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 an era where information moves relentlessly fast, managing communication and workflow with precision isn’t optional—it’s essential. Tools like Superhuman, Grammarly, and Coda io create a streamlined ecosystem that helps professionals process high-volume correspondence efficiently, polish every message, and turn email threads into clear, actionable tasks—transforming the path from inbox to execution.

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.

Elevating the support role goes well beyond tasks—it’s about adopting a service-first mindset. By thinking like a host rather than a responder, you anticipate needs, design experiences, build meaningful connections and transform daily interactions into seamless moments of value.

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.

When teams fall behind, it’s rarely about talent - it’s about ownership. Whether you're supporting the C-suite or guiding operations behind the scenes, the difference between surviving and thriving often comes down to one thing: shared responsibility. This isn’t just about who’s accountable for what. It’s about stepping forward, choosing to care, and leading from wherever you are. Explore seven ways Executive Assistants and Chiefs of Staff can help shift teams from blame to breakthrough—and build a culture where everyone delivers, together.

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.

To build a truly strong support team, it’s vital to differentiate between three distinct hiring profiles—each with its own purpose, skill set and impact. When you clearly define whether you need a strategist who drives big-picture priorities, an executor who masters operations and rhythm, or a specialist with deep expertise in a niche area, you avoid role confusion, set clear expectations from day one and dramatically increase your chances of hiring for success.

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.

As we navigate the post-pandemic world, many young professionals in their 20s are rediscovering the importance of real-life social connections. With the shift from college life to the workplace, the need for authentic, face-to-face interactions is more pronounced than ever. This period feels like a social renaissance, where people are embracing activities like joining sports clubs, participating in local events, or volunteering, all in the pursuit of building meaningful relationships beyond the digital space.

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.