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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?

4 Types of Personal Assistants

Image by Marissa Grootes

The Case for Executive Assistants

Harvard Business Review

The Case for Executive Assistants

by Melba J. Duncan

Summary.  As technology has transformed the workplace and organizations have downsized, companies have sharply reduced the ranks of administrative assistants. But many firms have gone too far.

In their zeal for cutting administrative expenses, numerous organizations now count on highly paid middle and upper managers to arrange their own travel, file expense reports, and schedule meetings. Some companies may see a type of egalitarianism in this assistant-less structure—believing that when workers see the boss loading paper into the copy machine, it creates a “we’re all in this together” spirit.

But as a management practice, that approach rarely makes economic sense. Generally speaking, work should be delegated to the lowest-cost employee who can do it well. Yet while companies seem to have embraced that logic by outsourcing work to vendors or to operations abroad, they ignore it back at headquarters.

In this article, Duncan, a longtime recruiter of C-suite executive assistants, argues that a good assistant is a crucial productivity booster for a busy executive—one that offers a solid ROI if he or she is deployed correctly.

Among the most striking details of the corporate era depicted in the AMC series Mad Men, along with constant smoking and mid-day drinking, is the army of secretaries who populate Sterling Cooper, the 1960s ad agency featured in the show. The secretary of those days has gone the way of the carbon copy and been replaced by the executive assistant, now typically reserved for senior management. Technologies like e-mail, voice mail, mobile devices, and online calendars have allowed managers at all levels to operate with a greater degree of self-sufficiency. At the same time, companies have faced enormous pressure to cut costs, reduce head count, and flatten organizational structures. As a result, the numbers of assistants at lower corporate levels have dwindled in most corporations. That’s unfortunate, because effective assistants can make enormous contributions to productivity at all levels of the organization.

At very senior levels, the return on investment from a skilled assistant can be substantial. Consider a senior executive whose total compensation package is $1 million annually, who works with an assistant who earns $80,000. For the organization to break even, the assistant must make the executive 8% more productive than he or she would be working solo—for instance, the assistant needs to save the executive roughly five hours in a 60-hour workweek. In reality, good assistants save their bosses much more than that. They ensure that meetings begin on time with prep material delivered in advance. They optimize travel schedules and enable remote decision making, keeping projects on track. And they filter the distractions that can turn a manager into a reactive type who spends all day answering e-mail instead of a leader who proactively sets the organization’s agenda. As Robert Pozen writes in this issue: A top-notch assistant “is crucial to being productive.”

That’s true not only for top executives. In their zeal to cut administrative expenses, many companies have gone too far, leaving countless highly paid middle and upper managers to arrange their own travel, file expense reports, and schedule meetings. Some companies may be drawn to the notion of egalitarianism they believe this assistant-less structure represents—when workers see the boss loading paper into the copy machine, the theory goes, a “we’re all in this together” spirit is created. But as a management practice, the structure rarely makes economic sense. Generally speaking, work should be delegated to the lowest-cost employee who can do it well. Although companies have embraced this logic by outsourcing work to vendors or to operations abroad, back at headquarters they ignore it, forcing top talent to misuse their time. As a longtime recruiter for executive assistants, I’ve worked with many organizations suffering from the same problem: There’s too much administrative work and too few assistants to whom it can be assigned.

Granting middle managers access to an assistant—or shared resources—can give a quick boost to productivity even at lean, well-run companies. Firms should also think about the broader developmental benefits of providing assistants for up-and-coming managers. The real payoff may come when the manager arrives in a job a few levels up better prepared and habitually more productive. An experienced assistant can be particularly helpful if the manager is a new hire. The assistant becomes a crucial on-boarding resource, helping the manager read and understand the organizational culture, guiding him or her through its different (and difficult) personalities, and serving as a sounding board during the crucial acclimation. In this way, knowledgeable assistants are more than a productivity asset: They’re reverse mentors, using their experience to teach new executives how people are expected to behave at that level in the organization.

Getting the Most from Assistants

Two critical factors determine how well a manager utilizes an assistant. The first is the executive’s willingness to delegate pieces of his or her workload to the assistant. The second is the assistant’s willingness to stretch beyond his or her comfort zone to assume new responsibilities.

Delegating wisely.

The most effective executives think deeply about the pieces of their workload that can be taken on—or restructured to be partially taken on—by the assistant. Triaging and drafting replies to e-mails is a central task for virtually all assistants. Some executives have assistants listen in on phone calls in order to organize and follow up on action items. Today many assistants are taking on more-supervisory roles: They’re managing information flow, dealing with basic financial management, attending meetings, and doing more planning and organizing. Executives can help empower their assistants by making it clear to the organization that the assistant has real authority. The message the executive should convey is, “I trust this person to represent me and make decisions.”

Not every executive is well-suited for this type of delegating. Younger managers in particular have grown up with technology that encourages self-sufficiency. Some have become so accustomed to doing their own administrative tasks that they don’t communicate well with assistants. These managers should think of assistants as strategic assets and realize that part of their job is managing the relationship to get the highest possible return.

Stretching the limits.

Great assistants proactively look for ways to improve their skills. When I was the assistant to Pete Peterson, the former U.S. commerce secretary and head of Lehman Brothers, I took night classes in law, marketing, and presentations to burnish my skills. Today I see executive assistants learning new languages and technologies to improve their performance working for global corporations.

In my work, I frequently encounter world-class executive assistants. Loretta Sophocleous is the executive assistant to Roger Ferguson, the president and CEO of TIAA-CREF; her title is Director, Executive Office Operations. She manages teams. She leads meetings. Roger says that he runs many decisions past Loretta before he weighs in.

Another example is Noreen Denihan, whom I placed over 13 years ago as the executive assistant to Donald J. Gogel, the president and CEO of Clayton, Dubilier & Rice, LLC. According to Don, Noreen fills an informal leadership role, has an unparalleled ability to read complex settings, and can recognize and respond to challenging people and circumstances. “A spectacular executive assistant can defy the laws of the physical world,” Gogel says. “She [or he] can see around corners.”

Trudy Vitti is the executive assistant to Kevin Roberts, the CEO Worldwide of Saatchi & Saatchi. Often when you ask him a question, he’ll say, “Ask Trudy.” He travels for weeks at a time and says that he has utter confidence in Trudy to run the office in his absence.

Compared with managers in other countries, those in the United States do a better job of delegating important work to their assistants—and of treating them as a real part of the management team. Outside the United States, educational requirements for assistants are less intensive, salaries are lower, and the role is more typically described as personal assistant.

You can often tell a lot about an executive’s management style—and effectiveness—from the way he interacts with his assistant. Can the executive trust and delegate, or does he micromanage? Do assistants like working for her, or does she have a history of many assistants leaving quickly or being fired? Not every boss–assistant relationship is made in heaven, but an executive’s ability to manage conflicts with an assistant can be an important indicator of his overall ability to manage people.

Finding the Right Fit

Hiring the right assistant can be a challenge. In some ways, it’s trickier than filling traditional management positions, because personal chemistry and the one-on-one dynamic are so important—sometimes more so than skills or experience.

Expert assistants understand the unspoken needs and characteristics of the people with whom they work. They have high levels of emotional intelligence: They respond to subtle cues and react with situational appropriateness. They pay close attention to shifts in an executive’s behavior and temperament and understand that timing and judgment are the foundation of a smooth working relationship. A good assistant quickly learns what an executive needs, what his or her strengths and weaknesses are, what might trigger anger or stress, and how to best accommodate his or her personal style. Good matches are hard to come by: That’s the reason so many good assistants follow an executive from job to job.

After many years of debriefing assistants who’ve been fired, I’ve identified several factors that make for bad relationships. The most common missteps an assistant makes are misreading the corporate culture, failing to build bridges with other assistants, failing to ask enough questions about tasks, agreeing to take on too much work, and speaking to external parties without authorization. Bosses usually contribute to these deteriorating relationships by not being open in their communications or not being clear about expectations.

There’s an assistant I placed recently who’s having trouble developing the right relationship with her boss. The executive called me and said, “Melba, I expected her to read through these memos and then get them out very quickly to my managers. But she left them on my desk, didn’t call me over the weekend, and didn’t send them out.” I asked the assistant about it, and she said, “He didn’t tell me it was important—I can’t read someone’s mind.” But in fact, in this job you’re supposed to be able to read minds—or, at the very least, you’re supposed to ask questions. 

Simply put, the best executive assistants are indispensable. Microsoft will never develop software that can calm a hysterical sales manager, avert a crisis by redrafting a poorly worded e-mail, smooth a customer’s ruffled feathers, and solve a looming HR issue—all within a single hour, and all without interrupting the manager to whom such problems might otherwise have proven a distraction. Executive assistants give companies and managers a human face. They’re troubleshooters, translators, help desk attendants, diplomats, human databases, travel consultants, amateur psychologists, and ambassadors to the inside and outside world.

After years of cutting back, companies can boost productivity by arming more managers with assistants.

After years of cutting back, companies can boost productivity by arming more managers with this kind of help—and executives who are fortunate enough to have a skilled assistant can benefit by finding ways to delegate higher-level work to him or her. Executive–assistant relationships are business partnerships: Strong ones are win-wins between smart people. In fact, they’re win-win-wins because ultimately the companies reap the benefits.


The Executive Assistant: The Unsung Leader At Every Great CEO's Right Hand

October 10, 2023 by Vince Molinaro

​You'll find the most powerful and capable leaders at the top of a company's hierarchy. The CEO and the senior executives yield great power and responsibility.

Yet, in all my years as a strategic leadership advisor, I have found another leader at the top of the hierarchy, one who yields a different kind of power and has their finger on the pulse of everything that matters in a company.

Who is this unsung leader? The CEO's executive assistant (EA).

They often operate in the shadows but are the linchpins that ensure the organizational machine runs smoothly.


While the boardroom celebrates praise for CEOs and senior executives, the vital leadership role of EAs often goes unnoticed and underappreciated. And when a CEO has a genuinely exceptional executive assistant, their effectiveness is greatly amplified. At the same time, when the CEO's EA isn't up to the task, the ramifications are visible to everyone.

So, what are the unique leadership attributes of great EAs? I've talked to many of them, and here's what I've learned.

1. Excelling In Diplomacy And Tact

Every day, EAs handle a myriad of tasks that require them to communicate with diverse sets of people. From senior executives to frontline staff, clients to suppliers and the board, they interact with everyone. The diplomacy and tact they display while managing expectations and resolving conflicts are hallmarks of effective leaders.

2. Confidentiality And Trustworthiness

Holding the fort means being privy to sensitive information. The discretion with which EAs handle this information, ensuring it remains confidential, speaks volumes about their integrity and trustworthiness—two vital leadership qualities.

3. Anticipating Needs And Shaping Circumstances

EAs are very good at scanning their day-to-day environment and predicting what the CEO or the organization will need even before it becomes apparent. This proactive approach—the ability to foresee and prepare for challenges—is a pivotal leadership trait. Related to this is the ability to shape things as they unfold to ensure they move in the direction aligned with the CEO's vision.

4. Making Decisions Under Pressure

While the CEO and senior executives routinely make big decisions, EAs often make countless decisions that ensure everything else functions correctly. Whether it's deciding on the scheduling of meetings, prioritizing tasks or managing unexpected challenges, their ability to make sound decisions under pressure is commendable.

5. Gatekeepers Of The CEO

Much like a lighthouse keeper, an EA ensures that only the most relevant and necessary information reaches the CEO's or senior executive's desk. They shield leaders from unnecessary distractions, allowing them to focus on the strategic aspects of the business.

6. Apolitical

At times, internal politics can run high among an executive team. EAs have the uncanny ability to sense the pulse of the office, understand unspoken issues and act as a bridge between the executive and the rest of the team. They also have the courage and a solid backbone to stand up to anyone trying to manipulate a situation to their advantage.

7. Continual Learning And Growth

The business landscape is constantly evolving and changing. The best EAs consistently adapt, learn and grow with it. This dedication to personal and professional development mirrors that of top-tier leaders.

Next Steps

If you are a CEO looking to bring a strong EA on board, here are some thoughts for you to consider.

1. Review the attributes described above and identify the top three that are most critical to you.

2. When conducting the recruitment process, don't over-emphasize traditional administrative duties. These are important, but the leadership attributes may be more critical.

3. Hire for complementariness. In other words, find someone who brings very different strengths than yours. So, together, you can become a dynamic duo.

With their multifaceted and demanding roles and unwavering commitment, executive assistants are undeniably leaders. They orchestrate silently, ensuring smooth operations and efficient functioning. In recognizing and celebrating their leadership, companies can boost morale and underscore the diverse ways leadership can manifest within an organization.

Dr. Vince Molinaro, CEO of Leadership Contract Inc., is a NY Times best-selling author & adviser on scaling leadership accountability.


Virtual Assistants for ADHD Entrepreneurs

January 23, 2023 by Richard A. Green

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

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.

Virtual Assistants for ADHD Entrepreneurs

Resources: Resources and Tips
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