Top 3 Things I've Learned Coaching Executives to Work Better with Their Executive Assistants

I serve in a role that allows me to work with a variety of executives, entrepreneurs, business leaders, and world-changers every day. They all desire to maximize the partnerships they have with their executive assistants, and they are all seeking input and coaching on how to make that a reality. 

It is so much fun to sit with an executive and hear all about the challenges they’re facing to move their business to the next level of success and then to begin the dialogue around collaborating with their executive assistant. There are countless ways executive assistants can come alongside these leaders and remove hurdles for them left and right. We spend time discussing short-term goals, long-term goals, and ways in which their EA can become a trusted partner and a loyal companion. An executive assistant can be a ‘secret weapon’ to unlocking a leader’s ability to pull from untapped energy they simply did not have the time or willpower to find. As we finish these meetings, there is usually a contagious and electric sense of excitement and optimism.

Does this sound too good to be true? Well, sometimes it can feel that way. As I spend time with these incredibly busy, high-impact leaders, I learn of the barriers to success they face in their relationships with their executive assistants and the challenges they need to overcome to truly leverage their EA’s value. 

Below are the 3 most common areas I find myself leaning into with executives and executive assistants as they navigate their relationships. If you are reading this blog and sitting in an owner, executive, leader, or C-level seat, I would like to invite you to join me in thinking through these areas and determine if you could implement some new ideas into your partnership. If you are an executive assistant, my challenge to you is to read and understand how you can help make some of these ideas a reality. I believe if you work together and invest time, your partnership can thrive!

1. If you do not prioritize partnership, it will NOT work.

Yes, I said it. If you are a leader, you must put your executive assistant in one of the highest priority seats for at least 90 days. If you are an assistant, you must work to find time to ensure this onboarding happens. These early days of onboarding (which I would absolutely recommend be 90 days) can be a little bit awkward. You are both learning about a brand new person - their personality and their work style.  As a leader, you are inviting your executive assistant into some of the most intimate areas of your business and life. You are often discussing past successes and failures, setting important expectations, and casting a vision you may have yet to share with anyone else in your organization. As an executive assistant, you are working on building trust with your leader. This is a season of listening well, learning who your executive is, and discovering what you can do to help them be more effective. This takes time for both of you and requires a level of vulnerability as you invite each other into your journeys.

For many of you, your partnership is well past its first 90 days. That’s okay. You just need to reinvest time and re-onboard. Do some of these activities, plan the next 90 days, and be intentional. You’ll get on track! 

Woah, that’s a lot.  

I recognize that your time holds significant value for your business, your direct reports, your family, and you personally. I completely understand the thought of adding additional meetings to your already packed schedule sounds nothing short of impossible. But believe me, the only road to successfully shift significant work from the executive's plate to the executive assistant's plate requires time invested in making this relationship a priority.

2. Can you take feedback? 

Feedback. Everyone’s favorite word. One of the questions I routinely (and bluntly) ask the leaders I work with is, “How do you give and receive feedback?” Oftentimes, their answers speak more specifically to the “giving feedback” piece of that question. However, I don’t let the conversation end there. Receiving feedback from your executive assistant is vitally important. The best leaders I have had the privilege of working with are men and women who are full of humility and are ready to collaborate with an executive assistant who can provide insights and observations into barriers that may be preventing a leader from pushing through to the next level of success. You may be wondering why the idea of feedback is so “sticky” for some executives. Truthfully, many people who work with successful leaders feel an undertone of superiority from them that can paralyze them from giving extremely helpful feedback. The nature of an Exec/EA relationship simply will not work if the executive assistant feels fear or hostility when offering observations related to topics like communication style, priority setting, and delegation. Sometimes, even executives need to be held accountable for the paths they lay out for business success.

If you are an executive assistant, you have to be willing to take the risk and give feedback to your leader. It is the only way to keep your partnership moving forward. You must also be willing to listen to and accept feedback as you seek to improve your partnership. Ask questions to clarify things you are unsure of, but most importantly, show that you want feedback and are listening. The moment you get defensive or push back on feedback is the moment you risk the feedback stopping. This can be the beginning of the end of what could have been a great partnership. 

3. Your fists are clenched.

I’m in a fun season of parenting. We have 3 young kids and many times throughout each day, there are screaming matches over who’s toy belongs to who. It’s not unusual to walk into the room and see two children holding tightly to one toy and pulling it in opposite directions. They are both refusing to release their closed fists while the energy is gaining steam with each passing second. 

So the question I pose to you leaders is, “Do you delegate?” Are you willing to open your fists and walk towards your executive assistant with a posture of delegation and trust? As an executive assistant, there is nothing more frustrating than a leader who asks you to own a task or project only to override you and redo 80% of the work and effort that you’ve invested. I absolutely appreciate that a lot of successful executives have spent their entire professional life, late nights, and early mornings laying a stable foundation to build their vision on. It is hard to trust others. However, if you don’t allow your hands to be open to helpful partners, you may soon find yourself completely depleted which often leads to your business being stuck with its tires spinning.

If you are an executive assistant who wants to take on more, always be looking for opportunities to take something off your leader’s plate and free up some of their valuable time. Try to understand how hard it can be for your leader to delegate and appreciate the level of trust being given to you each time something is released. Work with that knowledge and understanding, and do your best to complete the task or project in a way that your leader wants it. Be willing to accept feedback and incorporate it into the next task you do. Doing a task “just okay” is a quick way to reduce the amount of delegation you receive. Doing a task “great” is the best way to be given more.

In closing

I believe so fiercely in the executive-executive assistant relationship that I work to strategically help these partnerships on their journey to success. As I’ve journeyed with many leaders and assistants, I’ve learned that the above 3 areas often pose the biggest challenges preventing executives from moving into “The Land of Administrative Freedom” and keeping executive assistants from that great feeling of being trusted, valued, and indispensable.

It isn’t always easy to figure out how to make this a reality. Communication and being on the same page are keys to your success. Emmre has developed a tool that directly links an Executive and Executive Assistant and may be a great place to start in improving your communication in these 3 areas. This tool can help anchor the onboarding by being the place that holds all communications, tasks, projects, and priorities. It can create a channel for quick feedback loops and interactions, and its ability to keep things like accepting tasks, completing tasks, and prioritizing tasks visible can help with the delegation process.  

Do you find yourself struggling with prioritizing onboarding, taking feedback, or delegating thoughtfully and intentionally? Make these areas a priority. When I see the people that I coach shift their focus and ensure these things happen, I get the joy of watching their partnership grow and thrive. 

Don’s Comments

It’s great to read Anna’s insights here. She has such a unique perspective being an active executive assistant while also interacting directly with executives coaching them on how to better their partnership with their assistants.

As I read this, I could relate to each and every point. My partnership with my executive assistant really took off when I invested the time. When I blocked off chunks of time to go through how I did my calendar, my travel, my emails, etc., Kristie really began to take things off my plate, freeing up so much more of my time. The time I invested in onboarding was paid back 10-fold!

I learned early in my career the importance and value of feedback. Understanding that, however, does not always make it easier to hear. One of the best things I did in my partnership with Kristie was to try to foster an environment where she felt comfortable giving me feedback. Kristie had insights into me and into our company that nobody else had which resulted in her ability to give me feedback that no one else could. Executives, it’s imperative that you create that environment. Assistants, give your leaders feedback. It is so valuable!

Delegation is hard for us executives. As Anna wrote, we’ve built our early careers as excellent individual contributors and have high expectations for how things should be done. The reality is that executive assistants have done the same thing. They have very high standards for how things should be done and are in their current role because they do outstanding work. The breakdown usually occurs when there are unknown expectations or uncommunicated requirements. If you are an executive, clearly communicate how you want things done. Show your EA how to do things. Invest in training if need be. Give your executive assistant the chance to take on more and they will impress you with their capacity to do it and do it well! If you are an executive assistant, ask questions. Don’t take on something if you don’t understand the requirements. Your ability to successfully deliver on delegated tasks directly impacts future levels of delegation.

As you work on these 3 areas that Anna outlined, I know you’ll see improvements in your partnership. If you ever have any questions on any of the items we cover or have an area that you’d like us to write more on, feel free to reach out anytime! Don@emmre.com

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.