Finding the right assistant can be very difficult. Hiring the wrong assistant can be a major setback. But how do you discern the great applicants from the not-so-great? The key is knowing the right questions to ask during the interview process.

6 Questions to Ask Your Potential Assistant

These six questions are specifically designed to help you discern whether or not an applicant has the potential to be a rockstar assistant.

1. How much money do you need to make to be content?

Throw the topic of pay on the table right away. You don’t want to wait till the end of the process and realize your applicant has 3 kids, a mortgage, and student loans they need to pay off – making it impossible for you to afford them.

Ask them to be honest. Ask them how flexible they are. Find out how much they really need to make in order take care of their family. If they don’t have a family, find out how much they need to make to reach their goals.

This question will save you both a lot of headache in the process, but it also shows the applicant you value honesty and openness.

2. Do you like helping people?

An assistant’s job is to help you free up time and energy so you can do your job better. They spend most of their time serving you and your team. It’s a very self-less role.

Before asking this question, you could test them out. Ask them if they’d be willing to look over an email draft or a proposal and make suggested edits. Or ask them if they could grab coffee from the break room down the hall.

Now, in some settings, doing this might not be appropriate. But coming up with a creative way to ask them to help you – before you ask question #2 – could be a huge help.

Do they jump at the chance to serve? Do they have a pleasant attitude while doing it? Or do they look at you like you’re crazy?

Do they respectfully and kindly decline with, “I would be happy to help, but I don’t work for free!” This could be the answer you want to hear, depending on their attitude and your workplace environment.

The point is this – you want to hire someone who loves helping people.

3. Do you see this job as a stepping stone to your long-term career goals?

This question can help you gauge the applicant’s honesty. Follow it up by asking them about their long-term career aspirations. Where do they see themselves in 5, 10, 15 years? Do they respect life-long assistants or see them as weak and unskilled?

Most assistants I’ve met don’t want to be an assistant for the rest of their life. This isn’t a bad thing, unless you’re looking to hire a career assistant – someone who will stick with you for 5 – 10 years, or longer.

Some applicants may lie when asked this question. They believe if they say they do see the job as a stepping stone, they won’t have a chance at getting the job.

On the other hand, if an applicant honestly says they want to be an assistant until they retire, that’s great. As long as they are self-aware, and honest enough to acknowledge that things change.

Odds are, a potential rockstar assistant will answer with something along these lines:

“I enjoy being an assistant, and could see myself doing this job for the next 3-5 years, maybe longer. That said, if I was given the opportunity to move into a different role, I can’t say I wouldn’t consider it. I see this job as an opportunity for me to learn and gain crucial experience for whatever might be next in my career. But for the near future, I believe being an assistant is the best role for me.”

4. Do you like working behind-the-scenes?

Another critical characteristic of a great assistant is their ability to work behind the scenes, and be content with it. You don’t want an assistant who craves the spotlight. You want one who is ok with spending hours and hours working on things that no one else will ever notice. In fact, they need to enjoy behind-the-scenes grunt work.

Ask the applicant how they felt the last time they got credit for something. Ask them how they responded to the person who gave them credit.

You should encourage and give credit to your assistant, but not because they need it to have motivation to do their job. You should do it because they do an amazing job. If you hire someone who constantly craves attention and accolades, you’ll soon be looking for a replacement.

5. Can you keep a secret?

Confidentiality is one of the most important traits of any assistant. If you want to delegate your email and calendar management, and any personal tasks, odds are your assistant will come across private information on a regular basis.

You cannot have an assistant who goes around talking to other staff members about all the details of your emails. “Can you keep a secret?” is a good initial question because it will likely catch them off guard. This should get their attention and allow you to dive into the topic of sensitive information and confidentiality.

6. Do you have any questions?

This might seem like a cop-out on my end, but stay with me. An applicant who answers with, “No, I can’t think of anything,” is almost certainly NOT going to make a good assistant.

Great assistants ask clarifying questions. In fact, a rockstar assistant will ask so many clarifying questions, you will get annoyed. Over time, they won’t have to ask as many, but them doing so initially shows they are detail-oriented and thorough.

You want an assistant who understands the reasons why you want things done. They also need to understand exactly how you want things done. How can they get to this level of understanding with you? By asking clarifying questions.

So, when you ask the applicant if they have any questions, you should hope they ask several.

Good luck with the hire! Are there additional questions you would add to this list? Let me know by commenting below.

If you want more advice on what to look for in an assistant, check out my post, 7 Characteristics of A Good Assistant.

My goal with this blog – and my coaching services – is to help leaders like you find, equip, and empower an assistant. Contact me here if you have any questions or need help hiring an assistant.

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