A good assistant knows what you’re thinking and anticipates your needs. But do you know what your assistant is thinking? Do you know what they need? Do you even care? Why should you care?
9 Counterintuitive Questions to Ask Your Assistant - unsplash - helloquence_photos_5fnmwej4taa-small

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How would you feel if your long-time, rockstar assistant — who took you months to find — suddenly told you she’s quitting because she wants to become a photographer, or start her own business?

You’d probably freak out and say something like, “What am I going to do without you?! Why didn’t you say anything before?! It would have been nice to have time to prepare for this.”

To which she might reply, “You never asked.”

Quick side note: I’m referring to your assistant as a female because odds are your assistant is a woman. According to the US Census, between 2006-2010, 96% of secretaries and administrative assistants were women. Of course, my point applies to male assistants too!

Help Your Assistant Help You

I’m willing to bet you don’t want the above scenario to happen. Not that you don’t want your assistant to dream of a different career — even though you may selfishly want her to stay. But other than the convenience of having a heads up, wouldn’t you also want to know so you could encourage her, and maybe help her achieve her dreams?

If you knew your assistant’s long term goals, you could give her flexibility to take some photography (or business) classes. Maybe even have your company provide a scholarship to help pay for them.

Helping your assistant — you know, the one you can’t live without — develop skills to find work elsewhere sounds crazy, right? Maybe… but your assistant is the easily one of the most important employees in your company. Investing in her will positively impact the culture and reputation of your company.

Let’s say she takes some classes and eventually leaves the company. Don’t you think she would highly recommend working for you to everyone she knows? The quality of people who would apply to work for you would increase, making it easier for you to find a replacement.

Just Ask

In my years as an Executive Assistant, one of the most helpful things my boss did was show interest in my personal life. He allowed me the flexibility to do things I loved, and encouraged me to grow. Whether it was letting me drive to Kansas City to attend October baseball (Go Royals!) during a work week, or loaning a leadership development book to me, his care spoke volumes.

Every once in a while he would ask me questions that made me think outside the box and wrestle with my life goals. He would also ask questions about our work and offer to help find solutions to my problems — not just his. It always threw me for a loop when he asked, “Is there anything I can help you with?” Wasn’t it my job to help him, not the other way around?

You can call it what you want — employee retention, good leadership, or being a caring person. However you look at it, it will benefit your assistant greatly — and in turn, you — to just ask.

9 Counterintuitive Questions to Ask Your Assistant

I recommend asking your assistant the following questions — or your own variations of them to better fit your context.

  1. What’s one thing I could do to make your job less stressful?

  2. What’s your biggest frustration with me? How can I do better?

  3. Are you satisfied with how much money you’re making?

  4. Is there an online course or class you’ve been wanting to take that would help you grow — personally or professionally?

  5. Is there a way to rearrange our weekly schedule to make things easier, more enjoyable, and/or more productive for you?

  6. Could I help you finish or eliminate any tasks on your to-do list?

  7. Are you happy in your current role? If not, what would you change?

  8. What future goals do you have? Do you feel this job helps or hinders your desire to accomplish them?

  9. How’s your family life? Can we help you pay for counseling or a nice dinner with your spouse?

You don’t have to ask all of these questions in one sitting, but make it a regular practice and you won’t regret it. Also, if you don’t listen and take action on what’s possible to take action on, there’s no point in asking.

Comment below to let me know it goes, and feel free to share any additional questions you would add to the list!

Are you overwhelmed and on the verge of burnout? Get one-on-one help finding an assistant or developing your assistant, so you gain more time, energy, and success! Learn more about my coaching services here.

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