Season 2, Episode 8: The Most Important Person You Lack in Your Business w/ Gretchen Moran

An executive assistant needs a Swiss Army knife of skills.

Season 2, Episode 8: The Most Important Person You Lack in Your Business w/ Gretchen Moran

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If you start missing important meetings and deadlines, it may be time to bring on an executive assistant. David talks to Gretchen Moran once again to discuss finding, hiring, and training that crucial lynchpin in your organization to organize your time and triple or quadruple productivity in your business.

Show Notes

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Show Transcript

[00:00:00.000] – David Maples

Did you know that an executive assistant might be the most important person you lack at your business? How do you hire, promote, and grow these veritable Swiss Army knives in your organization? Today, an interview with Gretchen Moran on The Buck Stops Here.


[00:00:19.500] – David Maples

Today, we have Gretchen Moran here with us. She’s the owner of Simply Living KC. She’s a master organizer and served in the corporate sector as an executive assistant for decades. She’s worked in oil and gas and healthcare and accounting, auditing. She’s worked in a lot of different organizations with the very highest levels. And with all of that, today she’s going to share her information on how to hire that crucial linchpin in every organization. No, it’s not your bookkeeper; it is your executive assistant. If you are a business owner, then this is one of those things that can triple or quadruple your productivity, having the right executive assistant. Gretchen, I want to thank you, welcome you back to the show again. Thanks for spending time with me. That seems weird because you’re just on this show.


[00:01:08.000] – Gretchen Moran

Thank you, David, for having me.


[00:01:10.660] – David Maples

I’m so glad you’re here again. It’s amazing. So, you served as an executive assistant for years in the corporate space. Will you just, for those of us listening who are not familiar with what exactly an executive assistant does, could you talk a little bit about that and how that is different in many organizations from the administrative assistant. What is the difference? What do they do?


[00:01:33.230] – Gretchen Moran

I wouldn’t say it’s necessarily different. I think it’s maybe years of experience. As I started out in entry-level admin roles earlier in my career, I just built up a wider array of skills and knowledge and ability, professionalism. Then when I came into the world of executive support roles, it’s just a higher level of experience, higher level of confidentiality and trust and skill and ability as well.


[00:02:09.070] – David Maples

Okay. It sounds like this person is a Swiss Army knife of skills. They have to become good at a whole bunch of different things.


[00:02:16.370] – Gretchen Moran

I love that term that you have. I think it’s fantastic.


[00:02:20.140] – David Maples

So, tell me, at that level.. So, they’ve been doing this work for years and they have migrated into the executive assistant role. Now they’re working with people at the C suite. What does that job profile look like? What all do they do? What all do they handle? What are they trusted with?


[00:02:36.230] – Gretchen Moran

I would say for any C-suite level executive, number one is helping them to manage their calendar. As you can imagine, much like a business owner, a CEO has lots of supporting staff underneath them. Other executives may report to them. Supervisors, managers may either report directly to them or funnel to them through other more vice president or other supervisor director roles. And so that role is super vital with communication and calendaring between meetings and emails and just managing their day to day schedule throughout the day through the people that report to them, other people that they need to connect with, either in the organization or outside of the organization. So, they are the key communicator and scheduler of that executive.


[00:03:47.440] – David Maples

Why do you need them? I manage my own calendar. It’s totally fine, right? By the way, that’s a lie.


[00:03:53.740] – Gretchen Moran

I would say how’s that working for you?


[00:03:57.600] – David Maples

Well, that’s always a good question, right? Well, I guess the question is, so why do you need them? What does this really free up for the executive?


[00:04:07.300] – Gretchen Moran

I mean, number one, it frees up time for them. Like we talked about in our previous conversation, time is money. So, if an executive is spending, or business owner, is spending time in their day doing things that do not move the business forward or move the organization forward, they’re not necessarily spending their wheels, but they’re doing activities that are not moving things forward. So, the quicker that you can realize and determine what those activities are that you can delegate, the faster you’re going to be able to grow and be able to move things forward in your organization.


[00:04:52.620] – David Maples

So, I guess the follow up question for them is… Okay, so you’ve been running your organization for a while. What would of the – for lack of a better term – what would be the canary in a coal mine? The warning signs that you need these people?


[00:05:08.130] – Gretchen Moran

If you are missing important meetings, either something didn’t get scheduled on your calendar, or you missed an important communication maybe that came through your emails or came through the mail or a voicemail, something that you missed that was vital to your business, that to me is an indicator that you need some help. I would say not that it just happens one time, but if it happens multiple times, because what’s happening is you’re hurting your credibility and not showing up for a meeting that you were supposed to be at, or you were late, really late to a meeting and that happens consistently, that’s a key indicator that you really need some help managing your time and your communication a little better.


[00:05:59.520] – David Maples

This is the big part of this. What do you look for and how do you hire them? Because you said it’s a continuum, right? A lot of people starting out may start as an administrative assistant and they grow into this role. Big corporations are legion with the people who… And it said, some of the biggest corporations on the planet, SpaceX and Tesla Motors. Elon Musk had an executive assistant, and when she worked for the organization for 10 years, she was the person who’s like, oh, if you want to get something done, you talk to her. She puts it on the calendar, she makes sure these things happen. I have noticed that a repeating strong skill that seems to be across all these people, as I’ve read about books managing up these other things, they said that one of the things an executive assistant needs to be is a lot of times they can be a better communicator than even their boss because they have to, I guess they have to, grease the wheel, so to speak, with both the boss and… So, the boss says something and maybe it comes across in the wrong way. So, it’s like they’re doing a pseudo HR role a little bit.


[00:07:08.650] – David Maples

They’re sometimes putting out fires and say, well, what this person means to do, she meant the following, or this is what’s going on. Or you have to understand that the boss is incredibly busy right now. They’re working on 45 different projects. They just spent 115 hours getting this video game they’ve gone to gold with. They spent 115 hours the past four weeks in a row getting this to launch. So, they’re really short on sleep and time. So, I think what I’ve read about it is they have to be master communicators eventually, too. So, I digressed there. I didn’t mean to get off the subject and go further there. So, what do you look for? Because if you’re looking for one earlier on, as an admin assistant role, what skills are you looking for in these people?


[00:07:51.870] – Gretchen Moran

I think, first and foremost, you’re looking for a level of professionalism. How do they operate within your organization currently? I know a lot of organizations prefer to hire from within. I think that is very wise, because they already have an understanding of the culture that is within the organization. They already have an understanding of systems and processes that are in place. They already know who the resources are that they can pull from when you get to another level. You know who to call for IT problems. You know who to call to clean a bathroom, or whatever. You know who all of those sources are. So, having that person that has a good understanding of how the organization works is really smart if you’re looking to promote that person from within. Being confident. I can’t tell you how many times that I had to call a Senator’s office or a House Representative’s office or someone who is highly esteemed in the community and try to schedule an appointment with them and my executive. So, being able to have that confidence just to get on the phone and call someone that you feel is really important, it takes a lot.


[00:09:06.730] – Gretchen Moran

You can’t be timid in that kind of work. Even people coming into the office that are high-level individuals, you need to have that confidence about you, because you are that first face that people see when they come into your office or come to meet with your executive. So, you need someone that’s going to have that nice smile. It doesn’t necessarily have to be an extrovert, but they need to be able to be face-to-face with people in a confident way that represents your organization, represents your executive.


[00:09:51.540] – David Maples

We’ve had this brought up in the podcast episodes before. It’s like hiring from within definitely has some real advantages because these people are a known quantity to you. You already know some things about them. But let’s say you’ve got somebody in your organization who you think might be a good fit for this role and you put them in the admin assistant role, but they need to have a higher degree of professionalism or higher degree of confidence. Is this something you would recommend that they get some outside training on? Or what would you do if you needed to give them the skills to maybe help polish them up to be more of that role?


[00:10:24.210] – Gretchen Moran

Two ways I think that you could fill this role. One would be to have that person work with someone else, whether it’s a consultant from outside or a business coach of some sort to come in and work with that person for a short time and help them with those skills. Even online tutoring, online coaching. This world was not available when I was in the corporate world. You can just get a life coach or a business coach and get on a Zoom call. It just wasn’t a thing then. But now we have this tool that’s available. I think if that person, just like any other training, if you’re learning Microsoft Suite or learning any piece of technology, you can get on YouTube and find what it is you need to know. So, they could do a self taught thing. And then putting into place. Here’s a time frame, we would like to have these skills and abilities tuned up a little bit and have a time frame wrapped around that. The other option would be is to hire a headhunter. I had registered myself with several headhunters here in Kansas City, and I really loved working with them.


[00:11:35.700] – Gretchen Moran

They do a great job. Robert Half and Morgan Hunter are the two organizations here that I worked with. I think they’re all over the country, actually. They vet these people for you. They do the testing and the training for you. And then you just pay a fee on top of that, whether you want to do a temp-to-hire or you want to do a permanent placement. They will help you through that process, and then you just pay the company a fee to help you with that. Great way to be able to find a really good executive assistant that’s going to fit the culture that you need and then be able to try them out, like a temp-to-hire situation.


[00:12:14.920] – David Maples

That’s a really strong idea, actually. And yeah, Robert Half International, they actually… I guess there are some big organizations. I’ve never really thought about using a headhunter for an executive assistant, but I guess it makes perfect sense. If your executive is one of the most valuable people at the company and there were X hundred, thousand, or a million dollars a year, if they can increase your productivity by 50%, a fraction of that being spent on one of these people would be money well spent any day of the week, it sounds like. Let’s say you promote from within and maybe this is the other side of the coin. You promote within, what would be your deal breakers or the warning signs on these people to say, maybe I’ve got the wrong person in this role. Maybe this person wasn’t set for this thing. In the previous episode, you talked about promoting a salesperson to manager. And anytime we promote from within, that’s always been one of my concerns. It’s always like when you talk to these organizations, how do you know if you put somebody in the wrong role? What would you figure would maybe be, since this is such a key Swiss Army individual, what would be the signs you would look for them and say, hey, maybe this is the wrong fit for this particular role.


[00:13:28.160] – Gretchen Moran

A couple of different things. One would be personality and then the other could be their skill level. Depending on maybe which is more important to you, do you want that chemistry to be able to have really good communication between them? If that’s really important to you that you have really good communication and they’re really good at that, but maybe they need some help in fine tuning their skills, maybe with PowerPoint or whatever software program that you use, and maybe they’re just not quite to the level of expertise in some software program, you can get them training on that. That part is easy. But the personality, the chemistry, the morals and ethics, if something comes up that maybe looks a little shady that they’re doing, or they’re, God forbid, stealing from your company, or just those little small things, you can see those red flags. That stuff is not teachable. That’s within that person. So, stuff that’s trainable and stuff that’s just inherent. I think as a business owner, you’ve got to figure out which of those is more important to you and really concentrate on that one.


[00:14:43.760] – David Maples

So, you’ve got an executive assistant in the role. And the other thing I’ve seen when I’ve talked to business owners before is that they’re not sure they’re managing their calendar, but that’s the baseline type thing you want them to help you do. So, what would you say are ways you could really involve your executive assistant to really best utilize them? How do you maximize, not just production in that position, but how do you maximize their growth and the growth of your organization? What are the things that you should do as an executive with this really key person there? What things should you be looking at for them to do or learn?


[00:15:21.040] – Gretchen Moran

Well, from my experience, the best working relationships I had with my executives was sitting down and having conversation with them because I would let them know, hey, I have done these things in the past for other executives. I can do these things for you. Which makes most sense for me to be able to take these on so that you can go out and you can do the work that you need to accomplish today? What of these things that I’m good at that I can take off your plate? So, I think just being able to have that open line of communication and understanding what is this executive assistant’s skill level? What is she good at? What is her experience? And then what on my plate can I take off and give to him or her?


[00:16:08.830] – David Maples

I’ve had some conversations with some people at some very high levels, at some big companies, and I’ve had it said more than once by these people –  and it’s almost always gentlemen I’ve talked to in this role, not because there aren’t women in this role, but it just happens to be this conversation has happened – they said, if I could just get a Pepper Potts, like Iron Man had Pepper Potts. I always look at the guys and I was like, “You realize that is fiction, right?” You realize that that is, aside from the relationship thing, which is wholly inappropriate, you do realize that that is a fictional account, right? But I guess the idea is that you have this other person who really is a stand in for you. If you can’t be there, it sounds like, at a very high level, somebody’s executive assistant, if you couldn’t be there, they could pinch hit for you or something like that, for lack of a better term. I’ve always wondered what that comes down to. It’s just funny. Some of these conversations you have sometimes are just ridiculous. The things they ask for, can you get them to do X, Y, and Z?


[00:17:14.210] – David Maples

There’s probably limits. There’s probably a set of skills or things that they have. What additional training would you recommend for executive assistants beyond? So, let’s say you’re listening to this podcast right now and you’re in, I want to flip this on its head a little bit, and you’re in an administrative assistant role or an executive assistant role, what advice would you give to those men and women who might be listening who are in that role right now for them to grow their careers, or on their own initiative, how do they become more valuable to the organization or improve their position?


[00:17:45.280] – Gretchen Moran

I would say the number one advice I would give is to know your industry. The last job that I worked in the corporate world was in oil and gas. I had never been in oil and gas before. We had three publicly traded companies, and part of my job was to understand how the markets worked in the oil and gas industry and be able to put that information and data on a spreadsheet. And then my boss went out and took that information and presented it to investors. I had never done any of that before, but I still had an understanding of… I know where to gather the data. I can teach myself how to read this data and then translate it and put it into a format that will make sense to put it on a PowerPoint so that my boss can go out and give these presentations. So, it’s vitally important, whatever industry that you’re in, have a high level understanding, or maybe I should say a low level understanding, somewhere in the middle. Have an understanding of the industry that you’re in, the population that you are serving, who your client base is or your customer base is.


[00:18:59.760] – Gretchen Moran

Just having a little bit of information, so that when you do get phone calls, you do get emails, people are asking you questions that you at least have an understanding and you can make an intelligent response.


[00:19:12.390] – David Maples

I guess part of it is if your executive that you’re helping manage, if you have to go to them for every question or every answer, I think you lose a lot of utility or value in the role.


[00:19:24.870] – David Maples

I hadn’t thought about that.


[00:19:28.300] – Gretchen Moran

They need to be driven. They need to be self motivated. That’s not something that you can teach. It’s something that’s inside of here that if you can find the right person that is driven, that wants to do well, they want to learn more, they want to get up that corporate ladder, or they want to do the very best job that they possibly can, and they’re asking, what else can I do? That’s a golden nugget right there.


[00:19:58.450] – David Maples

I did want to talk about the… Well, this is not a question. This is more like the No BS portion of this episode. We had a thing before where we talked about in a very early episode of The Buck Stops Here, it was this idea that if you want more in life, you have to be more in life. I was talking to a lady who had been out as a graphic designer, and Catapult, the company I work for full time, we deal with a lot of graphic designers and things like that. I asked this lady, and she’d been out in her career maybe five years. She’s like, I really want to be an art director, creative director. I asked her, I said, so what have you done to say that you want to be more in this role? What time and energy are you putting into doing these things? If you want to be a creative director, and she’s like, well, I’m so busy at my job. I was like, well, how much does your job take out of your life? She’s like, 40, 45 hours a week. I was like, what do you do in your free time?


[00:20:51.260] – David Maples

Well, I’m off surfing or doing the following. I was like, None of that is about sharpening your skills outside of work. If you want more out of life, you’re going to have to be more. Because the people that you’re competing with who want to become art directors live and breathe this stuff. They’re out there doing these things. They have side projects where they are sharpening their own skills. They’re getting involved with other experts in the industry right now. They’re at least watching YouTube videos, and then they’re putting what they see into practice. So, to this episode’s point, if you’re an executive assistant or administrative assistant, you want to take that next leaf and move up in your organization. If you want to get paid more, you want to have more responsibility. If you want to grow in the organization, then you have to not only have, as Gretchen said here, the drive and determination, but you’re going to have to put the time in. There’s a good book called “Managing Up” that’s out there. You can look at that and find it on Amazon where it talks about managing and how you deal with the people who are above you in the organization.


[00:21:44.960] – David Maples

I’d recommend starting reading that. Just go look at these other things and find out. Go maybe talk to other executive assistants who work at other places in your industry. In any city you’re in, you can probably find some. Maybe go pick up a mentor or a mentee who can, a mentor in this particular case, who can maybe help you get to the next level. I guarantee you there are people out there that are executive assistants right now who see where you are and they see a version in themselves 10 or 15 years ago. I guarantee you they’d be more than willing to help you out. That’s the end of your No BS segment. If you want more, you got to go be more. In the No BS segment of this podcast, we just said, want more, be more. If you could go back in your career, and when you were either a young administrative assistant learning things out, or when you started becoming an executive assistant, what are the three pieces of advice or maybe one or two pieces of advice you’d go back and give yourself in that role? What would you go back and tell Gretchen?


[00:22:41.780] – Gretchen Moran

Don’t be afraid to ask for more.


[00:22:45.860] – David Maples

More to do? You mean more to get paid? What do you mean?


[00:22:48.770] – Gretchen Moran



[00:22:49.370] – Gretchen Moran

Don’t be afraid to ask for more work. If you find yourself sitting at the desk and you’re like, Oh, I don’t feel like I’m really earning my wages here. Ask for more work. See if there’s other people in the organization that you can take some of their work, take it off of their plate and do more. Or you may be on the other side of the coin and you may just be at top full capacity. Ask for help. You may need to ask for help. There’s so many organizations that I know of over the last, especially the last two and a half years, that jobs have been eliminated, positions have been eliminated, and they have taken two jobs and made one. Now, one person is doing the work of two people. If you’re at the level where you are just full up, your burnout is coming, your health is suffering, ask for help. If you are at that place and you know you can’t get the help, ask for more money. Because if you are truly valued in the organization and your boss values you, if you’re in a good place, they will value that and they will compensate you.


[00:23:59.680] – David Maples

I’ve always heard it said, if you don’t ask, you don’t get. So, that’s one of those things that’s important.


[00:24:06.570] – Gretchen Moran



[00:24:06.820] – David Maples

So, Gretchen, I want to thank you so much for coming on the podcast today. If you guys would like to know more about Gretchen, you can find her online. We have links to those places below. The name of her company is Simply Living KC. She is a master organizer where she manages and helps other people master the organization in their personal and professional life, and she comes in and does organization and some consulting for business owners. So, if you’re looking for more information, perhaps about how to hire an executive assistant or how to get some feedback, or perhaps even get some personal consulting or coaching for your administrative assistant who wants to become a better executive assistant, then Gretchen is open to that work. With that, Gretchen, I want to thank you for coming on today. It was a real pleasure getting to chat with you.


[00:24:49.730] – Gretchen Moran

David, this has been really great. I really appreciate it. I hope your audience got some good tools out of it today.


[00:24:55.210] – David Maples

Oh, I’m sure they did. I’d like to thank Gretchen Moran for coming on the podcast today. If you’d like to find out more about her consulting services, you can find out more at That’s If you liked what you heard here, please give us a thumbs up or five stars, or provide a comment if you’re on YouTube watching this right now. If you’re trying to share this with other people, you can find us on Apple, Google, Spotify, or wherever great podcasts are hosted. Again, I’ve been your host, David Maples. Go out there, be awesome, and have a great week.


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