Episode 208: How Executive Assistants Can Guide A Leader’s Professional Presence

You can run a flawless calendar, solve travel chaos, and defuse workplace fires before most people finish coffee and still get blindsided by one quiet risk: your executive walks into the room looking slightly off. Not scandalous, not sloppy, just misaligned enough to blur authority, weaken credibility, and chip away at the outcomes you worked hard to set up. That “unwritten responsibility” lands on executive assistants all the time, with maximum discretion and almost zero training.

I share the three moments where what your leader wears matters most: high stakes external visibility like board meetings and investor presentations, recurring moments like leadership meetings and all hands, and the last minute media request or VIP meeting that appears with 24 hours notice. 

If you want to support executive branding while becoming a stronger strategic partner, press play, then subscribe, share with an EA friend, and leave a review so more assistants can find this kind of support.

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Transcript

Welcome And The Hidden Job

SPEAKER_00 0:00

This is the Everyday Icon Style Podcast, the space for style-conscious, career-driven women who are ready to look like the next level version of themselves. Each episode helps you build a wardrobe that reflects not only your executive presence, but your real life. With a little bit of guidance, intentional edits, and no full-blown transformation required. Let's elevate your style and your authenticity one outfit at a time. I'm Tiffany, your style coach. Let's get started. You manage calendars, travel, communications, and crises probably all before 10 o'clock in the morning. And you are the person who makes sure everything runs smoothly, effortlessly, and flawlessly. And somewhere in the middle of all that, someone handed you an unwritten responsibility that nobody trained you for up until today. And that is making sure your executive looks the part. And it will happen gradually, a little bit at a time, and sometimes you won't even realize that it's happening. Because maybe you found yourself quietly stressed before a major board presentation because you know the suit or what they're wearing or plan to wear isn't quite right, but you're kind of hesitant to say, you know what, I don't think that looks right. Or maybe you've had this diplomatically suggest a change without making it awkward. Or even maybe you've been quietly managing this for years and no one has ever given you a single tool or framework to do it well until today. So welcome back to the Everyday Icon Style Podcast. As always, I am your host, Tiffany, and today this episode is for all of my executive assistants. Now, I am not an executive assistant yet, but I am on road and on track to be. So, but even as an administrative professional, I still do some of this even remotely in very small ways. And I want to what we're going to think about today. I want you to think about this with an open mind and see if you have done this or see where you could have done this, but maybe you are a little bit hesitant. And today we're going to be talking about how you, the EA, the executive assistant, can manage your executive's professional image because whether you believe it or not, you're doing it on a consistent basis, maybe not with what they wear, but definitely with everything else. And what I've come to realize is this you are the most underserved people in the professional image conversation because you deal with it every day, but just in a different way. Because you carry a level of responsibility for your executive's presence that most people don't even realize exist or care about. And you're expected to do it with zero training, zero resources, and maximum discretion. Because remember, we get a lot done before nine or ten o'clock every day. So today I want you to think about this, and I want to talk about this and a way to actually manage it without it becoming a source of stress, because we know we have other things that make our days and lives stressful at work. So, why is this your actual job? Well, it's easy. Now I know that there could probably be some guilt that can come along with being involved in how your executive dresses or even presents themselves. I get it. Because it can be a little bit um, a little bit touchy. And you actually may even feel sometimes that you're overstepping, like it's too personal to even bring it up. Sort of like it's not really in your your lane, and you like to stay, and we like to stay in our lanes. But I want us to reframe this starting today. Your job is to protect and amplify your executive's effectiveness. Full stop. And their professional image is a direct part of that effectiveness. It affects how they're perceived in the boardroom, how serious you they're taken in a pitch, how much authority they command when they walk into any and every professional room when it deals with their job. So I want you to think about it this way. If their image is off, it will affect the outcome of meetings that you have worked incredibly hard to get on their calendars. It affects the relationships you've begun to cultivate and build because you do that, and it affects the brand of the organization that they represent. So, yes, this is your job, and doing it well is a real skill that deserves real strategy. This is not something that you're going to be doing like all the time, but I'm about to actually tell you when you would need to actually do this, and they are the moments that will matter, and there are three moments that will matter. The first one is the high-stakes external moments, and that's something that we all should be very familiar with. So these are your board meetings, your investor presentations, your media appearances, even and including your speaking, their speaking engagements. Now there now, these are the moments where your executive is being being seen by people whose opinions can and will can hold and carry significant weights. The standard here is not, does this look fine? No. The standard is does this communicate authority, credibility, intentionality at the highest level? So in these moments, you want to be involved early, not early in the morning or the day of, but well, well, well in advance. So maybe if you know something's on the calendar a month before, maybe begin to brainstorm it then, keep it in the back of your mind. That's when you want to do it. So you do want to know what they're planning to wear in these moments. And you need to know the environment they're walking into, they have to know their audience, and if something isn't right, you need enough runway to address it without creating a crisis. So, as an executive assistant, all we do all the time is we go and we have to know who's going to be in the room, what the meeting is, who the audience is going to be, and that will kind of dictate how they dress. So you can say, Well, you know, you're going to speak to a college. Maybe they are having a tech fair and they're going to recruit and attract individuals to come work for your or be a part of the leadership development program. They don't need to be in a full three-piece suit. They need to be friendly, look friendly, be open, you know, something like some nice pair of slacks, maybe a branded polo or button-down, something of that nature, to where they can be relaxed and have a conversation as a porch as opposed to going to an investor relations meeting, to where, yes, that will require a three-piece suit, and everything is straight and precise and standard. That's these are the moments that we need to look at, and we need to make mental notes or put jot down notes when we're actually scheduling the meetings and as we're beginning to see where everything is. So next is the recurring visibility moments. Now these are going to be your weekly or monthly touch points. So your regular leadership meetings, your recurring client dinners if you have them, internal all hands presentations, and we know everybody has all hands because I have one next week for one of my leaders. And these matter more than people think or realize, even if they're virtual when you have them as well, because we can kind of see and feel their vibe and everything when it comes to that. Why is because it's being absorbed over time, it's building consistency over time. Remember, even with your executive, how they look, seven seconds or less, or nowadays, even a millisecond, all of it counts. And when they become inconsistent, it creates a subtle low-grade confusion about who their person is and what they represent. And of course, I want you to make sure that you realize is this is also going to depend on the industry that you work in. So if you're in banking, it's going to go look different, say than if you're in education, if you're in um higher education. So all of this is going to be completely different and going to depend upon what industry that you actually work in. So I do want to keep that, I do want to make note of that as well. And lastly, it's going to be that last-minute media request. And these impromptu meetings with a high profile or with a high profile client. And the event just got added to the calendar, like, I don't know, 24 hours ago, because we know how their calendars can be. These are things that come on, like, oh, can we do this a week and no? This is 24 hours or heck, sometimes even three to four hours before they go. And these are the moments where your preparation will actually and really pay off. Because if you've done the work of understanding your executive's wardrobe and what works, you can troubleshoot fast. And if you haven't, you're guessing under pressure. So you always want to keep that in mind, especially last-minute high-profile meetings that they may have to go to in a moment's notice. Even something as simple as if they have to attend something that somebody else was supposed to attend, say another executive was supposed to attend, and now they have to fill in. So we always want to keep that in mind. I know it's a lot, I know it's probably like, well, Tiffany, we have 50 other 11 things to do. I know, completely understand, but at the same time, this is just a very small piece, like maybe two, three percent of your job. So it's not the whole thing. So now you're probably wondering, well, how in the heck do we have this conversation? Because when we manage logistics and travel, that's one thing. We can probably do that in our you could probably do that in our sleep. Here I am talking about me, but I know you can do that in your sleep. But talking to your executive about their image is something totally different and probably a territory that you may or may not have crossed yet or entered into. But I'm gonna give you an easy framework for it. You will need to understand that this conversation is never ever about taste or personal style. This is always about the strategic outcome, just like everything else you do. It's always going to be strategic. So when you frame it that way, it will stop being personal and start becoming professional. We are doing this as a professional on a professional level, not anything outside of that we could care less. That's their own personal time. So instead of, I don't think that suit is the right choice. I want you to try something different and say, maybe for this particular audience, I want to make sure we're walking in with the strongest possible impression. Can we talk through what we're planning to wear? Here's an example. Say they are going to have a meeting and it's on a golf course. So you want to make sure that they go in with the right impression when they get on the golf course. Because some people can go on the golf course and they can just wear whatever because guess what? They're probably playing golf in their personal time, but they're going to have to wear something different playing golf in their professional life than they are in their personal time. So it might be, you know, a lot of us with our with our companies that we work for, they have branded, um, they have branded wear. So then we're probably looking at maybe not to over brand, but maybe they have golf club. Uh, got not golf clubs, golf gloves, not clubs. Maybe they have the branded nice branded gloves or nice branded polo shirt that they could wear when going out there and still making it look professional with what they do. Maybe they have a separate outfit that they wear for golf outings, and I'm just using golf as an example as opposed to what they wear when they go in their professional life. So small, just different things like that. Another thing could be instead of that doesn't look too hot, because we have to remember this is professional, this is not you telling, like, your sister, your brother, your cousin, your mama, your daddy, girl, boy, that don't look right. This is not what this is. But I want you to try to make sure that this presence matches the room, everything else with everything else that we've prepared. Let's look at a couple options. Now you're doing this weeks in advance, not the day before, because we always know that always can possibly turn into disaster. Now, you're not the fashion police, you are always and you are their strategic partner who understands that every detail of how your executive shows up absolutely matters. And when you position yourself that way, the conversation will land completely different. And if they by any chance are resistant or dismissive, which is valid, that's actually going to be information for you. And it often means that they haven't fully connected their appearance to their outcomes yet, because they are busy doing something else to where guess what? We are the ones that have to take everything else so that they can focus on what they need to focus on, their zone of genius. Dressing usually may or may not be their zone of genius, and they probably come in with the same old suit and tie combination or whatever combination that they wear. So this is where you come into detail and always looking, making that keen eye. And if you bring it up to them, they might actually be receptive or say, hmm, I never thought about that before, and notice and realize that you want to make sure that everything, the entire presentation, from the PowerPoint presentation to their speech, that everything totally and all together flows and makes a good impression. So don't doubt yourself when you feel that way. So now, because we deal in systems, we have to build a system for this. But we're not going to reinvent any wills. Remember, this is only like 3% of your job, so you're not necessarily going to always have to do this. So the EAs who will manage this best are the ones who build a system. Because winging it every time is exhausting and inconsistent. So if you're planning a meeting for him or her, you can actually build it into what you all whatever you already have, you can just add an extra point or two in there because the system is already built. You just have to maybe add one or two additional questions or a section that's just going to be focused on this. But before we kind of get to that point, you want to start with a wardrobe audit. Now you don't have to do this yourself, and honestly, this is a great place to bring in a professional. Hi again, my name is Tiffany. But at minimum, you want to know what your executive owns, what actually fits and works, and what the go-to options are for each category or the moment or a moment. Then from there, you need to just build a very simple reference. Even just a note on your phone or in your notes app if you use Microsoft Notes, or a shared document. High stakes external, these are the go-to options. Recurring visibility, these work well. Travel, here's what travels best. This is a great place to start is travel. Because they are traveling all of the time. So wouldn't it be great if you could ask them about? So when you travel, what do you take? And maybe help them say, build a small travel capsule wardrobe for them, you know, to help them so that they can, when they're packing to get dressed and get ready, they can just throw something in. Because guess what? They get called at last minute sometime to travel from here to New York City in a matter of a day. And sometimes they fly back. So even with that, what do you travel? What do you wear when you travel to go from here to there? Are they traveling commercial? Are they traveling by private? Can they change, you know, X, Y, and Z? Can they change if they're in the AMX lounge at the um at the airport? All of these, all of these are all of this is information and data points for you. So you want to use them so that you can help them with this to make their lives easier, because that is what we are here to do. And then from there, you can build a habit of looking ahead. And at the start of each week, you can scan the calendar, flag moments that require image attention, give yourself and your executive enough lead time to address anything that needs addressing. This system alone will take so much out of the stress, will take so much stress out of it. I don't want to add more stress, I want to add more value to what you do for them. That is what I want to do. More value for what we do. Now, this is what I want to leave you with here. The work that we do, the work that you do is not small. And I'm saying we because I too am on a way to become, I want to become and go to the next level of being an executive assistant. So that's why I say we or you. And we also want to make sure, and a part of this is making sure that they always show up at their best and looking their best consistently. That is going to be real contribution. And the EAs who do it well, who build the skills and the systems and the language to manage this with confidence, they will become indispensable in a way that goes far beyond logistics. So if you feel that you can do this, make this something now that makes you become indispensable because they see you as their strategic partner and not just somebody pushing and managing a calendar. I want you to think about the environment and the world and how jobs are changing these days. You are not just keeping the train running, you are literally. Helping shape how a leader is perceived, how seriously they're taken, and ultimately how effective they are. And I need you to begin to own that. Because managing your executive's professional image is one of the most nuanced and unappreciated parts of your role, but it doesn't have to feel like guessing in the dark. So now that you have a framework for thinking about it, language for talking about it, and a system for managing it, and if you have to rewind this and play it back a couple times, by all means do so. Because something you can do with confidence and clarity instead of stress and uncertainty, and your executive and their career will be much better for it. So I know this was a little different and a little taken. You probably thought as an executive assistant, I was going to talk about you and how you can dress well and all of the things. I got you. Because I am going to do a series specifically for executive assistants, because as I've stated in the podcast today, you are an extension and you are your executive's strategic partner, and you need to look like that as well. So I am going to work on a series. I don't know if it's going to be next month or the month after, but definitely this quarter. I am going to do something specifically for you and do a series for you so you can also begin to dress the part, and that you will be seen as their strategic partner that you are, so that you will also begin to shift how people see you and see not and see you less as someone that manages a calendar and someone that is actually a partner. So to start off with doing that, here's what I want you as the executive assistant to do. Every month I publish my newsletter, The Signature Edit. And here I share real actionable content on professional image, wardrobe strategy, and how to think about appearance as a leadership tool. And it's the kind of insight that makes you even better at what you already do. And most people don't cater to the executives and the executive, not only the executives, but anybody that works in an executive space. I'll put that's the easy way of saying that. And to make it a little fun and a little lighthearted and a little personal, I even include a section of what I'm loving right now. So it could be anything from the latest book that I'm reading, from the favorite way to enjoy my downtime, my travel plans, all of the things. And I want you to come and sign up and subscribe and join. The link will be in the description of this episode below. So I hope that I gave you something to think about and to pause and think about. And when you do, let me know over on Instagram, send me a DM, and also if you're while you're over there too, let me know what you want me to address when it comes to executive assistance and what it is that you are looking for when building your style so you can use it as a leadership tool is because guess what? You are a leader tool, too. Not tool, but tool. So I hope you enjoyed this episode, and I hope you enjoy and have an amazing rest of your day. Stay healthy, stay safe, and as always, I will see you next week in the next episode.