How to Hire an Executive Assistant for a CEO: Including an Interview Scorecard and What “Great” Really Looks Like

Hiring an Executive Assistant for a CEO is one of the highest-impact people decisions a business can make. When done well, the right Executive Assistant increases leadership capacity, improves decision-making, and creates measurable momentum at the top of the organisation. When done poorly, it becomes a costly mis-hire that drains time, energy, and confidence.

This is not a generalist hire. It is not about finding someone who can manage a diary. It is about hiring someone who can operate at the pace, judgement level, and complexity of a CEO.

Below, we outline how to approach Executive Assistant recruitment for a CEO, what truly differentiates high performers, and a practical interview scorecard, including example questions, to help you assess candidates with confidence.

What Makes a Great Executive Assistant to a CEO?

A great Executive Assistant is not defined by tasks. They are defined by outcomes.

At CEO level, the role exists to protect focus, increase leverage, and ensure the leader is operating at their highest level. This requires sound judgement, commercial awareness, emotional intelligence, and the confidence to operate autonomously.

In practice, a high-performing Executive Assistant:

• Anticipates needs rather than waiting for instruction
• Filters priorities and information with confidence
• Understands the CEO’s role in the wider business
• Acts as a trusted representative internally and externally
• Operates calmly in ambiguity, pressure, and change

Many clients tell us they want someone “exceptional”, but struggle to define what that looks like. The difference between good and great rarely comes down to technical ability alone. It is mindset, maturity, judgement, and presence.

Common Mistakes CEOs Make When Hiring an Executive Assistant

Executive Assistant recruitment often fails when urgency overrides judgement. The most common mistakes we see include hiring too junior for the complexity of the role, over-prioritising tasks over judgement, assuming all Executive Assistants operate at the same level, or rushing the process without properly scoping the role because the pressure feels immediate.

A strong Executive Assistant should reduce pressure, not add to it. That only happens when expectations are set at the right level and the role is clearly defined from the outset.

Executive Assistant Interview Scorecard With CEO-Level Questions to Ask

A structured assessment process is essential. Chemistry matters, but it should never replace rigour. Below is a practical scorecard designed specifically for hiring an Executive Assistant to a CEO, along with example interview questions that surface real capability.

Judgement and Decision-Making

A CEO-level Executive Assistant must make independent decisions and get them right.

Questions to ask:

• Tell me about a time you made a decision on behalf of your executive without being able to check with them. What happened?
• How do you decide what to escalate versus what to handle yourself?
• Tell me about a decision you made that did not land perfectly. What did you learn?

What great looks like:
Clear accountability, strong reasoning, and evidence of learning rather than defensiveness.

Anticipation and Proactivity

The role should prevent pressure, not respond to it.

Questions to ask:

• How do you stay one step ahead of your executive?
• Tell me about something you anticipated before it became a problem.
• What signals do you watch for that suggest an issue is coming?

What great looks like:
Pattern recognition, forward planning, and calm prevention rather than reactive firefighting.

Communication and Confidence

An Executive Assistant must communicate with authority across senior stakeholders.

Questions to ask:

• Tell me about a time you had to push back on your executive. How did you handle it?
• Have you ever had to say no on behalf of your executive? What was the outcome?
• How do you adapt your communication style for different personalities?

What great looks like:
Confidence without ego, composure under pressure, and strong emotional intelligence.

Organisation and Execution

This is about managing complexity, not simply staying busy.

Questions to ask:

• How do you manage competing priorities when everything feels urgent?
• What systems or tools help you stay organised and in control?
• How would you prepare a CEO for a critical board meeting?

What great looks like:
Structured thinking, strong prioritisation, and an instinct for preparation.

Commercial Awareness

A CEO’s Executive Assistant must understand business context and impact.

Questions to ask:

• How do you ensure you understand what matters most commercially in the business?
• Tell me about a time commercial awareness influenced how you supported your executive.
• How do you prioritise when business needs conflict with diary requests?

What great looks like:
An understanding of impact, not just activity, and the ability to prioritise strategically.

Discretion and Trust

Trust is non-negotiable at this level.

Questions to ask:

• How do you handle confidential or sensitive information?
• Tell me about a situation where your discretion was tested.
• How do you maintain boundaries in close-working relationships with executives?

What great looks like:
Maturity, professionalism, emotional stability, and ethical judgement.

Adaptability and Resilience

CEO environments evolve quickly.

Questions to ask:

• Tell me about a time you worked through significant change. How did you adapt?
• How do you stay effective in high-pressure or ambiguous environments?
• What do you do when plans change at the last minute?

What great looks like:
Calm under pressure, accountability, and the ability to stay steady in uncertainty.

What “Great” Looks Like in the First Six Months

A strong Executive Assistant makes a tangible impact early.

Within the first few months, CEOs often notice clearer priorities, fewer unnecessary meetings, stronger preparation for decisions, reduced cognitive load, and more controlled, intentional use of time.

When Executive Assistant recruitment is done properly, it consistently delivers one of the fastest returns on investment of any senior hire.

Getting the Hire Right

Hiring an Executive Assistant for a CEO is not about finding someone who can keep up. It is about finding someone who can elevate how the CEO operates.

At Lily Shippen, we work with CEOs and founders to define what the role truly needs to deliver before going to market. We focus on judgement, capability, and long-term fit rather than surface-level experience. The right hire accelerates growth, protects leadership effectiveness, and improves how the business operates at the top. The wrong hire creates drag, distraction, and unnecessary cost.

If you are hiring an Executive Assistant for a CEO and want support defining the role, assessing candidates at the right level, or ensuring you avoid costly hiring mistakes, we would be happy to advise. Our approach is consultative, discreet, and focused on securing Executive Assistants who genuinely elevate leadership performance and business outcomes.

To discuss your Executive Assistant hire, contact our team.