Jimi Smoot Entrepreneur / Software Engineer

Ultimate Guide to Working With an Assistant

The Ultimate Guide to Working With an Assistant

I wrote this ebook a few years ago because I noticed that there weren’t many strong or comprehensive resources out there when it comes to hiring and working with an assistant. To get the book you were originally required to subscribe. I have, however, decided to post it here so that it can reach a broader audience.

This book is something you probably won’t be able to read in one sitting so be sure to bookmark or pocket the page to come back to it.

If you want it in PDF form, shoot me an email and I will get it out to you.

It’s my hope that reading this book will offered you a bit of guidance and context around how you can go about supplementing your personal and professional life with an assistant.

I’m uniquely qualified to talk about hiring and managing assistants because I’ve worked with dozens of them over my career. A few years ago I even tried to make a business out of it by giving assistants superpowers using some techniques from the field of artificial intelligence.

What happened with that company is for another post. Until then, I give you The Ultimate Guide to Working With an Assistant.


Edison had Clarence Dally. Guy Kawasaki hired Peg Fitzpatrick to run his social media. Even Sherlock Holmes had Dr. Watson. Donna Karan started as an assistant to Anne Klein before building DKNY into a fashion empire.

Successful people tend to have at least one person helping them run things behind the curtain. An assistant is a person who can get things done on your behalf, making you more effective at the things that drive the most impact for you and your business.

How do you bring an assistant into your day-to-day? It all starts with a to-do list.

You’ve probably made your own to-do list before. If you’re really organized you may even start tomorrow’s to-do list today, adding tasks to it into the next morning to keep you focused for the day. It’s one of the simplest ways you can manage your daily productivity.

Take a quick look at your to-do list for the week. (If you don’t have one, jot one down quickly on a piece of paper.) Now draw a star next to the things you enjoy doing.

If you didn’t have to lift the pen much on the “star” portion of the exercise, you’re not alone. We perceive daily administrative tasks as necessary evils. It’s so much harder to see how all the little mindless tasks add up, especially when they appear so unrelated. Dropping off your dry cleaning and organizing your email inbox are significant to your success, for example, but seeing how they tie together to make you a more effective professional is tough.

Imagine if you could focus exclusively on the elements of that to-do list that you found personally fulfilling. The tasks that showcase your strengths. The projects you feel most passionate about. Employing an assistant is the quickest route to that kind of daily productivity and enjoyment.

Assistants aren’t just for Hollywood producers, Fortune 500 CEOs, and jet-setting celebs. They’re core to how any professional can get ahead in business. Between the sharing economy and evolving technology, it’s easier than ever for anyone to leverage the power of an assistant.

Working with an assistant means more time spent doing the things you want to do and less time spent on the tedium. Assistants can help you live a happier and more fulfilling personal life. You get more done overall, which makes you a more effective executive, entrepreneur, artist, salesperson, chef, parent, sibling, student, or human being.

If you’ve never worked with an assistant before, the idea of tracking one down and figuring out how they can best supplement your day can seem daunting. I put together The Ultimate Guide to Working With an Assistant to help you navigate your own experience with an assistant.

In this book, we’ll cover everything you need to know about working with an assistant, from why you need one and how they can make an impact to how to hire and the best ways to work with your assistant. We’ve also included email templates to help you ease communication with your assistant, ensuring nothing gets lost in translation.

To get started, let’s take a look at why an assistant can work for you, no matter what you do for a living.

Table of Contents

Chapter 1: Why assistants work

Chapter 2: Who needs an assistant?

Chapter 3: What an assistant can do for you

Chapter 4: How to hire your assistant

Chapter 5: Working with your assistant

Wrapping thing up -Resources and further reading

Chapter 1: Why assistants work

As humans, we’re not accustomed to change. When something works, we stand by it. When something doesn’t work, we frequently still stand stubbornly by it.

We get it: you’ve gotten where you are because you’re good at what you do. But a truly successful person keeps a critical eye open for opportunity. Much of the time, a great opportunity requires you to embrace change.

Think of hiring an assistant as an opportunity to hasten the change you need to make to rapidly grow as a professional and as a person. Your assistant makes you better not only because of the work they do for you but because they force you to hold a mirror up to yourself and understand how you can live a happier and more fulfilling life.

One of the hardest parts of being a successful professional is letting go. In this case, an assistant challenges you to let go of the tasks, projects, ideas, and habits that limit you and either delegate them so you can focus on the good stuff or eliminate them altogether.

Your assistant can supplement your professional strengths, bolster your limitations, and help you continue to grow and be more successful. In this chapter, we’ll discuss the practical ways this works.

To get started, let’s start with the most poignant argument for why you should be working with an assistant.

Get more sh!t done

No matter how much you grind it out or how much sleep you lose, there will never be enough hours in the day to get everything done. Even working more than eight hours a day can be counterproductive.

The biggest advantage of a hiring an assistant is giving you more time to focus on your strengths. These are the production-drivers, the factors that have the most impact on your bottom line. By focusing exclusively on the things you do well, you can multiply the impact of your work several times. To do that, you need to outsource the things you do less well.

It doesn’t have to end just at your strengths, either. You also want spend more time working on the tasks and projects that you enjoy grinding out. One of the most understated benefits of hiring an assistant is giving you time back to work on the things you love. It shouldn’t come as a surprise that happiness also has a huge impact on the bottom line. Working on what you love makes you happier, in turn making a positive impact on business results.

A good manager knows when to delegate. Strong delegating skills can help you rise above the minutia, giving you the clarity of vision you need to focus on the big picture. They’re absolutely critical when it comes to handling administrative overflow –less mindful but necessary tasks like paying bills or booking travel that help power personal organization and planning.

Freeing up time is just one way to look at the benefits of a personal assistant. Staying productive while you’re busy doing other things (like traveling, a big contributor to projects stalling out) is another huge benefit.

Multitasking done right

Sometimes we wish we could be in two places at once, the laws of time and space be damned.

We try to cheat those laws by working on two things at the same time. Unfortunately, this approach doesn’t allow to focus on either project. Research from the University of Michigan shows multitasking greatly decreases our ability to accomplish tasks.

You’re only one person. With an assistant, you gain the ability to work on more than one thing at the same time, adding a level of synchronicity to your presence that makes it easy for parallel projects to converge at the right time.

For instance, imagine you’re working on a pitch deck. As you finish chunks of content, your assistant could be designing and plugging it into a deck. By the time you finish your content, your deck is ready for review.

Waiting on hold is distracting. Your assistant can monitor the line while you work and let you know when the other party is ready to chat.

While you’re wrapping up one project, your assistant could be digging up research for the next project. As soon as you’re ready to move to the next thing, you have the research ready in your inbox.

These are just a handful of examples of how synchronous work helps keep the ball rolling at a fast pace. It’s important to take advantage of momentum when you have it. Instead of stopping at roadblocks, use your momentum to speed into the next thing.

When you take advantage of momentum by delegating certain tasks to your assistant, you’re also minimizing the opportunity cost associated with your time.

Waste not, want not

If you’re trying to optimize time against a revenue goal, every opportunity that comes to a salesperson must be weighed carefully TODO: fix link. Working on a high-value client, for example, is more valuable to your bottom line then spending an exorbitant amount of time with a lower value client.

Where opportunity cost can get tricky is assessing the future potential of that lower value client. Sure, they may not be worth as much to you now, but it could be worth laying the groundwork now for future revenue. Without the resources to work on both, it makes sense to spend more time on the high-value client.

Weighing opportunity cost is a fundamental part of smart economics, especially for people who run their own business. What exactly are you missing out on that an alternative decision could offer you?

With an assistant, you can accomplish your primary choice of work and the alternative. You reap the benefits of both options, which means you’re significantly lowering your opportunity cost. While you’re doing the groundwork on the high value client, your assistant could be spending time with a client that may have high yield in the future.

Tough decisions like deciding which client to spend more time on can be paralyzing. It can be tempting to put these decisions off, but you need to push through to ensure success.

Do it today, not tomorrow

We all fall victim to the Instant Gratification Monkey from time to time. Researchers estimate procrastination has quadrupled over the last 30 years. Even if you aren’t in the 26% of people who identify as chronic procrastinators, you’ve probably had your own experiences with regular mild procrastination and occasional debilitating procrastination.

We tend to put off projects because:

  • It takes a long time to see results. We crave that instant gratification associated with crossing an item off our to-do lists. Bigger projects with longer lead times can sometimes fall by the wayside – a shame considering they big projects frequently make the biggest impact.
  • We prioritize easier things. Sometimes you just want the brief rush that comes with crossing something off the list. We often tend to look for the low-hanging fruit and pick it first because it’s easy. But there are much sweeter berries higher up the tree and ripe for the picking.
  • It’s mindless work or work we don’t enjoy doing. You can force yourself to do something you don’t want to do but it takes a lot of conscious and subconscious negotiation. That kind of mental negotiating can get pretty exhausting.

By handing off the tasks that drain more of your mental energy, you’re doing more than freeing up time to accomplish more. You’re refocusing that mental energy towards projects you’re more naturally inclined to stay motivated working on.

A lot of the time, the mindless tasks are the ones that keep you organized. They have to get done to keep you looking like a consummate professional.

Look and act like a boss

You only get seven seconds to make a first impression. Even if you make a good one, you have to work hard to maintain a client, colleague, partner, or employee’s opinion of you. It takes a lot of organization to stay polished and on point.

Image is everything if you want to build the relationships that’ll take your business or your career to the next level. Luckily, an assistant can help you with:

  • Being timely: Punctuality can be one of the toughest parts of maintaining a full plate. Your schedule is jam-packed already. What’s a minute or two in the grand scheme of things?

Actually, that minute is just important to the person you’re working with as it is to you. Timeliness is extremely important to keeping a strong professional image. Scheduling and keeping you honest is your assistant’s job.

  • Staying organized: Organization is a professional’s best friend. It helps you stay on point when presenting to an enthralled room. It’s remembering someone’s name who you only met once at a party. Enlisting your assistant to help you with tasks that keep you organized is a huge advantage to keep your personal brand looking spiffy.
  • Keeping your cool: The more organized, timely, and confident presence your assistant inspires can help you stay at the top of your game. Keeping your cool is crucial to projecting the confidence you need to woo your audience.

So far, we’ve talked through some of the ways an assistant can help you be a better professional. But there’s much, much more to it than just business.

Make more time for the things that count

Your professional success is important for your personal happiness. But it’s not the only thing that matters.

Today’s pace of life is influenced by the always-on mobile experience. We’re constantly being bombarded with work-related information, even outside of typical work hours. This makes it really hard to enjoy the little free time we have for ourselves. It’s okay to maintain a “work hard, play hard” ethic, but there are limits to this kind of thinking. Working too much doubles your risk of depression and increases the likelihood of binge drinking.

We have a tendency to lose track of the important things outside work, leading us to an unsustainable pace of life that can easily cause burnout. Beyond productivity, delegating work to your assistant empowers you to enjoy things outside of your workday like family, friends, entertainment, hobbies, vacation, health, and personal betterment.

It can seem hard to keep your sanity in the face of the demands of ambitious career choices like entrepreneurship. Better work-life balance is an understated benefit of hiring an assistant. That way, you can spend more time attending your daughter’s softball games, keeping regular date nights with your husband, or grabbing a drink with your friends from college.

Hopefully, these examples of why you need an assistant resonated with you. Next, let’s see some practical examples of the kinds of people and professionals who are immediately suited to hire an assistant.

Chapter 2: Who needs an assistant?

Now you have a rough idea of why an assistant could come in handy. Some of you may still be wondering how this is relevant to you. Are you really the kind of person who needs someone to shoulder some of the load?

Who needs an assistant? Road warriors, big thinkers, wordsmiths, and negotiators, for starters. Assistants are for anyone who wants to up their game and become great at what they do, whether that’s closing business, being a mom, or playing gigs on the weekend with your Springsteen cover band.

This chapter details some of the common profiles of people who make the best use of assistants. These profiles aren’t meant to limit the list of professionals who need assistants. Instead, they’re meant to be examples that can help you form parallels to your own life. After all, we all have an entrepreneur, an executive, a salesperson, a freelancer, and a blogger inside us.

Let’s get started with a profile of a professional with one of the biggest opportunities to take on an assistant: the entrepreneur.

The Efficient Entrepreneur

Entrepreneurs are self-starters who give up a lot to see their big ideas come to fruition. To start your own business, you need the focus to wear a lot of different hats in a high pressure environment. Efficiency is your middle name whether you’re spending your own money or answering to a swath of investors.

More than half of adults around the globe think they have what it takes to start their own business. Only a small percentage of that half actually makes throws their hat into the ring. Those that do still have quite a bit of company. They also have quite a bit of competition.

The most successful businesses are the ones that differentiate themselves. Entrepreneurs that thrive see their goals clearly and follow the paths that help them achieve them. Those that succeed help shape marketplaces and solve real problems for consumers and businesses alike.

That’s not to say it’s all glamour. In fact, 70% of senior decision makers at surveyed small companies reported having to take out the company garbage at some point. The numbers are nearly as high for cleaning, maintenance, IT, and other tasks you wouldn’t usually write into the entrepreneur job description.

Nobody said being an entrepreneur was easy. That doesn’t mean you have to be a martyr, though. If you’re taking out your own trash, chances are good you have a lot more things you could shop out to an assistant.

Entrepreneurship is fraught with high impact challenges, intriguing problems that require creative thinking, and crucial relationship-building that can mean the difference between running a successful business or heading back to the drawing board. The minutia and the low impact necessities can and should be handled by an assistant.

The Efficient Entrepreneur shares many traits with our next profile, the Streamlined Executive.

The Streamlined Executive

Perhaps the most frequent association with assistants, the Streamlined Executive is an omnipresent face of the company, an extremely busy professional who constantly meets with clients, presents at conferences, deliberates with board members, directs vision, and communicates important concepts to the organization. It almost goes without saying that executive assistants are essential to effectively managing an exec’s day to day.

We’re pretty sure we don’t need to convince you that executives need assistants. If a C-level professional had to book her own travel, schedule her meetings, run errands, and generally spend a lot of time on administrative tasks, the tasks and projects that have the highest impact on an organization’s success would never get done.

Execs handle a lot of things internally and externally. But what about the people who represent the face of the organization outside its walls? Our next profile is the Savvy Salesperson.

The Savvy Salesperson

Eighty percent of sales require five follow-ups after an initial meeting. Landing the sale takes time, care, dedication, and focus. You have to nurture your leads.

But life and work get in the way. You meant to follow up on Tuesday, but you were too busy researching a new prospect. By the time you were finished, the East Coast business day is over. You don’t want to bother that prospect at home, so you’ll have to put it off until tomorrow.

Sound familiar? Even the best salespeople miss deadlines and blow opportunities. Between all of your responsibilities, you’re strapped for time and your focus is divided. All it took was sending off a check-in email – something that could easily be done by an assistant. In fact, the research you were doing also could have easily been done by an assistant, leaving you time to work on another prospect. There’s no doubt that an assistant can greatly amplify the reach and effectiveness of a salesperson.

The Savvy Salesperson is a road warrior, traveling nationally and internationally to develop the business that makes the organization tick. He attends conferences, books meetings, drops in on clients, manages accounts, and does the digital prospecting necessary to open new relationships.

Self-awareness is important for all of our profiles, but it’s especially important for the salesperson. To effectively sell, you must know your strengths and limitations. Knowing where you excel and where you could use a little help is essential to making the most of your experience with an assistant. The Savvy Salesperson is a perfect candidate for working with an assistant.

Our next profile is one part entrepreneur, one part executive, and one part salesperson. The Solo Business Owner could use a helping hand.

The Solo Business Owner

Last year, 15.5 million Americans were self-employed. The trend doesn’t show any signs of slowing down, either. The ability to for people to work remotely has greatly eased the freelance lifestyle, empowering stay-at-home moms and dads, creative workers, and people who just like a balanced daily routine to go into business for themselves.

Though self-employed people may have the benefit of skipping the daily commute, it isn’t all fun and games. Building a one-person business is hard and requires the patience, focus, and foresight to stay productive over the long term.

Sometimes a freelancer and other times a one-person corporation, the Solo Business Owner handles all of the aspects of maintaining a business, from setting up health insurance for herself and her family to paying quarterly and year-end taxes and from securing new business to completing the tactical frontline work. Considering there aren’t a bunch of employees that rely on you, it might seem like less work to the outsider to maintain a single-person business. In reality, it’s an extremely challenging job that requires the person to handle all day to day operations.

At-home businesses include a wide range of different professions and niches.

  • Online store management
  • Influencer marketing
  • Blogging and writing
  • Business development
  • Consulting of all different shapes and sizes
  • Designing websites and brands or doing publication layout and formatting
  • Babysitting, pet sitting, or dog walking
  • Bookkeeping and other accounting services
  • Carpentry, mechanic, and other related services

These are just a handful of areas where freelancers and single-business owners function on a regular basis. Each of these niches requires hours upon hours of administrative work to stay productive and keep clients happy.

Freelancers, self-employed workers, and at-home business owners have a great opportunity to leverage assistants to keep them on target. Organization and structure are key to the Solo Business Owner’s success. Contrary to what people believe, structure is also extremely important for people that fit our next profile, the Prolific Creative.

The Prolific Creative

There’s a pervasive myth that creative workers thrive in disarray. You might hear studies or statistics tied to the way a truly creative person’s brain works better through entropy and disorganization. According to one University of Minnesota researcher, it may be true that creative types are more disorganized. It may also be true that messiness and disorganization stimulates creative thinking.

Unfortunately, that also means you’re spending your creative energy navigating your own disorganization. What’s really happening here is that some creative people tend to be less organized, making it even tougher to push through the clutter and be productive.

Like any other person who wants to be good at what they do, creatives need the structure that will help set them on the right path for the day, week, month, year, and decade. Structure helps creatives slam through writer’s block, brainstorm great ideas, and stop procrastinating on projects with loose deadlines. By helping people in creative fields stay organized, assistants empower them with the structure they need to create successfully.

The same goes for helping power through writer’s block, an affliction that actually affects anyone in a creative field, not just writers. This kind of creative blockage happens because your brain may be in a state where it’s less inclined to create. To avoid the creative process, you’ll start thinking of all the other things you need to do that day. An assistant helps take care of the non-timely tasks that are constantly dragging you away from the creative process, taking away your brain’s excuse not to focus on creating.

Lastly, one of the most crucial parts of being a journalist, blogger, web designer, reporter, author, artist, architect, or feature writer is the mountains of research you need to make a compelling case for your content. Researching can be painstaking and time-consuming. As we’ll see later, assistants are there for all of your research needs.

Convinced that hiring an assistant could be the right move for you? Great! Now it’s time to get more tactical. What kinds of tasks would you assign to your assistant? Where can assistants make the most impact? Put simply, what can an assistant do for you?

Chapter 3: What an assistant can do for you

When you have time to focus solely on your strengths, you become better at everything you do. Before you can spend your time on the projects with the biggest impact, you’ll want to take some time identifying the areas where an assistant can offer you the biggest impact.

What your assistant can do for you is only limited to your imagination, though it’s good to scale the number and importance of tasks as you learn about each other and fall into a groove. In this chapter, you’ll find a long list of tasks and projects where your assistant could come in handy.

By no means is this an exhaustive list. You have unique needs, and your assistant will have unique talents. The main point to take away from this chapter is the breadth of possibility your assistant offers you. Use these examples as thought starters when you’re making your own list of tasks and defining your strengths and limitations (more on this in the next chapter).

First, let’s take a look at one of the least imaginative areas of focus (but nonetheless a huge time saver)for your assistant.

Shoulder the administrative load

Here’s the first sweet spot for your assistant and one of the areas where most people start when they imagine having an assistant. Administrative work is a crucial part of maintaining a successful career. Whether it’s pulling a report that summarizes your wins over the last quarter or taking notes during a conference call with an important client, administrative work is clutch for any successful businessperson.

As you’re forming a bond with your assistant, administrative work is the best place to start getting into a groove. Here are seven administrative areas where you can get your assistant up and running with quickly.


Whether you’re looking into the competition, tracking down potential new clients, writing an article, or creating a presentation for a conference, research can be incredibly time consuming. It’s also crucial to the success of those projects.

Your assistant can be a research machine. All you need to do is define clear guidelines for the research and define what kind of information should be included in the report (more on that in the last chapter where we include reporting templates).


You need reports for QBRs, sales presentations, internal communication, filling in the board, celebrating successes, figuring out expenses, and so much more. Reporting (and doing it well)is key to the success of every professional, no matter where you are on the ladder.

Pulling reports takes time. Here’s a great opportunity for your assistant to help you showcase your strengths while you continue to do work around them.


Whether for a letter, email, report, or website, formatting text, pictures, and other media is a crucial part of keeping your image polished and professional. Though it’s your job to put the content together, the sometimes timely task of formatting your content should fall to your assistant.

Note-taking & transcription:

You have to be poised and engaged during meetings, which is why burying your head in your notebook is out of the question. Having your assistant present makes it easy to engage without missing any crucial takeaways.

If you can’t take your assistant along to every meeting or conference, you can record them (when it’s appropriate and non-intrusive)or get recordings afterwards. Your assistant can also help with transcription if you want to read the notes later.

Summarizing & briefing:

Whatever your niche, there’s a lot to stay up to date on in your world – too much information for you to process on your own. To stay on top of the news and trends, you need a daily summary that highlights the most important information.

Your assistant should be able to keep you briefed on what’s going on internally and externally, pulling out the points that most impact your day. Staying knowledgeable and up to date is crucial, and this is an efficient way to do it without losing hours to searching for and reading stories.

Mailing & shipping

The death of snail mail has been greatly exaggerated. Traditional mail and shipping keeps the business world moving. If you opt for an in-person assistant, mailing and shipping are key tasks you should assign to him.

Data entry

You need to capture important non-digital data, whether it’s entering lead information you collected at a conference or scanning important tax-related documents for storage. Your assistant is there to help with all of your data entry needs.

Though administrative work is the first task your assistant should be able to handle, handling your logistics might be the next thing on your mind.

Handle the logistical details

When you travel frequently or attend lots of off-site meetings, logistics can feel like an extra full-time job. Planning out your days is tough enough when you’re trying to get work done, but when you’re on the go it can get downright meticulous.

Logistics shouldn’t bog you down. Planning trips, dinners, meetings, and the like are all perfect tasks to delegate to your assistant. They can handle things like:

  • Scheduling & reservations: Important business dinners, meetings with prospects or clients, or dinner with your wife – with a busy schedule, you better have these on the calendar or risk missing your appointments. Scheduling and making reservations are perfect logistical tasks to hand off to your assistant.

Your assistant can manage your scheduling from end to end, too. For example, if you’re running late for a meeting, it’s much easier to tell your assistant “Call my 2:00 and let them know I am running late” than it is to try to get through to your appointment directly when you have something more pressing in front of you.

  • Important reminders: When you’re focusing on the things you want to do and you’re good at, it’s easy to get in the zone. Sometimes you need a reminder to snap out of it so you remember to pick up the kids from school. Your assistant is there for you with a quick reminder whenever it’s time to switch gears, holding you accountable for the important things on your schedule.
  • Booking travel: Companies spent around $1.25 trillion (with a Ton business travel in 2015. It’d be hard to quantify the hours spent booking that travel and searching for the best deals, but suffice it to say it wouldn’t be small number.

Small businesses don’t always have people handling travel internally or travel agents they can call on to book for them. This is an essential role your assistant can fill, especially if you hit the dusty trail pretty often. (Don’t forget personal travel either. Booking a Eurotrip is a lot easier with a little help.)

Like administrative work, logistics is a no-brainer to assign to your assistant. But have you considered letting him take some of the heavy lifting out of your daily communications?

Strengthen your communication prowess

Strong business leaders are excellent communicators. Today’s always-on professional presents a dedicated and ultra-organized image by responding to emails around the clock – especially true for salespeople who need to allay client concerns and entrepreneurs and executives who need to sign off on projects that come in at varying times of day.

It’s also super important to make sure you’re prioritizing the right communication, rather than responding haphazardly to whatever comes in first. A good communicator understands which kinds of communication are timely and important and sends well thought out responses.

If your goal is work-life balance, you won’t get it responding to every email around the clock. You need to be extremely organized and ready to prioritize every phone call, email, or text at a moment’s notice if you want to be on top of your communication game.

Not surprisingly, some of the best business communicators out there have a little help. When it comes to business and personal communication, here are five ways roles your assistant can fill.


Picking up the phone every time someone called would be a major detriment to accomplishing your daily goals. Sure, things come up now and then that you have to address in real time. But more often than not, phone calls aren’t timely or don’t require an immediate response. You need someone to keep the gate or risk flooding your day with requests to chat that are low on the list of priorities.

Think of your assistant as an intermediary between you and your contacts, a role traditionally filled by a secretary or receptionist. When your assistant’s answering calls, the right ones get through at the right time while lower priority callers at least feel acknowledged and confident you’ll get back to them when you can.


We already saw how key to your image it is to stay organized. Your communication strategy is one of the most useful places to work within a structured, organized environment. Think of your assistant as the keeper of that strategy, the organizer responsible for putting everything in its place. Your assistant should:

  • Organize your inbox so you can find everything easily
  • Call out important emails and other communications
  • Filter unwanted correspondence


Sometimes you don’t need to be involved in communication at all. Usually this is when the message is clear and simple and able to be delivered without much relationship building or tactical knowledge.

Positioning your assistant as a communication initiator empowers you to quickly and efficiently take care of things like:

  • Getting in touch with airline support
  • Returning something you ordered online
  • Checking for fraud on your bank card
  • Waiting on hold with tech support

These are usually time-consuming tasks that don’t require much effort on your part. Therefore, they’re perfect tasks to delegate to your assistant.

Help desk manager:

As we’ve seen, running a small shop requires you to wear many hats. Managing customer support is a chance for your assistant to handle a task that directly impacts the bottom line but can be a distraction as you try to grow your business.


Or…social media coordinator, to be exact. Managing a professional social media presence can take a lot of time. But you need to have one so vendors and potential clients can vet you, for marketing purposes, and to build deeper relationships with the people to whom you’re already connected.

Make your assistant the master of your social media. That way, you won’t have to spend time managing what you post on half a dozen accounts.

Now that we’ve covered some of the most basic and obvious roles for your assistant, it’s time to jump into a lesser known area.

Keep the books

Forty percent of small business owners cite bookkeeping and taxes as the worst parts of entrepreneurship. That’s an incredibly significant number that says a lot about the complexity of accounting. For very small businesses and solo business owners, the task of keeping the books generally falls to the business owner herself, a line of business that may or may not be in her wheelhouse.

According to the same survey, forty percent of business owners claim they spend more than 80 hours annually on tax preparation. That’s two weeks out of the year – a significant opportunity cost for someone who relies on themselves to drum up business and execute on it. You simply can’t take that much time out of your schedule to work on something so complicated that people actually dedicate four or five years of school to it.

It’s expensive to hire an accounting department and messy if you try to do things yourself.

  • Billing & invoicing: You want to get paid, right? Billing is one of the most important parts of a business transaction, but it can also be one of the toughest. Some clients just take more time to pay than others. Have your assistant be the persistent billing presence so you don’t have to be.
  • Paying bills: Sometimes you’re the client the billing department is trying to track down. Whether it’s for business or personal bills, your assistant can help make paying your dues a snap.
  • Tax preparation: When tax season comes around, you have to crunch a lot of numbers and dig up tons of documentation from the prior year. As we saw earlier, this can be one of the most frustrating parts of small business ownership. Tasking your assistant with keeping the books assures a more organized experience come tax season.

Collecting and paying is only one part of managing your finances and expenditures where an assistant can be a huge help. How would you feel about having your very own personal shopper?

Run errands and shop for you

So much of our daily errand running can be done online with the help of Amazon. Still, not everything should be left to just any app-based service. Sometimes you need a deeper level of trust. Other times, you need something done as soon as possible (rather than having to wait a few days for delivery).

Your assistant should be able to handle errands like:

  • Getting the car fixed
  • Dropping off and picking up dry cleaning
  • Picking up office supplies
  • Represent you at an auction

It’s not just the in-person shopping that requires some legwork, either. You may know exactly what you want to buy online, but it could take some time to find the best price. Or maybe you only have a vague idea of what you’re looking for (a nice pair of casual shoes in the $150 range, say)and you want to see some curated options from someone who knows your style. Hand the directions off to your assistant so they can run with it.

Next, it’s time to have your assistant add a little structure to your life.

Make you super organized

It takes a village to stay organized when you’re busy. Between your physical and digital life, we tend to collect clutter and debris. The more we ignore it, the more it piles up.

Some people are naturally organized people. Others could use a little help. Whichever category you fall into, your assistant should be at the forefront of your personal and professional organization.

A good assistant can cover organizational tasks like:

  • Building shelves and other storage units
  • Structuring intranets and local or cloud storage systems
  • Filing physical documentation
  • Scanning physical documents for digital archiving
  • Keeping your calendar up to date
  • Organizing your email inbox
  • Holding onto important items while you’re at a meeting or event
  • Taking care of incoming mail

We’ve covered several practical areas where your assistant can help. Lastly, let’s talk about an area where there’s more to use your imagination.

Fill in the details

Let’s be honest: sometimes you only have time to paint the broad strokes. A good leader directs vision and delegates the details. It’s your assistant’s job to fill those details in using your vision for the project as guidance.

You do the work on getting the content out. Then your assistant takes the reigns to handle the time-consuming stuff. Here are six ways your assistant can help you fill in the details.

Create data visualizations:

You have the numbers. How do you present them in a context your audience will understand them? Visualizing data is crucial to making trends and large amounts of data digestible, no matter who your audience is. Of course, creating a strong data visualization isn’t easy. Get your assistant some training before they jump in.

Build presentations:

In the same vein as data visualizations, presentations have to be appealing to your audience if you want them to hit the mark. The details and time that go into a strong presentation can be painstaking. When you have higher priorities, outline your presentation and leave it to your assistant to fill in the details and design the framework.

Maintain your website

Every business needs a website. You probably don’t want to be wrapped up in the frequent upkeep your website requires, whether that’s uploading new content, renewing domains, or sorting through blog comments. A little training in content management for your assistant can go a long way.

Follow up with prospects

It takes a lot to maintain existing client relationships and do the groundwork for new ones. You should be spending your time on the business development grunt work that got you where you are today and leaving the follow-ups to your assistant.

Do prospecting for recruitment

Hiring a new employee is a significant decision that requires a lot of vetting. Spending hours sifting through social media profiles is a necessary part of the process and another great task to delegate to your assistant.

Help you brainstorm

To get a great idea on the page, sometimes you just need to talk it out. If you’re running a small business, it’s not always easy to get everyone to sit down in a room together to knock ideas around. Everyone wears a lot of hats and needs to focus on executing. Don’t be afraid to talk out those ideas with your assistant. More often than not, they’ll have the outside perspective you need to help you evaluate those ideas.

By now, you should have a good idea of what kinds of projects your assistant can help you get done. Take some time to look at your daily to-do list and pull out other items. Having a comprehensive list of what you expect from your assistant is crucial for the next chapter, where we’ll dig into the nitty-gritty of actually hiring an assistant.

Chapter 4: How to hire your assistant

Assistants come in all shapes and sizes. They can cost you anywhere from a few hundred dollars a month to a full six-figure salary depending on the range of work you’re looking to have done. It’s up to you to understand exactly what it is you want out of an assistant – someone to be there to take on administrative overflow when you need it or someone who’s more like a full extension of you, handling important correspondence and skilled tasks to double your efficiency.

On one end of the spectrum, you have assistants like Honey – working remotely, perhaps a little less experienced, and less expensive than hiring someone to hover nearby every day in case something important comes up. On the flip side, people like Shana Larson are career assistants who work closely with high level executives to help make business-critical decisions for major companies. You’re probably good to hire someone less experienced than Shana, but it’s up to you to find the right balance.

This chapter is dedicated to helping you find that balance – from crucial exercises in self-awareness and where to look for your assistant to weighing your options and making the right choice. Here, you’ll find everything you need to hire your assistant.

A word of advice: you shouldn’t hire an assistant just to handle menial daily tasks. This may be how you’ve always imagined the role of an assistant – the dirty-work coffee jockey chasing a Hollywood agent around with an armful of papers. Your assistant should add real value to your day to day, not as a luxury but as someone you can trust to handle the tasks that make sense for you to delegate. It’s about being more strategic in how you manage your day.

First, it’s time to get introspective. You’ll need to dig deep and look at yourself and your business critically in order to understand where an assistant can help you the most.

Understanding what you need from an assistant

Time for some professional soul-searching. Before you start looking for an assistant analysis is crucial. Understanding yourself, your business, and what you’re trying to accomplish will help you frame the conversation in a way that’ll set your relationship up for success.

To find the right assistant, you’ll need to put yourself in the right mindset. There are three keys to success here.

  • Self-awareness: Being self-aware is important for a laundry list of reasons. For our purposes, you need to take a realistic measurement of your strengths and limitations and understand what sort of work fulfills you on a granular level. (For example, saying that “running a successful business” is what fulfills you is less productive than recognizing the consistent fulfillment you get from programming algorithms.)
  • Workflow discovery: What are the workflows that power your business throughout the day? Identifying these and deconstructing them can help you recognize which tasks have the most impact throughout your day. Revisiting your workflows can help you work more efficiently and shed more light on where your assistant can make the biggest impact.
  • Goal orientation: Finally, no major change in the way you approach your business is complete without orienting around goals. Starting with your high level goals and working your way down to the details that’ll help you accomplish them ensures you’ll have a clear vision for your assistant when you go into the hiring process.

Self-awareness questions

You’ve gotten where you are today because you’re self-aware. You spend a lot of time analyzing your strengths and weaknesses, understanding what motivates you, and imagining how other people see you.

It’s important to frame your self-awareness through the lens of working with an assistant. This exercise is also important because you have a chance to put your findings on paper. Recognizing your strengths and weaknesses becomes far more actionable when you make them concrete, rather than just visualizing them.

Here are four questions to answer to enhance your self-awareness before you hire an assistant.

What are you good at? Where are you limited?

Let’s start with one of the hardest but most important parts of becoming self-aware: what are your strengths and weaknesses? It’s usually easy to see where you’re strongest as a professional. Successful salespeople tend to be patient, friendly, and well-spoken. Some marketers are really good at writing collateral, while others excel at crunching numbers and strategizing lead generation. Executives may be good at presenting but not as good at written communication.

To answer this question, it’s a good idea to get some outside perspective. You’ll need to put on a thick skin and try to take your ego out of the equation. Soliciting feedback from partners, colleagues, friends, and other people in your life can be difficult. It’s important to take a creative approach to feedback that can at least help you identify a handful of areas where you’re less advanced. It’s also good to get second opinions on your strengths. How other people perceive you may be surprising, which makes it even more productive and insightful for you.

What do you like doing?

Forget what you’re good or bad at for a second. What fulfills you? What kinds of projects do you fully lose yourself in? Which accomplishments make you most proud when you think back on your career?

Happiness is a significant part of your professional productivity. Even if you find you’re happiest doing something you identified as a limitation, that’s a call to action to work on improving. In the long run, being happy is what it’s all about. You want to hire an assistant who helps you achieve that happiness.

How could you get even better at the things you do well and the things you enjoy?

Now that you know where your strengths and passions lie, it’s important to recognize how you can get even better at those things. If you’re good at data science, for example, wouldn’t it be nice to have someone who could automatically generate and format reports, making it easier for you to spend your time searching for trends? People who like to write might benefit from having someone to do research, help outline, or copyedit.

This part of self-awareness is all about recognizing how you can supplement your strengths. (We’ll get into more actionable detail on how to do this in the next section.)Standardizing and automating repetitive or mindless elements of the things you’re good at improves your output, making you more productive.

What don’t you do that could take you to the next level if you had more time?

We only have so much time and experience to lend to our careers. That means things we may want to do to improve ourselves or our businesses can fall through the cracks. Maybe you wish you were doing more with social media marketing, for example. Or maybe you want to learn more about where your product could be closing gaps in the marketplace.

This is also a chance to spend time learning about areas you maybe haven’t explored much. Read a book about six sigma. Take a class on how you can improve as a manager. Do more yoga or take a kickboxing class. Self-improvement is core to your business success, and your assistant may be part of an opportunity to find more time to work on yourself.

Workflow discovery questions

Though more analytical people get it, getting scientific about your day may seem strange to some. Frequently, we throw together a to-do list without a full understanding of how one task leads to another, which task is reliant on another, or what order tasks are accomplished to complete a workflow.

For context, a workflow encompasses all of the processes a piece of work passes through before until it reaches its end state. Identifying workflows is crucial part of figuring out how any business can be more efficient.

Mapping out the workflows that drive you forward in your personal and professional life makes a huge difference. It gives you the chance to take a scientific approach to hiring and interacting with your assistant. You want to understand exactly what it is that makes your business tick. The better your understanding of daily workflows, the more efficient you can become.

Below are four crucial questions to ask in order to get to the bottom of your workflows.

Which workflows are most valuable?

Here, you want to find the workflows (especially repeatable ones)that have a direct impact on your bottom line or add tangible business benefits in other ways. It helps to try and quantify how much a workflow is worth.

Converting a customer is a typical sales workflow, where a salesperson nurtures someone from lead to completion. This is an easy workflow to quantify because you usually see tangible bottom line results from it. It’s also one of the most valuable things you can do to drive company growth.

What tasks make up the most valuable workflows?

Back to our sales workflow example. You can break customer conversion into tasks like:

  • Attending a conference
  • Having conversations and collecting business cards
  • Entering business card and lead information in Salesforce
  • Following up with a lead over email or phone
  • Scheduling and attending a meeting

Knowing exactly how these tasks work together to drive a workflow can help you evaluate what you’re doing right, what’s going wrong, and most importantly for our purposes, how you can delegate work to your assistant and still ensure a successfully completed workflow. It also helps you understand where different workflows interlap and become reliant on each other, which you need to know in order to plan how to stay efficient when you start to work with your assistant.

Where do I have workflow inefficiencies?

You’d be surprised at how many inefficiencies you’ll find in the way you and your company do things. That’s not to say you’re bad at your job. But a good professional can always be better.

With a concrete visualization of how you spend your day, you can find the places where you could be using your time better. You also want to make sure you aren’t duplicating workflows anywhere, especially when you have an assistant working hard on tasks that can supplement the high value workflows contributing to your personal success.

Which tasks and workflows can I delegate?

Now that you have full visibility of your workflows, you can choose which tasks and workflows you can delegate to your assistant. This will inform the qualities you’re looking for in an assistant.

Goal-setting questions

Like any aspect of business or personal development, goal-driven decisionmaking and planning will get you much, much farther than jumping in without a clear idea of where you’re headed and how you’ll get there. Once you have personal and business awareness, you’ll be better equipped to set strong goals that’ll keep you oriented as you search for the assistant that makes the most sense for you.

Here are three questions that’ll help put you on the right track for setting your goals.

How can an assistant help you supplement your strengths?

Here’s where you start to put tangible numbers on getting even better at what you do best. If you bring an assistant into the mix for your customer conversion process, for example, how many more leads do you expect you’ll be able to convert?

Which tasks does it benefit you to delegate? What kinds of skills or basic instruction do these tasks require from the person accomplishing them? Where can you reallocate the time you’ll save delegating these tasks to have the biggest impact for you? Tie the answers to these questions to tangible numbers so you can have achievable goals.

How can an assistant help you tackle obstacles?

You’ve identified workflow inefficiencies. How do you plan to attack them? Your assistant can help you get practical about making you more efficient at what you do through process improvements.

Once again, it’s important to get detailed about quantifying goals in addition to being descriptive in how you’ll achieve process improvement. How much revenue, how many hours, how many customers do you stand to gain by eliminating a specific workflow inefficiency? How do you hold yourself accountable for achieving these improvements when you bring your assistant onboard?

What original ways can an assistant contribute to your success?

Lastly, take a look at the value additions you identifying way back in the self-awareness section. How do you take your game to the next level? How can your assistant help you get there? Create scalable goals (like “Add 2 new customers who originated through our new Twitter channel”).

After you answer these questions, you can start setting your goals for what you want your assistant to accomplish. Remember that these goals should focus on what you are trying to accomplish. Setting goals for your assistant comes later, though those goals will be directly related to what you’re trying to accomplish for yourself and your business.

Once you have clear ideas of what you want to accomplish with your assistant, it’s time to look at the different considerations that go into hiring.

What to consider for hiring

Hiring is tough, but taking a goal-oriented, insightful approach to hiring your assistant should keep you on the right track.

Note: this is a book about getting the most out of your assistant. While there’s a lot that goes into the hiring process to fill any role, we’re not going to go into specific details of interviewing, screening, and other HR related activities here. That’s a whole different book entirely. Instead, we’ll go over some high level things that should help guide you in building a profile of your dream assistant.

There are a lot of ways to engage with an assistant. One of the most important distinctions, however, is whether you hire someone to work onsite or remotely.

The difference between personal and virtual assistants is huge. That doesn’t mean one is necessarily a more effective strategy than other. The exercises in the previous section should help illuminate which of these options is right for you.

A personal assistant usually serves as an in-person employee, often with secretarial and office management duties that can only be performed onsite. Though many personal assistants are full-time employees, you can also consider a part-time person for an onsite role.

A virtual assistant is typically located somewhere else, either within the country or overseas. Virtual assistants tend to work best for professionals on a tighter budget who need help with tasks that can be accomplished digitally.

Considerations that’ll help you decide on a personal or virtual assistant include:

  • Cost: Not everyone can afford to hire a full-time employee. Virtual assistants are definitely more affordable than personal assistants. If you do decide to go the less expensive option, hire based on the skillset rather than choosing the least expensive option. Consider the cost of an assistant an investment. You get what you pay for.
  • Distance: Is distance something you’re willing to overcome when it comes to working with your assistant? If you’ve decided your assistant’s most impactful tasks are to run errands, you’ll need to hire a personal assistant. If there are higher impact tasks you want your assistant to accomplish that can be done remotely, a virtual assistant obviously makes the most sense.
  • Communication preferences: How do you work best with people? A lot of management communication takes place over email, instant message, and other digital channels these days. Some people really can’t live without in-person interaction on a regular basis. With tools like Skype, you can still communicate face-to-face, but you definitely lose the benefit of the personal interaction. It’s a question of if you think you can maintain a successful working relationship without that frequent interaction.
  • Management experience: Managing people is extremely difficult. Your level of management expertise should directly inform what kind of assistant relationship you’re most comfortable maintaining.
  • Length & kind of employment: While we’ve laid out a pretty strong case for why you should always have an assistant, you may just want to engage someone for a short period of time (during an especially busy time of year, for example). Or maybe you can only afford to bring someone on part time. Whatever the case, this is an important consideration when you’re choosing between personal and virtual assistants.
  • Task difficulty: How tough are there tasks and projects you’re hoping to hand over to your assistant? Digital administrative work can easily be done remotely. But you may
  • Travel: If you travel a lot and don’t intend to bring your assistant along, it might make more sense to work with a virtual assistant. Lots of travel means you’d be working with your personal assistant virtually most of the time anyway.

Before you hit the ground running on the hiring process, it’s important to understand exactly how to work with your assistant so you can enter the relationship with the knowledge you need to make it work.

Chapter 5: Working with your assistant

Like with any new relationship, it’s important to kick things off on the right foot with your assistant. The precedents you set will help define the relationship from day one. As always, good preparation will help you set precedents for a successful experience working with your assistant.

The right kind of preparation involves goal setting. It means putting the framework and resources in place to ensure your assistant has what they need to succeed at their fingertips whenever they need it. All of this requires you to communicate well, set expectations, and empower your assistant.

You’ve already done a lot of groundwork to prepare yourself for an enriching and productive experience. Now that you know what kind of assistant you want to hire, it’s time to take a look at what you can do once they become a part of your day to day life. Your assistant can’t exist in a void. You have to plant the seeds of success in fertile ground. Only then can your assistant take the resources at their disposal and grow their impact on you and your business.

Let’s get started with understanding exactly what success looks for your new assistant.

Set their goals

“Begin with the end in mind.”* This is great advice from Stephen Covey, author of *The 7 Habits of Highly Effective People, meant to convey how important it is to set goals.

What you want to accomplish and what your assistant should accomplish to help you get there isn’t always as obvious as we think it is. If you don’t lay out a clear path for your assistant, you risk becoming a reactive manager, dealing with issues as they arise and spending more time problem-solving and micromanaging than you would have without an assistant.

In the last chapter, we looked at questions to help you set your goals for working with an assistant. Now it’s time to set your assistant’s goals. These can’t exist in a vacuum. They should be tied strongly to the goals you set for yourself and the goals of your organization. That way, you’ll have a clear path for success.

Here are four tips to help you set measureable goals for your assistant.

  • Make goals attainable: Though you may set aggressive goals for yourself, you’ll want to make sure the goals you set for your assistant are attainable, especially at the start of your relationship. As your assistant attains goals and grows more comfortable in the role, you can work on setting out a more ambitious strategy.
  • Be specific: For goals to be measurable, they must be specific. You should also be specific about how achieving this goal benefits you and the organization. Context and transparency will help your assistant feel ownership over their goals.
  • Ask for input: Another way to help your assistant feel ownership over their goals is including them in the process. Collaborating on goals ensures everyone’s on the same page.
  • Revisit and revise: Don’t be afraid to revisit and revise goals over the course of the evaluation period. If the original goals were far from the mark, it’s best to make realign towards something more realistic.

After you’re done setting your goals, you should have a clear idea of which tasks you want your assistant to tackle. Before they dig in, lay the groundwork they need to be successful.

Your assistant’s resource library

Though you should have an open door policy for questions, your assistant shouldn’t have to chase you down every time they have one. Create a strong library of resources for your assistant to keep you both organized and on target.

Below are seven crucial resources you should include in your assistant’s library.

A master task list

It’s pretty easy to collaborate on a master task list where you can add projects, track progress, and balance your assistant’s workload in real time. Your task list should be simple to categorize and organize. It should be stored and edited in the cloud so there’s only one copy floating around. Choose to use an easy project management tool like Trello or build a custom task list through Google Sheets.

Project briefs

Some tasks are self-explanatory, like “Pick up the dry cleaning” or “Scan these pages.” For longer term and more complex projects, it makes sense to create project briefs that give context and set the right tone. They could consist of a paragraph and a few bullets that explain the task and its purpose. This kind of information helps orient your assistant.

Templates & example work

Some projects you assign to your assistant will have precedent, like drafting an email, creating a presentation, or running your help desk. You’ve done all these things before, so it’s important to organize them and make them available for reference as your assistant starts to handle them for you. If you have time to make templates for standard projects, that’s also a great headstart and extra insurance that the project will be completed the way you want it done.

Confidentiality guidelines

For a lot of professionals and business, confidentiality must be kept at all times. Chances are good your assistant will be handling confidential and other sensitive information. Though you should train your assistant on confidentiality early on, detailed guidelines on how to handle this kind of information should also be available at all times.

Payment information

You may ask your assistant to buy things and make payments for you from time to time. Make sure they always have credit card, PayPal, and other payment information at their fingertips.

Login list

Your assistant shouldn’t have to track down login information every time they need to use your Amazon, Twitter, eBay, or other digital accounts. A handy list of logins that they can keep and update is an indispensible resource for your assistant. I recommend that you use LastPass for this.

Vendor list

What partners do you work with in your personal and professional life? It could be as simple as your dog walker or as advanced as your financial planner. Having a list of vendors at their fingertips makes it easier for your assistant to work on autopilot as new tasks come up.

Now that you’ve laid strong groundwork for your assistant, it’s important to understand how communication will continue to drive your relationship forward.

Communicating with your assistant over email

Like with any employee or direct report, effective communication is crucial to the success of your new relationship with your assistant. A patient but authoritative tone helps position you as a leader. If you’re working with a virtual assistant, scheduling weekly status meetings (or building a communication cadence that works for you)helps develop a stronger relationship.

Though these are important parts of the process, a lot of crucial communication will happen over email. Of course, it can be hard to get your point across over email. It takes time to craft thoughtful emails that don’t obscure the point. If the project is unclear, you’ll endure an onslaught of back and forth that can actually make the process take longer and become more inefficient than if you did it yourself.

Instead of spending your time drafting emails, we’ve put together some templates and thought starters you can use to help you communicate more effectively with your assistant. You can use these at the beginning of your time with your assistant. As you build a rapport, you can adjust these as necessary provide less information.

Planning travel


I need your help booking a trip to Miami for Art Basel from November 30 to December 5.


Depart: LAX > MIA (11/30/16)- arrive no later than 4 p.m.

Return: MIA > LAX (12/5/16)- arrival time is flexible

Important details:

- Nonstop flights only
- Prefer a window seat
- JetBlue preferred -- please get my frequent flyer number from the login list


Please book:

- Starwood hotel - please get my preferred guest number from the login list
- 11/30-12/5
- No more than 10 miles from Art Basel


- Set a meeting with Dan Johnson for 12/3 during any open block on my calendar before 8 p.m.
- Please ship 40 sales folders to the hotel under my name. 
- Email Pablo Rauschenberg to confirm dinner at Miami Steakhouse (7 p.m. on 11/30).

DELIVERABLE: Please send me the three least expensive options by EOD.

Thank you!

Touching up a presentation


I need your help touching up a presentation I’m giving at the conference next week. The draft slides are attached.

- Pictures: Can we add one relevant picture per page except ones where I’ve marked where we need charts?
- Charts: Please create line charts for the designated slides. Each slide has a link to a spreadsheet and notes on the data range I’m looking to visualize.
- Summary: Please add bullet points that summarize the notes I’ve provided in each slide.

I’m looking to have this by late afternoon today. Does that sound doable? If not, let me know what else you have on your plate and we can reprioritize. Thank you!

Scheduling a meeting


Can you schedule the following meeting as soon as you have time?

Attendees: Darren Smith, Anne Jones, Brittany Anderson

Where: Skype

When: Morning of Tuesday, April 12

Re: Project Highline check-in


Researching for a project


Can you do some research for a presentation I’m giving to the board next month? Here’s the gist.


The board has asked me to present on differences between us and our competitors. 


- A list of all ecommerce software providers on the market
- The difference between us and them in terms of 1. price and 2. features.


Please create a spreadsheet organized alphabetically that includes the prices of low, mid, and upper tier software packages for each provider. List any features they have that we don’t in one column and all the features we have that they don’t in another column. Thanks for your help!

Find a few more email templates for working with your assistant here.

Use these templates to help inform other tasks and projects you plan to send to your assistant. When you do go wrong, try to understand exactly how it happened rather than getting frustrated. Great communication with your assistant is the cornerstone to making you a more effective and more successful professional.

Wrapping things up

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Resources and further reading

Tags: assistant, productivity, and ebook