Bad Hiring or Bad Managing? The Pitfalls of Not Managing an EA Well

In the dynamic world of executive support, the relationship between an Executive Assistant  and their executive is both unique and complex. It’s a partnership built on trust, understanding, and seamless communication. However, when things go awry, it’s not always easy to pinpoint the root cause. Is it a case of bad hiring or bad management? More often than not, the answer lies in the latter. Managing an otherwise great Executive Assistant effectively is a skill that requires investment, not just in their role, but in their success and development.

The Nuances of the Executive Assistant Role

An Executive Assistant is far more than just a taskmaster. They are the gatekeepers, confidants, and often, the glue that holds the executive's professional (and sometimes personal) life together. Often they are the wizard behind the curtail, the air traffic controller, and the representative of their Executive on many levels. The nuances of this role demand a deep understanding of the executive’s preferences, relationships, goals, working style, communication habits, and even personal quirks and pet peeves. Without this understanding, the relationship can quickly become strained.

Here’s where the challenge lies: an EA cannot perform optimally without the right information, context, and clarity on what is expected of them. Unlike other roles where job duties are more rigidly defined or fall outside this intimate scope, an EA’s responsibilities can be fluid, adapting to the ever-changing needs, moods, goals, pressures, and priorities of their executive. They go to bed and wake-up thinking of someone’s life, who almost never thinks of them. This means that, as a manager, you must continuously provide context, share insights, and communicate expectations clearly and regularly.

The Role of Style, Preferences, and Context

Every executive has their own unique style. Some prefer to communicate through quick text messages, slack, during one-on-one phone calls, while others favor detailed emails, documents, tracking systems or consistent face-to-face interactions. Some executives like to be involved in every detail, while others prefer a more hands-off approach. An EA must learn and adapt to these preferences, but they can only do so if they are aware of them.

Context is king. It is equally critical to almost everything else. Without understanding the why behind a task or decision, an EA may struggle to execute it effectively. For instance, scheduling a meeting might seem straightforward, but if the EA isn’t aware of the underlying importance of that meeting, relationships, history, or how this meeting plays into other projects or priorities in the works, they might not prioritize it correctly. Providing context allows an EA to make informed decisions and support their executive in a way that aligns with broader goals.

Managing the Personalities and Chemistry

The relationship between an executive and their EA is deeply personal. Chemistry plays a significant role in whether this relationship thrives or falters. But chemistry alone isn’t enough. Both parties need to be committed to each other’s success. As an executive, you must be genuinely invested in your EA’s success, growth and development. This investment goes beyond just professional training; it involves fostering a relationship where the EA feels valued, heard, and empowered.

One of the challenges in managing an EA is that their success is often invisible. When things go right—when meetings are flawlessly scheduled, emails are meticulously handled, and travel plans are seamlessly executed—these successes can go unnoticed. However, when something goes wrong, it’s immediately apparent. This imbalance can create frustration if not acknowledged. It’s important to recognize the countless things that go right, not just the occasional mistake.

  1. Invest Time in Onboarding: Begin the relationship by dedicating substantial time to onboarding your EA. Share your preferences, communication style, and any unwritten rules or nuances that guide your daily operations. Provide them with the tools, resources, and context they need to hit the ground running. The more they know upfront, the better equipped they’ll be to support you effectively from day one.

  2. See Them as Your Success Partner: Recognize that your EA is not just an administrative support role but your day-to-day success partner. Their effectiveness directly impacts your productivity and overall success. To ensure they can continuously succeed, provide them with the resources, authority, and autonomy they need to excel. This includes access to information, systems, and decision-making processes that empower them to act on your behalf.

  3. Maintain Regular Communication: Keep the lines of communication open and consistent. Schedule regular check-ins to discuss ongoing projects, share feedback, and offer necessary context. These meetings are vital for ensuring alignment and preventing misunderstandings. Regular communication also gives your EA the opportunity to voice concerns, ask questions, and stay informed about your evolving needs.

  4. Provide Comprehensive Context and Background: Whenever you assign a task, make sure to provide as much context and background information as possible. Explain why the task is important, how it aligns with broader objectives, and any relevant history or expectations. This not only helps your EA execute the task effectively but also fosters a deeper understanding of your goals, leading to better decision-making and prioritization.

  5. Encourage Questions and Clarification: Cultivate an environment where your EA feels comfortable asking questions and seeking clarification. Make it clear that questions are welcome and that it’s better to ask upfront than to proceed with uncertainty. This approach reduces errors and builds confidence, ensuring tasks are completed correctly the first time.

  6. Recognize and Appreciate Their Efforts: Take the time to regularly acknowledge the work your EA does. Whether it’s a small task or a major project, recognizing their contributions fosters a positive working relationship and boosts morale. A simple thank you or acknowledgment in a meeting can go a long way in making your EA feel valued and motivated to continue performing at a high level.

  7. Create a True Partnership: Treat your EA as a partner, not just a subordinate. Their success is intertwined with yours, and a strong partnership can lead to greater achievements for both parties. Involve them in decision-making processes, seek their input, and be open to their suggestions. This partnership mentality encourages ownership and accountability, leading to better outcomes for your team.

  8. Play to Their Strengths: Understand your EA’s strengths and leverage them to maximize their effectiveness. Every EA has unique skills, whether it’s organization, communication, project management, or problem-solving. By aligning tasks and responsibilities with their strengths, you enable them to perform at their best, ultimately benefiting both of you.

  9. Be Patient and Supportive: Mistakes will happen, especially in the early stages of the relationship. Approach these moments with patience and use them as learning opportunities. Show your EA that you’re invested in their growth by offering constructive feedback and guidance. A supportive attitude fosters a culture of continuous improvement and development.

  10. View the Role as a Long-Term Investment: Don’t view the EA role as a transactional arrangement. Instead, approach it with a long-term perspective. Building a strong, enduring relationship with your EA takes time and effort, but the rewards are substantial. A long-term commitment to their success and well-being will lead to greater loyalty, trust, and productivity over time.

Managing an Executive Assistant properly is not just about assigning tasks and expecting them to be completed. It’s about building a relationship based on trust, clear communication, and mutual respect. When an executive takes the time to manage their EA effectively, the rewards are substantial, career changing even. Not only will your EA perform better, but they’ll also be more committed to helping you succeed. Remember, in the delicate dance of executive support, both parties must be in sync. When you invest in your EA’s success, you’re investing in your own.


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