While hiring an assistant is similar to hiring someone for any other position, there are key differences.

This person will serve as your right hand.

You must trust this person without any doubt. It’s also important to like them. You’ll be spending a lot of time together, so take the time to find the best person for the job.

Form your own questions.

  • Consider what you need done.
  • What will they take off your plate?
  • What do you need to find out about an applicant to determine if they’re the right person for the job?
  • What software programs do you use? Need Asana or Trello to be used well – find the person who knows how or can learn really easily and quickly.
  • What hours do you keep?

Create the questions that serve you and your purpose.

Ask the right questions to find the right person:

“Tell me about your last boss and why you left.”

Does the applicant take the opportunity to throw their last boss under the bus? Why did they leave? How was that handled?

“What would be your ideal work environment?”

Does that come close to the work environment you can provide?

“What makes you the best applicant for this job?”

Determine the applicant’s strengths.

“Tell me about two examples of projects you enjoyed the least and what you did to make them happen.”

Everyone has weaknesses. What’s important is managing them. Examples give you the evidence and not just a vision of what their weaknesses are.

“What would you like to be doing ten years from now?”

If you’re a movie producer, you might like (or not like) the fact that your future assistant wants to be a movie director.

“How do you like to unwind away from work?”

You need to know what makes your new assistant tick. Bear in mind they won’t always be working for you, 24/7/365 (even if you want them to), and so it’s vital that they have life away from work.

Be wary of hiring someone who only wants to look after you… your assistant needs to sharpen their saw somehow and take care of themselves. If they can’t or won’t look after themselves, they won’t be able to look after you!

“Tell me something about your current or last boss he wouldn’t want anyone to know.”

This is a trick question. Your ideal next assistant should be smart here and protect their current or last boss.

Ideally, the candidate will choose not to provide a specific answer.

The juicier the response, the less you’ll be able to trust this person to be discreet.

Ask a question that poses a problem to solve. For example,

“Tell me the criteria you would use to book a flight for me from New York City to Tacoma, Washington.”

You might have a computer available for them to tell you what flight(s) they would use. Do they put you on four connecting flights and take up 13 hours of your day?

Inquire about their previous experience as an assistant.

Tell me about a challenging experience and how you handled it.

“Explain the tasks you did on a regular basis. What did you like/dislike about that position? What did you learn from it?”


If you need some support or just a sanity check as to who your next assistant can be for you, please set up a strategy call with Helen here at Your People Partners. She’s helped hundreds of business owners like you hire their first and next assistant.

Here’s where you can book the call.