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Interviewing Your Future Employer: a Crucial Guide for Assistants


One thing I have learned over the years from being in various assistant roles is that it’s so important to look at the interviewing process as a two-way street. It’s so easy to want to impress the person you might be supporting but stepping into a partnership is a commitment, so you need to do your part to determine if it is a fit and that there are very few surprises.

It’s important to ask questions that will give you a clear view of the role, an accurate overview of expectations and a better idea of the personality of the person you would be supporting. We all want to ensure we step into a new job that aligns with our values, career goals and notion of work-life balance, so by preparing questions to gather this information you are increasing your chances of knowing if it’s a partnership that will mesh well.

Being prepared with questions not only helps for you to gauge if the fit is present but also shows your high level of interest in the role and your level of preparation. If you don’t ask questions you are running the risk of looking less interested in the role than other candidates. Also, a lack of question asking on your end can make you appear unprepared and like you simply showed up for the interview; your potential employer could translate that into you possibly not being the type of assistant that goes above and beyond.

I recommend making a list that’s longer than you think you need, around 15-20 questions. A large bank of questions covers you since chances are some might be answered along the way. The bulk amount also gives you the opportunity to pick and choose what is the most relevant based on where the conversation steers; this helps to keep the flow of the conversation and gives it more of a two-way nature. Moreover, make sure you prioritize your list and ensure the questions are concise; you don’t want to make your possible future employer glaze over due to unnecessary wordiness.

Remember to bring relevant printed copies to the interview to refer to when asking questions. Print the job description for you and your potential employer to refer to during the interview; you could highlight sections and add notes on your copy to reference during the interview process. Also, bring printouts from the company’s website that you might be asking about, such as the company’s core values and/or mission statement.

Questions for your potential employer

To help you get your question list started, do research to see if there are any additional details you could benefit from. I recommend looking at the following sources for this: the job description, the company website, all email correspondence about the role, your potential employer’s LinkedIn page and other helpful websites that provide information about him/her. For example, if the job description simply states “event planning” you could ask for specifics about the events you would be organizing (ex: Would the events I’d be organizing be offsite or onsite? Would travel be required for these events?). These details might shed light on aspects of the role that you wouldn’t know about otherwise, such as travel requirements, which could either make you feel even more sure about the fit or could be deal breakers.

Here are some possible general questions to ask your potential future employer to help you brainstorm what would be relevant for your list:

  • Could you please tell me more about your role and day-to-day responsibilities?

  • What is the biggest challenge you are facing in your role at the moment?

  • What would a “typical” day be like for me as your assistant?

  • What is the breakdown of the role and approximate percentage of time I’d be spending in each area? From the job description, it appears to be 25% travel management, 50% calendaring and 25% personal assistant related tasks. Does that sound accurate?

  • If I were able to provide support right now, what would be the top items I could take off your plate today to ease your workload?

  • What are some examples of big projects that I’d be working on?

  • What are the biggest challenges of this role?

  • How many assistants have you had?

  • How long was the previous assistant in this role?

  • Why did the previous assistant leave this role?

  • What qualities did your previous assistant(s) possess who excelled in this role?

  • Were there any areas your previous assistant(s) could have improved on?

  • What characteristics and personality traits are you looking for in your ideal assistant?

  • Is this a role where I’d be given more responsibilities over time?

  • How do you see this role changing over the next [insert time period]?

  • Is there someone who would provide backup for this role when I am away? Would I be backup for that person as well?

  • How would you describe the company culture?

  • How would you describe the company’s atmosphere?

  • Are there any changes on the horizon for the company?

  • What are examples of qualities someone in this role would possess that would show they embody the company’s core values?

  • What do you enjoy most about working here?

  • What is your preferred method of communication?

  • Do you require the person filling this role to be on call after scheduled work hours?

  • How often do you like check-in meetings with your assistant? Weekly? Daily?

  • What would my general schedule look like? Is overtime required?

  • How often do you travel?

  • Do you have a travel agent or would I be responsible for all travel research and bookings?

  • Would travel be required on my part?

  • What kinds of events would I be organizing?

  • How much of the day would you estimate involves calendar management?

  • What kind of personal tasks do you need support with?

  • Is there anyone else I would be supporting? What is the percentage of time I would be spending supporting them?

  • Who besides you would I be working closest with?

  • Is there anything not listed on the job description that you would need my assistance with?

  • Would I have a point of contact for general questions when I start?

  • What computer programs would I be using most often?

  • Do you use a task management program?

  • Will I be given a Mac or PC?

  • Are there opportunities for continuing education or development?

  • Do you provide ongoing feedback?

  • How often are reviews and what is that process like?

  • Do you have any concerns about me being a fit for this role?

  • What are the next steps?

  • What is your hiring timeline?

  • Could I please email you if any questions pop into my mind later? (Ask for their business card if you do not have their contact information.)

Be sure to take notes during the interview and circle back with clarifying questions if you need more detail. An example question is “Could you please give me more information about [insert topic] that you mentioned earlier?” This not only will help you to get those more precise pieces of information, but also will show the other person that you are a great listener, think about details and are a forward-thinking person.

Also, do your homework and try to learn as much as possible about the company (or companies) the person you would be supporting manages as well as what their job entails. This helps with tailoring questions to be more specific. There might be a certain aspect of their role you are unclear on which could help you to better understand how you would be providing support. Also, there could be something about the company that you need more clarification on which could relate to the support you’d be providing.

Questions to ask the previous assistant(s)

Sometimes you will be lucky enough to meet the previous assistant at some point in the interview process. I’ve interviewed several candidates who were either filling my current role before my departure or were being hired to work as part of my assistant team and I cannot stress how much of a golden opportunity this is. Here are examples of some questions for you to tailor to meet your interviewing needs:

  • How long have you been in your role?

  • Why are you leaving this role?

  • What do you like the best about your job?

  • What do you enjoy the most about supporting [insert principal’s name]?

  • What do you enjoy most about this company?

  • What have been the biggest challenges for you in your role?

  • What do you think are the biggest challenges I’d face in this role?

  • What would a “typical” day be like for me?

  • Is there anything not on the job description that you think I would be responsible for if I stepped into this role?

  • How do you usually communicate updates with [insert principal’s name]?

  • How often do you have regular check-in meetings with [insert principal’s name]?

  • How have you successfully managed your task list assisting [insert employer’s name]?

  • Does [insert principal’s name] provide sufficient details when assigning tasks?

  • What is a usual schedule for you? How often do you come in early or stay late?

  • Is [insert principal’s name] schedule back to back or is there typically buffer time?

  • Does [insert principal’s name] typically run on time or do you need to give warnings when it’s close to time for their next meeting? How have you gone about those reminders?

  • How would you describe [insert principal’s name] personality?

  • What are your favorite as well as least favorite parts of assisting [insert principal’s name]?

  • Who do you work closest with? What is their personality like?

  • Is there anyone who has been challenging to work with in this organization? How did you handle that challenge?

  • Do you have any general advice for me if I were to step into this role?

  • Could I please email you if any questions pop into my mind later? (Ask for their business card if you do not have their contact information.)

If you will be working alongside or under the other assistant, be sure to ask them about what they are looking for in candidates as well. A few examples are:

  • What qualities are you hoping the person in this role will possess?

  • What skills did the previous person in this role possess that helped him/her to perform well?

  • What tasks would we be working on together?

  • Are there any tasks I could take off your plate if I stepped into this role?

  • Check out their LinkedIn profile since they might have their current responsibilities listed, which could help for brainstorming questions.

In addition, if you would be working with the current assistant, ask questions to generally get to know them better. Not only is it flattering for people to know that the other person has a genuine interest in them, but you will be able to gauge if you would enjoy working with them. This is something you will need to feel out along the way and insert appropriate questions as the opportunity arises. Here are some example questions:

  • How long have you been a [insert their job title here]?

  • How did you end up in this field?

  • Keep your ears open for questions that you could ask them as well. Ex: They might ask “What do you enjoy doing outside of work?” After you answer you could ask, "What about you?"

As I mentioned in the previous section about the time with your potential employer, be sure to take notes during your time with the current assistant and circle back with clarifying questions. The assistant will most likely have significant weight in the final hiring decision and you want to treat your time with them with the same importance as you give your potential employer. They will notice how well you take advantage of the opportunity to learn their perspective. Take this time seriously and you will have a huge leg up.

Final thoughts

Finally, I want to close by reiterating that the interview process is an opportunity for you to properly weigh if the role would be a good fit for you, not just for the other side to assess if you are a possible fit. It’s important to make sure you would be happy, successful and your requirements would be met long-term. This is a big decision to make and asking questions will allow for a clearer assessment of the role and the type of partnership you would be stepping into.

What questions have helped you to determine if a role would be a great fit for you? Please comment below!

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