Interview with Colleen Illman

This week I am so excited to be interviewing Colleen Illman. Colleen is a seasoned Executive Assistant with over seven years of experience supporting C-suite leaders, orchestrating high-profile corporate and private events, and optimizing workflows so executives can focus on what matters most. Colleen has a reputation for discretion, adaptability, and an eye for elevated experiences.

Colleen, with over 7 years of experience supporting C-level leaders and startups, you say you "bring structure to chaos." Can you tell us about a time you walked into a chaotic situation and what your first three steps were to create order?

Absolutely - I really believe all EAs are wired to bring structure to chaos. That’s part of why we thrive in these roles!

One example that stands out is when I joined my current company. The executive team was going through several restructuring phases, and things were understandably a bit messy. Calendars were either completely overloaded or neglected, and there weren’t any clear meeting cadences across departments.

My first three steps were pretty simple:

1. Listen and observe – I took time to understand what was working, what was overwhelming people, and where things were falling through the cracks.

2. Tidy up the calendar – I restructured my executive’s schedule so that it actually reflected their priorities, while also carving out real focus time.

3. Create rhythm – I put meeting cadences in place so departments were communicating consistently and decisions didn’t keep stalling.

It didn’t take long before things started to feel less chaotic and more intentional. And honestly, that’s my favorite part of this role - helping leaders and teams breathe a little easier because the structure is finally supporting the work instead of getting in the way.

Your work has led to impressive quantifiable results, like a 30% reduction in scheduling conflicts and a 40% improvement in task completion rates. What's the most impactful system or process automation tool you've implemented that made these results possible?

I’d say the most impactful shift came from combining the right systems with simple visual organization. For me, that looked like introducing Trello, EOS tools, and color-coded calendars - each serving a different but connected purpose.

With Trello, I created shared boards for priorities, projects, and deliverables. This gave leaders and teams a clear snapshot of what was moving, what was stuck, and who owned what. It cut down on a lot of back-and-forth emails and really supported accountability.

Then, layering in EOS (Entrepreneurial Operating System) provided a framework for meetings, priorities, and measurable goals. Using tools like Level 10 meetings and scorecards gave structure so that time spent together was purposeful - which is where that reduction in scheduling conflicts really came from.

And finally, color-coded calendars may seem simple, but they were a game-changer. Having visual cues for focus time, external meetings, internal syncs, and personal commitments instantly made the calendar easier to navigate and protect. It turned the CEO’s schedule into more of a strategy tool than just a list of appointments.

Together, these systems created clarity and consistency, which not only reduced chaos but also freed up energy for the team to focus on actual execution - and that’s where we saw those measurable results.

Your event planning experience includes executing 20+ strategic meetings, company culture activities, and leadership events on time and under budget. Can you describe a particularly challenging or high-stakes event you managed, and what was your key to ensuring a low-stress execution?

One of the most high-stakes events I’ve managed was our company’s 35th anniversary Christmas party. It was a huge milestone celebration, and the pressure was on to make it unforgettable. We had multiple vendors, a large venue, intricate décor, and yes - even circus performers (which was such a fun twist!).

The scale could have easily become overwhelming, but my key to keeping it low-stress was meticulous preparation paired with strong vendor relationships. I built out a detailed project plan that included timelines, budgets, and responsibilities, and then held regular check-ins with each vendor to make sure everyone was aligned and confident.

On the day of the event, that groundwork paid off. Because everything had been organized and communicated clearly ahead of time, I was able to focus on troubleshooting the small things that always pop up instead of putting out major fires. The result was a seamless, joy-filled night that not only came in on budget but also left employees and leadership buzzing about how special it felt.

For me, the magic of event planning comes from creating experiences where the only thing people notice is the fun - not the work it took to get there.

What's the biggest misconception you think people have about the role of an EA in a remote-first, high-growth company today?

That’s such a great question. While I don’t currently work for a remote-first company, I’ve supported leaders remotely and I know it’s where a lot of high-growth companies are heading. Personally, my long-term goals don’t require me to be tethered to one location, so I’m definitely open to remote opportunities in the future.

I think one of the biggest misconceptions about an EA in a remote-first environment is that distance equals disconnect - that if you’re not physically in the office, you can’t be as effective or “in the loop.” In reality, the opposite can be true when the right systems are in place.

A strong EA doesn’t just manage tasks; they create alignment, protect focus, and keep priorities moving forward - all of which can be done seamlessly in a remote setting with the right communication cadence and tools. In fact, being remote often sharpens those skills, because you’re intentional about over-communicating, documenting processes, and making sure nothing slips through the cracks.

At the end of the day, the EA role isn’t about proximity - it’s about partnership, trust, and results. And those translate across any environment, whether in-person or remote-first.

As an administrative professional with a clear track record of bringing structure and efficiency, what's one piece of advice you would give to an EA who is new to supporting a fast-paced, remote team?

My biggest piece of advice would be: don’t rush to fix everything at once - start by listening. When you step into a fast-paced, remote team, it can feel tempting to overhaul systems right away, but the most valuable thing you can do is take time to understand how the team actually works.

Ask questions, observe communication styles, and learn what your executive’s true priorities are. From there, start small: maybe it’s organizing the calendar so it reflects those priorities, or setting up one tool that brings clarity to the team’s workflow.

And because it’s remote, over-communicate. Share updates, document processes, and make sure people know where to find information without having to chase you down. That consistency builds trust faster than anything.

Supporting a fast-paced team isn’t about doing it all - it’s about creating the right structure so the most important things get done without everyone burning out. If you focus on listening, clarity, and communication, you’ll naturally bring order to the chaos.

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Colleen Illman is a seasoned Executive Assistant with over seven years of experience supporting C-suite leaders, orchestrating high-profile corporate and private events, and optimizing workflows so executives can focus on what matters most. With a reputation for discretion, adaptability, and an eye for elevated experiences, she thrives in fast-paced environments - whether managing a remote team or curating a luxury, white-glove event. Colleen blends creativity with precision, ensuring every detail reflects excellence while staying under budget. Passionate about integrating wellness and productivity, she believes a balanced leader is a high-performing one. Outside of work, you’ll find her curating vision boards, lifting weights at the gym, or enjoying a perfectly brewed cup of coffee - ideally somewhere with a passport stamp.

Connect with Colleen on LinkedIn: https://www.linkedin.com/in/colleen-illman/