Interviews can feel like a one-way street, where you’re expected to prove your worth and demonstrate why you’re the right fit. But let’s be clear: it’s just as much about finding the right executive and company for you.
As a high-level Personal or Executive Assistant, you’re not just filling a role; you’re stepping into a partnership. You’ll be the strategic right hand, the problem-solver, the person who keeps everything moving. And that means you need to work for someone whose leadership style, expectations, and values align with yours.
The best way to ensure that? Ask the right questions…
This isn’t about surface-level chit chat like “What’s a typical day like?” (you’ll figure that out soon enough). It’s about getting a clear picture of the company’s direction, your executive’s working style, and whether this position will set you up for long-term success.
Here are five high-level questions that will not only help you stand out in the interview but also help you assess if this is the right role for you.
1. How does this role contribute to the bigger picture of the business and your long-term goals?
Why this matters:
You’re not just an assistant, in the words of the incredible Hallie Warner you’re a force multiplier. Your role should be directly tied to the executive’s ability to perform at their highest level and, by extension, the company’s success. Asking this question shows that you’re thinking strategically and ensures that the role is designed for impact, not just administrative work.
What to listen for:
- A clear understanding of how the assistant contributes to the company’s success.
- Signs that the executive values and respects the role.
- A roadmap for how this position will evolve over time.
There’s a red flag if: If they struggle to articulate why the role is important beyond scheduling and inbox management, the position might not be as high-level as you’d like.
2. What leadership qualities do you value most in an assistant?
Why this matters:
This shifts the conversation from “What do you need me to do?” to “How can I lead within this role?” It also gives you insight into whether the executive sees their assistant as a strategic partner or just a gatekeeper.
What to listen for:
- Do they mention traits like proactivity, decision-making, and problem-solving?
- Do they see their assistant as a leader in their own right?
- Does their answer align with the strengths you bring to the table?
There’s a red flag if: If their response is vague or focuses purely on admin tasks, it could mean they haven’t worked with a strong assistant before, or they don’t fully understand the value of one.
3. What are the biggest operational challenges you’re currently facing, and how do you see this role helping to solve them?
Why this matters:
A great assistant isn’t just there to do things, they solve problems before they even arise. This question allows you to understand where the pain points are and where you can have the most immediate impact. It also subtly positions you as a strategic problem-solver rather than someone who just takes direction.
What to listen for:
- A clear understanding of what’s not working and where you’d fit in.
- Realistic expectations for how an assistant can help.
- A willingness to collaborate and delegate effectively.
There’s a red flag if: If they say something like, “I just need someone to handle my calendar,” without acknowledging deeper challenges, they may not be ready for a truly strategic assistant.
4. How do you see this role evolving over the next three to five years?
Why this matters:
Longevity is key. You want to work with an executive who invests in their assistant and sees the role as a long-term partnership. If they’re thinking ahead, it’s a sign that they value stability and growth within their team.
What to listen for:
- Are they open to expanding the role as you prove your value?
- Do they see a future where your responsibilities grow alongside the company?
- Is there a commitment to professional development?
There’s a red flag if: If they say something like, “Well, I guess we’ll see how it goes,” or “I haven’t really thought about that,” it could indicate a lack of long-term vision.
5. What’s your leadership style, and how do you like to work with your assistant?
Why this matters:
The assistant-executive relationship is one of the most unique and personal in any organisation. You need to know if their leadership style aligns with how you work best. Some executives prefer high levels of autonomy, while others want constant updates. Understanding their expectations upfront will help set you up for success.
What to listen for:
- Do they value trust and autonomy?
- How do they communicate? Are they clear about what they need?
- Do they seem self-aware about their working style?
There’s a red flag if: If they say something like, “I don’t really know” or “I haven’t worked well with assistants in the past,” that’s worth digging into before committing.
Final Thoughts
You’re not just looking for a job, you’re looking for the right fit. The best assistants don’t just take jobs based on salary or title; they choose roles that align with their strengths, career goals, and values.
By asking these high-level, strategic questions, you’ll not only impress your interviewer but you’ll gain the clarity you need to ensure this role is one where you can thrive.
At the end of the day, the best interview is a two-way conversation. You’re not just being evaluated, remember that you’re evaluating them, too.
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