Imagine this — tomorrow morning you arrive at the office, say “Hi” to your assistant and ask, “Did you get my email? Is everything taken care of?”
Your assistant responds with, “Yes, I got your email. In fact, I got all 27 of your emails. Oh, and I stayed up until midnight meticulously taking care of each one of them. Just like I’ve done for the past three years. What about you — did you get my email? You know, the one I’ve sent nine times, but still haven’t gotten a response to? Or were you too busy checking twitter yesterday? It’d be nice if you’d do your share of the work around here.”

Ok, that probably won’t happen. At least I sure hope not. That said, your assistant may have legitimate concerns about their job.

If so, would they voice those concerns?

Is the environment you’ve created conducive to honest and open communication?

Is your assistant running out of steam, but too afraid to say it?

It’s time to find out.

Be a Better Boss

I suggest asking your assistant most — if not all — of these counterintuitive questions I put together.

But before you do this, I think it may be helpful for you to hear what assistants all over the world have to say about their bosses.

I recently asked dozens of assistants — from all types of industries — to complete the following sentence:

“I wish my boss would…”

Thankfully, I did not get what is apparently the number one way employees finish that sentence (at least when typing it into google search)…



As you read the responses below, think about how you are leading your assistant.

Note: I took out personal and business names for confidentiality reasons, as well as made minor edits for readability.

I Wish My Boss Would…

“…take 10 minutes to meet with me at the beginning of each day to go over the day’s calendar and to-dos. Then 5-10 minutes at the end of the day to download/catch up. We juggle a bunch of different shows, so it’s super easy to lose track of things. This would definitely help me visualize my daily goals (reminding him of appointments, deadlines, important calls to make), as well as keep us mutually accountable for what is still unfinished.” On this note –> Click to snag my FREE meeting agenda template to help you and your assistant be more productive when you meet – even if only for 5 minutes! 

“…have treated me more as part of his team instead of just “the help.“ I would have liked more responsibility in some positions. Top executives are so busy they forget they have a person that can take the load off a bit.”

“…show/verbalize confidence in my abilities.”

“…communicate exactly what he needs from me because I’m competent enough to do it all, but I cannot read minds.”

“…understand that people and various personality types process information differently. And while I foresee myself excelling in this position, oftentimes it’s difficult to know how to properly proceed without direct communication. I’m no mind-reader, and I often feel that I’m expected to “hit the ground running” and naturally know what to do with vague or incomplete instruction.

When I make a mistake, I would value using that as a growth opportunity, and I would listen to the constructive feedback and move forward. I feel that many individuals in management roles are so inundated with responsibility, they often neglect to properly communicate with the ones who are attempting to shoulder their load of stress.”

“…understand the importance of communication.”

“…understand I have their best interest at heart and my goal is always to make them shine (regardless of our interpersonal relationship). I’m a consummate professional and it is my job to do this, and do it well.”

“…give deadlines and expectations rather than just a request. For example tell me to set up a meeting with these people and it needs to occur within the next 5 days, or ask me to please submit such and such report to me by the morning of the 15th each month, because he must use it to report to the next level on the 16th.”

“…have an open door policy with all employees. This would allow us to stop by and be candid, direct, and assertive with him about what we are thinking. It would give us an avenue to share our ideas for the growth of the company.”

“…let me tackle more difficult projects.”

“…realize just how much hard work a personal assistant does behind the scenes. Things don’t just magically happen. Most of the time, they require lots of time and effort!”

“…continue to support and consider my position as a key role in the team.”

“…improve his time management.” –> Manage your time with my FREE ideal week calendar template.

“…provide more consistent feedback.”

“…appreciate every employee as much as he appreciates me.”

“…stop scheduling appointments on top of already scheduled appointments.”

“…slow down a little bit. We have a major project going on and he is running around like a headless chicken!”

“…pay me for the work I do for him and the other directors.”

“…read the wrap-up email we send at the end of the day! The email summarizes the accomplishments from the day, appointment reminders, etc.”

“…understand that when I have personal holds on her calendar, it’s to catch up on things so I can do my job better.”

“…communicate! He thinks I’m a psychic, which is true most of the time. But I really need his input to keep his practice going.”

Ask and Listen

Perhaps your assistant has similar thoughts. Or maybe reading the above responses gave you ideas on how to be a better boss. Either way, I would encourage you to ask your assistant to be honest, and listen to what they have to say.

And don’t forget, you can refer to these 9 questions if you don’t know what to ask.

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.

Download FREE Chapters