The 10 Worst Things You Could Say To Your Boss

I didn’t finish the project. I have no idea where your files are. I think I spilled coffee on your laptop. Clearly, these are incredibly obvious phrases you know your boss doesn’t want to hear. But, surprisingly, the majority of statements that make bosses cringe may seem like NBD to a lot of us. In fact, many of the lines most likely to irritate your boss are the ones you might utter because you think you’re helping them out.

So, we asked nine powerhouses across a wide range of industries to reveal the phrases that won’t score you a promotion anytime soon. Some of them learned these lessons the hard way while others dish on their personal pet peeves. Either way, they all provide universally useful insights — no matter your job. And, of course, it goes without saying that none of these are written in stone. In most offices, hard work and a good attitude are far more memorable than one slip of the tongue. Learn from your mistakes, move on, and when you’re the boss, make sure to tell your team the story of that one time when you said something you shouldn’t have. 10 WORST THINGS YOU COULD SAY TO YOUR BOSS:

1. You Should Never Say: “Do you really think you should do that? ” Kristin Newman, Screenwriter & Memoirist This comedy writer has written for small-screen favorites like That ’70s Show, Chuck, and How I Met Your Mother, and is the author of the travel memoir What I Was Doing While You Were Breeding. Here’s the trick that’s helped her stay on top in her career, the one that she wishes every career newbie knew. “Don’t try to teach your boss something they learned the first day on the job. One of the basic rules of comedy writing, the thing you learn in any ‘Intro to Comedy’ class at any community college, is to put the hard laugh at the end of the sentence. When I was a young writers’ assistant on the last season of Mad About You, I was taking dictation for a script from Paul Reiser. I decided he had buried the laugh in the middle of the sentence, and I asked if he wanted to reword his joke so it was at the end. The comedian — who was making a million dollars an episode — turned his head very, very slowly toward the 23-year-old trying to school him in comedy, and just said, ‘No.'”

2. You Should Never Say: “If I don’t get this, I’m going to quit.” Mike Indursky, Bliss World President Bliss Spas may be where you go to get an ahh-inducing massage, but that doesn’t mean the CEO thinks work is anxiety-free. Formerly the Chief Marketing & Strategic Officer of Burt’s Bees, Inc, Indursky says threatening to quit will definitely cause your boss’ shoulders to tense. “Never hold a gun to your boss’ head. When an employee gives an ultimatum, it tells me it’s not a matter of if they’re going to leave, but when. Instead, go into any negotiation with respect and good intentions.”

3. You Should Never Say: “I was waiting to see if [insert potential disaster here] would work itself out before telling you.” Leigh Belz Ray, Lucky Magazine Deputy Editor As an editor at a fast-paced magazine, Leigh Belz Ray needs to be in the loop on everything so that pages get out the door before deadline. Her advice: Trying to help your boss may end up hurting you in the long run. “No boss likes to be surprised. So, it’s always important to keep them looped in, even if it means telling them that something’s in the midst of going wrong. It’s better for any boss to have a heads up on a potentially problematic situation, as opposed to finding out in the eleventh hour that there’s an issue.”

4. You Should Never Say: “It’s just that so-and-so coworker is so [insert complaint here]. She’s ruining everything!” Elizabeth Chambers, TV Reporter A chief correspondent for the Human Rights Foundation and a co-owner of BIRD Bakery in San Antonio, Chambers has experienced a very wide range of workplace environments — but she finds certain truths remain constant no matter where you work. Specifically, drama is never going to score you points with the big boss. “It may be tempting to vent your frustrations about a coworker, but no one likes unnecessary drama in the work place. It’s best to vent at home and avoid unproductive negativity at work.”

5. You Should Never Say: “I don’t know…” Sarah Fincke, SoulCycle Director of Recruiting In order for everything at mega-fitness brand SoulCycle to, ahem, spin smoothly, it’s essential that staffers are confident in their problem-solving skills — and often that means bringing solutions to their bosses. Meaning, there are a few words that no SoulCycle staffer will ever utter, either on or off the bike. “Be solution-oriented, and if you don’t know the answer to something, come prepared with several possible ideas for how you think the problem can be solved. Approaching challenges as opportunities to learn something new and develop yourself professionally can make a huge difference in both your success and your company’s success.”

6. You Should Never Say: “We have a problem.” Kerry Diamond, Restauranteur & Editor As co-owner of three Brooklyn hotspots (Nightingale 9, Wilma Jean, and Smith Canteen), co-creator of the indie foodie mag Cherry Bombe, and editor of Yahoo! Food, Diamond’s juggling a lot. How she does it? By making sure the people she surrounds herself with are just as fast on their feet as she is. “Glenda Bailey, my former boss and the editor-in-chief of Harper’s Bazaar, gave me great advice one day. She said, ‘Don’t bring me problems, bring me solutions.’ It really changed my way of thinking and working with my superiors. Instead of telling them what went wrong or is wrong, reframe the issue. Your boss might not agree with your solution, but it’s better than dumping a problem on his or her lap!”

7. You Should Never Say: “As a millennial…” Josh Bank, Executive Vice President of Alloy Entertainment Overseeing the creation of major book-to-television crossover hits like Pretty Little Liars and Gossip Girl, Bank understands his audience. His finger is on the pulse of what millennials want — and what millennials shouldn’t say if they want to impress their boss. “Don’t begin any sentence with, ‘As a millennial…’ Ever. I get it. You are younger than me. Much younger than me. Telling me you’re a millennial is another way of telling me I’m a clueless old loser who’s going to die shortly. A good rule of thumb is that bosses don’t like to be reminded of their mortality.”

8. You Should Never Say: “I agree with you.” Sarika Doshi, Rank & Style Founder A former corporate lawyer turned member of a management team at a venture-backed company, Sarika Doshi knows how to work under pressure. So, it makes sense that she’s really thriving as founder of Rank & Style, a site that creates Top 10 lists of the most essential buys in fashion and beauty. Her thoughts on what you should and shouldn’t say: “I thrive on getting dissenting opinions from my team. Hearing an agreement too quickly or too often can be a red flag. While I think reaching a consensus is important in how companies make decisions, I thrive on getting dissenting, sometimes critical opinions from my team. When we all agree without much back and forth, it leaves me to wonder if there is a better way we haven’t considered. Challenging your boss (without overdoing it) demonstrates confidence, shows you are engaging, proves you are being thoughtful, and conveys passion.”

9. You Should Never Say: “It can’t be done.” H. Kim Bottomly, Wellesley College President Trained as an immunobiologist with a doctorate in biological structure from the University of Washington School of Medicine, H. Kim Bottomly is the first scientist to ever lead Wellesley College. Since her inauguration in 2007, Bottomly has received accolades for her work advocating women’s leadership in higher education, particularly STEM education. Here, her secret to coming out on top. “I have spent the majority of my career testing out new ideas — from when I was a child conducting lab experiments in my parents’ basement (the ‘boss’ of my younger brother and reluctant lab assistant), to teaching immunology and running my own lab at Yale, to now, as president of Wellesley College. As a scientist, and especially as a woman in a male-dominated field, I have learned that you must have enough confidence in your own original thinking to be willing to test your ideas. Saying ‘it can’t be done’ is the easy way out. Instead, step outside of your comfort zone to figure out a way that it can be done. Ask challenging questions, experiment, and draw conclusions based on good data. I recognize that scientists are more accustomed to this way of thinking and working — but, if more of us were willing to test out our new ideas, perhaps we could make even more positive change in this world and find many things that can be done. Albert Einstein told us that we can’t solve problems by using the same kind of thinking we used when we created them.”

10. You Should Never Say: “I need a raise.” (Ed note: Just to be clear, you should absolutely ask for a raise when you deserve it — just be smart about how you position that request.) Dante Gaudio, Healthline SVP Of Sales As a SVP of one of the top-rated health information and technology portals on the Internet, Gaudio manages a steadily growing national sales team and forges relationships with a clientele that includes IBM and UnitedHealth Group. “Rather than telling me you ‘need’ a raise at the review, convince me of why you deserve it. It’s extremely helpful to present to your boss the value you’ve delivered to the organization and the responsibilities or projects you’ve taken on. Almost everyone needs more money. So, make it clear why I should stick my neck out to my boss and fight for your higher compensation.”

Originally published on Refinery29:


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