The art of balance: How Nicky supports CEOs while working remotely

Meet Nicky Simons, one of our Executive Assistants who will share her Headroom story with the world!

When did your EA journey start, and how?

After making a life changing decision to split my time between two countries with very different cultures, Headroom became the perfect match for me in April this year. I was introduced to the company through recommendations from others in my network, and I quickly saw how aligned my skills and values were with what Headroom stands for. People often say I’m living the dream life. I get to work in the countries I love, with a company I genuinely enjoy being part of.

What’s your favorite thing about working at Headroom?

What I love most about Headroom is the sense of freedom and trust I feel. The company allows me to do my work without needing to be micromanaged and trust me to get my stuff done. In today’s world, where many workplaces are returning to traditional office setups, the sense of autonomy and flexibility at Headroom is truly special.

As an executive assistant, what do you find most rewarding about supporting CEOs in their day-to-day operations?

I love creating space for our members so they can focus on their priorities and really be the stars of their own show. My role as an EA allows me to clear up the clutter, whether that’s managing schedules, inboxes, or organizing tasks, so they can concentrate on what matters most to them. To be honest, I’ve always had a passion for organizing. Even as a child, I loved cleaning up when I visited friends’ houses. Now, even my phone is color-coded and neatly arranged, which brings me real peace!

Can you tell us about a challenging situation you faced as an EA and how you successfully handled it?

One of the key challenges in my role as an EA is learning to negotiate effectively. It’s about finding the right balance between being assertive and flexible. For instance, I’ve negotiated much lower rent for a luxury villa in France, secured significant discounts when booking hotels, and helped create more open schedules by understanding the urgency of meetings. These experiences have taught me that negotiation is not just about saying ‘no’, it’s about finding solutions that work for everyone.

What are some skills you believe every executive assistant should have, and how do you continuously improve those skills?

As an EA, strong organizational skills are essential. You need to be proactive and stay on top of everything, but continual growth comes from stepping outside your comfort zone. Whenever I face a task I’m unsure about, I research how others approach it, and then make it my own. One of the biggest lessons I’ve had to learn (and am still learning) is the importance of embracing mistakes as part of the process. After all, mistakes are meant to help you grow, not define you.

You’ve been working closely with different entrepreneurs and high achieving individuals: what’s the secret sauce to a successful Executive – EA partnership? What’s a non negotiable?

Clear and transparent communication, ongoing feedback from both sides, and a personal touch are essential. Also, I believe humor adds value, as it allows a more relaxed and open communication during serious business talks.

How do you prioritize tasks and manage time efficiently in a role that often demands multitasking and quick decision-making? What is your secret productivity hack?

Call me old fashioned, but I enjoy writing down my to-do list. It helps me see clearly what’s urgent and what’s not. I start with the most urgent tasks, followed by the ones that are less enjoyable and might take longer. You’ll notice that once those tasks are done, you have much more mental space.

Collaboration is key in any workplace. How do you maintain strong relationships with colleagues, especially while working remotely?

I try to chat with a colleague daily about something non-work related. A quick virtual coffee break does wonders for team spirit.

Where do you see Headroom in 10 years?

On an international scale, with EAs from around the world. The Headroom concept is fantastic, and I believe it can be just as effective in other countries. If we can connect these companies with an EA who understands the same language and culture, it would be a significant step forward.