You are missing meetings. Important emails slip through the cracks. You are constantly running late. These are not signs of a busy executive—they are signs of an executive who needs help.
The Role Most Leaders Underestimate
On The Buck Stops Here podcast, David Maples interviews Gretchen Moran, owner of Simply Living KC and former executive assistant across oil and gas, healthcare, and accounting industries. Her message is clear: an executive assistant is not a luxury—it is a necessity for leaders who want to maximize their impact.
An executive assistant represents years of accumulated administrative experience. The role differs fundamentally from entry-level positions through enhanced professionalism, confidentiality, and broader skill development.
Warning Signs You Need One Now
- Missing important meetings repeatedly
- Overlooking critical communications via email or voicemail
- Consistently running late to appointments
- Spending hours on tasks that do not require your expertise
These gaps do not just affect your productivity—they damage your credibility and organizational efficiency.
What to Look for When Hiring
Professionalism and Organizational Knowledge
Internal candidates often have an advantage—they already understand your culture and systems. But whether internal or external, look for someone who grasps how organizations function.
Confidence
Your assistant will contact high-level individuals on your behalf. They need to do so without hesitation and represent your organization professionally.
Master Communication Skills
The best executive assistants become diplomatic translators between leadership and staff. They know how to deliver messages appropriately in both directions.
Adaptability
Moran describes the role as being a “Swiss Army knife”—requiring diverse competencies and the ability to handle whatever arises.
The Non-Negotiables
Some things cannot be trained:
- Personality fit: If the chemistry is wrong, no amount of skill compensates
- Ethical foundation: Integrity issues signal wrong-fit placement immediately
Technical skill gaps are addressable through training. Character and integrity issues are not.
Development Options
If you find someone with the right character but gaps in skills, you can develop them through:
- Business coaching
- Online training platforms
- YouTube tutorials for specific skills
- Headhunting services like Robert Half International or Morgan Hunter, which vet candidates and offer temp-to-hire arrangements
Maximizing the Relationship
Success depends on open dialogue. Discuss:
- What tasks drain your productivity that could be delegated
- Your assistant’s capabilities and past experience
- Communication preferences and working styles
- Growth opportunities within the role
For Aspiring Executive Assistants
Moran offers career advice for those in or seeking the role:
- Understand industry fundamentals relevant to your organization
- Develop self-motivation for continuous improvement
- Confidently ask for expanded responsibilities when you have earned them
- Seek mentors and attend industry networking events
- Read books like “Managing Up” to sharpen your skills
Advancement requires intentional effort beyond work hours. Those who demonstrate commitment through continuous learning will outpace those who simply show up.
This article is based on Season 2, Episode 8 of The Buck Stops Here podcast: “The Most Important Person You Lack in Your Business” featuring Gretchen Moran.