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

The executive assistant role is a challenging one—that’s why Base is here to give you the confidence to ask your executive to invest in you. When it’s your job to cater to every detail behind the scenes so your executive can tackle their strategic goals, it can be easy to neglect your own needs when it comes to professional development. 

However, this doesn’t have to be the case. Executive assistants (EAs) are a pivotal part of any business. Executive and employees would not be able to do their job effectively without an EA. (At Base, we believe every knowledge worker should have access to an assistant!) Don’t discredit yourself or allow accolades, appreciation, and development to fade into the background. You are deserving of it all!

We know this job requires you to be confident and take charge of any situation to get the job done. We encourage you to take this same approach when advocating for yourself, whether for a raise, recognition, or a monthly budget for software or professional development.

The bottom line: employers need to take care of the EA’s overall needs. This can be by purchasing quality EA software (might we suggest Base?), enrolling in a project management webinar, or attending a conference. 

Convincing Your Executive to Invest In You

How you approach your executive about these costs is important and requires some work on your part. Learn the steps to take below:

1. Do Your Research

When it comes to executive assistant software, there are a few things to consider to ensure this is a wise investment for both you and your executive. You’ll want to be familiar with all the different features, the full cost (including taxes or recurring fees), and how it will improve your overall work—since these are likely questions your executive will ask. 

For conferences or professional development, make sure you study the agenda or curriculum to get a clear view of what’s offered. You’ll also want to tally up all associated costs so your executive can get a good idea of what the investment will cost them (don’t forget about associated expenses like travel, food, and supplies.) It’s a good idea to come prepared with an outline that highlights this investment will specifically benefit you and your work.

Come to your executive with all the information upfront. When you already have all the answers to all their possible questions, it makes it a lot harder for them to say no. Supportive executives will see that you know your stuff and won’t hesitate to invest in you if they are able. Here are some broader questions to consider before chatting with your executive:

  • How many hours will the investment take? 
  • What happens while you’re away? 
  • What is the cancellation policy? 
  • What are your goals related to this tool or event?

2. Look at It From Your Executive’s Perspective

While you can’t read your executive’s mind, you can start to think of things from their perspective. It’s important to remember that many executives are physically unable to spend the extra time, money, or resources right now. Even if your executive can’t support you in the way you want at this time, you can still make your needs known.  

If you can think of any reason your executive might say no to investing in you, these are good to consider when planning to approach the conversation. We’ve listed some questions for you to think about below:

  • 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? 

3. Know Your Worth

When you know your worth, confidence follows. Make sure you enter the conversation with a positive attitude and assume that your executive has the best intentions. At this point, you know that there are many reasons an executive may say no, and most of them have nothing to do with your worth or performance. 

You are a professional and a valued part of the executive team; your job satisfaction is of utmost importance. If updating your EA software or learning a new skill means you are happier in your role, it’s certainly important enough to warrant a real discussion with your executive.

4. Schedule Time to Discuss The Plan With Your Executive

Take time to practice how you’ll pitch this plan to your executive, then schedule a meeting to discuss the fine details. While sending this type of request via email may sound less intimidating, it may make it easier for your executive to put off a decision or dismiss it altogether as just another task they need to address. 

Talking about your needs face-to-face is the most effective way to get your executive to focus on you. This way, they can hear the passion in your voice when you talk about your goals and needs, which may make them more inclined to support you. 

Enhance Your Executive’s Investment With Base’s EA Software

As an EA, your role is integral to your company! It may be your nature to put everyone else’s needs before your own, but you must remember to fill your own cup. The Base platform was designed by executive assistants, for executive assistants. We can confidently say that our EA-focused software improves the role of EAs, as well as the course of success for executives and their employees. 

Advancing your career as an executive assistant often means having a fully-faceted view of your responsibilities and streamlined communication with your executive. Base houses everything EAs need to do their job in one convenient location. Rather than having to fish through Slack, email, and various other tools to gather the important information you need to get in front of your executive, features like Decision Stream create a single feed that you can text or Slack to your executive for instant feedback.

Did we mention Base gives EAs the ability to see how their executive spends their time? It’s true! With so many leaders concerned about productivity and how it affects their bottom line, being able to analyze your executives’ day-to-day productivity can be a huge selling point in getting them to invest in our helpful, EA-centric software. 

With Base, you’ll get a visual representation of how your executive’s day, week, or year is divided between meetings, travel, value-add activities, and more. You can use this data to start thinking about the executive assistant goals you want to accomplish and why you’re worth investing in. Once you know where your executive needs more help, it will be simple to take this information and create goals around it. That’s something any smart executive will be able to get behind.

Taking care of yourself as an EA ensures you have plenty of energy, motivation, and drive to continue to take care of others. It may sound intimidating to ask your executive for a favor at first, but we’re here to promise you’ll never regret investing in yourself.

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

Put 4+ hours back into your week.

Base helps 1,000s of assistants put time back into their week, be more productive, and impress their executives.

About the Author

Mallory Greer

Mallory Greer

After graduating from Wofford College, Mallory spent 10 years at Blackbaud, a global leader in software and services for nonprofit organizations, in roles ranging from Support to Renewals and Customer Success. After having her first child, she decided to move away from the corporate world and spent two years as an Executive Assistant at 33Vincent. Mallory joined the Base team in December 2019 as a Customer Success Manager. In her free time, Mallory likes to run and spin (she lacks coordination for organized sports), read, and explore her hometown of Greenville, SC (breweries, playgrounds and the like).