EA Importance

What Finally Pushed Me To Hire An Assistant & How It Changed Everything

Never Enough Time...? Why your Executive Assistant is your single most important hire.

As leaders, we know we need a great team.  Sales, operations, technical leaders, as well as other executives, are essential to our success. 

But I have come to believe that your Executive Assistant is your single most important hire.

Why is that? 

You only have so much time in a day.  The things you do, the things that ONLY you can do, often get moved to the back burner for things someone else can do.  You know you need to find ways to be twice, three times, or even ten times more productive with each moment and yet your days are full of inefficiencies.  A great executive assistant is the only person capable of changing this.  Sound too good to be true?  Just a short time ago, I would have agreed.

Never Enough Time  

Five years ago, I found myself frustrated and struggling against a complete lack of time. Usually, a lack of time would have felt normal.  Throughout my 20-year career, I’d taken on many demanding roles and had become very familiar with working long hours.

But this was different…

The Inaccessible Executive 

At that time, as an executive leader of a SaaS company where I later became the CEO, I had just completed reviews with my leadership team.  In our reviews, we always asked the questions, “What does your leader do that frustrates you?” and, “What could they do better?”

The overwhelming feedback I received was that I was inaccessible, was rarely available, and I wasn’t timely in my responses when a team member would reach out.  This was incredibly painful to hear.  I have always cared deeply for my team, and I’ve always tried to serve them well.  But it was obvious I was falling short of expectations, theirs and my own. 

Initially, I tried to let myself off the hook. 

“They don’t realize the demands on my time.”

“They can’t see how busy I am.”  

“Their expectations are unreasonable.”   

But the more excuses I came up with, the more I found that they were falling flat.

Something Had to Change

I was a roadblock.

I was hurting my team’s ability to get things done.  I wasn’t serving them the way I wanted to. 

Something had to change. 

Around that time, someone recommended I hire an executive assistant.  I remember initially dismissing the idea.  

“I’ve gotten to where I am without an EA,”  I said to myself.  

“I don’t have time to hire and train someone. It would be faster to just do things myself.”

There were additional mental barriers preventing me from embracing the idea of hiring an EA as well.  For one, I can be particular about how I do things. I also struggled to believe that anyone would want to or be able to learn all the systems and processes I have in place for myself.  I also struggled with not wanting people to think that I was “above” administrative work or that I was passing off the tasks I deemed unpleasant to someone else. (I mean, does anyone like administrative work?  -  I’ve learned the answer is “Yes!”  And they are also 10x better at it than I am.)

With these misperceptions in my mind, I delayed.  But my work hours continued to grow, and my effectiveness and responsiveness were still falling short of expectations.  I was tired of working so hard only to have the same problems.  I was tired of letting my team down.  So, I finally decided to enlist the help of an executive assistant.  This was a daunting task that was only made possible with the help of an amazing executive assistant, Anna McIldoon.  Anna was the Executive Assistant of the Founder and CEO of the company I was with at the time. (I’m excited that Anna is now a part of our advisory board so you will have the opportunity to hear from her frequently.)  After a lot of interviews and trepidation, I finally pulled the trigger and hired Sarah.  Everything changed from that point forward.

Sarah was the first executive assistant that worked directly for me. I had the privilege to work with Sarah for 1 year before she decided to cut back her hours to spend time with her young children.  At that point, I hired Kristie as my executive assistant (I introduced Kristie in last week’s post, here). I worked with Kristie for almost 4 years.  She has played a huge role in getting Emmre where it is today and will continue to have a significant impact moving forward as a member of our advisory board. 

Everything Changed - My Most Important Hire

Five years after hiring my first executive assistant, I can truly say that it was the most important career hire I’ve ever made. I learned very quickly how a great EA will help you improve as a leader, and I even began seeing positive changes in my personal life.  I remember my wife commenting on how glad she was that after hiring an EA, I was getting home earlier, making it to all of my kids’ events, and I seemed less stressed.  The difference was unbelievable.

The year after I hired my EA, my team reviews were remarkably different.  My team expressed how accessible and responsive I was.  Don’t get me wrong, I was still busy.  But with my EA’s help, I was able to better protect my time, be there for my team, and prioritize my time to do the things for the company that only I could do.  For me, the value was enormous.  It wasn’t without an investment of time and energy on my behalf, but that investment paid off with huge dividends. Shortly after this, I was asked to take the CEO role for the company.  I do not believe I would have had this opportunity without Sarah and Kristie and the invaluable help they gave me.

Since this time, I’ve spoken to many leaders and heard story after story very similar to where I had started.  Burn-out, long hours, and a general feeling of being ineffective plagues many leaders.  It became clear that this was a widespread problem, and I wanted to help.

My goal is to share more about this journey of learning to work with an assistant and the lessons we’ve learned as we worked to maximize our partnership.  In future posts, I’ll share more about my experience hiring an EA, key onboarding lessons, and how the right EA will do significantly more than you realize if you empower them to do so. My hope is that these lessons will be valuable to assistants and executives alike.

It Might be time to hire an Executive Assistant!

I don’t know your situation, but if you think you’re in need of an executive assistant, please strongly consider hiring an EA.

Don’t continue with the stress, long hours, and burn out.  

Don’t continue doing the administrative work that drains your energy and that someone else is more skilled at. 

If You’re an Executive Assistant

If you are an executive assistant, thank you!  Thank you for the work that you do on behalf of your leader, your team, and your company!  You make a huge difference! I hope you feel valued and appreciated.


Introducing Anna McIldoon

Last week I had the privilege to introduce Kristie Webber, my former Executive Assistant and a current member of Emmre’s Advisory Board.

This week I’m excited to introduce you to Anna McIldoon, another member of our Advisory Board. In this week’s post I mentioned how Anna played a significant role in convincing me to hire an Executive Assistant and an even bigger role in helping me hire my first EA.

Her encouragement of me to see and experience the incredible value of working with an EA has transformed my professional career, given me more time to spend with my family and even helped influence us as we started Emmre! I am so thankful that Anna was there for me during this critical time.

Anna is a servant-hearted leader who values integrity and loyalty. She looks for ways to add value and think strategically to create efficiencies and effectiveness in all areas of her life. She is an experienced Executive Assistant and Project Manager who started her administrative career in her local church missions office managing thousands of short term mission trip participants.

She transitioned into an Executive Administration role at Church Community Builder in 2015 and had the opportunity to serve the CEO and Founder of this business where I worked with her extensively. During that season, Anna was foundational in helping me learn how to build a strategic partnership with an executive assistant.

In addition to her EA role, she does project management, serves as a board member with The James One 27 Initiative, volunteers with JDRF advocating for a cure for Type 1 Diabetes, and does executive coaching to help executives create better working relationships with their assistants.

Anna’s numerous years of experience as an Executive Assistant combined with her experience coaching executives to work better with their Executive Assistants will bring an extremely valuable viewpoint to our blog. I’m confident that getting the perspective of a veteran assistant who now coaches Executives will be impactful, whether you’re an Assistant looking to improve and better understand how to work well with your Executive or you are an Executive who wants to maximize your working relationship with your Executive Assistant.

We are so grateful that Anna brings these experiences to Emmre as an Advisory Board Member. We’re so excited to welcome her and look forward to all of the wisdom and experience she has to share!

Anna’s Comments

Anna McIldoonAs someone who has years of experience serving in the Executive Assistant role and working with Executives and EAs to refine and build their processes, I could not agree with Don more on the importance of the executive assistant hire.

I have spent countless hours speaking to executives who know they need help and simply don’t know how to take the first step. It can feel overwhelming, daunting, and almost not worth the effort; I urge you to avoid this dangerous cycle! A stellar EA can change the trajectory of your professional story by lifting burdens you might not even realize weigh you down in the daily demands of your role.

The executive assistant...the thought partner...the door-holder...the gatekeeper...the anchor. If you are sitting in the seat of an executive assistant, you are certainly indispensable and responsible for much more than the eye can see.

When I think back to the season where Don was finally ready to hire an EA, I remember a leader who was primed and ready for an EA to come in and start leading him through the delegation process. Don and I began to dialogue about ways a forward-thinking, administrative professional could be instrumental in helping him lead our SaaS company forward.

It is such a rewarding process to have conversations that invite leaders to consider all the things they would be doing differently if they just had the right person cutting back the weeds and revealing the path forward. That is where a skilled executive assistant can shine. We collaborate, we remove barriers, we color the illustration and allow our leader the opportunity to draw the next picture. I am excited to be joining Don and the Emmre team, and I look forward to continuing to unpack the value in the Executive and Executive A partnership. An executive assistant is truly the most important hire.

Emmre - Software for Assistants and Leaders

Emmre is executive assistant software created by an executive and assistant for executives and assistants. Emmre's mission is to help supercharge productivity and maximize the strategic partnership between executives and executive assistants.

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