Questions to Ask in an Interview for Assistants

Okay, you made it. You’re at the end of the interview and you’re feeling pretty good. The vibe between you and your potential new executive is positive and you feel like you have a pretty solid knowledge about the company and the job duties. Then she asks…

“Do you have any questions for me?”

You choke for a minute. Your brain is spinning. Was there something we didn’t cover? What will sound clever? Ugh – a million questions, but what’s appropriate right now?

You take a deep breath and the only comment you can muster is a chipper, “Nope! Not at this time.”


This is a common mistake in interviews in general but can be a huge mistake for assistants. Never miss the opportunity to ask additional questions of a potential executive. Especially if you can ask questions that speak more to their personality and needs.

You see, most executives think in terms of tasks. They need someone to book their flights, file their expense reports, put together their presentations, etc. Maybe they have personality or work style in mind. However, assistants think in terms of future needs and environment. Duties listed on job descriptions are nearly identical across the board. Assistants want to know what it’s like to work with someone. Digging for this information usually falls to the assistant.

So, how do you dig up these nuggets about the executive? Here are a few questions to get you started.

1. What is the biggest challenge you are facing in the next six months?
Aside from showing a genuine interest in the state of business and their workload, this gives you valuable insight into the environment you will be entering. Are sales down? Will he be frequently traveling? Is the company going through a branding overhaul? Listen carefully and find opportunities to reassure the executive that you are the right person to partner with them for these challenges. For instance, learning that their top priority is evaluating cost-saving process improvements and at a past job, you successfully ran a program that saved the company a significant amount of money opens the door to share your experience and show you’re the perfect fit!

2. How would you describe your communication style?
Do they like context and details? Or are they strictly “be brief and be gone” people? What tools do they primarily use to communicate – text, email, phone? Are they app-friendly or stick primarily to traditional manners of handling business? Communication will be your biggest tool and can also be your biggest downfall. Knowing how they communicate helps prepare you for your first day and every day after.

3. What do you not do well for yourself?
This is your super tool to find out how you can fill the gaps in their life. Maybe they aren’t good at follow-up from meetings or making time for family. Regardless of what it is, you will know where to focus additional attention to add value. I also like this question because it invites the executive to be a little vulnerable and be honest – step one to building trust!

4. From your perspective, what is the most difficult part of this role?
Asking this question will give two pieces of valuable insight. First, your executive will reveal what parts of your role or the company are sticking points. For instance, I once had an executive reveal that his micromanaging style irritated some assistants. Knowing this would drive me nuts, I was grateful I knew this at the time an offer came and I politely declined. Second, you may just get a nugget of what the last assistant struggled with or, if the executive was lucky, handled with grace. Hopefully it will align with your strengths and open the door for another quick anecdote about your superpowers!

5. How do you invest in your administrative staff? 
This is my favorite question and one I insist upon discussing in every interview. I’m not talking salaries and benefits here. I’m talking professional development. Will the company be willing to send you to one conference a year? Maybe they will invest in online administrative training and allow you to carve out time to take webinars on the clock. Will they buy you resources like training manuals and books? Maybe they will pay for your professional membership fees. Ask the question. I beg of you, ask the question. This changes the tone of the conversation from hiring “just an assistant” to hiring someone who is serious about a career as an assistant.

These questions are just to get your wheels turning.

What other questions would you add to the list?

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