Episode: How to Hire a World-Class Assistant

Michael Hyatt: Hi, I’m Michael Hyatt, and this is Lead to Win, the weekly podcast to help you win at work and succeed at life. In this episode, we’re talking about the biggest problem most people face in using an executive assistant: how to find one. Megan Hyatt Miller is still on parental leave. She’s spending some time with her newly adopted daughter Naomi. Today I’m joined, as always, by Larry Wilson. Hey, Larry.

Larry Wilson: Hi, Michael.

Michael: Since we’re talking about hiring, we’ve brought in our resident expert on the subject, our HR manager, Danielle Rogers. Hey, Danielle.

Danielle Rogers: Hey, everybody. It’s good to be here.

Michael: Welcome from Florida.

Danielle: Thank you very much.

Michael: Did you have a good trip?

Danielle: I did, and I appreciate the nice weather here too.

Michael: Really? You call this nice?

Danielle: I think it’s nice. The overcast is good. It’s not too hot.

Michael: Well, that’s good. I call it hot and humid, but I digress.

Larry: Hey, Michael, we are so excited about the launch of your latest book, Your World-Class Assistant: Hiring, Training, and Leveraging an Executive Assistant, so we want to talk about that again today. Last week we had Jim here and talked about how to use an assistant, how to get the most value. Danielle is here today to talk about how to find one. Why does a good assistant seem to be so hard for people to find?

Michael: Well, actually it’s not. I would say that, for most people, that’s in their head; it’s not true in reality. If you know the right process, which is exactly what we’re going to be talking about today, it’s not that difficult. I can tell you when I was trying to hire my first virtual executive assistant after I left the corporate world, I did think it was hard, so I can definitely relate. I thought, “Who do I know? I don’t know that many people. Most of the people I know are employed. I’m not sure I want to hire somebody who’s not employed.” I went through that whole gyration.

That was before I discovered (and this is not going to be a promotion for BELAY Solutions, which is the company we recommend)… I got in contact with them kind of by accident. I sent out a tweet trying to find some kind of resource that would help me, and Bryan Miles, who is the CEO at BELAY, contacted me and said, “Hey, we can start with 10 hours a week.” I thought, “Whoa!” That wasn’t something I was expecting. So with the right process, with some of the stuff we’re going to talk about today with Danielle, this is going to seem super simple. You just have to have the right process.

Larry: All right. Well, we have that ready and lined up. Seven steps to finding and onboarding a world-class assistant. Now, we kind of added that second part in there. That’s really important too, isn’t it, Danielle?

Danielle: The onboarding piece? Absolutely. Onboarding is essential, and being intentional with how you onboard. I would say the main reason that’s important is because it helps to prevent misaligned expectations from the employer side and with the employee. When you hire someone who’s fresh and new, they have a desire to please. They want to do the job well. They want to understand what it means to be successful. So it’s our job, as the employer, to help define what those expectations are so that it’s clear when they have met the mark and when they need to improve.

Larry: Let’s get right to it. Step one for finding and onboarding your world-class assistant: pick a staffing strategy.

Michael: You have to decide whether you want somebody full time or part time. Do you want an employee or a contractor or is it going to be remote or on-site? We’ve done a little bit of all of those options. Some of them are better than others, but it all depends upon where you are in your journey. So we want to pick that apart, but maybe we should have Danielle talk about the pros and cons of each one of those.

Danielle: Yeah. Each one of them definitely have their pros and their cons to weigh. I would say for full-time traditional roles, those are people who you know you’re committed to. They fit the company culture, the values are aligned, and you see yourself working with them long term. Now there is an additional cost to having someone full time. You’re usually paying for benefits and health care. It’s a lot more expensive to keep them engaged long term, but it’s fully worth the while, if this is the right person for your staff.

When you’re looking at someone who is going to be just a contractor to work with you, it can be something where it’s kind of an extended interview. You’re getting to know the person, what their work ethic is like, how they perform with the project-based work you give them, and they’re also checking you out to say, “Hey, is this employer really who they say they are? Could I see myself working here long term?” Typically, with a contractor, they usually have some kind of a defined start date and end date and some clear guidelines for what the role looks like, but it’s not as comprehensive as having someone full time.

Michael: It’s usually not as big of a commitment either.

Danielle: Exactly.

Michael: Like, if you need to terminate a contractor, that’s a lot easier than terminating an employee. Hopefully you don’t have to do either, but it’s just less of a commitment.

Danielle: Totally agreed. Then the last option, which I think is a really great one that we’ve used here at Michael Hyatt & Company a lot of times, is remote work as well, which is something to consider if you don’t need as much in-person collaboration and coordination but you really need to hire an executive assistant who’s going to help you with taking notes, help you with travel, help you to organize your day, to be your gatekeeper to manage your calendar, but maybe they don’t need to be there in person to run as many errands. Perhaps you can even hire a personal assistant or someone to help you with those smaller in-person tasks while really testing out someone remote to see if they’ll be a fit as well.

Michael: That can totally work in any of those contexts, whether it’s a contractor or an employee, whether it’s part time or full time. In fact, you, I think, before you were our HR manager, started as an executive assistant for us and working remotely. I mean, you’re still remote, although you’re here today, which is delightful.

Danielle: It is.

Michael: But you’re usually not here, and that works fine. We make that work.

Danielle: It does. I think it works really well, too, when you provide different opportunities for your employees to really become immersed in the culture and to build strong relationships. Even when you’re working apart and are far from one another, you know who’s communicating on the other end, you understand that they have your best intentions at heart, and you can communicate at a higher level even about the difficult things.

Larry: This decision boils down partly, I think, to finances and what you think you can afford to do, but a lot of it boils down to what you want that person to do for you, and that really brings us to the second step, which is to create a job description. You must have done that a time or two, Danielle.

Danielle: A few times. A few times in a week. Yeah, creating a job description is something that’s essential before you get far along in the process, the reason being you want to clearly define what the needs are for this role. What are your needs of the business that this role is going to help to provide or make possible? It’s important that you do that before you have a person in mind, because you can inadvertently end up crafting a job description to a person and not to your true business needs.

You want to think about things like what the business needs, some core competencies for this role, and experience this person should bring to the table before they even come through your doors. Also, just from a personality standpoint, what are you looking for in terms of character, core values, and how do those things need to align with what your company represents?

Larry: Do you think, Michael, it’s an advantage to have Danielle create job descriptions? Obviously it is in terms of time, but where does the input come from the executive? If you have an HR department or an HR manager, how does that work where someone is creating a job description for the person who’s going to work for you?

Michael: I think it has to start with the hiring manager. Do you agree, Danielle?

Danielle: I would agree. I think in instances where the hiring manager is extremely taxed and really busy, it makes sense to do what I call a job vision interview, where I’ll sit down and ask you a few questions. Either way, it still starts with you. You can help to inform my process as I begin to write the job description.

Michael: I think the reason I said what I said is if the hiring manager isn’t clear on what they need, I’m not sure Danielle can find them the person. They have to get clarity first, and the job description does that. I agree with you. So many times we go out and start looking for somebody and don’t have a clear job description, so how do you know when you’ve achieved the goal?

It begins with clarity, and the job description brings clarity, and you’re much more likely to have aligned expectations if it’s written out. And not just aligned expectations with candidates but aligned expectations internally, because once Danielle has clear expectations and a written job description with the hiring manager, she knows what to start looking for.

Larry: So, Danielle, what do you put into a job description? If somebody had never created one before, what are the elements that make a good job description?

Danielle: That’s a great question. Some of the first things you want to include is you want to sell your company a little bit and define the company culture. It’s important to have a little about the employer or about the company section. It’s brief, nothing too extensive, maybe about a paragraph that describes your mission statement, why you exist, because you want employees to connect to that first and foremost. When people lose their why they lose their way.

So that’s really important. I think also defining what the benefits look like, which are also attractive to people who know they’re going to connect with your mission statement. Then beyond that, they want to know, “How is this going to benefit me and meet some of my natural needs that I have?” So that’s the first part, and then beyond that, you want to really dig into what the desired outcomes for this role are.

As a leader, when you’re looking at success, you’re not necessarily looking at the entire process of what it takes to get there but the desired end result, so it’s important to quantify it with numbers whenever you can. Then after that, you want to look at some key characteristics or personality traits. Do you want someone who has a strong attention to detail, an ability to work and communicate with others from different departments and collaborate? What do those things look like?

Then from there, you also want to look at some of the job requirements in terms of educational background. We don’t usually require a college degree, but a lot of times it’s preferred, because we’re looking for someone who has a higher level of thinking that oftentimes is developed during that time frame of going to college and obtaining career roles that usually require a college degree. So those things are important to outline in the job description. Of course, if there is anything else you’re looking for that you know your leader specifically needs in terms of personality criteria, you want to include that as well.

Michael: One of the things I wanted to talk about a little bit… You talked about having the mission statement and all that, which is great, but one of the things we’ve done at Michael Hyatt & Company is we actually have a Careers page. You guys can look at this by going to We think of that internally as a sales page that sells prospective employees on the company.

So we have our mission, our vision, our core values, a little bit about our history, what it is we do. We’d like them to come to us kind of presold on the company so they know our why so they can see if it aligns with their why. Then we’ll have open positions at the bottom of that. Anything you want to add to that? Does that help, by the way, from your perspective?

Danielle: That completely helps. I would just say whenever you are posting externally to other job board sites, it is important to have that brief blurb about your company, because other people may be familiar with the name of the organization, and it may help to jog their memory that they’ve heard a podcast, heard one of our speakers speak before, when they hear more about the mission that’s in the brief job description.

Larry: What’s more important in hiring for a position like this: skills or attitude?

Danielle: I think both are essential, but attitude is something you can’t really teach. You want someone who comes to the table with some of the basic core competencies, but you may want to be creative about how you look at whether or not they possess those things. Maybe they haven’t had as much professional experience, but when you look closely at their résumé or have conversation with them, you may notice that maybe they were a volunteer leader at their local church or maybe they were a leader on the HOA board of directors for their townhome complex where they live.

So there are other ways for you to figure out if that person brings leadership equity to the table or the right administrative skills or servant-hearted nature to be able to serve their leader well. Attitude is something you definitely can’t teach, and intelligence you can’t teach, but there are certain competencies you can continue to build upon over time through training and through culture immersion.

Larry: Well, so far, we’ve covered step one: the staffing strategy, so you know if you want full time, part time, remote, on-site. Step two: the job description, so you know what you want this person to kind of look like when you’re searching. Step three: find your ideal candidate. How do you do that?

Danielle: Well, there are a lot of ways to do it. My favorite way to do it is to just continue to communicate with your sphere of influence before you even begin to hire. It’s great if the people in my community, the people on my social networks, are already aware of how amazing my company is and that it’s a great place to work, because they’re literally waiting and anticipating for us to open up the next position, and that’s ideal.

That’s, I think, the best place to start, because great people oftentimes know other great people. Referrals are one of the strongest ways for Michael Hyatt & Company and many successful organizations when it comes to hiring great employees and also having very high retention.

Larry: That’s kind of like letting your tribe do your work for you.

Danielle: Yes. It’s working smarter, not harder.

Larry: Yeah, because they know you, they know what you’re looking for, and they know the potential candidates, so they can do a little prescreening for you.

Danielle: They can. And it doesn’t hurt to also have… If you’re using tools like LinkedIn, which is an amazing tool I’d recommend if you want to do some proactive recruiting of people who maybe are already employed at jobs where they think they’re satisfied. They kind of like what they do, they see some meaning in it, but they could love working for Michael Hyatt & Company.

It helps to think in advance about what the copy, what the email communication will look like to end up in someone’s inbox and get their attention in 30 seconds, to say, “Hey, you know what? I’m glad you reached out to me about this opportunity; I might be interested” or “My friend who I used to work with down the block I think would be a great fit for this.” So that’s a great tool as well, but you want to think about what that short-term, quick communication looks like to grab someone’s attention.

Michael: Yeah, this is really good. I thought of another question I wanted to ask you. A program we just implemented recently… I don’t know what we call it, but I think of it as a bounty program, where we pay our employees if they bring to us a great candidate. Could you explain that?

Danielle: Employee referral program.

Michael: Oh, you don’t like “bounty”?

Danielle: Not so much. I could think of some other titles to call it, so we’ll go with employee referral program. It essentially is a way to incentivize our employees to continue to be on the lookout for other rock stars, other high performers to bring to the team. They have a personal vested interest in this; first, because we pay them, but second, because they want to bring someone who’s going to be solid, who’s going to carry their own weight when they get here to the workplace.

No one wants to bring their friend in who’s going to make their life harder and not going to be able to get the job done. So it’s a win-win on both sides, and it helps them to continue to remember that they are also partially responsible for helping us to recruit great talent and keep this as an amazing place to work.

Michael: That’s great. How do we get the word out in addition…? You mentioned email, but what would be the checklist of how you think about getting the word out to find the ideal candidate?

Danielle: There are a few different ways. The first one is, of course, posting to your careers page, and we are fortunate enough where we’ve developed a large enough following where people check that pretty often. You want to also give people the opportunity to receive alerts whenever you have a new position that’s open, so, people who follow you but maybe don’t have the time to check your Careers page every Monday, but they want to know when something new is available.

Those are some key places to start, and then beyond that, you want to just take a moment to look at your networks. Look at your social media, who’s within your sphere of influence that you can send direct messages to, post on their page, or even ask them to share about your position. Then there are some really great free tools. offers a great service for employers to post for free about their jobs and post the job descriptions.

That’s one of the most widely used tools nationwide for people to find jobs online, and they can do it simply by searching for your company name, searching for the job title, or just searching for jobs in the Franklin, Tennessee, or Nashville, Tennessee, area. So there are a lot of ways for your job search to pop up and for them to find it. Then, of course, there’s also using some of the more professional network tools, like LinkedIn, just to leverage your networks that you have in existence.

Also, you can sign up for LinkedIn recruiter access, which gives you access to people who are outside of your typical two or three degrees of separation, where you can search for people who have had experience with certain employers, who have certain job skill sets, or even live in a certain geographic location. It allows you to have very targeted recruiting that otherwise you wouldn’t have access to as a normal LinkedIn member if you sign up for that recruiter access.

Larry: What’s interesting to me in all that, Michael, is that what I would think of as the first step, which is to post to job boards, is actually the last step. You start with your network, the people closest in, and then work out, because you want quick referrals and trusted sources.

Michael: Part of the reason I like doing that is because it better ensures that we get a candidate who already gets us, who is familiar with our content, familiar with our values, so we don’t have to do a lot of selling on that part of it or hope there is an alignment on that part of it. So often, when an employee doesn’t work out, it’s because there’s not a cultural fit. Not always, but that’s a big reason why there’s not a fit. If we can recruit somebody from our tribe, somebody who’s already using our products, they kind of come preloaded with a base of knowledge that’s really helpful.

Larry: Danielle, I have two questions for you. The first one is this: Do you ever use headhunters, professional recruiters?

Danielle: We do. I would say, specifically, for two reasons: whenever you’re looking for a niche or a hard-to-fill role. If you have some experienced HR professional on your team, I would at least give them a shot at trying to fill the role first, if you have the bandwidth and the time to be able to do that, but oftentimes, when you’re looking for very niche, specific roles that are maybe heavily technology-oriented in a field where the demand is much higher than the supply of workers, you may need to employ a recruiter who has had ongoing relationships with people who are trying to obtain a new career change or obtain a new job in their field.

That’s when it’s really important to reach out to a recruiter, because they have had the time to specialize in searching for someone who fills that one specific criteria for months at a time. You are typically, as an employer, filling a lot of different various roles. That includes things like sometimes maybe even a CFO or a heavy technology role are things you might want to consider hiring a recruiter for if you can’t first try to fill it internally.

Larry: You wouldn’t necessarily recommend it for hiring an executive assistant? Or would you?

Danielle: I think it’s very helpful to use it for an executive assistant, especially if you’re looking for a lower quantity of hours, because in the very beginning, it may not be worth you taking all of that time to search for an executive assistant on your own if you don’t have a pool of candidates readily available on your own if you’re looking for someone for 5 or 10 hours a week. When you do the math, it just may not be worth it. There may not be a high enough return on your investment of time.

Michael: That’s one of the reasons we recommend BELAY Solutions. You’re going to pay a little bit more, just to be honest, than you would if you just went out and found somebody off the street, but you’re going to get somebody who has already been prescreened. They have outstanding executive assistants, and you can hit the ground running. I think that just starting out, especially, it’s often worth it.

Danielle: That’s what we did at Michael Hyatt & Company.

Michael: And still do.

Danielle: Exactly.

Larry: My second question for you is this: You hired me, made the employment offer. Did you check my references?

Danielle: I did check your references. I think these days a lot of people discredit checking references or don’t see the value in doing it, but we have a little bit of a tip or a hack we use. In one of our very first interviews, I sit down with the candidate and say, “Listen. I would love for you to tell me about your most recent supervisors and how you think each of them would rate your performance, not if but when I talk to them as a part of the reference check process.”

Michael: Brilliant.

Danielle: That’s kind of a gut check, because it helps people in terms of honesty. They come forward and say a lot of things they wouldn’t otherwise say, because most people are inclined to say, “Oh, I was awesome; I was great,” and they have all of these stellar examples. Even the most problem employees have great examples to choose from.

So it’s a gut check and an honesty check from that standpoint, but it also prevents me from being blindsided. If I check a reference and maybe something comes up, at least I have context, and now I can use my emotional intelligence to weigh out what really happened in the situation and ask better questions and take better notes.

Larry: There are some psychological assessments and tools people use in hiring. Is there any one you would particularly recommend?

Danielle: There are a lot of them out there, but I have to say, by far, I would highly recommend using the Kolbe assessment. It’s something created by Kathy Kolbe decades and decades ago, so it’s not a new tool. It has been tried and true and gone through a lot of case studies. It helps to measure how a person responds when they are striving toward something.

Each of us has a different MO, so to speak, a mode of operation, and the Kolbe measures that. We use the Kolbe to line it up with what kind of MO or how we need people to strive and take action in a specific role, and we line up their Kolbe results with what we need to see if it will be a right fit or if it will create stress and strain long term.

Larry: Awesome.

Michael: Danielle is certified in that, by the way, which is hugely helpful.

Larry: Well, this is HR 2.0, Michael.

Michael: Man, I’m learning like crazy. I’m taking notes here.

Larry: Yeah, me too. Well, you’ve found your ideal candidate and you’ve made the offer. Now you’re ready to onboard, and we’re going to get to that, starting with step four, which is to clarify expectations. How is this different than a job description?

Michael: One of the things I’ve found helpful (and I picked up this tip from Dan Sullivan) is clarify at the outset of the relationship how to win with you. In other words, “Here’s how to be a hero with me,” on the one hand, “And here are the things that drive me crazy.” The more clear you can be about both of those things, the less likely it is that they have to read your mind to succeed in the role.

I never want to have to depend on mind reading for success. I don’t like it when I’m put in that position. I don’t think anybody else likes it. So the more explicit I can be as the hiring manager, as now the new boss, in terms of how to win with me and how to lose with me, I think that goes a long way toward making sure they succeed.

Larry: Danielle, do you just sit people down and have a brain dump on what you expect or how does this clarification of expectations work in practice?

Danielle: It’s helpful for your new executive assistant to know where the tools are that are going to help them to be successful. During our new hire orientation, we go through the process of showing them our company drive, which is our internal method of keeping files and documents and resources…where those things are, how they can find them.

We also go through talking about the different contacts even within the company. Who is the best person to go to when you’re trying to learn more about booking a venue or if you need to have more training on how to work on booking travel? Who are the key resources you can go to for those kinds of things, and how often will you be meeting with those people?

We have the privilege of having an internal executive assistant mastermind team that meets internally and is coached by our senior director of operations, but it’s important for the executive assistant to know not only what tools help them to be successful but how they can continue to build their equity and become more of an expert in their fields.

One of the great resources we use at Michael Hyatt & Company is we have a detailed Excel sheet that provides the executive assistant with a list of questions to ask their executive, including their travel preferences, their social security number, their passport information, that helps them to really get down to the down-and-dirty nitty-gritty to help to serve their leader really well.

Michael: This is so unbelievably comprehensive. I mean, Jim knows, based on the data in that Excel spreadsheet, where I like to sit on an airplane, restaurants I like, restaurants I hate, what my food preferences are when he’s ordering out for a meeting we’re going to be doing inside the company, all that stuff.

By the way, when you buy a copy of Your World-Class Assistant, we have a link to a blank copy of that comprehensive Excel spreadsheet so that those of you listening can get this information to your executive assistant so they can better serve you. If you’re an executive assistant listening to this, this will amaze and blow the mind of the person you’re working for. That’s free when you buy the book.

Danielle: It’s a total game changer.

Larry: I would add to that, Michael, there is a whole list of downloadable resources that are mentioned in the book, and they’re all free and cover all aspects of working with an executive assistant. That alone is worth the price of admission.

Danielle, you are a high-achiever, which we hire a lot of around here, because you actually covered step five just now, which is to share information. We’ve talked about that. Let’s move on to step six, which is to grant access. Now this one puzzles me a little. Doesn’t your executive assistant have access to you all the time?

Danielle: Well, I think there’s a temptation to just kind of want to dump and run. When you get an executive assistant, you’re so glad to have that relief you want to just give them everything and run away or you’re still apprehensive and you want to keep things close to you, because it takes a level of trust to be able to share such detailed information with people.

What we suggest, oftentimes, is taking a moment to stairstep it by providing access to your email and providing access to your calendar and to be able to make appointments, but then maybe it will take a few weeks for your executive assistant to get really familiar with how to respond on your behalf.

It takes a level of trust, for sure, but when you hire someone you’ve screened for honesty and integrity, you’ve also done a background check, and you have great references, you can really be confident that you have the right person in this role and begin to let go of the reigns to allow them to really help to allow you to lead at a higher level at the capacity that you need to so you can understand what’s happening on a larger scale so you can work on the business and not just always in the business.

Michael: I can’t emphasize enough the importance of not just communication but over-communication, especially in the first 90 days. Again, your executive assistant cannot read your mind. I’ve talked to leaders who get frustrated. They say, “Well, they’re just not getting it.” Well, have you been explicit? Have you expressed it or are you just expecting them to read your mind?

If they do something you don’t like or maybe it needs to be tweaked a little bit, that first 90-day period is the time to say that. Everybody expects to be corrected. Everyone expects clear direction, so do it. Don’t put yourself in a position of thinking, “Well, this might hurt their feelings.” No. Forget that. Basically, “I’m going to coach you on how to win with me, and here’s what you need to do that’s just a little bit different than how you did it.”

Danielle: That’s good.

Larry: So there’s really a balance here between your EA giving you the freedom and privacy to get your work done and you being responsive to their need for information and their need for direction.

Michael: Well, that’s where you need a regular communication rhythm. Don’t leave this to chance. Don’t leave this to “When I can get my head above water, I’ll spend some time with her or him.” Instead, establish a communication rhythm. One of the things Jim and I do is we communicate, first of all, every day. I’m sharing my Big 3. I’m sharing any obstacles I see in the way every day. We talked about that on the previous episode.

In addition to that, we’re meeting once a week just for half an hour. By the way, we met more than that at the beginning, but now our rhythm is half an hour once a week and then as needed through the week, but at least there’s that regular meeting that’s on the calendar so I know I don’t have to interrupt Jim every time I have a thought. If it can wait until that regular meeting, both of us do that. If not, then we communicate with each other.

Danielle: And knowing what is important and what’s on your executive’s calendar that’s high leverage helps to empower your executive assistant to feel a sense of authority and accomplishment, because they’re helping to protect your most priceless time to do your best work.

Larry: Well, today we’ve learned you really can create your own world-class assistant in just six steps: pick a staffing strategy, create a job description, find your ideal candidate, clarify expectations, share information, and grant access. Michael, Danielle, any final thoughts for our listeners today?

Danielle: I would say, imagine a world where you are more freed up to focus on the things you love and are really great at doing as a leader, and just know that those moments of what you’ve been dreaming about are just around the corner and an executive assistant can help to get you there.

Michael: You can find an executive assistant that is beyond what you expect. I’m amazed that we have a company full of these people, who, by the way, often don’t stay in those positions, because they’re so good they get promoted out of them. I could list specific examples here. But you can find a world-class executive assistant, and all you have to do is follow the process we’ve outlined.

Larry: Michael and Danielle, thank you. Very practical blueprint that I know people can use as a pathway to success.

Michael: Thank you, Larry. Thank you, Danielle. And thanks to all of you for being here. Join us next week for another brand-new episode. Until then, lead to win.