human being but a poor leader to make them tolerable every day. But if they already lack that and act like an asshole about things that damages their character, it’s too much.  Sometimes, it’s worth jumping ship when you get a new job offer and simply call the very brief employment so far a misstep and you aren’t sure you can truly see no way to fix it within a year so ready to explore options because this company interviewing you is one you can believe in. Don’t jump to jump. Find the right jump. And Remember, leave and job better than when you found it.


Second Boss Type

  1. Real Deal.

They’re like your tour guide along your own adventure and eventually they let you explore on your own and just check in and talk analytics, give you feedback and ideas when you need them. They have your back and make decisions.

They either inherited dad’s company, have a little Spicoli in them, came from a true climb of blood, sweat and tears to get passed the “Hey Bosses”. There’s many stories of how leaders got to that place. You might find a podcast or two about them.

Anyway, they’re a little older and saw something in you they’ve seen or have themselves and truly admire. They see your potential because they aren’t threatened by talent, they embrace it so they can chill out and coast if they want 20+ years inside the hustle. They still got it to help and teach and guide you, but they don’t expect to take the credit for it. Your success reflects their efforts. The more you can do on your own, the less they are needed and can focus on life balance for time served and be used for wisdom, direction and experience in growing others.

It’s a great place to be because of that leader, even if they have their moments of doubt with the leader somedays, they are genuine people who don’t hide or judge flaws.  Usually, you end up sticking in for the higher probability of 7+ years because starting over gets tiring sometimes when you have the perks and affordable pay, even if the work gets so hard at times. Either way, you both buckle in and go for it and push past any barriers that would hinder anyone growing themselves,  the company, the profits and what’s even better – the people within it.

Then, at least you are growing and exploring together with a perk you can’t explain. An extension of your home. Your biodome. Your life. That’s something you can believe in and find purpose in.


My own personal experience of probability on the boss gamble when accepting a job on terms you see as mutually beneficial? 80/20. And of the 80% of “Hey Boss…” you get, I’d say 1/4 of that is also capable of being a dick. 20% chance. So, it’s the same odds that you’ll either get a dick or a great leader but 80% of the time you’ll have some form of “Hey Boss…”


But on the flipside of the bosses who have to hire new people- same equation backwards.

Want to know my odds of hiring new positions or replacing failed positions (Could be my fault, could be theirs but either way it was a clash of the misunderstood performance and growing speed) with people who make us better and are growing in career as rapidly as they are perks to match their talent growth? 80/20

But man, does that 20 shock our eco system sometimes. Scary.


So which is more worth it? I bet 80% of the time you have a manager that’s the “Hey, Boss” and you learn anyway while getting what you want out of what you’re doing. It’s ok. Even the bad ones are good because you learn exactly what not to do. Reflect, don’t regret.

Just think – some of the best life lessons is experiencing all of these bosses to figure out which one suits you best.


Every type of boss is everywhere and every type of employee is everywhere.

Last point to make – if I were to ask you the difference between a woman or man boss – what does it matter? The odds of the two types above do not know a gender. They are behaviors. Behaviors are what set us apart. Not gender discrimination.

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