9 Ways To Dazzle Your Boss In Your First “Real-World” Corporate Job


Throughout the years, I’ve run the gamut of work experiences, ranging from pretty awful to quite idyllic. Through both the good and the bad, I’ve learned a few simple truths that will help dazzle your boss in a corporate setting. As it’s likely we will work for someone at a point in our lives, here are easy ways to achieve “rock star” status in your boss’s eyes.

1. Remember that it all boils down to keeping people happy. Make sure that your boss sees you as a “value-add,” and not a “value-detract.” How do you become a “value-add?” This is simply corporate jargon for “make her/his life easier.” Simple things, like bringing her a printed copy of an email if she prefers reading on paper rather than on the computer screen, or asking if she wants a coffee when you go out and get yourself one, or presenting her a super-organized binder of materials that she requested that you print, or sending her a morning “sync-up” list that gets her organized for the day. While you may be in a position that is more elevated than an assistant/secretarial role, little things like this count and add up.

2. Manage expectations – underpromise, and overdeliver. (Not the other way around.) “Managing expectations” seems to be the buzz word of corporate America, but its where all of us struggle the most. “Managing expectations” means that you have to proactively make a push to have the other party understand what is realistic in terms of timing of delivery of a product. For example, when I worked at Benihana’s as a hostess during college, we would always tell our customers there was a 15-20 minute wait even if there was a table available in 5 minutes, to ensure they wouldn’t be annoyed or frustrated and so that we could “look good” when we get them in even faster. Can you imagine if it were the reverse, and you told the customer 5 minutes, and it ended up taking 15-20 minutes? I myself would walk out and go to the nearest Panda Express. By underpromising (tacking on extra time that you think it will take to deliver a project/memo/presentation) and overdelivering, you will always look good to your boss, instead of missing the mark on expectations. This goes to both (a) expected turn-around of something and (b) the content of the deliverable. If you are able to effectively manage expectations, you will always make yourself look good.

3. Manage up. And often. You should be well aware that your boss is a busy person with competing demands. In addition to managing you, your boss is likely managing many others around you. As such, take a load off her back by “managing up.” I like to think about things as a funnel analogy. Whereas you are handling the narrow layer at the bottom base of the funnel, they are handling the top layer, which encompass much wider responsibilities. You will be seen as quite the “value-add” if you are able to manage your boss effectively, as in TELL HER what needs to get done and what you are doing to help move that process along. By doing so, you are removing the step of her having to think about what she needs to tell you to get done. Also, this way, you can better frame/brace your boss for any outstanding issues that you may need to delicately present. Make sure that you keep her posted in frequent intervals (determine how frequently your boss would like to check-in with you) to cover yourself as well.

4. Keep lists for your boss. This is a form of “managing” up, and an excellent “CYA” tool. The real world, you will quickly learn, is all about these three letters: C, Y, and A. You must make sure you protect yourself from any shifting of blame down to you, or else your job will be in peril. The corporate environment is a vicious one where mistakes are not tolerated and one where people are quick to blame the lowest on the totem pole, so to make sure you don’t “mess up,” document EVERYTHING. Be careful of what you put in an email, as anything is easily forward-able and bcc-able (i.e., don’t trust the recipient not to pass on your email to outside parties and make you look bad). One way to ensure you and your boss are on the same page is to keep a daily (or bi-weekly, depending on how frequently your boss would like to be bothered) list between the two of you, to make sure you guys have a mutual understanding of the scope of work that needs to be completed. I do the same with the people I manage, and name these lists a slightly silly combination of our names, like “Josh-een” or “Pie-Lee” (last names merged together) to make it less intimidating/formal of a process.

5. Always be prepared/efficient with your boss’s time. Time is money, and money is time. Going along with 4 above, if you always show up with a list when you meet with your boss, you will be extolled as someone who is prepared and efficient. While this is not to say that organic conversation can’t result and stray from the list, your boss will appreciate it that you take the time to organize yourself prior to approaching her. This way, you don’t dawdle in front of her and look like a buffoon.

6. Send articles that you think your boss will find interesting. Bosses generally become bosses because they have a constant thirst for learning and curiosity. You don’t get far in your career without these two things. That being said, good bosses are constantly trying to grow and learn, and there is no better way to grow and learn than reading new articles and books on topics of interest. You will become an “indispensable” (more corporate speak) team member to your boss, as well as promotable, if you show that you similarly have this thirst for learning and curiosity. As such, if you run across any great or relevant article that you think your boss would find interesting, go ahead and send her a link to it with a subject line indicating it is solely “FYI” and an “interesting read.” Some bosses despise an influx of email (considering their inbox pings about every 2 seconds with new ones), so consider printing and handing a file folder of articles to your boss every month if that is the case.

7. Make your boss look good to others. One of your functions is to make your boss look good to others. One way you do so is by making sure she is always prepared at client meetings or filled in with relevant details prior to meeting someone. Another way you can do so is promote, promote, promote. Talk your boss up in front of other important people (instead of griping – if you have gripes, address them with her privately and directly), and be the first to sing her praises. In turn, your boss will want to promote you. All relationships are reciprocal, and the more respect and trust you give to your boss, the more respect and trust will be given to you.

8. Show that you’re thinking and make sure to challenge/raise questions when appropriate. Your job, as an underling, is to be the “attention to details” person and catch things that your boss may not necessarily catch, being that she/he is busy managing a million other things and does not necessarily have the time to devote to a granular review. So make sure you show your boss that you are paying attention, and catching her typos and asking questions when things don’t appear to add up. Don’t worry about looking smarmy – if anything, it makes YOU look good that you are smart enough to raise questions when appropriate. There is nothing that makes you look dumber than staying quiet and never broaching any issue that you see as a potential yellow or red flag.

9. If you work for several bosses, make sure you raise your hand and say “hell no” when you’re overwhelmed. I think this is something that I personally struggled with the most in not knowing how to set limits and boundaries and focus on pleasing one person (namely, the most important/powerful person in the room). If you’re a natural people-pleaser like me, you’ll want to make everyone happy, and in the process, make no one happy. Thus, it’s a much better idea to latch onto one or two bosses who will keep you busy and then respectfully make those bosses aware when you are feeling like you are being deluged with work assignments from other people. Let them duke it out with whoever is throwing work your way, and keep you out of it.