Why Cultural Fit Matters When Hiring an Executive Assistant
WRITTEN BY: NATALIE DOWSETT, FOUNDER, THE EXECUTIVES SUITE
When you make the decision to bring in support, it isn't just about finding someone who can organise emails and manage a diary. It's about finding someone who gets you, your business and your slightly obsessive colour-coded filing system (if you have one of course). Because in all honesty, skills can be taught, but the right attitude and cultural fit? That's pure gold.
Bringing in an EA is also one of the biggest, most positive steps you can take as a business owner. It's a powerful move that shows you recognise you can't (and shouldn't) do everything yourself. It signals growth, ambition and a decision to protect your time, energy and sanity so you can focus on the work that matters.
What Do We Mean by "Cultural Fit" Anyway?
Cultural fit isn't about shared hobbies or whether you both enjoy a cheeky Friday night prosecco (though that always helps IMPO). It's about shared values, working styles and expectations. It's about whether they understand the beating heart of your business and can slot seamlessly into your rhythm without missing a beat.
If your business thrives on structure, precision and a sprinkle of sass, you need someone who respects that energy. Equally, if you're more laid-back and creative, hiring someone who demands a rigid nine-point plan before they breathe is going to be a car crash in slow motion.
Why Cultural Fit Makes or Breaks the Relationship
A skilled EA already knows how to confidently manage your day and protect your time. What truly sets the right EA apart is their ability to care about your clients as deeply as you do, to mirror your communication style effortlessly and to instinctively understand when you need a detailed breakdown and when a simple "all good!" update will suffice.
When you bring in support that matches your business culture, everything feels easier. Communication is smoother, misunderstandings are rarer and you don't find yourself gritting your teeth because "technically" they did the task but completely missed the tone.
How to Find Your EA Soulmate
Finding the right EA is part science, part magic. Here's how to stack the odds in your favour:
1. Be brutally honest about your business culture:
If your vibe is "organised chaos with a side of banter", say so. Pretending you're ultra-corporate will just attract the wrong people.
2. Focus on an energy check, not a formal interview:
You're not conducting a corporate job interview here. You’re checking if the energy aligns. Chat casually. Notice if the conversation flows easily, if they intuitively understand your vision and if their vibe compliments yours.
3. Don’t be afraid to ask questions:
Chances are, you are new to this, so it’s OK to need guidance and for the process to be explained clearly to you
4. Shared values and vision:
Your ideal VA will align with your core values and be genuinely excited about the direction you're heading in.
5. Proactive communication:
Look for someone who keeps you updated without needing to be chased, and who communicates clearly and professionally.
6. Flexibility and adaptability:
A great VA can roll with the punches, shifting priorities without losing momentum or focus. They will take full ownership of their tasks and outcomes, celebrating wins and learning from challenges alongside you.
7. Energy and enthusiasm:
You want someone who brings positive energy into your business and who genuinely enjoys contributing to your success. They should feel like a true extension of your team, invested in your success and keen to build a lasting, collaborative relationship.
The Power of Alignment
At the end of the day, hiring a Executive Assistant is a bit like dating. You can swipe right on a hundred profiles, but the magic only happens when you find someone who really "gets" you. They will amplify your business, not just support it. They'll anticipate needs, smooth out bumps and make you feel like you've finally got the partner-in-crime you deserve.
So take your time when deciding, because you don't just want an EA who can do the work, you want one who makes you wonder how you ever coped without them.
ABOUT THE AUTHOR
Natalie has an impressive 20+ years of experience supporting high-level executives and busy professionals. She founded The Executives Suite to deliver the same level of professional administrative support virtually. Natalie has worked across various industries, honing her ability to adapt, anticipate needs, and handle complex tasks with precision. She’s a long-term member inside The HoLT, and is a helpful, supportive and kind individual with a bubbly personality and commitment to going above and beyond for not just her clients, but her fellow members. Find out more and connect with Natalie below:
READ MORE FROM our expert guests 👉
YOU CAN JOIN THE HOLT WAITLIST TODAY 🎉
Once a month, there are 25 new spots in The HoLT up for grabs.
This is so we can protect the experience of our existing members and grow gradually.
