Managing the Executive Assistant Relationship for Maximum Performance
Hiring an executive assistant is the beginning. Managing that person well is the ongoing work that determines whether the relationship delivers its full potential value. In entertainment and media, where the assistant’s effectiveness is closely tied to the CEO’s own performance, the quality of this management relationship is a direct factor in business outcomes.
This guide provides a practical framework for managing an executive assistant in entertainment and media, with specific attention to how the relationship should evolve, how to provide effective feedback, and how to build the trust that enables genuine partnership.
The Management Mindset for This Relationship
Managing an executive assistant is different from managing most other roles. The relationship is unusually close, unusually trust-dependent, and unusually consequential for the CEO personally. This requires a management approach that combines high standards with genuine investment in the person’s development and success.
The most effective entertainment CEOs manage their executive assistants with three principles:
Clarity over assumption. The assistant cannot meet expectations they do not understand. Clear, explicit communication about preferences, priorities, and standards is more effective than expecting the assistant to figure things out through osmosis.
Trust over control. Micromanaging an executive assistant defeats the purpose of having one. The goal is to develop the assistant’s judgment to the point where they can operate independently on the vast majority of decisions. Getting there requires giving them autonomy and accepting some imperfection in the process.
Investment over indifference. The assistant’s development is in the CEO’s direct interest. An assistant who is growing, learning, and deepening their understanding of the business becomes more valuable over time. Treating the role as a static position rather than a developing partnership wastes this potential.
Establishing Clear Operating Protocols
In the first weeks of the relationship, invest time in establishing clear protocols that define how the CEO and assistant work together. These protocols should cover:
Communication Preferences
How does the CEO prefer to receive updates from the assistant? What channel should the assistant use for urgent items (text, instant message, a knock on the door)? What should be batched into the daily check-in versus surfaced immediately?
In entertainment, where urgency is frequent and interruptions have real costs, clear communication protocols prevent the assistant from either interrupting the CEO unnecessarily or holding back information that should be shared quickly.
Decision-Making Authority
For what categories of decisions can the assistant act without seeking approval? The answer should be broad enough that the CEO is not being constantly consulted on routine matters. At minimum, the assistant should be empowered to: schedule meetings within the established priority framework, book standard travel within defined parameters, send routine correspondence on the CEO’s behalf, and handle vendor logistics independently.
The narrower the assistant’s authority, the more the CEO functions as a bottleneck. In entertainment, where pace matters, this is particularly costly.
Scheduling Philosophy
Share your calendar philosophy explicitly. What time of day is your best creative work time, and when should you not be scheduled for administrative meetings? Which relationships always get priority in scheduling? Which types of commitments can be declined without asking? How long before a meeting do you need preparation time?
This context allows the assistant to make intelligent scheduling decisions that reflect your actual priorities, not just availability.
Daily and Weekly Rhythms
The Daily Check-In
A brief daily check-in (10-15 minutes) is the most important management rhythm for this relationship, especially in the first year. This meeting covers:
- The day’s schedule and any changes
- Time-sensitive items that need the CEO’s attention
- Open questions the assistant needs guidance on
- Quick feedback on any items from the previous day
In entertainment, where every day can bring unexpected demands, this check-in ensures alignment before the day’s complexity unfolds.
The Weekly Review
A longer weekly meeting (30-45 minutes) allows for more substantive review of the week ahead, feedback on the previous week, and discussion of strategic priorities that should shape the assistant’s focus. This is also the forum for addressing any patterns or issues that need direct conversation.
Providing Effective Feedback
Feedback is the primary tool for developing the assistant’s judgment and performance. In entertainment, where many situations involve judgment calls that cannot be scripted in advance, the quality of feedback determines how quickly the assistant develops the independent judgment the role requires.
Be Specific
Vague feedback (“I just need you to be more proactive”) is less useful than specific observation (“When I have a meeting with a studio executive I haven’t seen in several months, I’d like you to include a note on what we last spoke about and any news about their projects since then”). Specific feedback is actionable.
Be Timely
Feedback is most useful close to the event it addresses. If the assistant scheduled a meeting in a way that did not reflect your priorities, address it the same day rather than storing it for the quarterly review. Timely feedback prevents the incorrect behavior from being repeated.
Be Balanced
Noting only mistakes sends the signal that adequate performance is invisible and only errors are acknowledged. Make a practice of specifically naming what the assistant did well. In entertainment, where the pace is relentless, moments of explicit recognition are meaningful.
Have Direct Conversations
When there is a significant issue with the assistant’s performance, address it directly rather than hoping it resolves. Indirect feedback in a close working relationship creates confusion and erodes trust. A direct, respectful conversation about a performance issue is more effective and more respectful than hoping the person reads between the lines.
Managing Through Entertainment’s Intense Periods
Entertainment has natural seasons of intensity: production launches, award seasons, festival circuits, deal closing periods. During these times, the demands on both the CEO and the assistant peak simultaneously.
Managing effectively through these periods requires:
Pre-season preparation: in the weeks before an intense period (like Sundance or a production launch), review the upcoming demands together, identify what additional support or resources the assistant needs, and adjust priorities proactively.
Clear communication during the period: maintain the daily check-in even when it is harder to find the time. During intense periods, alignment is more important, not less.
Post-period recovery: after a peak intensity period, acknowledge the effort, review what worked and what could be improved for the next time, and ensure the assistant has the recovery time they need.
Building Trust Over Time
Trust in this relationship is built through consistent experiences of the assistant making good decisions, handling sensitive information appropriately, and representing the CEO professionally in challenging situations.
As trust builds, the CEO should actively expand the assistant’s authority and scope. This signals confidence, accelerates development, and creates the conditions for genuine partnership rather than supervised execution.
According to Harvard Business Review research on executive assistant relationships, the most effective CEO-EA partnerships are characterized by deep mutual trust and the assistant’s near-complete understanding of the CEO’s judgment. This level of partnership requires deliberate investment in the management relationship over time.
See our what CEOs should delegate.
See our EA training for entertainment.
Managing an executive assistant well is not passive; it is an active investment in one of the most impactful working relationships you have as an entertainment CEO. The return on this investment, measured in time recovered, opportunities captured, and decisions made with better information, is among the highest available to you.
Related Reading
For further context, explore Animation Studio CEO Time Management Across Long Development Cycles and Automation Tools That Free Up Entertainment Company CEOs for Strategic Work.