What 2026 Will Demand of Executive Assistants and Chiefs of Staff
Executive Administration support is changing fast, and 2026 will not be a year for hesitation. CEOs who want stability, precision, and strong judgment in their leadership offices must face what is coming. The role of the Executive Assistant and Chief of Staff is no longer administrative; it is strategic. The expectations are higher. The stakes are higher. And the talent gap is widening.
Being in the business of Executive Assistant search, I see the trends firsthand. I make it a point to educate both candidates and clients on what is happening in the market so they can make wise decisions and align their careers and businesses strategically. My role is to help them stay ahead of the curve and move forward with clarity and confidence.
This is what I recommend executive leaders and HR professionals pay attention to and understand now as they plan their upcoming 2026 C-Suite administrative hires.
1. New Expectations for Executive Administrative Leadership
For decades, EAs kept operations steady and the executive’s schedule clean. That foundation still matters, but 2026 brings a new layer of responsibility.
Today’s EA and COS must:
Manage cross-functional priorities without needing hand-holding.
Serve as the point of alignment between the CEO, the board, internal teams, and external partners.
Uphold judgment equal to a senior manager.
Anticipate problems early and prevent small issues from becoming costly distractions.
The days of hiring someone solely because they are “organized and friendly” are behind us. CEOs must hire individuals who also bring operational intelligence, business acumen, and maturity, as well as the discipline to handle daily pressure. Anything less will not keep pace with 2026.
2. The Rise of AI Competence and Executive-Level Judgment
AI is no longer optional. It is an expectation. Regardless of where your company is in the adoption of AI within the business, make note.
Hiring managers are already screening candidates for:
AI literacy and workflow automation
Ability to evaluate AI outputs for accuracy
Judgment in determining what should not be automated
Understanding privacy, confidentiality, and ethical use
In 2026, the best administrative leaders will be those who pair authentic human judgment with AI skill. This combination allows an EA or COS to protect executive time at a level we have never seen before.
The truth is simple:
If your administrative team cannot work alongside AI, you will fall behind competitors who can.
3. Why CEOs Must Hire Strategically in 2026
The market is shifting. CEOs are asking more of their support staff, yet the pool of qualified professionals is shrinking. Many companies are discovering that hiring incorrectly, especially in the CEO’s office, has real consequences:
Lost revenue
Poor decision support
Burnout at the top
Inefficient operations
High turnover in roles that should remain stable
In 2026, CEOs will be rewarded for approaching their EA and COS hires with seriousness, clarity, and strategy. It will punish those who delay, settle, or assume the role is interchangeable.
Steele Recruiting. This is retained search territory. Not staffing. Not luck.
Precision matters. Fit matters. Judgment matters.
4. Emerging Pay Trends and Structural Shifts in EA/COS Teams
Compensation for top talent will continue to climb, especially in Minneapolis, New York, California, Texas, and Florida, where the markets are demand is surging.
Current trends heading into 2026 include:
Senior EAs supporting CEOs: $110,000–$165,000+
Chiefs of Staff (non-technical): $150,000–$250,000
Executive-Support Pods or “Office of the CEO” teams- replacing lone-wolf structures
Additional investment in fractional EAs and project-based administrative specialists
A growing recognition that high-caliber support prevents costly executive burnout
You cannot hire a 2026-ready administrative leader with a 2018 mindset or a 2020 budget. The best-in-class talent market will not respond.
5. A Call to CEOs: Prepare Now And Partner Early
If you wait until Q2 or Q3 to build out your 2026 administrative structure, you will be too late. The strongest talent is already in motion now. Smart CEOs are securing support early, clarifying expectations, and investing in stable leadership around them.
If you want:
An EA or COS who can keep up with you and operate at your level
Someone who protects your time like an asset
A leader who understands or is willing to embrace AI and modern operations
A professional who brings judgment, stability, and long-term value
Then it is time to approach your search with precision and not convenience.
Steele Recruiting is here to help you do it the right way.
We have been placing Executive Assistants, Chiefs of Staff, and Personal Assistants supporting CEOs and UHNW leaders for more than twenty years. We understand the discipline required to match a leader with the right administrative partner. Retained search is not a transaction. It is a strategy.
2026 will demand more of administrative leadership. The question is whether your organization will be ready.
If you are planning to hire in Q1, Q2, or Q3, or know of someone who is, start the conversation with us now. Let Steele Recruiting handle the search so you can stay focused on leading your business.
Steele Recruiting LLC | diane@steelerecruiting.com | 952-484-4217
Call us for a free consultation.
