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5 Lessons Learned from a Silicon Valley Executive Assistant

If you’re overwhelmed by the challenges you face as a professional administrator, know that you are not alone. As the executive assistant for a very busy, very connected CEO for an outsourced financial services firm, I have faced my share of challenges — and I continue to face challenges on a daily basis (which keeps me on my toes!).

But, for the most part, I’ve managed to conquer the biggest challenges through experience, trial and error, extreme organization, and a handful of must-have apps. Hopefully, my lessons learned can help you to slay your own work dragons and be more efficient.

In my experience, these are the biggest challenges admins face on a daily basis, and some helpful tips:

Challenge #1: Not Enough Time
Solution: Prioritize

The common refrain of all busy admins (myself included) is that there just isn’t enough time. This is why it is so important to time track and prioritize. Most of my tasks now are routine, so I know exactly how long each takes. It’s become a time management exercise: how can I fit it all in given how long each item takes and how many hours there are in each day? Sometimes you’ll need to defer to your executives for help prioritizing. List all of the items on your to-do list and ask your executive to rank the items in order of importance.

Challenge #2: Too Many Side Tasks – You Find Yourself Wearing Too Many Hats
Solution: Outsource

Just because an efficient admin can literally do it all, doesn’t mean she should. Ironically, the company I work for helps other companies outsource their financial and administrative pain points, but, soon after starting at Early Growth Financial Services, I realized I had no help myself. Fortunately I was able to convince my executive to identify all essential functions and create an organizational map. This led to us hiring a new office manager and outsourcing some non-core functions, which freed me up to focus on my core responsibilities.

Challenge #3: Lack of Organization
Solution: Putting systems in place

I have a confession to make: I’m an organizational junkie! When I was starting out, there were no systems in place; a few tools later, I have everything under control. For example, I have a bunch of different apps I use for email, most notably Boomerang which helps me keep my goal of a clean inbox and schedule up to 60 appointments per week. When I first came on board, all of our documents were hard copy. So I scanned for three weeks straight until we had digital copies of all of our documents. This took time, but in the long run this paperless solution is more efficient, easier to maintain, neater, and more environmentally conscious.

Challenge #4: Work / Life balance
Solution: Boundaries

How can you create boundaries and make time for yourself when your work is never-ending? Especially when you’re young and just starting out and trying to advance your career, it is so easy to fall into the trap of having no boundaries. To create some semblance of work/life balance, you need to create a strict routine. in which the boundary lines are more pronounced and it’s harder for you — or others — to blur them. For example, I just went to London on holiday for a week. During this time, I agreed to work, but I set limits: 2 hours a day, 3 days a week for a total of 6 hours. The rest of the time? My time!

Challenge #5: Boredom
Solution: New projects

Once you’ve got your systems in place, know how to schedule a high volume of appointments, and are set up for success, boredom can creep in. This is when I find myself looking for new projects or optimization opportunities. Most recently, I’ve started assisting with social media. This is a totally different area for me, and one I find really interesting. It’s forced me to learn new things and create new systems for social media management.

Sometimes the biggest challenge to being an admin can be how isolating it is. Sometimes you feel like you’re all alone behind the curtain, holding the pieces together, making sure that everything gets done. At times like these, it’s important to remember how integral your work is to the success of your company and how there are lots of people within your organization who can lend a hand, and lots of people outside of the organization who are willing to share their insight and support.

 What are your biggest challenges — and how do you overcome them (or not!)?


  1. Signed up today for Office Ninjas … thanks for the tips & ideas. I’ve been an administrative assistant 34 years at my present job; I always welcome new ways of getting the job done. Awesome site!

  2. I love baydin. I don’t know what I would do without!

    To get my contacts into a spreadsheet, I have added them onto my cell phone (which syncs with my google contacts) then exported the google contacts into a .cvs file, then converted the .csv file to an excel file.

    If you have a better process, please let me know!

    Thank you!

  3. Good Morning Janine,
    I loved your suggestions for organiztion and was wondering if you would be willing to share what other apps you use to help keep yourself and office organized?

    1. Good Morning Monica,

      Here are a few of my favorites (on top of the usual – Google Calendars/Drive/Etc):

      CardMunch – My boss is a huge BD guy. He ends a workday with stacks of business cards. There is nothing I hate more than data entry. CardMunch allows you to take a picture of the business card, save the information directly to your phone (and mine is set to back up on Google Contacts), and quickly add the contact on LinkedIn!

      Boomerang Calendar – I DON’T KNOW HOW I EVER DID MY JOB BEFORE I DISCOVERED THIS APP! (Can you sense my excitement?!) When I am scheduling, rather than flipping screens, the app will pull up my executive’s calendar, and allow me to click on open slots. Then it will compose an email with the options. It also gives you the option to mark the items as “tentative” on your calendar so you know if you already offered the time slot to someone else.


      Do any of these times work for you?

      Monday, Aug 12, 3:00 PM – 4:00 PM (PDT)
      Wednesday, Aug 14, 1:00 PM – 2:00 PM (PDT)
      Thursday, Aug 15, 11:00 AM – 12:00 PM (PDT)

      Hootsuite – If you handle any of the social media, this makes life much easier. I am able to manage twitter, FB and LinkedIn from one place.

      Expensify “Expense reports that don’t suck!” – Such an easy way to create expense reports!

      I have all the Google Apps on my phone just in case I get an email on the go. How often do you step out to lunch, put your car into reverse, then get an email requesting that a document be sent “ASAP!” (daily, right?) So I keep the Google Drive app on my phone.

      I make a point to keep everything I possibly can online and in a Chrome app. I am never in the same place two days in a row, and need everything to be easily accessible.

      … and does the Starbucks app count as a productivity app? ;)

      I hope this helps!

      1. Great tips, Janine! Looks like the folks who created Boomerang Calendar has a lineup of other productivity tools.

        With CardMunch, have you found a way to export the contacts into an excel spreadsheet?

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