Questions to Ask

A common struggle for assistants is (ironically) communication with our bosses. We have the most to share with our leaders, but often the least amount of time to discuss it. As assistants, we strive to be "high capacity and low maintenance" so we avoid making time to ask questions, because we feel like that would make us "high maintenance and low capacity". Unfortunately, our NOT asking questions or getting clarity (both in general and on specific situations) only leave us more vulnerable to guesswork and susceptible to mistakes.

I have had the honor of serving my boss for six years, but I still regularly evaluate my role, ask questions, and seek clarity (because even after years, I drop a ball almost every day and can always get better at what I do). If you have NEVER met with your boss to hear their expectations, preferences, and language, or if it has just been a while, I would HIGHLY encourage you to set up time to meet (you have their calendar). Once you have had an initial conversation, there is an open door to continue this dialogue at any time. It doesn't have to be anything super formal, just a chance for them to share clearly with you. Here are some questions that I try to ask my boss at least annually (I don't ask all of them at one time): 

In the questions below, "you" refers to the boss and "me/I" refers to the assistant. However, it would be equally helpful for you (the assistant) to have your thoughts/responses on these as well, in case the conversation is reversed.

What are your expectations of me as your assistant? (i.e.:work hours, dress code, responsibilities)

How can I add the most value to you, your family, and this company? 

What are your top priorities or big rocks to land this year? How can I help lighten the load of these, move them forward or keep them in front of you? 

Are you feeling healthy in your priorities and schedule? 

What are your pet- peeves? (i.e.:margin in calendar, meetings starting on time, unconfirmed appointments, incorrect grammar in emails) 

What am I doing that really helps you? (this is an opportunity for you- the assistant- to share what you love most about your job as well)

What are some things that I could work on? (this is an opportunity for you-the assistant- to share things that you feel weak in)

We have worked together for ________, in what areas do you feel I have grown as your assistant and how can I improve?

Do you like the way I handle the areas you have entrusted to me? Is there any major changes you would like to make? (i.e.: print out all emails, set up a daily hour meeting with assistant, or change calendar scheduling)

How can I better serve you? 

How can I be a better assistant for you in this season? (i.e.: personal tasks, events, speaking preparation, travel preparation, vacation planning)

Is there anything else you would like to share that can help me be a better assistant to you and your family? 

Is there anything you notice in me personally that you feel I need to work on? (i.e.: don't take things so personally, work on time management, better communicate your coming and going)


Your Turn: Do you regularly evaluate yourself? What are some questions you ask your boss?