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4 Types of Personal Assistants (2 of Which You Need To Avoid)
by David Finkel for

April 19, 2018

Tired of doing your assistant's job for them? You should take a moment to think about the four kinds of personal assistants and which one is right for you. (Hint: You need to avoid two of them!)

Are you hiring personal assistants who save you time or who cost you time?

Recently, I invited thirty-five of my top business coaching clients to a private retreat in Jackson Hole, Wyoming, where I live. We were discussing the various aspects of leadership - the ways that business owners can create strategic advantages and breakthrough results for themselves and their companies - when somebody asked me about time management.

That question prompted a lively conversation about the best ways that each of us had found to leverage our time. And it became clear that the extraordinarily successful entrepreneurs whom we had in that room were losing valuable time because their assistants weren't capable enough or empowered enough to do the work required of them. So I started to talk about the importance of hiring assistants who best suit your needs - and what you can do to help them help you.

In twenty-five years at different companies and in different cities, I've had assistants who have worked from my office, assistants who've worked remotely-but-locally, and assistants who've worked literally a thousand miles away from me. In the process, I've discovered that there are really four levels of assistants. And that hiring the right kind of assistant is critical for leveraging your time.

Level 1: The Gofer

Assistants at this first tier require direct instructions and close supervision. They can move objects from point A to point B. They can send emails on your behalf - when told exactly what to write. They can take transcriptions and scan documents and file those documents in folders according to your instructions. With gofers, you're giving them directions every step of the way

So you do save some time -- after all, your gofer is the one who's actually doing the task - but, really, you have to do all of their thinking for them. Which puts a hard limit on the amount of time that you can really leverage by working with a gofer.

This is obviously not the kind of personal assistant you should hire.

Level 2: The Administrative Assistant

An administrative assistant or "admin" is somebody that can handle many tasks well, just so long as there's a clear process laid out for them and those tasks are well within the boundaries of what they're expecting or what they're used to handling.

The good news is that admins are considerably more autonomous than gofers. Admins can really help to leverage your time as long as they're following known processes and procedures to get known results. They excel with concrete, defined tasks.

But they get into trouble when things become ambiguous - when they're asked to handle tasks where success isn't guaranteed. They get scared about messing up. They get scared about making a mistake. Because they know that they'll be held accountable for their errors. They might get in trouble. That's they they're reluctant use their own discretion.

So admins can help leverage considerably more of your time than gofers can, but they'll shy away from the tasks where help could be most valuable.

Level 3: The Executive Assistant

Executive assistants aren't put off by uncertainty. They can take an unclear assignment and actually figure out, within certain boundaries, how to make it work. They can handle tasks that are sketched out instead of being engineered out.

Engineered assignments - the kinds of assignments with which administrative assistants feel most comfortable - are really well processed-through. The necessary steps are laid out clearly in advance.

By contrast, when you give an executive assistant a sketched-out assignment, you'll usually say something like,  "Here's what I'm trying to accomplish. Here are a couple of variables at play. Here are some things you might want to take under consideration. You figure the rest out."

Executive assistant are highly autonomous; they just need help understanding the context of your requests. They need a certain base amount of information to help them make good decisions on your behalf. They need you to communicate your expectations and preferences.

For instance, when it comes to travel, you'll want to let them know under which conditions you like to upgrade to a higher class of airplane service, what kind of hotels you like and what kinds of neighborhoods you prefer to stay in.

That context can also go much deeper. For my part, I like to have my executive assistant inside my inbox. Partly that's helpful because it reduces the number of emails I need to handle: if I get a hundred emails a day, I'd say that my executive assistant handles, redistributes, or deletes about fifty to seventy of them.

But having her there is also helpful because she sees the context of my business. Because she knows what I'm working on and with whom, she can make better decisions about who should get meetings with me. For instance, if she sees that I'm exchanging a lot of emails with Joe about a particular project and then Joe asks for a meeting and says that it needs to happen before a certain deadline, she can determine that the project is really important to me and that the meeting probably is too. So she'll take the initiative to set up that meeting for me and just drop me a note to the effect that, "Joe said he really needed to meet with you in advance of this deadline, so I fit him in for half an hour, from 2:45 to 3:15."

Executive assistants can really help you leverage your time, just so long as you give them good context.

Level 4: The Chief of Staff or The Executive Officer

Finally we have the chief of staff - or, in the military, the executive officer. This assistant is like a personal COO for your business activities. They understand your objectives. They know who all the key players are. And they're capable of getting results on their own while taking much - or even most - of the administrative load off of your shoulders.

A chief of staff will take initiative and actually follow up and check in with your direct reports on your behalf. Whereas an administrative or executive assistant might take notes in a meeting, your chief of staff will spot items that need to be followed-up on and do that follow-up themselves. Your chief of staff will take it upon themselves to circle back with Cindy after the meeting to make sure that she really did have a clean hand-off of those four items and then check back two days later to see how she's doing on them.

Unfortunately, most people hire gofers and administrative assistants - people who can only help with clearly laid out tasks. But as business owners, most of us aren't too process-oriented; we live in a world that's fuzzier. And so we really need, at a minimum, an executive assistant who can handle more ambiguous situations.

And while chiefs of staff are great, you'll usually only find them at mid-cap and larger companies. If you have a smaller company, you'll probably have a chief of staff type person on your team, but they won't be assigned exclusively to you. They might run your operations instead, or, if your business is a little big larger, they may be your COO.

And that's an important thing to note as well that these titles are arbitrary. Plenty of people who are titled "Executive Assistants" are really just gofers. And plenty of people who are hired as gofers really perform at the executive assistant level. (The latter is particularly common in the entertainment world.)

So, as you think about hiring your next assistant, consider which type of assistant you need. And, whatever you decide, be sure to search for those qualities during interviews.

Finally, a bonus pro-tip: hire someone with a little bit more capability than you think you'll need. After all, you want your company to grow, don't you?

If you enjoyed the ideas I shared, then I encourage you to download a free copy of my newest book, Build a Business, Not a Job. Click here for full details and to get your complimentary copy.


ADHD and Entrepreneurship
by Krysten Merriman for

October 20, 2020

Excerpt from 10 Tips for Optimizing Your Life as a Business Owner with ADHD


There’s a reason this is at the top of the list. Even if you read and agree with everything on this list, you will not execute all the suggestions without help. You need to be reminded. Cajoled. Coerced, even. This has to be someone you like enough that you won’t avoid them when they inevitably pester you. But not someone so similar to you that they share your weaknesses. Complementary skills are what we’re going for here. Coming up with ideas is your innate gift, but your success will be determined by the amount of work that you finish.

So find someone who genuinely enjoys executing, and is happy to let you be the ‘ideas person’. And then delegate as many of your Dread Tasks as possible.



You’ll be more likely to finish your projects if you have someone else to bounce your ideas around with. Note that this person is probably not your spouse and definitely not your assistant. Your spouse may listen patiently while you ramble on about your current obsession, but their excitement may be dampened by other aspects of your relationship (see #6). Your assistant’s job is to help manage your creative impulses by relieving you of routine tasks and reminding you of things you’re likely to forget.

Bonus: sometimes you really just need to talk to people who get you. These days, there are lots of online forums where you can connect with other ADHDers, including Reddit and Facebook groups (and this curated list of Twitter users).


Virtual Assistants for ADHD Entrepreneurs
by Gina Pera for

January 23, 2023

How can virtual assistants help ADHD entrepreneurs and others?

 As I gear up to offer in-person workshops and webinars, it’s become clear: I need some help. But what kind of help? The tasks are myriad and sporadic. Then a friend mentioned, “Find a Virtual Assistant.”

After researching a bit, I concluded working with a VA  would not only be a good idea for me, it also would be just the ticket for many of my friends who have ADHD—especially entrepreneurs.

Then, a friend introduced me to a VA who happens to specialize in working with clients who have ADHD. I asked him to write a brief explanatory piece about how it works. He kindly agreed.

—Gina Pera

By Richard A. Green

Meet Marie. She’s a whiz in the kitchen! A few years ago, she even invented a new kitchen gadget and started a business to sell that along with her unique recipes.

As a person with ADHD, however, this solo entrepreneur struggles with:

  • Getting organized

  • Focusing

  • Starting tasks

  • Completing tasks

  • Being on time

  • Prioritizing tasks

For several months, Marie tried to run her entire business herself. In a short time, she found herself always late shipping orders and responding to customer inquiries.  As a result, she was losing orders and becoming increasingly overwhelmed. This stress served only to increase the severity of her ADHD symptoms—and make her wonder why she got into this mess in the first place! Her business was on the brink of bankruptcy when she hired a Virtual Assistant, or VA.

What Is A Virtual Assistant?

More than 50 percent of small businesses fail in the first five years. For entrepreneurs to be successful, they must pay close attention to their business. That means being organized, managing time well, and minding the details.

Yet, people with ADHD tend to struggle with activities they find uninteresting or repetitively monotonous. Consequently, they are tempted to place those tasks on the back burner.

To maximize their potential, it’s in the best interest of entrepreneurs with ADHD to focus on what they do best and leave the rest of the work to a support team. Yet, how do you have a team when you are a “solo-preneur”?

A Virtual Assistant (VA) can be an ideal resource to provide support to entrepreneurs.  Simply defined, a virtual assistant is a person who works remotely from their own home office to provide professional administrative, technical, or creative assistance to clients.

A VA can perform tasks that:

  • the entrepreneur doesn’t like to perform (or doesn’t have the time!)

  • the entrepreneur knows must be done but don’t get around to

A VA can also provide accountability for entrepreneurs—in whichever way they prefer—to ensure important deadlines are met. For example, one person might want daily check-ins via email. Another might want verbal reminders at the end of each day: “This is due tomorrow; how are you doing with it”? Another might want a daily To-Do List reminder sent via email.

How a Virtual Assistant Helped Marie

To bring order to her chaos, Marie hired a Virtual Assistant to do the following tasks for her:

  • Process and ship orders

  • Respond to customer inquiries within 24 hours

  • Purchase product components and related accessories

  • Manage the offsite assembly team

  • Manage company finances (using QuickBooks)

  • Update her website as needed

  • Create, edit, and schedule the monthly e-newsletter

  • Manage her social media accounts

By taking the above tasks off her plate, Marie was able to:

  • Restore order to her business

  • Run her business efficiently

  • Increase sales

  • Have more time to focus on her true passion (creating recipes and experimenting with new kitchen gadgets)

  • Have a better life—more time to spend with family and friends and more free time for herself

  • Reduce stress

  • Have peace of mind that her business was being run professionally

If it takes an entrepreneur with ADHD 3 hours to do a task, it may take a VA considerably less time (perhaps 45 minutes) to do the same task. Why? Because the entrepreneur might spend most of that time distracting herself from the task at hand, procrastinating, and so forth.

Marie makes more money by delegating to her VA the tasks she does not want to do and focusing on the activities that fueled her business.  Even after the VA is paid, Marie is still ahead financially. Bonus: She doesn’t have to do the tasks she doesn’t want to do.

Other Benefits of Working With a VA

  • No need to provide office supplies, equipment, and space

  • Virtual Assistants pay their own taxes and benefits

  • No need for ongoing training of administration staff

  • No need to advertise for and interview administration staff

  • Fewer costs associated with projects – pay for time used only

  • Fresh ideas and perspectives on management for your business

  • Partnering with a professional whose success is based on your success

The Task of Delegation

It takes a bit of work to get to the point of effectively hiring a VA. It’s critical to understand exactly what you want to delegate and be able to communicate that clearly. That is a challenge for entrepreneurs in general.  It is more so for many people with ADHD.

Here’s an easy way to determine which tasks you can delegate:

  • Make a list of all of the tasks you perform in your business.

  • From that list cross off all of the tasks only you can do—typically, those tasks related to income-producing activities and growing your business.

  • What’s left on your list are the tasks you can delegate to a Virtual Assistant.


Virtual assistants are a great way to ease the workload of many busy professionals. They can help to keep things moving and reduce the stress of running a business while it grows. Freed-up time can be used in areas of the entrepreneur’s strengths.

If you’re an entrepreneur with ADHD, imagine how your personal life and business could be improved by hiring a VA. Wouldn’t it be a great relief not being bogged down with the tedious tasks that come with running a small business?

Are you ready to reap the benefits a Virtual Assistant can provide?  If so, you can find plenty of sources online by searching for “virtual assistant”.  You can also read this comprehensive guide from Thinkrific: How to Hire a Virtual Assistant.

Resources: Resources and Tips
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