In honor of 35 years of inspiring administrative excellence, this feature highlights shining stars of the administrative profession: trailblazers who are excelling in their roles and their advice for other administrative professionals.
Q: Can you share the story of how you began your career as an executive assistant and what inspired you to pursue this path?
A: I got my start as an administrative professional while I was still in high school. I went to a specialized magnet school where I double-majored in accounting and office technology. My older brother was interning as a drafting assistant at a state government office, and almost every day after school, he’d call me asking how to do something in Microsoft Office. Eventually, he convinced his manager that instead of him calling me to complete the tasks she was assigning him, she should just hire me instead. And that’s precisely what she did. I became their first high school work-study intern—and the youngest employee in the office.
Fast forward six years, and I was supporting a CEO, CFO, and Senior VP at a different organization. However, when I got that first job as a high school senior, I had no idea what I was walking into. It was just an opportunity for a nice, “cushy” office job. I come from a construction family—my dad, grandpa, uncle, cousin, older sister, and even my brother were all in the industry. My brother was getting ready to start learning how to operate a concrete pump, and meanwhile, all I knew was that I didn’t want a job where I was on my feet all day. And I didn’t want to work in construction. Sixty to ninety-hour workweeks outside in the desert? Hard pass. My goal was simple: get an office job. At the time, I didn’t fully know what that meant. My family always joked that I’d be the one who didn’t go into construction. And yet—here I am, over 20 years later, an administrative professional in none other than the construction and engineering industry.
I may have stumbled into this career by accident, but once I got here, I was all in. I fell in love with the role. I wanted to keep growing, keep learning, and keep finding new ways to support my team. I pushed myself to take on more challenging work and move up the administrative ranks. What started as a job I took just to avoid working outside turned into a career I’m genuinely passionate about. Funny how life works out sometimes.
Q: What would you consider your most significant achievement as an executive assistant, and why does it stand out?
A: Oh wow, that’s a tough one! Do I have to choose just one? Honestly, quite a few significant achievements stand out to me, and each one felt like the biggest achievement at the time it happened. They all had different impacts because they were different milestones, but that doesn’t make any of them less important than the others. I love looking back at each one and being equally proud of them for their uniqueness and significance in that moment.
I believe we should celebrate all of our big wins without constantly comparing them to each other. If you achieve something amazing and then say, Yeah, but it’s not as big as what I did two years ago, it immediately takes the joy out of it. It drains your motivation and kills the momentum that keeps you pushing toward that next big thing.
For example, last year, I wrote and published a 100-page guide. I was so excited to put it out into the world! Then, an admin organization asked me to write an article for their publication. Writing a short article isn’t the same as writing a complete guide—but does that mean I should be any less proud of it? No! I was just as thrilled to be asked and even more excited when my article got accepted and published. Whether it’s a 100-page guide or a three-page article, both are about sharing knowledge and best practices with other administrative professionals, helping as many people as I can.
So, I guess my most significant achievement isn’t just one specific thing. It’s not the guide. It’s not the article. It’s the fact that I’ve gotten to a place where I’m doing this—putting myself out there, overcoming my fear of public speaking, pushing past the fear of judgment, and sharing what I’ve learned to help others. That’s huge for me. I started my own LLC to make this possible—to create content, write guides, speak at conferences, and coach other administrative professionals.
My biggest achievement isn’t about what I’ve done. It’s about why I’m doing it. It’s about making an impact, helping others grow their careers, and sharing the things I wish I had known earlier. And that’s something I’ll never stop being proud of.
Kayla's Guide for Administrative Professionals
Q: What are the top three skills every successful executive assistant should master, and why?
A: There are a lot of skills that make a great Executive Assistant, but there are a few that have been absolute game-changers for me—helping me elevate my career and build a strong strategic partnership with my executive. These same skills have also helped me excel in other areas of my life.
1. Effective Communication: This is the big one. But when I say “effective communication,” I don’t just mean being able to send a well-written email or speak confidently in a meeting. True communication is a combination of several skills that work together to make sure your message lands the way you intend it to.
One major piece? Adaptability. Every person you interact with communicates differently. Your executive, your colleagues, your clients, your vendors—they all have their own styles. The best EAs know how to adjust their approach depending on who they’re talking to. This helps avoid confusion, tension, or unnecessary friction.
Then, there’s “Executive Speak.” Learning to speak the language of executives—the strategy, the business objectives, the financials—not only helps you understand what’s happening in those high-level meetings but also gives you the ability to contribute in a way that earns you a seat at the table. If you can speak their language, you gain automatic credibility and respect.
Another key aspect? Reading the room. Knowing when to speak up (and when to hold off) is just as important as what you say. This applies to everything from asking for a raise to pitching an idea at the right moment. Timing is everything, and picking up on nonverbal cues can be just as powerful as the words you use.
And let’s not forget emotional intelligence. A simple sentence like, “I need to talk to you,” can cause instant panic if not delivered with the right tone, inflection, or body language. Mastering how to phrase things in a way that gets your message across without unnecessary stress or confusion is a skill that will serve you well.
At the end of the day, as an EA, you are your leader’s representative. Whether you’re scheduling meetings, negotiating with vendors, or interacting with stakeholders, you’re constantly communicating. And how you do it directly impacts both your credibility and your leader’s.
2. Strategic Thinking: This is the skill that genuinely elevates an EA from a rock star assistant to a Strategic Business Partner. It’s more than just being a step ahead of your executive—it’s about seeing the bigger picture, identifying risks, and proactively working through solutions before problems even arise.
Strategic thinking means looking at a situation holistically—whether it’s a project, an issue, or a long-term goal. It’s about figuring out where you want to go (or what needs to change) and then working backwards to build a plan.
It also involves:
- Risk assessment & mitigation – spotting potential obstacles before they become major roadblocks
- Cost vs. ROI analysis – ensuring that time, money, and resources are spent wisely
- Change management – figuring out the best way to implement something without causing chaos in the organization
When you master strategic thinking, you become an essential part of the decision-making process. You’re no longer just in the room to take notes—you’re contributing valuable insights that help drive the business forward. And that’s when you truly become indispensable to your leader.
3. Adaptability & Resilience: If there’s one thing you can count on in an EA career, it’s change. Leadership shifts. Priorities get turned upside down. Technology evolves. And let’s be honest—some days, it feels like everything is on fire. If you can’t roll with the punches, this job will eat you alive.
Adaptability and resilience are what separate good EAs from great ones. It’s about being able to pivot quickly, problem-solve on the fly, and keep moving forward—without getting stuck in frustration.
Think about how much the role of an EA has evolved. Decades ago, assistants were typing away on typewriters. Then came desktop computers, then laptops, then cloud-based apps, and now AI is changing the game again. The assistants who resisted change got left behind. The ones who adapted? They thrived.
And let’s talk about AI for a second. There’s been a lot of talk about whether AI will replace assistants. Spoiler alert: it won’t. But it will replace those who refuse to adapt. AI is just another tool—like the first word processors were back in the day. The EAs who embrace it will find new ways to streamline tasks, free up time for high-value work, and make themselves even more valuable.
Adaptability and resilience aren’t just about technology, though. They come into play constantly in our day-to-day work:
- Does your caterer cancel the morning of a big meeting? You figure it out and get lunch delivered another way.
- A major deadline gets bumped up unexpectedly? You take a deep breath and shift priorities without missing a beat.
- Company leadership changes overnight? You adjust, build new relationships, and keep things moving.
Change is constant—but if you master adaptability and resilience, you won’t just survive it—you’ll thrive because of it.
These three skills—effective communication, strategic thinking, and adaptability & resilience—are what have made the biggest impact in my career. Mastering them has allowed me to not only support my executive at the highest level but also grow into a leader in my own right.
EAs are so much more than just “support.” We’re problem-solvers. We’re strategists. We’re the glue that holds everything together. And when you embrace these skills, you don’t just elevate your own career—you elevate your entire organization.
Q: Are there any tools, apps, or technologies that you rely on daily to stay efficient and organized?
A: Yep! There are definitely tools and apps I use daily to stay efficient and organized. I use some of them because they’re my leader’s preferred method, which makes collaboration more straightforward and more seamless. Others are my own personal go-to’s—what works best for me right now. But I’m constantly adapting and evolving, trying out new tech, best practices, and apps as I discover better ways to work.
MS To-Do – My Leader’s Task Tracker: My leader likes using the MS To-Do app to track what we’re both working on, so that’s where I go to see what tasks he’s added for either of us. These can be quick tasks for the week, long-term projects that will take months, or even future ideas he just wants to park somewhere for later.
He also adds his own tasks, so I can help keep him accountable and jump in where I can assist. This tool has actually led to some tremendous strategic conversations about the best way to tackle tasks and even improve the original goal. It’s not just about tracking work—it’s about making it smarter.
Outlook Calendar – My Follow-Up System: I live in Outlook Calendar—it syncs to my phone, and I use it to block time for projects and set reminders for follow-ups. Adding follow-up tasks to my calendar ensures that no matter how crazy my day gets, I will remember to check in on that critical invoice, meeting request, or pending response.
I also use it for lower-priority tasks my leader asks me to handle throughout the week—because let’s be real, those are the ones that can slip through the cracks if they’re not tracked.
MS Word – My Living 1:1 Agenda: This one is a game-changer for my weekly 1:1 meetings with my leader. I keep a working agenda open on my laptop all day, every day. This running document serves two purposes:
Capturing questions & discussion points – Instead of interrupting my leader every time I have a non-urgent question, I add it to our Agenda. Whether it’s a process clarification, a training request, or a business term I need defined—if it can wait, it goes on the list. This reduces decision fatigue for my leader and keeps our conversations focused.
Tracking updates & action items – This is where I log status updates on projects, travel plans, and anything else my leader has asked for. During our 1:1, I also jot down anything new that comes up—meetings to schedule, travel to book, upcoming deadlines, etc. Our 1:1 meetings run like clockwork because of this system. We start with calendar updates, review last week’s priorities, check the MS To-Do app for new tasks, and set priorities for the week ahead. It keeps us both aligned and makes sure nothing falls through the cracks.
ChatGPT – My Ultimate Efficiency Booster: This one isn’t about organization—it’s about getting stuff done faster. And honestly? ChatGPT has saved me HOURS of work. It’s hands down one of my absolute favorite tools.
I was skeptical at first (because, privacy concerns), but once I learned how to use it well? Total game changer.
One example—writing Standard Operating Procedures (SOPs). I’ve had to create SOPs for different companies, and instead of starting from scratch, I ask ChatGPT for an SOP outline, add my specific details, and boom—done in minutes instead of hours.
Another time? I was asked to write a template business plan, something I’d never done before. Instead of spending hours researching and structuring it from the ground up, I asked ChatGPT for a business plan tailored to that industry. Five minutes later, I had a solid draft. My leader gave feedback and asked for a few additions, and in another five minutes, I had an updated version ready to go. Instead of spending days figuring it out, I had a high-quality plan in under 10 minutes.
ChatGPT has become such a staple for me that I even signed up for a class on AI tools for business—because if it can save me this much time, I want to know what else is out there!
There are plenty of other apps and programs I use, but these are my heavy hitters. MS To-Do, Outlook Calendar, my 1:1 Agenda, and ChatGPT keep me efficient, organized, and ahead of the game. But, like anything else, my tools evolve as I discover better ways to work. The key is to stay adaptable and keep looking for ways to improve—because the more efficient I am, the more valuable I am to my leader and my organization.
Kayla Hutchens
Executive Assistant
Midnight Sun Consulting
Kayla Hutchens brings over 20 years of hands-on experience as an Administrative Professional, working in environments as diverse as start-ups, global corporations, privately held companies, and government agencies. She’s worn every hat, tackled every challenge, and supported amazing leaders, as well as both toxic and simply misaligned leaders, gaining firsthand experience in navigating the complexities of the workplace.
What makes her truly stand out isn’t just her years of experience—it’s her passion for helping other administrative professionals succeed. Having earned Several top-level certifications, she’s now channeling that expertise into empowering others. But what really defines her isn’t just the accolades— it’s her unwavering passion for helping you avoid the mistakes she made and fast-track your growth.
Whether through mentoring, workshops, or sharing her hard-earned lessons in her writing, Kayla is all about making sure the next generation of administrative professionals feel supported, equipped, and ready to take ownership of their careers. Having been in the trenches herself, she believes that you are not defined by the challenges you face at work— but by how you choose to rise above them.
When she’s not busy writing, speaking, coaching–or still working as an executive assistant–you’ll find Kayla connecting with fellow administrative professionals, sharing what she learned the hard way–so you don’t have to. Proving to them–and now you–that with the right mindset, you can create the career you deserve.
