Biggest Challenges Faced By An Executive Assistant At Boost VC

The biggest challenge right now, in my role at Boost VC, is that I haven't been here long. I'm not yet in a position to do more for my boss. Getting to know your executive takes time, and that's the biggest hurdle.

I need more time to ask questions that will help me grow and then help him. This is crucial for any executive assistant, especially in the first 90 days. You'll hit roadblocks because you won't have all the necessary information.

This leads to a constant battle: should I make an executive decision or wait? You face the fear of reprimand. Or perhaps it's a legal issue, like a contract that needs a signature, and you can't move forward without it.

The biggest challenge with a new boss is getting started. You're organizing their life and building trust, which takes time. Some bosses expect instant results and may wonder why you don't already know everything.

It's about managing expectations. The way to overcome these challenges is through clear communication. Not being able to help my boss more is a challenge because I don't know him well enough yet to take things off his plate.

My goal is to handle mundane tasks so he can focus on what he does best. I wouldn't know how to advise someone on dissolving their company or handle a co-founder breakup. These are far more important than minor issues like a DoorDash being a few minutes late.

Some companies make a huge deal out of small things and will reprimand you. Prepare to be blamed for things that aren't your fault. This requires thick skin and resilience.

While some workplaces have constant issues, others, like where I am now, don't. If I make a mistake, I own it, fix it, and move on. People will get over small mistakes; they won't remember them years from now.

The key for executive assistants is proper communication and keeping that line open. One of the most helpful pieces of advice, which I learned from my teaching career, is understanding different learning styles.

I always asked students what kind of learner they were. Similarly, you should sit down with your boss and ask how they like to communicate. Do they prefer text, Slack, or WhatsApp for urgent matters?

What's their response rate for emails? On day one, discuss how they communicate and handle problems. Some people want to address mistakes immediately, while others prefer to schedule a meeting.

Understanding these preferences and establishing clear communication on day one is part of building trust with your boss. Facing challenges is inevitable, but clear and open communication upfront is the best way to mitigate them.