Are you ready for National Boss Day?

Like most Americans, I've started preparing for one of the year's most festive holidays: National Boss Day.

Oct. 17 is right around the corner, and workers everywhere are out shopping for the gift that says "Thanks for making work a fun place to be!" or "Thanks for ruling over me like a dictator with a mood disorder and slowly wearing me down to a soulless shadow of my once-great self!" Whichever is appropriate.

For those of you who don't know, National Boss Day began in 1958 when Patricia Haroski, a State Farm Insurance secretary from Deerfield, registered the date with a national calendar listing called Chase's Annual Events. It took some time to catch on: Hallmark didn't start offering a Boss Day card until 1979.

But since then, of course, it has become a treasured tradition in every office in the land.

OK, that might not be entirely true. But it does exist, and that allows me to address an issue many workers struggle with: How can I be nice to my boss without seeming like a toady?

The employee-boss relationship is inherently oppositional, in large part because our society and our popular culture have cast that narrative in steel. Even if you kind of like the boss, the reflexive tendency is to gripe about her or him when you're around co-workers.

Not helping matters, a study that came out recently found that one of every 25 bosses could be diagnosed as a psychopath. Presumably, the first thing everyone thought upon reading that was, "Yep, that's my boss. I knew it!"

The problem with always viewing the boss as the enemy is that it can become a self-fulfilling prophecy.

Evelyn Williams, a professor and associate vice president of leadership development at Wake Forest University Schools of Business, noted that, from a pragmatic standpoint, people should strive to get along with the folks who sign their paychecks. And while you can't control how your boss behaves, you can alter the way you frame the relationship.

"If you have a positive mental orientation about someone, if you look at them as someone who might actually be an ally and not an enemy, your body language is going to be different; you're going to have different phrasing and communication styles," Williams said. "I realize that can be hard, and I don't mean to sound Pollyanna-ish. I just think no matter what you get as a boss, it's a dependent relationship. And you need to figure out how to make the most out of that relationship."

A first step?

"Try to understand the preferences your boss has when it comes to decision making and how they like to get information," Williams said. "These are things that are easy for you to do. You're not compromising your integrity by conforming to some of your boss' work-style preference. You want to know how you can be productive with them and understand them better."

As always, the best way to accomplish this is to be direct. If you're putting together information for the boss, ask something like, "How do you want me to share this with you? Do you want me to give you just a big-picture overview or do you want me to give you all the details?"

Look, I can sense the emails you're planning to send me, saying you've tried this and it doesn't work, and your boss is a communist and I'm a communist and blah blah blah. But let me reiterate Williams' earlier point: You have a vested interest in forging as good a relationship with your boss as possible. So why not make sure you're going the extra mile?

A final point from Williams, and one that I promise will get us nicely back on track with National Boss Day, is that the people in charge like to know when they're doing something right as much as anyone else.

"You have to remember that your boss is human, and most all of us want some form of positive recognition," Williams said. "Try to think of what would be positive for this individual that I work for to hear."

And what better time to do something like that than … NATIONAL BOSS DAY!!

This admittedly fabricated holiday does provide workers an opportunity to get to know their bosses a bit better and to possibly take a step or two toward building that better relationship.

Victoria Washington, a career service coordinator at Computer Systems Institute in Chicago, agrees it's a fine line between recognizing National Boss Day and behaving like a loathsome suck-up. She suggests a group effort, possibly offering to take the boss out for lunch or coffee.

"Maybe even a small party with all the staff coming out and a card, something to show your boss that you all appreciate what they do," Washington said. "Especially at big companies, not everyone knows who the boss is. When you have a group event, it gives you a chance to talk, maybe ask a few questions just get a better sense of them."

Barring widespread organization, you also might consider just shooting the boss an email saying something nice.

"Even if you don't like your boss, it's still not bad to show some appreciation," Washington said. "You still have a place to work. It could be far worse."

Once all you skeptics out there have put this information to practical use and developed healthy relationships with your superiors and received generous bonuses, I hope you'll remember me. Because I've started National Workplace-Advice Columnist Day.

It's Nov. 1.

I like chocolates.

TALK TO REX: Ask workplace questions — anonymously or by name — and share stories with Rex Huppke at, like Rex on Facebook at and find more at

Copyright © 2015, RedEye
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