Annie [00:00:01]:
Welcome to the Whole Assistant Podcast, where assistants come to embrace their badassery and discover how to show up more strategically for their careers, their executives, and most importantly, themselves. I'm your coach, Annie Kroner. Join us as we dive into the skills, strategies, and mindset that will help you unleash your full potential. Let's go. Hello, hello everyone. Today I am answering questions submitted under the Ask Annie Anything tab, so if you'd Scroll down to the show notes. There's a place to submit a question. So if you have a question that you would like me to answer on this podcast, please feel free to submit a question and I'll probably be doing more episodes like this.
Annie [00:00:43]:
Today I'm gonna be answering 3 or 4 questions and we'll just see how I do on time. The first question is really pertinent to the theme of this month, which is boundaries. If you did not listen to last week's podcast episode, I highly recommend that you go back and have a listen. Where I share my own personal story of boundaries. This question is really relevant, and honestly, I get a lot of questions around boundaries and what they should look like. So this question was submitted by Jira Porin, and she said, or they said, thank you for the good podcast. Could you perhaps share how you set boundaries in the case the executive has some emergency issues? I mean, is there any exception on helping him on a Saturday or Sunday. How do you normally set boundaries for this? As a PA, I mostly deal with personal stuff for my executive and his family, and it's difficult for me to set this kind of boundary.
Annie [00:01:36]:
Yes. So first of all, boundaries are all about self-discovery, and I think that a lot of us think that boundaries are hard and fast, but I actually think that boundaries can breathe a little, and we can set parameters around our time and energy that do accommodate certain situations. So if you have an urgent item that comes up over the weekend, or there's an emergent item that needs taken care of and your executive turns to you, you can absolutely do that task even though you've set maybe the parameter or boundary that you will not work during off hours or during the weekend. I had similar boundaries with my last executive, and yet I still wanted to be in the know. I wanted to know if something urgent came up and something needed to be changed last minute. I was totally willing and able to accommodate that, and I wanted to maintain boundaries cuz I had babies at home, started to have kids. And so I really had to adjust my boundaries to match my values during that season. And I will say that boundaries tend to shift and change with time and circumstance, and it's totally okay to be accommodating to your executive's life, to their world, to any situation that may arise with my last executive, I also managed a lot of personal things as well.
Annie [00:02:48]:
Jeroporn. So I just want you to know that I wouldn't do anything that I felt like his kids should be doing for themselves. That was the one boundary that I had set up. And yet there were times where the family was leaving out of town and I needed to do something for them. And I'd reiterate the boundary to my executive, be like, under normal circumstances, your kids should be doing this, but because you guys are going out of town, I don't mind managing this for you. And I was always really respected in that my executive understood those boundaries and why I had set them up. So my core values around that were resourcefulness and resilience and training kids to be resourceful and resilient in particular was something that I really valued and I just wanted to pass on to my executive's children because it was such a high value for me. And I think that it's also okay to recognize and realize that you may differ from your executive's values, and that you guys may have values that are honored more with one person than another, and you can find that middle ground.
Annie [00:03:48]:
You can find a workaround, and you can allow your boundaries to breathe a little bit. Another thing I also like to point out here is that boundaries can be iterative. Oftentimes we don't know what boundaries we want to put in place until something rubs us the wrong way until we bump up against something. We're like, this doesn't feel quite right to me. I should probably not be managing this thing that I've been asked to manage. You can always circle back. I don't think that they have to be hard and fast rules. I don't think that they have to be one and done.
Annie [00:04:18]:
I think that we can allow them to breathe a little bit. And I would caution that the number one violators of our boundaries is often us. Like, we set the parameter, we set the boundary, and then somebody checks the boundary, somebody pokes at the boundary, somebody pushes up against the boundary, and we're like, oh, okay, I'm just gonna do it, instead of actually holding to that and reminding the person of the conversation that you previously had with them, explaining that this is a good example of that, and moving forward. And I think that's just a normal part of the boundary-setting process, is having people test the boundaries. It's human nature. But in your case, Jeraporn, I do think that If there's an emergency, you can totally meet your executive in that in a way that feels good to you and good to them. Okay, moving on. This is kind of a long question, but I'm going to read it regardless because I do feel like it will be helpful.
Annie [00:05:12]:
And this comes up a lot too, I've noticed online. This question was submitted anonymously, so I'm not going to read the person's name. This person is an EA and she says, I have recently been assigned to work for the GM's office in the sales team. In this office, there's also a chief of staff whom I've worked closely with as she is a sounding board of my GM. I find the lines get blurred when the COF starts making changes and updating the calendar and some minor admin comms that she insisted she wanted to do, even though I offered to help. I come with more than 15 years experience supporting senior execs directly. The COS is an experienced people manager too, but came from a totally different field. This is her first year being a COS.
Annie [00:05:55]:
I also find it difficult to juggle between my core duties and the work that the COS picked up and wanted me to follow up on. To clarify, I report to my GM, but we need to manage different stakeholders on a daily basis. I wanted to find out if it's normal for a COS to be working at this level, and what is your experience working with one? I have great respect for the COS being a strategic partner to my GM, but things just are getting blurred when working on op— on an operational level. Thank you. Oh, this is so challenging because whenever you're managing, it's like two people managing the executive office and figuring out what those lines are. You had mentioned Anonymous that this COS has never sat in a COS role before. This person has obviously never been an executive support person. You mentioned that they were a people manager before, and I think it's always good to get clear on who's going to be managing what part of the executive office.
Annie [00:06:48]:
So sitting it down and having that clear conversation around roles, around those lines and also staying in communication when it comes to rhythm of business, because she may, or they may be making adjustments to the calendar based on rhythm of business initiatives that the executive actually wants. So it's gonna be challenging for sure, but I do think that actually having a real clear conversation and maybe even looping in your GM may be the way to go here. And it is challenging to work with somebody else in this capacity where the lines are blurred, and especially if the per— this person has never been in an administrative role before and now they're a chief of staff and you're trying to manage the executive and this other person's trying to manage the executive, it's gonna be very challenging to know how to do that. I do think that really keeping those lines of communication open and even like asserting yourself and being like, oh, actually that's my lane. I will go ahead and send the calendar invite for this meeting. And almost managing up. And I know it can be challenging cuz a lot of us manage up with our executives. We're constantly trying to figure out how to navigate, making sure that our executives are where they need to be, making sure that they are staying in line with their objectives and their KPIs and their goals and managing everyone else's expectations as well.
Annie [00:08:03]:
So this is gonna be an added layer of complexity to that because you're gonna be managing the chief of staff's expectations as well., and I see nothing wrong with maybe even putting on a calendar a weekly or biweekly touch base with your COS so that you guys can remain in sync and you can understand the COS's objectives. And for those, I'm sure everyone listening to this podcast already knows, but COS is short for Chief of Staff. So we definitely wanna be making sure that we are keeping those lines of communication open, staying in touch with the Chief of Staff so you know their objectives. You also understand the executive's objectives, and maybe the Chief of Staff could also keep you in line with the rhythm of business, cuz that's a large part of the chief of staff role is managing the rhythm of business and the overall arc of the company and the department. So I definitely think those are some strategies I would try. And Anonymous, please report back and let me know if this was helpful and if you actually were able to navigate this relationship with your chief of staff. Okay. The next question comes from Stephanie who asked, how can I be demanding but not offensively? And I think.
Annie [00:09:10]:
What this person actually meant, or how I'm interpreting this question, is how can I be assertive without being aggressive? Which is just a fine line to walk, right? Because oftentimes we do need to assert ourselves, we do need to use our voice, we do need to speak up, we do need to actually put ourselves out there and ask the questions. And it can be challenging when you are afraid of coming across as pushy or demanding or offensive or bossy. I see this a lot with people who are managing executive assistant teams or trying to lead a group of executive assistants, but they have no real authority. They're trying to get everyone on the same page with professional development or processes or procedures. And it can be a fine line because we don't wanna come off as offensive, and yet we want to create a standard operating procedure for the office. We wanna create procedural guidelines that will be helpful to everyone. How do we actually navigate that? And Stephanie, I hope I'm hitting this right on the head for you. I hope that I actually understand the spirit of your question.
Annie [00:10:19]:
I know that I've had been asked this question a lot as a coach and as a trainer in our space, and it's just gonna be a fine line to walk and, and we're really gonna have to stay in touch with our inner spidey sense, that, that intuition that helps us navigate these situations because you know your situation, you know what will be helpful versus what will be offensive to people, and I think Also, watching the spirit in which you speak can also be really helpful here. We know when we are giving a defensive response versus when we're giving a compassionate one. So really tapping into curiosity with people so that you fully understand what they are saying, really tapping into your sense of compassion for others, really getting curious and approaching any situation from a curious vantage point will give you more information that you can then address and speak to. So more data points so that we can release that drama piece and really dive into how we can address those data points without being abrasive or offensive or coming off as someone who doesn't care about the individual that you're sitting across from. So those are my best strategies for showing up in a way that feels authentic and genuine and genuinely caring about other people and still using your voice. It's a fine line to walk, but Stephanie, I believe you can do it. So please email me, let me know how that goes. Hey there, quick pause.
Annie [00:11:53]:
Do you wanna grow in your career but don't have a ton of extra time, money, or let's be honest, energy to commit to leveling up? If this is you, I have got you. Empower Seat is my intentionally affordable membership for busy executive assistants and support professionals who are done white-knuckling their careers in isolation Inside Empowered Seat, you get support that's actually built around you. You're gonna get access to me inside of our VIP online community. You're gonna get 2 monthly calls with me as well, a monthly training session you can watch or listen to on the go. It's prerecorded, so you can either listen through our private podcast or in the vaults. It's affordable, practical, sustainable growth built by someone who gets it. If this sounds like what you've been looking for, you can learn more and join Empowered Seat at wholeassistant.com/empoweredseat Or just click the link in the show notes below. Now back to the episode.
Annie [00:12:53]:
Okay, the next question is from Amanda in Oklahoma City. She says, how do you handle differing opinions with the executive team? Sometimes my CEO and founder clash. I'm EA to both. There have been a few times one said one thing and the Others said the exact opposite. It's this new startup and I wear many hats at this moment. I have been tasked with creating culture and company policies and have ran into them not agreeing at times while trying to make certain policies. Okay, so Amanda, that's not your problem. If you are trying to make policy and you have been tasked with making policy and leadership cannot agree on what the policy should be, you want to facilitate conversation between the two of them and take yourself out of the middle., and it can be really challenging whenever we feel like we're pulled in two different directions.
Annie [00:13:46]:
And in those situations, I just like to dismiss myself and I like to set up a meeting for the two leaders to discuss so that they can get on the same page and then you can execute. Okay. And I think often also that we take on so much responsibility and we make that mean it's something about us, or we make it mean that we should be the peacekeeper or whatever, instead of facilitating the conversation and detaching from the outcome. And that detachment from the outcome, while challenging, can be hugely helpful for you because once you recognize what is yours to own and what is not yours to own, it will be tremendously helpful for you in moving you forward and actually in getting the policy that you need in place. I would also caution that you may wanna actually consult with an actual HR professional when it comes to policy. I have a training inside of Empowered Seat that I held last month in February of 2026 that spells out what administrative professionals can be handling in terms of policy and what they cannot be handling in terms of policy. What's an actual liability for you to handle in terms of creating policy and where somebody with an actual HR training and a background in HR can be tremendously helpful in the liability piece when it comes to that policy piece. And I know that sometimes a especially in startup environments, it can be super challenging, which is exactly why I sourced this training.
Annie [00:15:12]:
And it took me like, man, a year and a half to find somebody to come and train on this because most people wouldn't touch it. And I'm like, I just need some guidance for my people because I can't guide them because I don't know, because I've never been an HR professional before. I know what feels intuitively like it may be a liability, and I know what feels intuitively like it may be putting my people at risk., but I don't know for sure. So really leaning into that intuitive piece as well and relying on an HR professional when it comes to creating the policies and also creating the culture. I'm a firm believer that as a support professional, you are the keeper of your company culture, but you are not solely responsible for it. Okay? And I know it can be super challenging when you've got two leaders who are at odds with one another. But there again, we can facilitate a conversation with them and you can tell both of them, I cannot move forward until you guys get on the same page with this. And take yourself out of the conversation that way and facilitate a conversation between them.
Annie [00:16:13]:
I've actually run into this quite a bit where there have been two founders, two leaders, maybe a CEO and a COO who co-founded a company and they're at odds with the vision, they're at odds with certain intricacies or certain policies or certain way things should be run. And as a general rule, I don't wanna be a part of that decision-making process. I wanna remove myself and I may give feedback and I may give my vantage point if it will be helpful and useful, but more often than not, it's like I will facilitate a discussion between you two. And that is my best advice for you, Amanda. I hope you find it helpful. Okay. And our last question For today comes from Sandra from Seattle, and she asks, how do I get started in this career? Do I need a certificate or school for this? I get asked this a lot about certifications in our space, and you absolutely do not need a certification in order to get started as an administrative professional. You can, if you feel like it would be helpful and give you a framework for managing things or a framework for expanding your knowledge base in the space, you can absolutely get a certification.
Annie [00:17:24]:
There's a CAP, there are a couple of others, but you do not need a certification in order to get started. I would get started at an entry-level position, probably if you're searching for a new role or you're shifting fields, or you are new in the workforce in general and you've just graduated high school or college and want to dive into a role in administrative function. That's how I got started. I actually was offered a job when I was in college working at this country church, and I told my then boss, I'm like, I have no knowledge of administrative roles. And this person was like, great, then I can mold you to be exactly what I want you to be, and I can help you to show up in a way that will actually serve and support our office. And she was actually really instrumental in me becoming more proactive and actually gave me some good food for thought for how I could offer value in that first role. And then I did administrative roles all through college and then graduated college, moved to Boston, became the receptionist at a consultancy there, and the rest is history. I've since steered my career to become like a really effective executive support person to C-suite executives and people in the venture capital and family office spaces and I believe that you can start from anywhere.
Annie [00:18:42]:
I think that it takes a level of resourcefulness. I think it takes a level of resilience, and I think it takes a level of being able to troubleshoot anything. You have to be really resourceful in administrative roles. So that's where I would start. And if you want help with finding a job or knowing how to frame your search or anything like that, I actually have a course. That you can go ahead and take, and it's pay what you can, because I understand that those looking for jobs may not be able to afford to pay a lot of money based on your financial situation. So it really is pay what you can. And I actually break down all my knowledge with regards to finding jobs and how to frame your resume and how to frame your search and how to position yourself in the marketplace and, um, how to set up your LinkedIn profile and all of those bits and pieces in this course.
Annie [00:19:36]:
And I will link to that course below in the show notes. But really, the way we get started in these roles is to just get started in these roles. So Sandra, I hope that was helpful for you. If you want a list of certifications, if you feel like you would benefit from certifications, you can go ahead and email me at annie@wholeassistant.com. I will say that I don't think that anybody needs a certification in order to be successful in a lot of fields. Obviously, in certain fields, like if you're going to be a therapist, you definitely want to have a degree that will be conducive to that. And certain fields require certain certifications and whatnot, but this field does not. And I sought out certification as a coach because I loved a specific framework.
Annie [00:20:22]:
And actually I'm certified in two different modalities for the coaching, but I sought out certification because I wanted the knowledge and because I knew it would help me become more effective as a coach. And I also utilized those skills prior to becoming a coach and found them so helpful. So I went to school to get that certification. Because I wanted to, not because I was hanging my hat on finding a job or being hired as a coach as a result of getting that certification. So I believe that if you wanna expand and grow and you want to gain that knowledge, absolutely get the certification, but you don't have to. And I would venture to say too that in the administrative function in particular, I would wanna get my feet wet first to make sure that it was something I wanted to pursue before I ever pursued a certification. As an administrative professional. So those are my thoughts on certifications.
Annie [00:21:15]:
They are not required in order to find a job. Most places will not require you to be certified. And honestly, I've had people in the past come to me and they're like, I just got certified, so I should get hired any day now. I'm like, nah, I don't think that's how this is gonna work for you. I'm sorry to say, but that's just something to bring your awareness to. I would get my feet wet first, and then if I decided to pursue a certification, I would pursue it because I wanted to, not because I was hanging my hat on it helping me find a job. Okay guys, so that is what I have for you today. Really fast, quickfire, rapid-fire questions.
Annie [00:21:52]:
I hope you found it helpful, and I will see you next week on the podcast. That's all for now. If today's episode gave you language clarity or just a quiet, oh, It's not just me. I am so thrilled you're here. If this podcast has been helpful for you, the easiest way you can support the show is by taking 30 seconds to rate and review it on Apple Podcasts or Spotify. This helps more assistants find this work. And if you're ready for ongoing support, guidance, community, and growth that actually fits into your life, Empowered Seat is where we continue this work together. It's affordable, flexible, and designed for assistants who are done white-knuckling their careers in isolation.
Annie [00:22:33]:
You can learn more and join at wholeassistant.com/empoweredseat or click the link in the show notes below. And until next time, go embrace your badassery.
