Office and Admin Professional Development

Top 4 Challenges for Executives and Assistants

Written by Miranda Pennington

According to founder and CEO of Office Dynamics International, Joan Burge, “There is no greater relationship in the workplace than that of an executive and an assistant.” This may seem like hyperbole if you haven’t had a really terrific working relationship with an executive or an assistant who “gets it.” If you’re at the top of the food chain, try to see your assistant as a strategic partner; if you’re in a support role, take advantage of these tips to improve your standing and the dynamics at work!

1. Bandwidth

Nobody has enough time in the day. Executives may have more than one assistant, or assistants may be supporting more than one executive (every one of which wants to feel like your Top Priority). Between the two of you, you may be fielding as many as 400 emails a day—have systems in place and revise them as necessary! Be aware of the speed and intensity of the information flowing across your executive’s desk, and let that inform the pace of your interruptions, meetings, and independent work.


2. Digital Dependency

They’re working from multiple devices and may ask you do to the same. While that may make them feel independent and tech savvy, it’s important (for them and for you!) to realize that an empowered executive assistant is as valuable as the Cloud in terms of coordinating information and monitoring plans.


3. Delegating

With all the self sufficiency of scheduling software and remote access, it’s easy for executives to forget how to use their assistants most effectively. Companies lose time and money when execs underutilize support staff. Know your role, advocate for appropriate ways to expand it, and always be a reliable asset.


4. Frustration in Communication

With complaints ranging from “I don’t have time to teach my assistant to do this job” to “I have no idea what this executive wants from me,” some of the hardest aspects of the relationship to master are the simplest—how you perceive one another and what you expect from one another. Be verbal, follow-up, and be willing to disagree and resolve it! Don’t be so wrapped up in status you forget to think like a team.


Tips for Assistants

  • Initiate Conversation
  • Talk about your relationship as a team
  • Get clarification on likes and dislikes
  • Put yourself on the exec’s calendar and leave it, unless there’s an emergency
  • Think like an executive—anticipate needs and prioritize accordingly
  • Go the extra mile
  • Attend meetings
  • Read everything
  • Understand the scope of their word


Tips for Executives

  • Have clear assignments and deliverables
  • Demonstrate the qualities you want to see
  • Be comfortable with disagreement
  • Rely on your assistant; don’t micromanage
  • Be appreciative—post-mistake shouldn’t be the only time you give feedback
  • Recognize that your assistant’s job requires skill

Executives and Assistants are Struggling Today


About the author

Miranda Pennington

Miranda K. Pennington is a freelance writer and editor whose work has appeared on The Toast, The American Scholar, and the Ploughshares Writing Blog. She currently teaches creative nonfiction for Uptown Stories, a Morningside Heights nonprofit organization. She has an MFA from Columbia University, where she has also taught in the University Writing program and consulted in the Writing Center.