kara mckeage leader assistant podcast

Kara McKeage is the founder of Pepper’s Personal Assistants, a sourcing and placement agency for highly vetted personal assistants.

In this episode, Kara talks about outsourcing, matching personal assistants with executives, interview questions to ask applicants, setting boundaries with principals, communication between executives and personal assistants, and more.


Don’t be intimidated by what you don’t know. That can be your greatest strength and ensure that you do things differently from everyone else.

– Sara Blakely


kara mckeage headshot leader assistant podcast


Kara McKeage is passionate about helping successful women ease the mental load with skilled household support. She is the founder of Pepper’s Personal Assistants, a sourcing and placement agency for highly vetted personal assistants. The company has grown organically to a team of 24 employees. She believes that it’s time for professional women to let go of the shame around outsourcing household tasks so they can find more time, feel organized and have peace of mind.

ezCater large logo

ezCater is the nation’s most trusted provider of corporate food solutions — the best way for companies to order food for daily employee lunches, meetings, and events of any size or budget. ezCater’s simple-to-use platform provides a network of over 100,000 restaurants nationwide, business-grade reliability, food spend management tools, and 24/7 support from their highly trained customer service team.

To explore corporate food solutions or place a catering order, visit ezcater.com.


To learn more about how you can join growth-minded Leader Assistants, check out our Leader Assistant Premium Membership for ongoing training, coaching, and community.


Download the first 3 chapters of The Leader Assistant: Four Pillars of Game-Changing Assistant for FREE here or buy it on Amazon and listen to the audiobook on Audible. Also, check out the companion study guide, The Leader Assistant Workbook, to dig deeper.


Check out our constantly updated schedule of events for admins and assistants at LeaderAssistantLive.com.


Join the Leader Assistant Global Community for bonus content, job opportunities, and to network with other assistants who are committed to becoming leaders!


Subscribe to The Leader Assistant Podcast so you don’t miss new episodes!

You can find the show on Apple PodcastsSpotifyGoogle Podcasts, Pandora, and Stitcher.

Join my email list here if you want to get an email when a new episode goes live.


If you’re enjoying the podcast, please take 2 minutes to rate and review the show on Apple Podcasts here. Each review helps me stay motivated to keep the show going!


Kara McKeage 0:00
Hi, I’m Kara McKeage and today’s leadership quote comes from Sara Blakely. Don’t be intimidated by what you don’t know that can be your greatest strength and ensure that you do things differently from everyone else.

Podcast Intro 0:19
The leaders assistant podcast exists to encourage and challenge assistants to become confident game changing leader assistants.

Jeremy Burrows 0:33
With so much on your plate, wouldn’t it be nice if ordering food for the office were easy and reliable. My friends at easy cater our workplace catering pros helping you find food for everything from daily employee meals to staff meetings and special events. With easy caterers network of over 100,000 restaurants nationwide, you’ll have a huge variety of options near you for any group size, dietary need or budget. Your food arrives on time as ordered all supported 24/7 by easy caters team of experts. Visit easycater.com/leaderassistant to find out more. Hey friends, welcome to The Leader Assistant Podcast. It’s your host Jeremy Burrows and welcome to episode 217. You can check out the show notes at leaderassistant.com/217. And today I’m excited to be speaking with Kara McKeage. Kara is the founder of peppers personal assistants. Kara How is it going today?

Kara McKeage 1:38
Great, doing Good.

Jeremy Burrows 1:40
What part of the world are you in?

Kara McKeage 1:41
I’m in Seattle, Washington.

Jeremy Burrows 1:44
Okay, are you from that area? Yes. Okay, so do you like rain?

Kara McKeage 1:49
I do. I do like rain. I like the sunshine when it comes out to though.

Jeremy Burrows 1:54
Yeah. Makes you appreciate the sunshine when you know when it rains that much, right? That’s not like. So tell us about your your career. What did you do before you founded peppers, personal assistants, and why did you found this business?

Kara McKeage 2:13
Yeah, so my background is mostly in admin support. I’ve always found joy in helping others succeed and making their life easier. And then I was able to stay at home with my two boys for eight years. And really enjoyed that. But once my youngest started school, I was ready to get back into the workforce and wanted to find something that, you know, helped me kind of keep that stay at home moms status. I really enjoyed being a part of their lives and being active in what they were doing. And so I started doing this part time for a friend and loved it and used all of my skills and provided flexibility and brought me a lot of joy. So I started looking for more clients, and it just kind of grew from there.

Jeremy Burrows 3:07
Nice. How many kids do you have?

Kara McKeage 3:09
I have two boys. They’re now teenagers. So I started Pepper’s. 11 years ago when they were much younger. Now I have my youngest son’s a junior in high school. So

Jeremy Burrows 3:21
awesome. Yeah, I have two boys as well. So have I think having boys is awesome.

Kara McKeage 3:26
Yeah, it’s a lot of fun, for sure.

Jeremy Burrows 3:30
Awesome. Well, what did you do to kind of was it all organic growth? Did you? Did you do like paid advertising? Like, how did you grow your business and find more clients? And then when did you start? Actually? So let me clarify. So does peppers, personal assistants? Are you kind of like a firm that has a lot of assistance that you provide for different clients? Or are you more of like a recruitment for clients? And then they kind of just go off and work with them? Does that make sense?

Kara McKeage 4:07
Yeah, so we have two arms of the business in Seattle, we’d hire personal assistants. So they’re our employees, and we play some with our clients. But we also have a national placement agency. So you know, anywhere in the US, we’ll do all the recruiting and getting everybody set up and placing them with clients. So doing all the hard stuff. And helping support, you know, the Getting Started as the hardest part. So we help with that. That part of it. Okay, so

Jeremy Burrows 4:43
then when you got started, what was what was kind of the busiest or what was the biggest part of the was it the recruitment side or was it just you had a bunch of clients that are like I need I need one of you.

Kara McKeage 4:59
Yeah, Well, when I first started, I was doing like anything that came my way. It was like, you know, returning shoes to Nordstrom and dogs sitting and you know, just like one time jobs. But as we started to grow and get more recurring clients, you know, we created packages. So on Seattle, it’s a weekly package with a six month commitment. But, yeah, we just, we’ve grown organically still, you know, to this day, I’ve really controlled growth to make sure we’re focusing on quality and taking care of both both sides, the client and the personal assistants.

Jeremy Burrows 5:43
Okay. And then how many about how many assistants do you have on your team?

Kara McKeage 5:48
Right now? I think we’re around 30. Part time of personal assistants.

Jeremy Burrows 5:56
Wow. And so does that mean you support about 30? Clients? Or do you have some that maybe support multiple?

Kara McKeage 6:04
Yeah, there’s a few pas that, you know, are working for, for a few clients. But yeah, we’re around 3035 clients so

Jeremy Burrows 6:13
great. And how have you? Well, before I get into some more nitty gritty, what would you say is the biggest difference between a personal assistant and, and executive assistant?

Kara McKeage 6:30
Yeah, so I find it interesting, because when I started the company, 11 years ago, there wasn’t really a term that I felt like my business fit in. Now, I’d probably, you know, name at like household assistants, or household managers. But at the time, in my mind, it was, you know, executive assistant, as somebody that’s supporting somebody in the office, and the personal assistant is supporting somebody more in their personal life. I know and in office setting there, there are personal assistants. In on, so it’s a little bit of a gray area. But, you know, we’re like, if you can get an executive assistant in the office and a personal system, that home that work together to make your life easier, like, to me, that’s a dream. For these busy executives, you know, that they can focus on, you know, the things that that they enjoy doing, and kind of their zone of genius, and have everything taken care of at both places. So

Jeremy Burrows 7:36
yeah, what have you had a lot of, or, you know, what’s maybe the percentage of the of your team members who have been executive assistants in the office and then kind of converted over

Kara McKeage 7:48
to the Personal System? To many, we find that people either really enjoy office work, or really enjoy, you know, household management, there’s not a whole lot of crossover there. Either direction I found, you know, they’re much different jobs. The goal is the same to support the person but the actual tasks, you know, are much different. So,

Jeremy Burrows 8:17
yeah, yeah, I have been a CEOs assistant for, I don’t know, 12 plus years now. And an assistant for for 17 plus years, but specifically CEOs assistant and when I’ve been this, really even when I wasn’t the CEOs assistant, I was still doing some personal assistant stuff. But definitely as I’ve been supporting as an executive assistant to CEOs I have also done personal stuff because I kind of see it as in my executives do as well. They see it as you know, we have one life we don’t have a work life and a personal life and you know, social life and whatever, we have one life and so it’s worked well. For me to be kind of involved on the personal side and coordinating things with their spouse and coordinating things, travel with kids involved in all that kind of thing. But what’s been interesting and what’s been nice in my current role is I brought in a household manager slash personal assistant to really support my executives, spouse, and so it’s, it’s been fun to have someone on site and especially since I moved four hours away during COVID and work remote now. Because when I was living in town as it is obviously easier for me to run over to the house and meet a contractor or whatever. So it’s been fun to work with the assistants slash household manager, like you said that titles kind of a little bit of everything. But what’s something that you encourage or even train your assistants, your personal assistants? To help them work well with their principals, executive assistant? If they have one? Like, how is there a? Is there a formal process on that? Is it just like, some tactics and tips on? On? Hey, you need to double check with their executive assistant, you need it, you know, those kinds of things? Yeah, so

Kara McKeage 10:34
every relationship is different, you know, some executive assistants of our clients are very hands on, some are more just, you know, scheduling the meetings and that sort of thing. We have one client that has operations manager that we work with closely, so we really tailor it to the relationship, but we’re very involved in, you know, especially the beginning of like, figuring out like, do those two need to be having a one on one each week to check in? And then we do a lot of training on communication, like, that’s really the key to success, you know, it’s making sure that you’re communicating with the right people. So

Jeremy Burrows 11:21
how often does the executive assistant delegate tasks to the Personal System?

Kara McKeage 11:28
Yeah, it’s not too often. You know, the, the operations manager, I would say, is probably the most involved out of all the clients that we have, where her job really is to, like, be the front person, like we go to her first, you know, if there’s any questions or issues, which is really nice to have, you know, it makes it so easy to make sure that we’re meeting his needs and kind of nailing it for him. And then there’s others that, you know, it’s only if we need to, like set up a one on one meeting with the client or something reached out to her to get that scheduled. Yeah.

Jeremy Burrows 12:10
Awesome. And what about if there are assistants listening, who are in office assistants, which I don’t really have the exact numbers but in don’t really have a way to do this, really. But I would guess that most of the assistants listening are corporate or nonprofit in office, executive assistants, Administrative Professionals. Many of them have personal assistant tasks as well. But if they’re considering or have considered making the jump from the office to the household, what are what are some recommendations you have? Or what are some maybe even just questions to consider for determining whether or not that’s would be a good move for them? But

Kara McKeage 13:03
yeah, yeah, I think looking at, you know, what brings you joy, like, that’s a big part of our most important task is matching up a client and a PA and making sure that the client’s needs is what the PA enjoy. So, I think looking at, you know, what are the things that I’m really good at? And that I enjoy doing? And is that something that would fit in with a personal assistant, you know, our pas are doing things like laundry and vendor management and going to Costco and, you know, running errands, that sort of thing. So, you know, if that’s something they think that they would enjoy, you know, definitely should should look into it. But yeah, typically, I think most, I would think, just based on interviewing a lot of admin assistants are like, No, thanks. That’s not for me, I enjoy, you know, the different tasks that admins do is it’s more in their line of what they enjoy. So, yeah.

Jeremy Burrows 14:17
What, what about tips for, you know, I was, I was helping my principal find the household manager, Assistant, what’s the best place to find them? What are maybe even tips on, you know, maybe examples of interview questions to ask, potential? And then how do you deal with security and background checks and all that?

Kara McKeage 14:43
Yeah. So I think, you know, for this type of a position that’s good to kind of start with friends, people that you know, and even like neighborhood groups or that sort of thing. stay at home moms can be really great candidates for these positions, you know, that are looking for kind of a mom hours when the kids are in school. And, you know, the type of questions that we asked we, we go through a very lengthy process, there’s, you know, two to three interviews where we’re really diving deep with people. And I think one of the great questions is just to ask them, you know, why did they apply what appeals to them, and you’ll get a lot of information, we look for people that are like, I just love helping people, it brings me joy, you know, to make their life easier, those kinds of things, and making sure it’s of values, but obviously, making sure they have experience with running a home are the tasks that you’re looking for. And then the other thing, I guess, kind of backing up is, you know, really having a list of what it is that your executive is looking for, and kind of prioritizing, like, what are the must haves, you know, the type of tasks? And what are the kind of nice to haves? Like, do you need somebody that can meal prep? Or, you know, are you mostly just focused on, you know, kind of the day to day tasks that are not sort of thing? And then asking the applicant? You know, what do you think is gonna be a slam dunk for you what, you know, do you think you might have some challenges with Are there any concerns with the newbies and, you know, to make sure that it’s a good long term set, you really want to be clear with what the job is, and what the expectations are? And so that, you know, something peppers does is we do a really deep interview with the client and with the employee and and make sure that it’s a great match. Okay.

Jeremy Burrows 16:56
Awesome. And what about, could you talk about boundaries, and maybe job descriptions even because I know, a lot of times, it’s super blurry. There was even an article recently that just was going around social media viral about this job description that was like, you know, you got to be the gardener, and you got to be the this and you got to be like six jobs, it literally said six jobs in lawn or something like that. And then it was like, the salary is $60,000. And everybody’s like, so how do you? How do you? And this is applicable to assistants in office as well? That how do you set clear expectations and set boundaries on hey, listen, I’m not the gardener. You know, I’m not the, you know, whatever the whatever the job is, it’s like, I will help facilitate, maybe, but I’m not actually the person to do that.

Kara McKeage 17:51
Yeah, exactly. Yeah, pepper is like the Seattle based with our employees, we have very strict like boundaries with that, just because we’re managing it. So we focus on what we’re really good at training people on and managing and everything. And so, you know, we don’t do child care, we don’t drive people. for insurance purposes, we don’t do executive admin work, you know, mailing things, or that sort of thing, you know, kind of like admin work will do. But it’s very clearly defined the household management tasks that we do with the placement agency, we can be a little more flexible, because we aren’t going to be managing that person. But we still discourage people from blending roles of like, you know, you don’t want to have the nanny, focus on household tasks, they should be focused on the kids, you know, like, again, a little bit of like cooking dinner, or maybe doing a load of laundry, or that sort of thing, but or, you know, the executive admin, you know, it’s better to have those roles separate. You know, so the person, you can make sure you find the person, that’s the perfect fit. Because that unicorn can be really toss, you know, to find that person that sets all of the things. So it kind of goes back to what I was saying of like prioritizing, like, what is your biggest need and hiring for it that?

Jeremy Burrows 19:26
Yeah. Do you have any painful stories or examples of clients or assistants that you assigned to clients, and it just did not work?

Kara McKeage 19:39
Oh, yeah, for sure. It happened,

Jeremy Burrows 19:42
and why didn’t it work?

Kara McKeage 19:44
Yeah, you know, one of the biggest things is, and that we’ve learned, with experience making the mistake is that communication in the first 30 to 90 days is the most important and so we’ve actually We made it mandatory for our clients to set aside at least 15 minutes a week to meet with their PA, because we’ve found that can make a huge difference in the long term success, because oftentimes, its clients not giving feedback, you know, in a timely fashion. And so, you know, we’ll have our 30 Day check in with a client, and they just start spewing all these things that are going wrong, that we had no idea, you know, and so we do a lot more check ins than we used to do, just to make sure things are going okay. And then also coaching clients on how to get feedback, you know, both make sure you’re giving positive feedback and constructive feedback of how the PA can improve. But oftentimes, it really is just communication. We’ve never had like, somebody like a client, or an employee that was just a horrible person or anything like that not being, you know, disastrous in that way. Thank goodness. But we do a lot of vetting beforehand. So that helps for sure.

Jeremy Burrows 21:10
So yeah, you mentioned meeting at least once a week, is that pretty standard? Like are we were what other types of chickens? And how frequently do these assistants me? Is it typically just a once a week thing? Or?

Kara McKeage 21:25
Yeah, so like, if, you know, one of the admin assistants is hiring for their executive, we recommend you know, what that kind of a relationship is like, the first month, you know, probably meeting for 30 to 60 minutes, a week is good, because you’re just really building that relationship. And, you know, it can take time to learn, I always say like, I would be a billionaire, if I had the magic one that was could read people’s minds and meet their needs without any work on their part. But the beginning it does work, you know, you have to put time and energy into the relationship. And the more time you put into it, the quicker you get to that place where you’re, you know, Pa will know what you need before you do like, that’s our goal. Eventually, you know, us to get there. So So those check ins are just so valuable, because it’s time to give feedback both directions, and make sure nobody is blocked on anything or unsure.

Jeremy Burrows 22:33
Great. And what about practically speaking, do clients, principals, households? Do they typically? What’s what’s more common for hiring personal assistants and working with purses? Do they provide things like health insurance or phone stipends or anything like that? Or with your case? Is that something that you provide for them? And then the client just pays you like? I’m just curious, because I’ve had that question come up a couple times, it’s like, hey, you know, the household manager? Are they expected to provide insurance for them? Or is it just more of a part time contracted role? So I’m just curious to hear your experience on that.

Kara McKeage 23:16
Yeah, it really varies. For peppers, our employees, we offer a health care stipend for full time employees, everybody gets a technology stipend, we do a 401 K with matching. Washington state has sick time, as required. And then we have PTO even for part time employees. So I feel like whatever you can afford, like the benefits are an important piece of it. But it really, you know, our employees aren’t with us, because of the pay or benefits. There’s a lot more that we focus on what’s culture, and those are the things that they value. But, you know, with people looking to hire, it’s definitely not a requirement, you know, to have insurance and that sort of thing, but you know, recommend doing what you can to make them feel valued, even if it’s not pay or benefits. So, yeah.

Jeremy Burrows 24:22
So you’ve been doing this business for what, 11-12 years or so is that right?

Kara McKeage 24:27
11 years Yeah.

Jeremy Burrows 24:27
How many years? What What’s the longest that one of your team members has been with a with a client?

Kara McKeage 24:35
Um, I think probably about five years. You know, we, we have like good retention rate for sure. Like clients tend to stay with us for a long time because they’re looking for for long term. You know, we have an employee that’s been with us for seven years, a lot of employees that have been with us for five years. So yeah, We focus on making sure they stick around. So

Jeremy Burrows 25:03
yeah. Well, you mentioned it earlier about, like, starting with your friends network and people you trust. Like, if you’re gonna let somebody in to your house, you have to trust them.

Kara McKeage 25:14
Yeah, yeah, that was one thing we didn’t talk about is definitely make sure you’re doing background checks, reference checks, that that piece is really important.

Jeremy Burrows 25:26
Yeah. So kind of the last thing I wanted to ask about is, and I’ve experienced this in my career as well. But why do Why do women in particular, struggle or wrestle with or hesitant to maybe even have shame around outsourcing for household help?

Kara McKeage 25:48
Yeah, it’s, it’s a big problem, I like to call myself a shame Buster, I’m like giving women permission, it’s okay to outsource smart people outsource. And I’m not entirely sure, you know why? There’s a lot of reasons, I think, but you know, women typically feel like, you know, have that feeling like, we should be able to do it all. And it’s like, even if you could do it all, doesn’t mean you have to do it. Like, you know, I’m a big, like, encourage women to outsource as much as you can afford, even if it’s, you know, the teenager down the street, you know, to come break down your boxes, and put out the trash and recycling each week, you know, whatever it is that you can afford to do, like, it frees up your time to really focus on things that bring you joy. I think the other thing is fear, you know, there’s this fear that, oh, it’s gonna be more work, right to hire somebody to do something that I can just do myself, it’ll be easier to do it myself. And, and that really just takes some training and some practice of being able to delegate and empower people to make decisions on their own and, you know, something that we help coach our clients on of, you know, how to give clear communication and, you know, be able to teach somebody how to do it so that, you know, you’re not spending too much of your time teaching training, and getting to that place where it’s freeing up your mental load because somebody else to have covered so

Jeremy Burrows 27:39
great. And I actually thought a one more question. I’m curious. How many of your systems and have you seen clients want the personal assistant to set up a sort of manual for their house? You know, here’s how you change the filter and air conditioner. And here’s how you do this. And this and that, is that a pretty common request?

Kara McKeage 28:02
Yeah, we have peppers has our own household guide that we start all clients with, and that’s a huge valuable resource. You know, we we kind of get it started just by listening to the client and kind of their needs, and you know, a little bit about their family and the PAs get an hour, two hours a month, paid time to keep it up to date. So it’s like haphazardly like their shirts folded, where’s the laundry detergent, who was the last vendor that was in the house, you know, because five years from now you’re like, who was at that service, the, you know, the furnace or whatever, it’s very easy to go back and look, and it’s great to if there is, you know, a new pa that comes in, makes it very easy for them to get up and running to have all of that history, armored in there and saves the client a lot of time because the PA is not coming and asking, you know, the same questions that’s documented, then the PA can use that as a resource. So

Jeremy Burrows 29:07
yeah, that’s great. Do you have that resource on your website? Or is it something just for your your client?

Kara McKeage 29:11
It’s just for our clients. Yeah. Yeah.

Jeremy Burrows 29:16
Well, Kara, thank you so much. It’s been great to chat. Is there any any any last words you’d like to share with assistants listening?

Kara McKeage 29:25
No, um, it’s been great chatting with you. I just encourage everybody, like I said, outsource as much as you can, even if it’s the grocery shopping, you know, get get some stuff off of your plate and go have some fun.

Jeremy Burrows 29:40
Love it. Love it. Well, what’s the best place for people to reach out if they want to learn more about you or connect with you or learn more about peppers? Personal Assistants?

Speaker 1 29:52
Yes, our website is Paseattle.com. And we’re on Facebook Live. A little bit on Instagram. So under peppers pa so and my email is pepper@paseattle.com If anybody wants to reach out in the chat

Jeremy Burrows 30:15
perfect well I’ll put that in the show notes leaderassistant.com/217. And thanks again Kara. Best of luck to you and appreciate you taking time.

Kara McKeage 30:25
Yeah, thanks Jeremy.

Jeremy Burrows 30:37
Apple podcasts

Unknown Speaker 30:45

Download FREE Chapters