• Mark Olivito

BOSS: A 4-letter Word?

Updated: Jul 3

I’ve become a huge fan of Stitcher Radio PODCASTS. One episode became the inspiration for this post: Masters in Business with Barry Ritholtz. The guest was Scott Adams, Creator of Dilbert (transcript link). This podcast covered a ton of ground, but what caught my attention is Adam’s view on what launched his desire to leave corporate America, all things related to “boss.”

“….Because I noticed that the common element was having a boss because my success or lack of it in the corporate world didn’t have anything to do with my ability or how hard I worked, it was entirely up to what a boss decided for the bosses and the company’s own reasons. And I thought well I’d like to be free of that so I’ve tried a number of things over the years, cartooning was the one that worked….”


So why does this matter?

The vast majority of people will NOT own their own business, they work for someone else (the Boss). Whether you like it or not, the Boss holds a DIS-proportionate impact (good or bad) on the quality of your life, and possibly your ability to advance/grow/develop. Outside of your immediate family, I’d argue that this one relationship is absolutely critical to get right, in a way that works for YOU.

Of course, how you view your job is multi-faceted, your co-workers, customers, vendors, etc all shape whether your happy, not or just “ok.”

But admit it, it’s impossible to think of how you feel about your job and/or company without quickly thinking about your boss, right?

Some have learned to cope/tolerate. Some employ the wishful thinking strategy: Pray they leave, get transferred, move on. Or that the boss’s boss (or higher) finally wakes up and recognizes there’s a bad apple in charge of people’s careers. (Note that “bad apple” could be simply in the eyes of the employee, and the boss has real value to the company.)

I would argue that wishful thinking or “Hope” is not a strategy for taking control of your own happiness at work, and how your relationship with your boss impacts that. Hustle, is of course a VERB.

HOWEVER, business isn’t all about Hustle: The drive to grow, make more $’s, deliver better results. There’s another major H, and it’s called HEART. It takes Heart AND Hustle to create successful, meaningful relationships.


The BOSS relationship is like none other. This person has the ability to impact a paycheck (or at least heavily influence it), and not many people can afford to NOT take their responsibilities to family into consideration, and therefore tread very lightly around their boss. Totally understandable, and I wouldn’t any form of reckless approach.

Some things to think about for getting off your heels on the Boss topic….

  • Make yourself a list of what truly matters to YOU in terms of how you want your relationship to start, build and evolve over time with your boss. What matters most?

  • Do you care to get to know them, vice versa beyond work? OR do you just want to do your time (like jail), leave it behind you and collect your check? Some people love their life and this works, no further thinking/energy needed!

  • Does it matter to you how “good” your boss is at their craft? Do they have it mastered, or are they learning on the fly? Are they better TODAY at what they do than 2 years ago? In other words, is learning from your boss very important to you in terms of how you “score” your relationship?

  • Who do THEY report too, and how good are they? What’s your boss’s “cred” within the organization? Respected? OR are they viewed as a ______?

  • If you left today, would your boss miss you, or would they breathe a sigh of relief? If they would miss you, should they be “taking care of you” (however you view that) RFN (Right _F’n__ NOW)? Said differently, will it take you finding an opportunity for them to “set right” whatever it is that’s causing you to look for a change and would it even matter if they tried to give you a “counter?” Said differently, to what degree is your boss vested in YOU?

  • Is it important for your boss to make you better, however you define that? If so, if you look at where you were at the start of your relationship with your boss, vs where you are today, how do you feel about your growth?

  • Does Loyalty Matter? Do you need to know that your boss has your back when you are not in the room?

  • Have YOU made a game changing (or minimal) impact on your boss? Relationships, even this one, are 2-way streets.

Everyone has a different score card for what matters most in a boss/employee relationship.

The key point is this:

No relationship, no matter how out-sized in terms of impact is worth approaching PASSIVELY. Think through what matters to YOU, then get off your heels and initiate that first conversation…..no relationship improves without that first, direct conversation.

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