Giving a great interview takes practice, but once you discover which questions yield the most illuminating responses, you’ll be able to ferret out the best candidate in no time!
Show the candidate that you’re serious about finding the right person for the job by being prepared and engaged. Ask purposeful questions that get you the important information you need to make a decision. Your passion for finding the right person for the role will energize the candidate and leave the impression that the role is important to your success and to the success of the company. When you give a thorough and memorable interview, candidates will leave energized, hoping they made a good enough impression to get the job.
Read the resume in advance. Do not waste valuable time with candidates simply reviewing their resume and their previous jobs chronologically. This is your chance to really get to know who they are and how they could be a real asset to your team, so make sure you maximize your time with them!
The Questions/Prompts
Explore KangarooStar’s list of interview prompts/questions, try a few that are new to you, and see what works for your process.
Tell me about your background and how it has prepared you for this role.
Why this prompt is a good one: This gives candidates a chance to advocate for themselves, especially if they haven’t had traditional experience or education. It will also give you a chance to see how they see themselves in the role you’re offering.
What you should look for in the answer: Self-confidence and the sense that the candidate sees a career trajectory. One thing leads to another, and the relationships between each step along the way are important to understand and appreciate. You want an assistant who has aspirations beyond the current role, so you can eventually promote them or enhance their assistantship role to include more responsibility.
Describe a typical day in your current job.
Follow-up questions: Which parts do you like best, and which parts do you like least?
Why this prompt is a good one: You can learn so much from a candidate with this question. First, you want to get a sense for their current workflow and how they’re accustomed to moving throughout their day. Do they gravitate toward liking routines or do they thrive in a constantly changing environment? Does their current typical day and responsibility set mirror the opportunity you’re offering or is it substantially different?
What you should look for in the answer: Look for cues that their likes/dislikes match the role you’re offering. If they really dislike coordinating schedules, let’s say, and the role you’re offering requires this skill in spades, this may be a consideration in your hiring decision.
What do you love about your existing role?
Follow-up question: What would be the one responsibility you would give up if you could?
Why you should ask both of these questions: Fit is so important when it comes to job matching, so you want to not only understand each candidate’s preferences, but the parts of their job they don’t like so much.
What you should look for in the answer: Just by listening to the candidate’s assessment of their current role, you should get a good sense of whether they’ll fit into your office/team culture. You should also get an idea of the areas where they’ll excel. Or where they might need a little more training or encouragement. Humans tend to shy away from doing things they don’t understand or where they don’t excel. If you run across a candidate who dislikes an aspect of their current role, ask them why. It may be because they just need proper training and mentoring. (This is good advice for managers, too, by the way! Instead of throwing the baby out with the bathwater, as they say, teach the young one how to be a better swimmer!)
Tell me about a time when you were truly challenged by your job.
Follow-up questions: What was the situation? How did you handle it? What was the outcome? How did it change you?
Why this prompt is a good one: You want to hire someone who isn’t afraid of a challenge, someone who will recognize a challenge and rise up to meet it.
What you should look for in the answer: Take note of what the candidate considers a “challenge” on the job. It’s not how they solved it—though give extra points for creative solutions, for sure—but how they handled it. You want an assistant who can stare down any challenge, no matter how big, and come out victorious.
How do you manage people or tasks that all demand to be prioritized?
Follow-up questions: Can you share a time where you created a solution in which everyone was happy? Can you give an example of a time when you had to prioritize in a way that left someone unhappy with the outcome?
Why you should ask these questions: The answer should help you see the candidate’s agility quotient. Can they stop short, regroup, and change directions in the blink of an eye? You need someone who’s able to see priorities changing in real time and act accordingly.
What you should look for in the answer: A good juggler! In other words, can the candidate manage multiple priorities and make sure all deliverables are met? Do they see how all the pieces of a working home or office fit together? And … are they okay with not being able to please everyone at once?
Tell me about your biggest professional mistake?
Follow-up questions: What was the situation? Who was impacted? How did you resolve it? How has this changed you?
Why you should ask these questions: Everybody makes mistakes. Owning up to them, learning from them, and moving on knowing you’ll never make that same mistake again are the hallmarks of an excellent hire.
What you should look for in the answer: Look for humility. Look for someone who understands that mistakes happen, that sometimes there are consequences, but that it’s not the end of the world—especially if you do all you can to make it right.
Describe a time when you failed to be discreet to the level your employer required.
Follow-up questions: What was the situation? What was the mistake’s impact? How did you reconcile the situation?
Why you should ask these questions: Showing a lack of discretion is a little trickier than merely making a mistake. Everybody makes mistakes. But an assistant who is lacking in discretion is in the wrong line of work.
What you should look for in the answer: You want the candidate to assure you that they’ve never failed to be the soul of discretion. If they do admit to a small misstep—leaving confidential documents on the copier, for example—it shouldn’t be a deal-breaker. But if the candidate fesses up to a real zinger—accidentally spilling the beans on a corporate merger, say, or sharing their employer’s private financial details with a friend—you’ll have a pretty bright, red flag to consider.
Everybody makes mistakes. Owning up to them, learning from them, fixing them, and moving on knowing you’ll never make that same mistake again are the hallmarks of an excellent hire. You’re not looking for a perfect human here, you’re looking for someone who has integrity, is honest, and who will do what it takes to fix their mistakes.
Tell me about a time when you saved the day.
Follow-up questions: What was the situation? Who was involved? How did you create the solution? What was the result? How did that change you?
Why you should ask these questions: EAs are known for all sorts of heroic, day-saving acts. Little ones and big ones. You’ll likely hear a relatable story while getting a feel for what the candidate thinks is heroic. Is it staying late to support the team until a project is finished? Is it putting out a fire before it bursts into flames? Is it being prescient enough to see that the office coffee stocks are low? You want to understand what “above and beyond” and “impact” mean to the candidate. Will they have an impact on your business? What does hard work mean to them? Are you aligned?
What you should look for in the answer: Look for a candidate who knows their worth and sees their role as an important one to your success. Look for pride (with a dash of humility). And if you get an EA that says, “I save the day every day!”? Hire them!
Where have you made a significant impact on your team or boss’s success?
Why you should ask this question: You’re looking for a forward-thinking assistant who recognizes the impact they have on your bottom line and/or brand/personal reputation. If they have a great answer for this question, you’ll know you’re looking at a strong, capable candidate.
What you should look for in the answer: Evidence that the candidate sees the difference between just doing a job and having an impact on the team’s success.
What would your current employer say are your three greatest strengths?
Follow-up question: Where would they say you were still working to improve?
Why you should ask these questions: The answers here will tell you whether the candidate has a good connection with their employer’s needs and expectations, which is key in assistantship roles.
What you should look for in the answer: Self-awareness.
With your previous/existing range of responsibilities in mind, what might be different in this new opportunity?
Follow-up question: What about this new opportunity is exciting for you?
Why you should ask these questions: The answers will not only give you a good idea of the candidate’s strengths, they’ll indicate whether this candidate is motivated by new challenges.
What you should look for in the answer: Evidence that the candidate has really read and considered your job description and is energized by the opportunity to work for you.
Do you have any questions for me?
Why you should ask this question: A candidate who’s truly interested in the opportunity you’re offering will have questions.
What you should look for in the answer: Evidence that the candidate has been listening to you, number one. And number two, evidence that the candidate understands the role and can see themselves in it.
