Sponsored by Oregon Business

How to use your new virtual assistant

| Print |  Email
Business tips
Friday, August 23, 2013



08.23.13 Blog VirtualAssistantCEO Kathy had just decided to hire a virtual assistant, Sissy. (I’m coaching Kathy.)

“I’m trying to get ready for my first meeting with her, and I’ve got so much she could help me with,” Kathy said.

“What does ‘so much’ mean?” I ask.

“Well, lots of administrative stuff,” Kathy said, her voice becoming uncertain.

“Can you give me three examples?” I ask.

Long pause.

Kathy is about to re-create the train wreck I had when I hired my first virtual assistant in 2008.

You can’t delegate things that are vague. And boy was I vague.

Thousands of dollars later, I had spent more time haggling with the oversees “virtual assistant” firm than it would have taken me to do the work myself. Their attempts to set appointments for me alienated my prospects. The spreadsheets they sent me were impossible to read. And I felt … lost … as I tried to describe what I needed.

Jump forward to a slightly smarter me.

“Kathy, here’s what you might try,” I say.

First: Use your assistant as an attentive listener.

It’s very common to want to hire an assistant when your head is swimming with too much work. However, even a psychic assistant who can “read minds and see around corners” can’t help you yet — because your head is swirling too much.

Here’s how to move rapidly to clarity.

First, tell your assistant to take notes and ask questions, and then start dumping out what’s in your head. (Use a digital audio recorder if you talk faster than he types.) No organizing (yet), no ordering or prioritizing. Just dump:

  • The trip to be planned
  • The proposal to be made
  • The followup call you owe Fred
  • The rattling sound in the front suspension of your car
  • The billing change the client requested
  • Everything else you think of, as it occurs to you

Now go through your calendar and look for more dangling issues. Appointments from last week that remind you of something you need to do. Anything. Everything. Just keep talking out loud. (Don’t be afraid to let silence stretch as you look for things.)

Now go through your executive notebook and look for more dangling issues and unfinished business. Keep talking out loud.

Now start at the left edge of your desk and look at each object (piece of paper, business card, whatever) you encounter. Does it involve an unfinished task? Say it out loud. Work your way from left to right across the work surface. Keep going until you run out of objects.

For a stack of 18 business cards you collected at a trade show, put a rubber band around them and treat them as one thing (for now). Don’t go crazy deep.

Second: Use your assistant as a typist, transcriptionist, and thinker.

Now, take a break and work on something, while your assistant types these up — in a spreadsheet — as a list of items to be resolved.

At first the spreadsheet will only have one column:

  • Issue or Item (what you said out loud)

Now, ask your assistant to add these columns:

  • Priority (from 1 = low to 5 = high)
  • Topic Area (5-7 topics like ‘personal’ or ‘admin’ or ‘clients’)
  • Immediate Next Step (leave blank for now)
  • Who will do it? (You or your assistant or someone else)
  • Context (more below)

To help your assistant grow, ask him to make a guess on each item for Priority and Topic Area. The idea is not that he’ll guess right on everything, but rather to get him to make some guesses at what your priorities are. Long term, you need your assistant to know your priorities — so this is your first step at educating him.

Plus, his guesses will tell you a lot about his thinking style — and what impressions you give people about priorities.

Now walk through the list with him. If you’re highly social, do it interactively on a big computer screen, you talking and him typing. If you’re solitary, print the list and mark it up with a pen. If you’re more verbal and don’t process written words well, have him read each item aloud. In any case, take time to share your thinking about priorities and topic areas.

Take time to fill out each column.

Example dialog

Assistant: “This item just says ‘Mom.’”

You: “Ah, right, I’m taking my Mom out for her birthday. It’s next Thursday.”

A: “My guess is, Priority 5? And Area is ‘Personal’?”

Y: “Yes and yes.”

A: “Immediate next step – make a reservation?”

Y: “No… I want to scan a list of Ethiopian restaurants and pick one we haven’t been to before. Can you do that?”

A: (Good naturedly): “Of course. I’ll have the list to you by 5 PM tomorrow. Email OK?”

Y: “Yes. Context for the Next Step for this item is ‘Computer.’ So we’re done with this item. What’s next?”

The Importance of Context

Every To-Do list should have a ‘Context’ for the task (hat tip: David Allen) — this is the tool you will be using, or the place you need to be, or the person you need to be with, in order to do the task. Contexts are things like ‘Phone’ and ‘Computer’ and ‘Desk’ and ‘Assistant.’

It’s very powerful to sort your to-do list by Context, figure out your current context, and knock out half a dozen tasks quickly. It’s much easier to make 6 phone calls in a row than to jump between phone calls, emails, letter writing, and filing.

Congratulations. You and your new virtual assistant are now on the road to an excellent working relationship.

Tom Cox is a Beaverton consultant, author and speaker. He coaches CEOs on how to boost performance by building workplace trust.



+1 #1 Excellent ArticleGuest 2013-08-24 11:27:19
Great article! As you point out, ensuring you provide specific details for every virtual assistant task is essential for a great working relationship. I often just use the 5W's (Who, What Where, When, Why) to provide the structure for tasks I delegate to my VA's.
One thing I'd add: Ensure right from the start that you ask your VA, "What's the best way to communicate with you?" as obviously communication is the most important aspect of any working relationship. Maybe they communicate best talking over Skype. Maybe its Google Chat. Maybe just email will work. Regardless, unless you can communicate and communicate well, none of these ideas you list will work.
Thanks again for the great info!
George Smolinski, M.D.
Four Hour Physician
Quote | Report to administrator
+1 #2 Michell jackelGuest 2014-04-10 18:48:26
But what you think about professional virtual assistant should I treat him like this first time. I hired dedicated resources for my business.
Quote | Report to administrator

More Articles

Make the business case, governor

Linda Baker
Thursday, November 05, 2015
aoikatebrownthumbBY LINDA BAKER

Gov. Kate Brown delivered the keynote speech at the Associated Oregon Industries annual policy forum yesterday.  Speaking to a Republican-aligned audience of about 100 business and public policy leaders, the governor was out of her comfort zone.


5 questions for Ruby Jewel creator Lisa Herlinger

The Latest
Saturday, October 24, 2015

What's it like working with your sister and how do you compete in Portland's crowded artisan ice cream space?


Big Geek

October 2015
Monday, September 28, 2015

To attract technology companies, the U.S. Bancorp Tower repositions itself as open, light and playful.


Salad Days

October 2015
Monday, September 28, 2015

How Portland's Garden Bar plans to become the Starbucks of salad.


Photo Log: Vigor Industrial, Swan Island Shipyard

Tuesday, November 03, 2015



Planter's Punch

November/December 2015
Wednesday, October 28, 2015

Molly Rogers believes she has found the solution to excessively syrupy cocktail mixes. She first just needs people to understand her product isn’t foliage.



November/December 2015
Wednesday, October 28, 2015

The world's second-largest wind energy project yields costs and benefits for a sheep-farming family in Eastern Oregon.

Oregon Business magazinetitle-sponsored-links-02