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“Am I an Overpaid Messenger or Executive-in-Training?”

Your boss knows he needs help and is willing to pay well for it, but that doesn’t mean he knows how to delegate

I was hired as an executive assistant to a CEO with multiple businesses in the real estate field, and was excited to learn more about the industry up close. Since I’ve been hired, though, I haven’t had a chance to learn much; my boss is keeping me busy with data entry, scheduling tasks, and running both personal and business errands on his behalf. I’m getting paid well, which makes me confused about why I’m being given low-level work. Is this what it takes to grow, or am I wasting my time? 
—Not Sure If I’m an Overpaid Messenger or Executive-in-Training 


IT seems like you both came in with a two-for-one expectation: Your boss thought he was getting a personal assistant along with the executive assistant, and you thought you were getting a mentor along with a boss.

When your boss decided to hire an executive assistant, he probably didn’t sit down and write up a detailed job description, or contemplate whether the position’s title should be executive assistant, personal assistant, or the new trending term: EA/PA, a combination of both. But there is a big difference between the two, and it’s your job to let him in on that little detail, unless you’re fine with scheduling his haircuts and ordering his kids’ school supplies between business meetings.

When you accepted this job, you recognized that although it may not seem glamorous, it would be a step on the ladder, allowing you to learn more about a potentially lucrative industry. You assumed that the boss, who obviously knows a lot about what you’d like to know more about, would teach you a thing or two. And while training sessions over hot coffee and Danishes may not be a realistic wish, it sounds like you may not be getting even the on-the-job exposure you were hoping for.

I’m going to guess that you’re the first person your boss hired for this particular role, which means that the formula to succeed is to actually create your own job profile.

Your boss knows he needs help and is willing to pay well for it, but that doesn’t mean that he knows how to delegate. Helping him delegate is your first and most important task. Pay attention to what he spends his time doing, think of what you can take off his plate, and then suggest a solution:

“Would it be helpful for me to set up a software that automates your scheduling?” “Would it be helpful for me to prepare meeting notes and send follow-ups after every meeting?” “I’ve created email templates for responses I noticed we use often. Here’s how to use them.”

Instead of you being another task for him to manage, take the initiative to take on more of his existing tasks.

Being busy with busy-work may or may not actually be a waste of your time. Many successful executives have worked their way up from the bottom of the data entry pile. The question is whether what you are doing is useful to the business, increasing your value, and teaching you something — even indirectly.

Consider that the CEO himself isn’t above the tasks you described, and if he weren’t delegating these tasks to you, he’d be doing them himself. We often underestimate the value of daily tasks as building blocks on the way up. The barometer of success is whether you are gaining responsibility, experience, and knowledge over time.

I suggest scheduling a monthly review for yourself and consider your perspective on your job when you zoom out of the daily grind. If it consistently feels like a bad fit, perhaps it is, and don’t be afraid to look for your next opportunity, which checks off more of your goals.

My hope for you and your boss is that you each learn from this experience and support each other’s career growth. And if you each gain a bit more than that, consider it a bonus!


(Originally featured in Mishpacha, Issue 979)

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