4 Tips for Having a Successful One-on-One with Your Boss

By Naomi Fink on October 18, 2020

Being employed and having an income are wonderful things. However, there are also a lot of responsibilities and challenges that come along with having a job. For one thing, it means you probably have a boss — and having a conversation with the person who tells you what to do, approves your paycheck, and can potentially write you a future recommendation can be intimidating. Whether you’re looking to find a new job opportunity, get a raise, express concerns, or just check in, here are four tips to help you have a successful one-on-one with your boss.

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Prepare in advance

Knowing what you want going into a one-on-one with your boss will make you more likely to get it so make sure to prepare in advance. Make a list of topics you want to bring up, questions you want to ask, goals you want to work towards, and, if you have a particularly big request in mind, reasons why you’re deserving. When you’re facing a one-on-one with your boss — or anyone for that matter — it’s important to advocate for yourself (no one else is going to do it for you!). Practice what you want to say beforehand so that your ideas come across respectfully and persuasively.

Depending on the context of the one-on-one with your boss, you can also prepare in advance by doing your research. Does your department have an upcoming presentation you could help out with? Does your boss have a preference for a certain writing style or formatting technique? Flattery can only get you so far; impress your boss with your knowledge, skills, and dedication to your work!

Take notes 

A lot of information can be thrown around during a one-on-one with your boss and there’s nothing wrong with taking notes! In fact, if your boss is giving you new assignments or detailed instructions during the course of the one-on-one, the responsible thing to do is take notes. This will help you remember all the tasks you need to accomplish and all the specifics of how to accomplish them to your boss’s liking.

While taking notes, however, also remember to be friendly and make eye-contact. If your boss only wanted to give over instructions, they could have sent you an email. Use the time with your boss to get to know each other better and form a relationship. Your boss is human too. A simple and genuine, “How are you?” can go a long way in developing your relationship and setting you apart from your co-workers.

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Take time to think before saying yes or no

During a one-on-one with your boss, you may be asked to do busywork, lead a project, or take on additional responsibilities. Perhaps you may even be offered a promotion! Whatever’s being asked of you, request time to think about it before giving an answer, even if you’re pretty sure of what your answer is going to be. Having time to think will allow you to take a step back, consider your options, look at the situation from multiple perspectives, weigh pros and cons, and ultimately make an informed decision in which you hopefully feel confident.

As psychologist and Holocaust survivor Viktor Frankl famously wrote, “Between stimulus and response there is a pause and in this pause lies our power and our freedom.” Create a pause for yourself by taking time to think about your decisions before saying yes or no.

Be flexible

While it’s important to know what you want and take time to think about your options, part of being a good employee is being flexible. Things are going to come up last minute and you’re going to have to take on tasks that may not be particularly enjoyable. This is what it means to part of a team. No one wants to be a pushover yet no one wants to hire or work with someone who can’t pitch in. Be flexible and communicate with your boss if you feel like you have too much on your plate.

Working for a startup the past several months, I’ve definitely learned the importance of flexibility. At times it can be extremely frustrating when plans change or you have a sudden looming deadline approaching. Yet there’s something really special about picking up the slack for someone else and knowing that if you need, they’ll pick up the slack for you too. Flexibility goes both ways so remember to maintain a positive attitude.

No matter the topic of discussion, having a one-on-one with your boss is an excellent way to form a relationship and showcase your skills as an employee. Though these conversations can initially be intimidating, the more of them you have, the more comfortable you’ll become. Set up regular one-on-ones with your boss to create an open line of communication and use these four tips to ensure that every conversation is a successful one.

Naomi Fink is a rising sophomore at the University of Pennsylvania. In addition to being a Uloop writer, Naomi is the Marketing Manager at Positive Voices. Some of Naomi's hobbies include hiking, volunteering, yoga, swimming, art, and of course, writing!

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