In today’s fast-paced world, the role of the Executive Assistant is evolving — and mastering tools like ChatGPT has become a true game changer. When used intentionally, ChatGPT can draft polished emails, conduct detailed research, streamline workflows, and provide rapid clarity, allowing assistants to step out of reaction mode and operate as strategic partners who anticipate needs rather than simply respond to them

In our guide on Slack (Slack) “101: How to Communicate and Collaborate,” we highlight how Slack transforms team interaction—from structured channels that keep conversations organized to real-time features like huddles and clips that replace endless email threads. By leveraging its integrations and promoting clear communication norms, assistants and support professionals can turn Slack from a chat tool into a strategic collaboration platform.

In today’s high-velocity support roles, the right digital tools aren’t a luxury—they’re essential. The most effective apps help Executive Assistants streamline scheduling, manage overflowing inboxes, automate repetitive tasks, and maintain clarity even in chaotic environments—freeing time and energy for deeper, more strategic work.

Planning business travel isn’t just about booking flights and hotels - it’s about creating a seamless experience that allows your executive to stay focused, prepared, and stress-free. From understanding their preferences to managing last-minute changes, this guide equips executive assistants with everything they need to plan smart, anticipate needs, and execute each trip with precision. Whether it’s their first trip or their fiftieth, you’ll be ready to make it smooth, strategic, and successful.

Every role that supports an executive becomes more powerful when it’s built on structured systems, not just completing tasks. The real leverage comes from designing repeatable workflows, automating routine steps, and bringing deliberate clarity to priorities—so the professional becomes a driver of strategic momentum rather than merely a responder.

Every role that supports an executive becomes more powerful when it’s built on systems, not just tasks. The secret lies in designing repeatable workflows, automating routine steps, and creating clarity around priorities so the executive assistant becomes a driver of strategic momentum—not just a responder to requests.

Starting a side business can feel overwhelming, but with the right tools and a step-by-step approach, you can get up and running smoothly. From incorporating your business using Stripe Atlas to setting up a professional website with Squarespace or Wix, there are solutions that make the process easier. Don’t forget to open a business bank account, manage your finances with QuickBooks, and create a professional email through Google Workspace. If you need to pay employees or contractors, Gusto can simplify payroll. With these essentials in place, you’ll be well-equipped to launch your side hustle successfully.

Achieving your goals doesn’t happen overnight—it’s the result of consistent effort, thoughtful planning, and habits that align with your vision. Success starts with clarity: defining what you want and breaking it into manageable steps. By establishing daily routines, visualizing success, and regularly assessing your progress, you create a system that supports growth. Remember, the secret isn’t in occasional leaps but in the small, intentional actions you take every day. As John C. Maxwell wisely said, "The secret of your success is found in your daily routine." Let’s explore how you can put these principles into practice.

Our environment plays a powerful role in shaping our behaviors and limiting our potential. Just like fleas conditioned to stop jumping high in a jar with a lid, we often let past experiences or the expectations of others create invisible ceilings in our lives. To achieve success, we must challenge these limits, push past fear of failure, and take action when opportunities arise. In this post, we’ll explore five common mistakes to avoid if you want to break free from constraints and reach your full potential.

In today’s evolving workplace, traditional incentives like bonuses and promotions are no longer enough to motivate and retain top talent. Employees now seek purpose, growth opportunities, recognition, and work-life integration. This blog post explores innovative strategies for employee empowerment, from fostering a sense of purpose to promoting continuous learning and recognizing individual contributions. By embracing a positive, inclusive work culture and empowering decision-making, companies can create an environment where employees feel valued and motivated. These approaches not only boost employee satisfaction but also drive organizational success.

In this exclusive interview, Pennyworth Projects sits down with luxury travel expert Stuart Marra to uncover the secrets behind seamless executive travel. Discover how executive assistants can collaborate with seasoned professionals like Stuart to curate bespoke, unforgettable trips that perfectly balance business and leisure. Whether you're planning a remote getaway or a high-profile business trip, this conversation is packed with insights on elevating every travel experience.

Interviews often feature familiar questions like "Tell me about yourself" and "Where do you see yourself in five years?" but sometimes, you’ll encounter unexpected questions that challenge your thinking and reveal deeper insights into your personality and problem-solving abilities. In this post, we’ve gathered 15 unconventional interview questions designed to keep you on your toes and showcase how you handle the unexpected. Prepare to explore questions that go beyond the typical script and offer a unique opportunity to demonstrate your adaptability and outlook on life.

Onboarding new employees should go beyond administrative tasks—it's about fostering a welcoming and supportive environment that empowers them to contribute effectively from day one. A thoughtful onboarding process sets the foundation for long-term success, significantly influencing a new hire's productivity, satisfaction, and commitment to the organization. To avoid overwhelming new employees, focus on creating a structured yet positive experience that ensures they feel valued and prepared.

In the dynamic world of executive support, the relationship between an Executive Assistant and their executive is both unique and complex. It’s a partnership built on trust, understanding, and seamless communication. However, when things go awry, it’s not always easy to pinpoint the root cause. Is it a case of bad hiring or bad management? More often than not, the answer lies in the latter. Effectively managing an otherwise great Executive Assistant requires a commitment to their growth and success, investing not just in their role but in their development as a key player in the executive team.

Starting a side hustle can be an exciting journey filled with new opportunities. Whether you aim to earn extra income, pursue a passion, or transform a hobby into a business, promoting your side hustle is essential to achieving success. Fortunately, you don't need a marketing background to get started. By using creative and effective strategies, you can easily spread the word and build a client base. In this post, we’ll share fresh insights and actionable tips to help you market your business like a pro.

In a world where demands on our time are constant, mastering productivity is essential for achieving meaningful progress without burning out. Productivity isn’t about doing more; it’s about focusing on what truly matters and using your time wisely. As philosopher William James noted, "The great use of life is to spend it for something that will outlast it." This post presents 15 research-backed strategies to help you maximize your day, whether you’re a seasoned professional or looking to fine-tune your approach, ensuring your efforts leave a lasting impact.

A sharp memory, enhanced brain power, and increased productivity are essential tools for excelling in both personal and professional spheres. In a world overflowing with information and short on time, optimizing cognitive abilities can be the key to thriving, not just surviving. While the brain's capacity for information is vast, many struggle with memory lapses and mental fatigue. The good news? Simple, effective techniques can unlock your mind's full potential. In this blog, we explore eight practical strategies to help you boost memory, sharpen focus, and increase productivity, allowing you to tap into the remarkable power of your brain daily.

In today's fast-paced digital world, Executive Assistants are becoming strategic partners, playing a crucial role in their leaders' success. With the rise of Artificial Intelligence (AI), assistants can now enhance their workflows, increase productivity, and elevate the level of support they provide. AI is transforming the role of assistants, making it an essential tool for maximizing impact. This guide offers practical insights on how Executive Assistants can effectively integrate AI tools into their daily routines, helping them thrive in their evolving responsibilities.

The role of the Executive Assistant has always been one of agility, foresight, and relentless dedication to keeping an executive’s professional life running smoothly. With the rise of technology and the integration of artificial intelligence (AI), this crucial position is evolving in exciting ways. Are we under threat? We get asked this question in various forms at least once a week. What’s going to happen to the role of EAs? We see it differently. We believe EAs are not just gatekeepers, time managers, and logistics wranglers; they are becoming strategic partners, thought partners, and curators. Leveraging AI will enhance EAs' efficiency, productivity, and overall effectiveness. But is the role disappearing? Absolutely not, especially at a high level. While some tasks like long-form writing and calendaring may become more hands-off, EAs will continue to be the curators, gatekeepers, sounding boards, and central hubs of their executive’s life. The essence of the EA role is here to stay, evolving with technology to become even more integral to executive success.