Tips to Support Eas in Career Development

Are you an Executive Assistant navigating the job market right now? As someone who's helped EAs through career transitions and worked alongside top executives, I know firsthand how competitive this space can be. But with the right strategy, you can stand out and land that role that truly leverages your organisational superpowers. Here's my expert checklist to supercharge your job search—tailored specifically for EAs. Print it out, pin it up, and check off as you go: ✅ Polish Your Professional Presence: Update your LinkedIn profile with a professional headshot, a compelling headline (e.g., "Detail-Oriented Executive Assistant | Streamlining Operations for C-Suite Leaders"), and a summary that highlights your key achievements—like managing complex calendars, coordinating international travel, or implementing efficiency tools. Quantify your impact: "Reduced executive travel costs by 25% through optimised planning." ✅ Tailor Your Resume for Humans: Customise your resume for each application, incorporating keywords from the job description (think "executive support," "confidentiality," "project coordination"). Focus on transferable skills like discretion, multitasking, and tech proficiency (e.g., Microsoft Office Suite, Google Workspace, Asana). Keep it to one page, with bullet points starting with action verbs. ✅ Network Strategically: Reach out to your existing connections—former bosses, colleagues, or EAs in your network—for informational interviews. Join LinkedIn groups like "Executive Assistants Network" or attend virtual events via platforms like Eventbrite. Pro tip: Offer value first, like sharing an article on productivity hacks, to build genuine relationships. ✅ Leverage Job Search Platforms: Beyond LinkedIn, check specialised sites like Indeed, Reed or SecsInTheCity, or executive search firms. Set up alerts for "Executive Assistant" or "C-Suite Support" positions. Don't overlook company career pages for hidden gems. ✅ Upskill and Stay Relevant: Brush up on in-demand tools—learn AI assistants like ChatGPT for drafting emails or Notion for advanced organisation. This shows you're proactive and adaptable. ✅ Prepare for Interviews Like a Pro: Practice common EA scenarios: "How do you handle conflicting priorities?" or "Describe a time you managed a crisis." Prepare questions for them, like "What's the executive's preferred communication style?" Role-play with a mentor to build confidence. ✅ Track and Follow Up: Use a spreadsheet to log applications, interviews, and follow-ups. Send personalised thank-you notes within 24 hours—reference a specific discussion point to jog their memory. ✅ Prioritise Self-Care: Job hunting can be draining, so schedule breaks, exercise, and celebrate small wins. Remember, rejection is often about fit, not your worth. What's one tip you'd add to this list? Let's discuss in the comments! #ExecutiveAssistant #JobSearch #CareerTips #ProfessionalDevelopment

📢 Onboarding matters! In my career, I had only one manager who took a lot of time out of his schedule to fully onboard me. It truly helped me to find my role. Executives understand the importance of building a strong, agile team to drive forward their vision and goals. However, one area that often goes overlooked is the onboarding of their closest allies: Executive Assistants and Chiefs of Staff. While they invest time and resources in onboarding other critical roles, many executives don’t allocate enough time to onboard the very individuals who will amplify their effectiveness and help navigate challenges. A rushed or inadequate onboarding for EAs and Chiefs of Staff can lead to missed opportunities, miscommunications - issues that could easily be avoided with the right onboarding approach. Here are my key steps to enhance the onboarding process for these essential roles: 💡 Provide context, not just tasks Go beyond the job description. Share insights into the organizational culture, values, and your strategic vision. These roles thrive when they understand *why* things are done, not just *how*. 💡 Schedule quality time An EA or Chief of Staff can’t support you effectively if they don’t know you. Dedicate time to discuss work style, communication preferences, and both short- and long-term priorities. Allow them to be your shadow. 💡 Create access to key stakeholders Build connections by introducing them to other executives, key teams, and decision-makers. This gives them the context they need to anticipate your needs and run initiatives on your behalf. 💡 Encourage an open feedback loop Build a culture of two-way feedback from the beginning. These roles are designed to optimize your productivity, so empower them to share ideas and improvements for your benefit. 📢 The time you invest in onboarding today pays dividends in team alignment, efficiency, and overall effectiveness tomorrow. Let’s ensure we set our Executive Support Staff up for success from day one. #Leadership #ExecutiveOnboarding #ChiefOfStaff #ExecutiveAssistant #TeamSuccess

You can invite your EA into the most senior meetings. You can give them a seat at the table. You can even tell them, "I want you to use your voice." But if you really want to change the game, it has to be bigger than the symbol of inclusion. It has to start with how you publicly value your assistant: ▪️ How you introduce them to others. ▪️ How you describe the scope and importance of what they do. ▪️ How you develop them — not once, but consistently. ▪️ How you coach and mentor them, the same way you were coached throughout your career. It starts with ensuring they have access to the conversations where real context happens — beyond inbox threads and surface updates. It starts with your broader teams understanding that if your EA requests time to learn more about their world and priorities, that’s not just a courtesy — it's a strategic investment in organisational success. It starts with creating a culture where development, not lip service, defines how we treat the people who keep everything moving. As a former career EA turned in-house trainer, consultant, course creator, and mentor, I see the same patterns today that I experienced firsthand: 👉 Onboarding programs that skip the EA entirely. 👉 Loose language about being “part of the leadership team” — without the development, visibility, or opportunity to match. 👉 A quiet epidemic of imposter syndrome — not rooted in individual self-doubt, but in systems that leave EAs isolated and under-supported. Very rarely have I met an EA who isn’t great at what they do. What I see far more often are great EAs who’ve simply hit the limits of what self-led development can unlock. Not because there’s no more potential — but because nobody can do it all alone. If you want to unlock the true value of your EA function, you have to ask: 🔑 Are we giving lip service — or are we creating the conditions for them to thrive? I do my part every day — training EAs to shift their mindset, uncover their value and impact, and show up in a way that changes perceptions. And encouragingly, the chorus is getting louder. More executives and leadership teams are reaching out to me than ever before, asking: 💬 "How can we help?" 💬 "How can we build the environment where EAs thrive?" That’s the momentum we need — and it's growing. But we still have a way to go and it starts with this understanding: An empowered EA doesn’t just support a leader. They shift the trajectory of businesses. 💬 I'd love to hear — what would meaningful change for EAs look like in your world?

Being a high-level Executive Assistant is not about taking orders. It’s about taking ownership. After 15+ years supporting C-suite executives and board members, here’s what I know for sure: the most effective EAs don’t just make things run smoothly. They make impact. If you’re stepping into this space or leveling up, here are my top tips to truly excel: 🧠 Think like an executive Understand the business. Know the goals, the pressure points, the decision-making process. Anticipate what's needed before it’s requested. 📅 Master calendar strategy, not just scheduling You’re not managing time. You’re managing energy, priorities, and outcomes. Be intentional. Know when to say no or reschedule. 🚪 Be a gatekeeper and a bridge Balance access with protection. Communicate clearly and graciously. Know when to shield, when to inform, and how to keep momentum. 🔍 Stay three steps ahead Prep for board meetings early. Confirm logistics down to the last detail. Think ahead so your executive doesn’t have to. 🧭 Manage up like a pro Learn your executive’s style, pace, and preferences. Tailor your support to how they work best and help them stay at their best. 🤝 Build trust relentlessly Integrity, discretion, and follow-through earn influence. That influence allows you to make things happen behind the scenes. 📚 Stay curious. Keep learning Learn the language of the business. Ask questions. Understand the why, not just the what. 🏛️ Own the room, even when you’re not in it When an EA is sharp and aligned, people notice. Meetings flow, decisions stick, and everything runs smoothly. 💡 Balance fierce efficiency with human warmth Systems matter, but so does emotional intelligence. Be the calm in the chaos. The one who remembers both the details and the people. 📣 Know your value. Act like it This is a strategic role. Advocate for your seat at the table. And when you're there, use it to elevate others too. Being an EA at this level takes more than coordination. It takes clarity, confidence, and leadership of your own. If you’ve been in the EA seat at the top level, what would you add to this list? I’d love to hear what’s helped you thrive.

Let's end the stigma of EAs being "stuck" in their roles. Every day, I hear of EAs leaning into their power. And I will never stop shouting it: you can be anything you want to be. Executive Assistants have the gift of seeing their company from the top. And with that, comes lots of opportunity.... Here are 8 SIMPLE STEPS to help EAs start to navigate potential career transitions ↴ 1) Start observing the functions & people in your company and notice which ones you’re organically drawn to. 2) Set up coffee dates (in person or virtually) to get to know and ask questions of people in roles you’re interested in. 3) Ask to sit in on as many meetings as you can to be in the middle of the action, and the learning. 4) Consider what you're great at and lean in: what company problems are you well-suited to solve? 5) If you have the bandwidth, take on small projects within different functions that you may be interested in. 6) Share your goals with your leader and ask for their support as you explore what's next for you. 7) Focus on your mindset & confidence: you CAN do a different job, and you will use the viewpoint of your EA role to help you learn, grow, and get there. 8) Invest in opportunities to level up, that make sense for your goals & your bandwidth. Just like anybody else... EAs can be anything they want to be. Let's end the stigma of EAs being "stuck" in their roles. 💪 __ ♻ Share to help spread power & possibility 👋 Follow Maggie Olson for content like this #chiefofstaff #EA

If you're struggling to find strong operational talent, take a hard look at whether you're actually developing the person sitting right outside your office. Your assistant already sees how the business operates. They just don't get invited to participate in the strategic thinking - and that's entirely on you. How to create genuine upward mobility: 1. Expose them to strategy - Bring them to meetings where decisions actually get made, not just where notes get taken. They need to learn how to think beyond logistics. 2. Delegate projects, not just tasks - Instead of "book this" or "send this," try "own this project end to end - budget, timeline, stakeholder management." Projects build business muscle. Tasks don't. 3. Invest in their education - Sponsor finance fundamentals, leadership development, project management certification. You're signaling "I see your potential beyond support work." 4. Give them visibility with other executives - Loop them into cross-functional initiatives. Let them give updates in leadership meetings. If you want them to grow, other leaders need to see them as more than your admin. 5. Coach them on judgment and discretion - These roles are built on trust. Share your thinking, your reasoning, your why behind decisions so they start learning how to make those calls themselves. You grow people by trusting them with meaningful challenges where they have room to fail safely and learn from it. Sign up to my newsletter for more corporate insights: https://vist.ly/4efhm #leadership #talentdevelopment #executiveassistant #leadershipdevelopment #careeradvancement #chiefofstaff #managementtips #executiverecruiter #eliterecruiter #careergrowth #succession

One way Executive Assistants become Chiefs of Staff: developing a strategic mindset 🧠 Having witnessed several executive assistants (EAs) transition into chief of staff (CoS) roles, it's clear that developing a strategic mindset is a pivotal part of this journey. Here are some insights on how EAs can evolve into strategic thinkers and prepare for a CoS role: 📌 Master the Basics: As an EA, mastering organizational skills and managing logistics and communications flawlessly is fundamental. This solid foundation is essential for any advanced role. 📌 Understand the Business: It’s crucial for EAs to learn the intricacies of their business beyond their direct responsibilities. Understanding how different departments contribute to the overall goals equips them with the broad perspective needed for a CoS role. 📌 Take Initiative: Successful EAs often take on projects that stretch beyond traditional duties. Whether it’s leading a cross-departmental initiative or organizing a major event, these experiences showcase their capability to manage and execute strategically. 📌 Develop Decision-Making Skills: Observing decision-making at the highest levels provides EAs unique insights. Learning from these can refine their own decision-making processes, preparing them for the broad responsibilities of a CoS. 📌 Build Relationships: A chief of staff needs to work effectively across all areas of the organization. Strong, cross-team relationships built during their time as an EA can be a huge asset in a more expansive role. 📌 Seek Feedback and Mentorship: Engaging with mentors who can provide guidance on strategic thinking and leadership skills is invaluable. These relationships often help EAs transition smoothly into more complex roles. 📌 Be Patient and Persistent: Transitioning from EA to CoS is a marathon, not a sprint. It requires patience, persistence, and continuous effort to develop and showcase strategic capabilities. For those in the throes of this transition or aspiring to one day make it, remember: a strategic mindset starts with curiosity about the bigger picture and a commitment to grow beyond your current role. What else should aspiring EAs be doing? #leadershiplevelopment from #executiveassistant to #chiefofstaff

📌If you’re an Executive Assistant (EA) or a Project Manager (PM) aiming to become a Chief of Staff, the smartest move is to start taking on special projects. ♟️Same strategy, different execution: 🏅EAs should showcase their ability to distill key information, build executive decks, and their synergy with the Principal. It should feel natural to step into projects related to organizational strategy—OKR planning, business process improvements, board reports and presentations, etc. 🎖️PMs should showcase their ability to drive cross-functional execution, identify operational gaps, and offer strategic recommendations. Volunteer for high-impact initiatives that need structure, strategy, and leadership. This should also come pretty naturally, you’ll flex a muscle that’s there but hasn’t been focused on. A special project requires strategy. Your Principal hands you the project, the purpose, and the goal, and you run with it—often building the plane while flying it. It requires initiative, leadership, and strategy. When done well, these projects stand out because you amplify your Principal as you take work off your their plate, allowing them to focus elsewhere. This is how you get the “COS experience” to set the stage for your Chief of Staff pitch. ‼️But remember‼️you have to be vocal about your career goals. You can either stay a top performer in your current role or position yourself for COS. The difference? How well you make the case for yourself.

Why Your EA Needs a Career Path, Not Just a Task List Here’s a truth founders can’t ignore: Retention fails when Executive Assistants (EAs) feel stuck in “admin land” with no vision for growth. When your EA is seen as just a task manager, you miss out on the true leverage they can bring. A scalable support system goes beyond delegating duties, it gives your EA a defined role with upward trajectory. EAs driving transformation and overseeing projects can increase a founder’s leverage and organizational stability. What Founders Should Do Next: • Build a framework for your EA’s progression (think roles, not just responsibilities). Invite them to leadership meetings, champion their professional development, and map out milestones together. • Assign project ownership, not just calendar invites. Empower EAs to drive outcomes across teams, giving them opportunities to strengthen business acumen. • Recognize and reward initiative. Celebrate when your EA identifies process gaps, proposes solutions, or upskills themselves. The outcome? When your EA grows, your leverage grows with them. Investing in your EA’s career path transforms support into strategic partnership. Are you giving your EA a vision for growth or just a checklist? Share your experience or tips in the comments below!