You’re Worth It! Convincing Your Executive to Invest in You

The Executive Assistant role is a challenging one—your job is to remain behind the scenes and take care of the small details so your executive can tackle strategic goals. However, this can often mean that EAs fade into the background when it comes to accolades, appreciation, and development.

As an EA, you have to be comfortable in a service role; but we all know you also need to be confident and take charge of any situation to get the job done. This is no different when it comes to advocating for yourself, whether for a raise, recognition, or a monthly budget for software or professional development.

While EAs may buy a favorite notebook, pen, or even coffee cup to use at work, employers should take care of the EA’s overall needs, whether that be purchasing EA software (might we suggest Base?), enrolling in a project management webinar, or attending a conference. How you approach your executive about these costs is important.

Do your research.

For software, be familiar with all of the features, the full cost (including any taxes or recurring fees), and how it will improve your work. For conferences or professional development, study the agenda or curriculum, tally up all associated costs (don’t forget travel, food, and supplies), and outline how it specifically benefits you and your work.

Come to your executive with all the info; have the answers to all possible questions, so it’s easy for him or her to say yes. (How many hours will this take? What happens while you’re away? What is the cancellation policy? What are your goals related to this tool or event?)

Look at it from your executive’s perspective.

Think through all the reasons your executive might say no. Are there budget constraints at the moment? Will they be worried about how much time off you’ll need? How does spending this money benefit their work and the company in general? What tangible benefits will they see? Is there a sharp learning curve?

Be confident and know your worth.

Enter the conversation assuming the best intentions and with a positive attitude. Know that there are many reasons an executive may say no, and that most of them have nothing to do with your own worth or performance. You are a professional and a valued part of the executive team; your satisfaction with your job is important. If updating your software or learning a new skill means you are happier in your role, it’s important enough to warrant a real discussion.

Schedule time to discuss your plan with your executive.

Take some time to outline how you will pitch this to your executive, then schedule a meeting to discuss. Sending this type of request via email may work, but it will also be easier for the executive to put off a decision or dismiss it altogether as just another of the many tasks they need to address. Talking about your needs face-to-face means he or she is focused on you, listening to your goals and needs, and more inclined to support you. 

Remember, your role is integral to your company! It’s so easy for EAs to put everyone else’s needs before their own, but you must remember to fill your own cup and take care of yourself, so that you have plenty of energy, motivation, and drive to continue to take care of others.

Looking for more information on how to advance your career as an EA? This article can help!

About the Author

Crystal Esquivel

Crystal Esquivel

Crystal has served as an Executive Assistant to a variety of leaders, including CEOs, Chairmen, Executive Directors, and Founders. She has managed weeklong food events in multiple cities, authored two books about food in her hometown of Austin, Texas, and contracted to support chefs, photographers, and cocktail experts. Crystal is Chief of Staff of Base and is focused on building a strong and supportive EA community packed with resources and relevant content. She lives in Greenville, SC with her husband Justin and their little black cat.