The search for the right EA is one of the most arduous processes a manager faces. Many have likened the search for a great EA to the search for the perfect mate; but as it stands, it’s easier to find a date or a dog walker than it is to find a quality assistant.

Since the actual system by which we hire and streamline this relationship and workflow is the biggest hurdle in the EA industry, for the purposes of this blog topic – I sat down and reviewed everything written or spoken by one of our times’ most influential thinkers on creating healthy systems, Simon Sinek. Below you will find my codified application of his most helpful advice and strategies to the EA-Manager operation.

Searching for the Right EA

To break it down, there are currently 3 avenues a Manager can take to hire a new assistant: (1) if their current assistant is good – they task him or her with vetting, hiring and training their own replacement, (2) if they don’t have an assistant, but don’t have time to do a thorough search themselves, they might outsource it to a staffing agency, or (3) if they don’t want to spend the money on an expensive headhunting agency, the Manager might post an advertisement on Craigslist, Facebook and various nanny websites.

Let’s be honest, nothing about this process screams: hire me! It is more like a chaotically unorganized waste of free time which is, in essence, the opposite of what it should be.

Even if you do make it through the 3-6 months it can take to find a promising assistant, they still need training. What does your typical day look like? How often do you actually have a ‘typical day’? What do you like? What do you hate? What cues do you prefer to give verbally and which ones are associated with a smile or a pursing of the lips? Do you hate the smell of popcorn? Are you allergic to peanuts? There may seem to be no cohesion to this list, but these are the details that can make or break your relationship with your assistant and, in turn, your success as a team.

Finding the one for a manager is harder to do than finding the one for life.”

In such an intimate relationship it is also incredibly difficult to remain objective rather than subjective. Managers and Assistants spend so much time together and connect in such a mystical and synergized way that the line of employment can easily be overshadowed by the emotional elements. When emotions get involved, this professional bond turns into one similar to a familial bond. Even still, at the end of the day, if the relationship goes sour – neither party is under any obligation to love the other. The unhappy dissolution of this relationship is then likely to unravel into negative complications and outcomes.

There are many ways to avoid this scenario, so let’s take a look at some of the qualities that make for a great fit in the Assistant-Manager relationship.

What Makes a Good Fit?

Managers know why they’re searching for Assistants. They want someone to not only alleviate their workload, but to also rid their free time of the nagging concern that a responsibility isn’t being handled well. So, when searching for the right EA, a great manager must first figure out the EA’s why.

Inspired leaders and innovators all think, lead and communicate from the inside out. Simon Sinek calls this cycle The Golden Circle. It starts with: Why? Which is followed by: How? And lastly we reach: What?

WHY: We know the WHY element as being “like-hearted.” According to Sinek, success hinges on this initial distinction, because at the core of human behavior – people don’t buy what you do… they buy why you do it.” 

Identifying the WHY in the early stages sets a clear outline of a Manager’s goals. Those goals allow that Manager to identify the criteria necessary to hire the candidate best-suited to meet his needs. In this relationship, the Manager’s need is an Assistant, but his “goal is not to hire people that need a job.” Instead, “the goal is to do business with people who believe what you believe.” Simon Sinek: How Great Leaders Inspire Action

HOW: Once a Manager has determined that you are like-hearted, they begin the process of determining whether or not you are also like-minded. Now that they know WHY you’re an Assistant, they want to see HOW you assist. Perusing an EA resume provides an outline of their work history, but the real meat of their capabilities is best demonstrated in one-on-one interaction.

At this stage, they look for hustle – they want to see that their EA will work for them the way that they work for themselves. They look for honesty – after all, they are placing their lives in someone else’s hands. This leads them to review the length of relationships. Prior work history not only demonstrates your capabilities, but the duration of the relationship sheds light on the reciprocal nature of commitment. Can you commit and can other people commit to you?

Here are a few other important factors to note:

  • Organizational skills: Sometimes a Manager has no organizational aptitude, so their assistant’s organizational skills need to be their superpower.
  • Composure: By the nature of this relationship, an assistant is an extension of their Manager. An insecure demeanor or a wrinkled dress doesn’t present the best foot forward.
  • Excellent networking skills: An EA might not be the leader all the time. Even still, EAs are expected to lead by example all the time and all eyes will be on their ability to do just that.
  • Flexibility: Take some yoga classes. Learn to juggle. Flexibility increases your ability to master the mental arts of contingency planning and spin control.
  • LACK OF DRAMA: There is a fundamental leadership role required of an EA position. There’s a quote by Simon Sinek that says: “Leaders eat last.” He actually wrote an entire book about it. Real leadership at the macro level starts at the micro level. If you’re causing drama, you aren’t eating last – you are eating first.
    Simon Sinek: Why Leaders Eat Last

*Lessons In Leadership: Effective Leadership – Seven Employees That Drive Managers Crazy

WHAT: If an EA makes it past WHY and HOW, chances are high that they deserve the WHAT. In this system, the WHAT is an opportunity to join a team.

If you hire people just because they can do a job, they’ll work for your money. But, if you hire people who believe what you believe, they’ll work for you with blood and sweat and tears.” – Simon Sinek

Unsuccessful Hiring

What happens when you hire someone just because they need a job and they work for you just because they need your money?

Instead of recounting another story depicting my career of seemingly harmonious Manager-Assistant interactions, let’s switch gears to a story of something that didn’t work.

Much like a scene out of The Devil Wears Prada – a while back, I worked as the First Assistant for an extremely busy executive. When the work became too much, we decided it was time to hire a Second Assistant. What we learned from this experience is that a healthy relationship with one assistant is not indicative of a healthy relationship with another assistant. Leading by example can and does often end with the Second Assistant rising to or surpassing the rank of the First Assistant, but in this story – that was not the case.

Here are some reasons this scenario didn’t work:

Mistake #1: The nitty gritty of the story resulted from a relationship born out of necessity and not one of mutual synergy and excellence.

Although the new hire appeared externally composed, the Second Assistant was actually desperately in need of a job and teetering on the edge of depression. With a looming large scale, our team was also desperately in need of help. Through the referral of a friend, we hired this seemingly normal and intelligent assistant to help run the event and even take over many of my duties as the First Assistant. Because of the firsthand referral and our time crunch, we didn’t run extensive background checks or thoroughly identify the Second Assistant’s WHY.

Mistake #2: Communication expectations were not outlined prior to employment.

Although my relationship with our Manager was built on a reciprocal portal to open and honest communication via: calls, texts, emails, Facebook messages, voice notes, handwritten letters, etc… the Second Assistant preferred to communicate only via written text and only on that EA’s terms. These misaligned expectations caused immediate resentment. As we’ve discussed in prior posts, once resentment exists it is extremely difficult to quash.

Mistake #3: Due to the time crunch, the EA’s HOW was not thoroughly fact-checked against the purported resume.

While we had outlined our needs and the EA had guaranteed a willingness and ability to perform, the Second Assistant was ultimately unable to deliver.

Mistake #4: The first hint of theatrics and round of excuses were flags of a flare for drama.

Although I listed lack of drama at the end of the list of necessary EA requirements, it is an element that must be present from the beginning. True colors always eventually shine through, but you can save a lot of frustration if you adhere to red flags early on. In our case, many flags were overlooked and ultimately, the external personal drama that swirled around the Second Assistant, infiltrated our professional relationship and ultimately doomed it.

Building Trust and Communication

As a Manager, you must allow your EA to do his or her job. Micromanagement is not only deadly to a relationship, but it is also deadly to productivity. Many times, Managers are unable to release attachment to visions, possessions and control, but the best way to streamline workflow is to allow the person who stands at 30,000 feet do the streamlining.

To make us feel safe. This is the job of leaders… Great leaders extend the circle of safety to the outermost edges of their organization, so that even their most junior employee feels safe and feels like he or she belongs… The value of group living means that if I trust you and you trust me, I can fall asleep at night and trust that you will alert me to danger. If I don’t trust you, I can’t go to sleep at night. It’s the same in our companies. If we trust each other we will turn our backs. We will take risks. We will innovate. We will do things that will change the course of our world. If I don’t trust you, I can’t do that.” – Simon Sinek

The best way to remove yourself to a position of macro-management in lieu of this counterproductive counterpart is to build a foundation of trust and communication with your Assistant. Once you’ve achieved this goal – that’s what Simon Sinek would call a highly effective operation.

If trust is so critical, you’re probably wondering how to avoid the stressful situation depicted above? The answer is easy but the solution is long – you take the time to start with WHY and make the effort to build a relationship from the inside out.

It can be scary to loosen the reigns on your life, but if you started with WHY you are probably in good hands. Instead, redirect that attention to ensuring that your employee feels safe and valuable. If you are able to do so, you will allow your EA to stop feeling self-interested and start focusing his or her energy on protecting your brand.

Here are some helpful pieces of advice for finding and working harmoniously with your assistant:

1. Remember what it was like to begin at the bottom of the totem pole. Kevin Spacey often speaks to the importance of this simple action. In fact, he started a foundation devoted to what he calls: “sending the elevator back down.” The saying comes from his mentor, Jack Lemmon, who actually encouraged Kevin Spacey to become an actor and develop his craft. Could you imagine a world without House of Cards? American Beauty? The Usual Suspects? I sure can’t.

When I first started out, I was lucky enough to meet Jack Lemmon who encouraged me to become an actor. He subsequently became a great mentor in my life. Jack had a phrase he used all the time that I’ve now adopted as my own. He believed that if you’ve been successful in your chosen path, if you’ve been able to realize your ambition, then you are obligated to: ‘Send the elevator back down.’ That’s why I set up The Kevin Spacey Foundation.”

2. Determine your brand and hire an assistant that is also a brand ambassador. Know your WHY and HOW to communicate it to an eager early adopter. That early adopter will sell your brand to everyone else. 

If you talk about what you believe, you will attract those who believe what you believe. Why is it important to attract those who believe what you believe? Something called The Law of Diffusion of Innovation… if you want mass market success, or mass market acceptance of an idea, you cannot have it until you achieve this tipping point between 15% and 18% market penetration…We all have about 10% that just get it…The problem is how do you find the ones that just get it before you’re doing business with them versus the ones who don’t get it?

So it’s here – this little gap that you have to close. As Jeffery Moore calls it “Crossing the Chasm because you see – the early majority will not try something until someone else has tried it first…People don’t buy what you do, they buy why you do it. And what you do simply proves what you believe.” – Simon Sinek

3. Be clear with your communication style, preferences and needs. 

From the horror story described above, you can see the importance of taking the time to ensure both you and your Assistant are on the same page. As I became more active as an advocate in my community, I found that more people sought out my advice. In my experience, if I articulate my communication style at the beginning of the interaction, I actually maximize the benefit to both parties. We eliminate many of the insignificant squabbles over too many phone calls and that makes me more excited to be of service.

4. When well-intentioned mistakes happen, and they will happen, it is your responsibility as a leader to lead. Never intentionally throw your Assistant under the bus. 

Leadership. Alpha. It comes at a cost. You see, we expect that when danger threatens us from the outside, that the person who is actually stronger, the person who is better fed, and the person who is actually seeming with serotonin and actually has more confidence than the rest of us – we expect them to run toward the danger to protect us. This is what it means to be a leader. The cost of leadership is self-interest.

If you’re not willing to give up your perks when it matters, then you probably shouldn’t be promoted. You might be an authority, but you will not be a leader. Leadership comes at a cost. You don’t get to do less work when you get more senior, you have to do more work. And the more work you have to do is put yourself at risk to look after others. That is the anthropological definition of of what a leader IS.

Leadership is not a rank. Leadership is not a position. Leadership is a decision… If you decide to look after the person to the left of you and look after the person to the right of you, you have become a leader…. It’s the shield that matters, not the spear. It’s your willingness to sacrifice yourself…. It’s your shield, your willingness to protect someone so that they feel safe – that’s what makes you a leader.” – Simon Sinek

5. Say thank you. Give praise. Be kind.  

This one is simple. You have the ability to inspire greatness: greatness for yourself and greatness for those inside your circle of safety. Happiness creates success, not the other way around.

Wrapping Up

Finding the right Assistant is difficult, but keeping the right one is one of the most important steps you can take on your path to wellbeing and success. The relationship between Manager and Assistant is intricate, but it deserves to be well kept and fluid. Open lines of communication, defined and realistic expectations, and consistent gratitude and praise are just a few of the ways to ensure that the relationship stays healthy and equitable.

As Shawn Anchors once said,

Happiness raises nearly every business and educational outcome: raising sales by 37%, productivity by 31% and accuracy on tasks by 19%.”

What actions are you taking to make your work relationship happier?

Download Your Free Toolkit

Download this week’s toolkit for tips, industry advice, and interviews.


Want to follow along? Subscribe to our newsletter to receive new posts in your inbox as well as news, tips and industry spotlights.

Leave a Comment