During the first call I had with my executive coach, he asked me about my executive assistant (EA), and I told him that I didn’t have one. Without hesitation, he told me that if I didn’t have an executive assistant, then I was the executive assistant. 

I’ve always had the mindset that “if you want it done right, you need to do it yourself.” However, I realized that perfectionism is the enemy of progress. While initially I didn't think I needed an executive assistant, I wanted to follow the advice of someone who had been where I was now and follow his steps towards business and personal growth. 

Not knowing where to start, I began by evaluating how I spent my time. I created a spreadsheet and documented each task I performed over a few days. Then, I categorized each task with one of the following labels:


      Incompetent - Task that I’m not good at doing

      Competent - Task that I’m okay at doing

      Excellent - Task that I’m good at doing, but don’t enjoy

      Unique - Task that I love doing, and would do for free


I quickly identified how much of my time was consumed by the first three categories, and better understood my frustration with not having more time to do my ‘unique’ tasks that energized me. In my efforts to do everything myself, it was at the expense of opportunity cost. What opportunities was I sacrificing while I was booking my travel arrangements or rescheduling meetings? 

So, my mind was made up about the need for an EA, and now I had the basic job duties for creating a position description. I really wanted to be more effective and efficient as a CEO, and now I knew how to better achieve that goal. Hope filled my heart as I realized that help was on its way.


Identifying important skills and characteristics in my future EA

Armed with a list of duties on the position description, I identified character traits, skills, and personality type in an EA that I felt would best support me. 

Character is important to me. I wanted to hire someone who demonstrated integrity, honesty and openness, a willingness to learn from mistakes, and a desire to continually learn. A person who is professional, ambitious, respectful, reliable, and exhibits a history of trustworthiness. 

To identify the skills that were important to me for my new EA, I started with a list of areas I’d like to be better in (aka, my weaknesses). I wanted to find someone whose Kolbe Index was the exact opposite of mine, a yin to my yang. From that list, I added the skills that I knew were most important for working within my company since it is an entirely remote workforce. The candidate needed to have a black belt in communication skills, which included demonstrating active listening skills, sharing ideas in a logical and concise manner, and exhibit professional body language. The candidate needed to be tech savvy, demonstrate meticulous attention to detail, an astute multitasker, follow detailed instruction, be mega-organized, have research and analytical skills, and demonstrate creative resourcefulness. I also needed someone who understood my business and vision; someone who could anticipate needs and conflicts, prioritize tasks and demands, break down the big picture into sequential steps, bring solutions to problems, and work independently while thoroughly communicating with me. Maybe I even needed someone who could read my mind. Basically, I needed a superhero. 

One really important aspect in a successful CEO/EA relationship is compatible and complementing personalities. This new EA would be a person I share my highest highs and lowest lows about my business, have unwavering mutual trust, and spend a lot of time together each day. I wanted to work with someone who’s personable, enthusiastic, positive, and upbeat, authentic, and a genuinely kind person. I love humor so I wanted an EA who had a great sense of humor and appreciated my humor.  

To find the right person, I shared my search for an EA online and with my network. I provided specific instructions on how to apply for the position, which included having each candidate write “Interview Me” in the email subject line. I asked each candidate to identify one of our core values that resonated with them and explain how they demonstrate that value in their own life. And, to get a better idea of their personality and ease with technology, I requested that they accompany their cover letter and resume with a video highlighting their experience as an EA. I felt like each of these requests would give me a greater perspective into their character, skills, and personality.


How my EA has helped me as an entrepreneur and CEO

As CEO, there is a constant barrage of communication and competing demands from my team. Mind you, I am very driven and work long hours, but sometimes I would allow the ‘squeaky wheel’ to get my attention, allowing other tasks to be pushed aside. One way my EA helps me is by holding me accountable. With a smile, she checks in with me to make sure I’ve completed tasks by the deadline. Meeting deadlines has improved my stress level, as well as improved my leadership because my team knows that I won’t let them down. 

Through the process of understanding how an EA would help me, I realized I was really looking for a Strategic Partner, and not just an assistant. My EA triages and prioritizes deliverables, messages, and meetings. She manages details of multiple projects and lets me know the progress and what she needs from me to keep the project moving along. In a way, she is my ambassador who represents me and my brand to colleagues, clients, and other professionals. The skills that come so naturally to her complement my weaknesses, which enables me to gain traction and productivity in my entrepreneurial areas of expertise.

The most significant intangible benefit of having an EA is delegating tasks and projects, which free up my resources to focus on growing my business. I’m maximizing my opportunities because I’ve given ownership of these responsibilities to my EA. I am more productive and spend my energy and time on landing new accounts, finding new acquisitions, and maximizing my ‘unique’ abilities. 

My executive coach was so right: I make a much better CEO than an EA, and my EA supports and helps me be a better CEO. 


Jason Hennessey jason@hennessey.com