A Conversation with Aileen P. Charland

Leadership is often discussed from the perspective of CEOs, founders, and senior executives.

Yet the people who work closest to those leaders often gain a unique perspective on how decisions are made, challenges are handled, and organizations move forward. Throughout her career, Aileen P. Charland has had a front-row seat to leadership in action.

As Executive Assistant to the CEO and CFO at TRUMPF North America, Charland supports executive operations, coordinates complex projects, and keeps priorities moving across the organization. She also recently joined the Board of Directors at MakerspaceCT, a nonprofit innovation lab in Downtown Hartford, Connecticut that is dedicated to bridging the gap between traditional skills and advanced technologies through education, collaboration, and hands-on learning. Her career has included leadership roles in university, community service, global trade show logistics, and executive support. Along the way, she has gained a unique perspective on what separates effective leaders from ineffective ones.

Aileen shares lessons from supporting senior leaders, navigating high-pressure situations, and building a career based on preparation, trust, and consistency.

Many people think leadership happens in boardrooms and presentations. From your perspective, where does leadership actually show up day-to-day?

Leadership often shows up in the small moments. It can be how someone responds when a project is falling behind or how they communicate during a stressful situation. The strongest leaders I have worked with are usually very consistent. They don’t only step up when everyone is watching. They show leadership through their actions every day, especially when challenges arise.

You work closely with senior executives. What is something people often misunderstand about leadership roles?

I think many people assume leaders always have all the answers. What I have observed is that great leaders spend a lot of time asking questions. They gather information, listen to different perspectives, and work through problems with their teams. Leadership is often more about learning and adapting than having all the answers.

After years of supporting decision-makers, have you noticed any habits that separate effective leaders from ineffective ones?

Preparation stands out more than anything. The most effective leaders are usually the ones who arrive prepared. They understand the issues, know the details, and have thought about possible outcomes before discussions begin. They also respect people’s time and come into meetings ready to make progress.

You’ve had a front-row seat to countless meetings and projects. What are the small behaviors that reveal whether a leader is prepared or not?

You can often tell within the first few minutes of a meeting. Prepared leaders ask focused questions and keep conversations moving forward. They know what they want to accomplish. Unprepared leaders tend to spend more time reacting than directing. Small things like reviewing materials in advance or anticipating questions make a noticeable difference.

In your experience, what tends to create more problems for organizations: poor decisions or poor communication?

Poor communication. Even good decisions can fail if people don’t understand them. In roles involving executive support, project coordination, and logistics, clear communication is essential because so many people depend on accurate information and expectations.

You once managed global trade shows and freight logistics. Was there a moment when a project nearly went off the rails, and what did it teach you about leadership under pressure?

There was a trade show project where a key vendor became unavailable much later in the planning process than anyone expected. It created a lot of uncertainty because the event was approaching quickly. What I learned is that pressure can push people to make rushed decisions. Instead, we focused on evaluating our options carefully and finding the best solution available. We ultimately found a stronger vendor, and the event was a success. That experience taught me that staying calm often leads to better outcomes.

Executive assistants often see challenges before anyone else. How important is anticipation in a fast-moving organization?

It is extremely important. Anticipation allows you to address issues before they become problems. In my role, I am constantly thinking about what might happen next. Whether it is scheduling, travel, or project planning, looking ahead helps prevent surprises and keeps things running smoothly.

You have said you like to think several steps ahead. Has there ever been a situation where that mindset prevented a larger issue from developing?

In my role, thinking ahead is part of the job. Looking at schedules, travel, and upcoming priorities helps reduce surprises and keeps things moving smoothly. Often, the biggest successes are the problems that never happen because someone planned ahead.

Business leaders often receive public recognition, while support professionals work behind the scenes. What have you learned about influence from a role that doesn’t always receive the spotlight?

I’ve learned that influence is not always tied to a title. Throughout my career, whether serving on community boards, including my recent appointment to the Board of Directors at MakerspaceCT, or supporting executive leadership, I have seen how trust and reliability shape outcomes. People tend to listen to those who consistently follow through and contribute solutions.

You’ve watched workplaces evolve throughout your career. What changes have improved the way organizations operate, and what changes have made things more complicated?

Technology has made communication and collaboration much easier. Teams can work together more efficiently than ever before. At the same time, the pace of work has increased significantly. There are more messages, more meetings, and more information to manage. Finding ways to stay organized has become increasingly important.

You serve leaders while also leading projects and coordinating teams yourself. How do you balance supporting others with having confidence in your own voice and ideas?

I think it comes down to understanding your value. Supporting others doesn’t mean remaining silent. There are times when sharing a different perspective or raising a concern is important. Throughout my career, I have learned that thoughtful input can be valuable regardless of your title.

After spending years around senior leaders, what is something you’ve changed your mind about?

Earlier in my career, I thought leadership was mostly about having the right answers. Over time, I’ve realised it’s often about listening, adapting, and being open to different perspectives. The leaders I’ve respected most are not always the loudest people in the room. They’re usually the ones who stay curious and continue learning.