My first job as an Executive Assistant (EA) was in 2007. Honestly, I did not know if I could do the job because I had never done it before. I was both scared and anxious as I was assisting the then Chancellor of District of Columbia Public Schools (DCPS). Given the responsibility, intensity, and attention the role of DCPS Chancellor encompassed, I knew this EA position would be complex to say the least, requiring a strong mix of operational, strategic, and political skills. With every job that I’ve ever had, I recall my mother’s words to me on my graduation day from middle school: “I don’t care what you become –a doctor, lawyer or garbage man– but whatever it is, be the best!” Those words have stuck with me over the years; and when I was about to take on the EA position at DCPS, I held those words close
Once in the role, I quickly realized how important the job was. I oversaw the day-to-day operations of the Chancellor of DCPS, and it was a lot. I didn’t think of my role as merely the Chancellor’s “scheduler” or front desk assistant; I thought of the role as being an extension of the person I was supporting. Now, after spending 18 years assisting various high-level executives across many sectors and starting my own Executive Assistant company, I am clear on how important the job is and why it is important to hire the right person.
One of the first things I tell prospective clients is that you should not change Executive Assistants every few years. As an executive, you should not be sharing confidential information with many different people. The relationship between EA and executive needs time to develop, get into a good rhythm, and grow. That typically takes six months to a year, but you should be patient, especially if you see great potential in the EA. I’ve made many mistakes (as have some of my executives), but if the trust and belief in the potential of the relationship is there, we discuss those mistakes, find solutions, and move on. That kind of patience and investment in each other can yield incredible results in a symbiotic relationship that maximizes the executive’s impact.
If you take the time to hire the right EA, here are some of the benefits:
- Meticulous Organization: The EA will create and maintain a highly detailed, precise, and orderly system where every item has a designated, labeled home. It requires thorough and careful planning that clears up mental and physical space and maximizes efficiency.
- Partner in Strategy: The EA knows the business better than most and can help with providing great insight for decision making and goal setting. That means you’re hiring someone who knows the role is more than scheduling and processing expense reports; you’re hiring someone who understands those tactical operations connect to a larger strategy. A great EA knows that understanding that larger strategy and the “why” and “how” of the company that is the foundation for all those critical operational decisions.
- Gatekeeper: The EA is the first line of defense for calls, emails, and requests, making sure that the executive is only focused on critical matters to run the business. This requires a deep knowledge of the business and the (small or big “p”) politics involved, so that the EA proactively handles requests and relationships as an extension of the executive.
- Clearer Lines of Communication: All communication starts and ends with the EA. This ensures that the executive is getting clear communication from leadership, internal and external clients, and stakeholders, minimizing errors and miscommunication.
- Simplified Operations: The EA creates systems that streamline processes to ensure that the business runs smoothly and consistently, both for the executive and all those who rely on the office of the executive.
- Improved Decision-Making: The EA supports better decision making by researching and providing data to offer additional ideas and suggestions.
- Stronger Relationships & Culture: The EA is an extension of the executive and therefore can help build bridges with broader staff and the leadership team. This helps improve morale and creates a positive work environment.
- Confidentiality & Trust: The EA handles sensitive information with discretion, protecting the executive and the organization’s interests.
Final Thoughts
Taking the time to hire the right EA will save you time, increase your productivity, and help you focus on the things that will help grow your business. I believe it’s one of the best investments for any organization.

