Executive Assistant Insights

Most people are surprised when I share that in the early days of Google, nearly 𝙚𝙫𝙚𝙧𝙮 𝙨𝙞𝙣𝙜𝙡𝙚 𝙤𝙣𝙚 𝙤𝙛 𝙤𝙪𝙧 𝙀𝙭𝙚𝙘𝙪𝙩𝙞𝙫𝙚 𝘼𝙨𝙨𝙞𝙨𝙩𝙖𝙣𝙩𝙨 on the Product Team had a master’s degree. This was by design. It was one of our drivers of growth. One of the things I see leaders get wrong in their critical growth window is treating support positions as low-level jobs. They are anything but that! When optimized correctly, your EAs, Senior EAs, Chief of Staff, and Executive Project Managers are not silent, reactive contributors – they are proactive, highly skilled, intellectual equals, sparring partners, and proxies. When hired and empowered correctly: -They are the ones who hold your executives accountable for deliverables. -They are the ones who can sit in a meeting and respond how you would respond. -They are the ones that are critical to translating your vision into trackable action items. -They are your eyes, ears, and heart connection to your team. -They are an extension of you and effective in a way you could never be for yourself. In fact, when I was Eric Schmidt’s Chief of Staff, he routinely tossed (quite literally) newspapers, magazines, and books to me while we traveled together. He was never looking for just a distillation or summary. He wanted me to read through them and see what correlations, insights, ideas, and recommendations he may not have gleaned at first glance. This intellectual partnership brought out the best in both of us and made each of us more effective at our jobs. Remember, your “support staff” can be the factor between a 2x C-Suite and a 10x C-Suite. Hire, train, and promote accordingly. #leadership #scale #culture #growth

An Executive Assistant (EA) can be a game-changing hire for a CEO. If you find the right person, set the right expectations, build the right relationship, give them the right authority and have them work on the right things they can make you 20% more efficient and effective. I know that a lot of CEOs, especially first time CEOs, don’t see the value in hiring a full time EA. They think calendly, an AI notetaker and a virtual EA can deliver the same things. I speak from experience when I say that the right EA will literally change your life as a CEO. Here are all the things that a great EA can and should be doing for you: - Calendar management - If you’re the CEO of a growing company your calendar will inevitably become crazy. A great EA will not only handle scheduling meetings but will be constantly moving things around (without asking you) to ensure that they’re removing or working around conflicts (including personal conflicts), prioritizing the right meetings, coordinating meetings that are a quarter or a year out (i.e. board meetings) and making sure that they schedule according to your preferences (i.e. back to back all day, 10 min breaks between meetings). - Coordinating deliverables - In an ideal world, everyone would get everything done the right way and on time, in reality that doesn’t happen. A great EA can be the air traffic controller for things like collecting slides for a board deck, ensuring that your team gets you their one on one topics 24 hours before your one on one, capturing follow up items from your weekly leadership meetings and ensuring they get completed by the agreed upon date, making sure that you’re adequately prepared for any presentations you’re doing. - Event management - Most companies will do things like all hands, leadership team offsites, company kickoffs, board dinners, team dinners, holiday parties, etc. Different companies have different people or departments owning these events but if you can find an EA that can own some or all of these events then the ROI on that person is extremely high. - Daily digest - This is the real unlock. I’ve attached an image of a real one that I received from Dani H. (my EA for many years at BetterCloud who taught me these lessons). This is an email that your EA should be sending you every day. She’d make sure I understood who I was meeting with, the context, the last time I met with them, their linkedin profiles. She would include the one on one agendas that she had to chase people down for. The presentations I was going to use for different meetings. She was able to give me a pulse on the sentiment of the people I was meeting with. And every digest had a list of to-dos or decisions I had to make at the bottom. Imagine that you never had to worry about any of the items listed above, imagine that you never had to context switch into your calendar, imagine that you didn’t have to remember and chase people for deliverables… how much better would you be at your job?

The Executive Assistant manages calendars, filters information, handles logistics, and serves as the critical interface between leaders and everyone seeking access to them. Today, #AI can automate perhaps 80% of these tasks with remarkable efficiency. But I believe automation will not eliminate this role, it will elevate it from #assistant to genuine partner. The future EA will spend less time on bookings and more time on judgment calls: deciding what deserves the executive's attention, prioritizing competing demands, analyzing plans before they reach the decision-maker, and anticipating needs before they become urgent. Throughout my career, my executive meetings were scheduled twelve months in advance, requiring thoughtful planning rather than reactive scheduling from assistants who knew what truly mattered. The qualities that make an exceptional EA cannot be automated: making #leadership possible, providing the human touch that keeps intense schedules bearable, and demonstrating the loyalty built through years of consistent judgment. These are delicate, well-compensated roles that are becoming more valuable as AI handles the routine and frees these professionals to focus on what truly differentiates them. What roles in your organization will AI elevate rather than eliminate?

I’ve been thinking a lot about what makes an exceptional Executive Assistant. Not just a good one. But the kind of assistant who transforms the way an executive operates. Who quietly (or not so quietly) holds the rhythm of an entire organisation in their hands. And I keep coming back to this: EA = (S + T + P + EQ + AI) × V Where: S = Strategic Thinking T = Technical Proficiency P = Proactive Initiative EQ = Emotional Intelligence AI = Agility in AI and Tech Adoption V = Value Multiplier (Trust × Communication × Business Impact) The administrative profession has outgrown the box it’s been kept in. This isn’t just a clever formula. It’s a framework to define the full scope of a modern Executive Assistant. One that goes far beyond tasks and dives into the strategic core of what the role can be. This formula reflects the real job - the one that rarely makes it into a job description. S = STRATEGIC THINKING You’re not waiting for instructions. You understand your executive’s goals and anticipate what comes next. You think in terms of business priorities, long-term impact, and operational rhythm. You don’t just react - you lead. T = TECHNICAL PROFICIENCY You don’t just use the tools. You master them, whilst keeping one eye on emerging technologies which could help you perform even better. From calendars and CRMs to project platforms and travel apps, you operate with fluency and confidence, often training others in the process. P = PROACTIVE INITIATIVE You see the fire before the smoke. You solve problems before they escalate. You step in without being asked and add value that others didn’t even know was needed. EQ = EMOTIONAL INTELLIGENCE You navigate difficult personalities. You influence without authority. You handle pressure, feedback, and complexity with grace. Your diplomacy and empathy are strategic advantages. AI = AI AGILITY You’re not afraid of the future - you’re building capacity with it. You understand how AI can streamline workflows, analyse data, and reduce repetitive work. You’re no longer doing the admin. You’re using AI to manage the admin, creating more time for high-value, strategic support. V = VALUE MULTIPLIER But it’s the Value Multiplier that changes everything. When an assistant is trusted, heard, and strategically aligned, they don’t just add value. They multiply it. That’s why so many executives will tell you their assistant is their competitive advantage. And why so many businesses miss the mark when they treat the role as purely operational. If you’re still measuring assistants by how many meetings they book or how well they take minutes, you’re looking through the wrong lens. This profession is evolving - fast. And the assistants who are growing with it? They’re not asking for a seat at the table. They’re building new tables entirely. Download my full EA Formula Explainer below. 🔁 Repost to share 👉 Follow me Lucy Brazier OBE for administrative profession related content and inspiration.

As an Executive Assistant, this is how you use AI beyond “write this email for me” Over the weekend, I was on a call with my Executive when he said “Clara, AI will replace a lot of assistants o… actually, it’s already replacing them” But I told him “Sir, AI isn’t replacing Executive Assistants. It’s replacing Executive Assistants who only do what AI can do” So if your entire skill set can be summarized as “I write emails and book meetings”… then yeah, you’re in trouble🥹 My Executive’s response to what I told him was “Well, you better start teaching Assistants how to use AI like you o” So let me show you how I use AI like a Boss Behind The Boss 1. I Train AI to Think Like My Executive (So I Don’t Have to Ask 47 Questions a Day) ❌ Basic: “Should I schedule this meeting Tuesday or Wednesday?” ✅ What I do: “Based on my Executive’s goals this quarter(I feed AI the goals), create a decision-making framework I can use to evaluate all meeting requests without asking them” Your Executive hired you to KNOW, not to keep asking. AI helps you build that mind-reading superpower faster 2. I Make AI Sound EXACTLY Like My Executive ❌ Basic: “Write a professional email declining this” ✅ What I do: I feed AI examples of my Executive’s emails, their tone, phrases, and priorities, then ask: “Draft this response in their voice while keeping the relationship warm” Now I can handle 50 conversations at once and nobody knows it’s me🤷🏽♀️ 3. I Use AI to See What Everyone Else Is Missing ❌ Basic: “Summarize this Slack thread” ✅ What I do: “Review this team Slack thread and point out (1) Decisions that seem stalled (2) People who haven’t responded but need to (3) Questions my Executive should ask in the next leadership meeting based on what’s being discussed” AI is REALLY good at finding patterns you’d miss while drowning in 1000 messages. So why not use it to your advantage? 4. I Let AI Challenge My Ideas (Before My Executive Does) ❌ Basic: “Is this a good idea?” ✅ What I do: “I want to block 30-minute strategy time in my Executive’s mornings. What could go wrong? What would make this backfire?” AI becomes the friend who tells you the truth BEFORE you embarrass yourself in the meeting. You’re welcome 😂 The Bottom Line AI won’t replace you if you’re doing work that requires ➖Strategic thinking ➖Relationship intelligence ➖Contextual judgment ➖Proactive problem-solving But if your job stops at just taking instructions and not thinking beyond the tasks, then yeah AI is coming for that ♻️ Repost this if you know an EA who needs to see it At Boss Behind The Boss, We are building Executive Assistants who’d thrive using AI. You should join us😊 Firmly rooting for you, Clara Chukwu 🥂 Helping Executive Assistants build Systems, Confidence & Clarity

The impact of a great Executive Assistant is often invisible — until they’re gone. From the outside, the role can look operational: managing calendars, coordinating travel, organizing meetings. But at its best, the Executive Assistant role is far more strategic. A strong EA doesn’t just support an executive — they amplify them. They understand priorities at a deep level. They anticipate challenges before they escalate. They safeguard time and attention — two of the most valuable leadership assets. They manage relationships with discretion and intelligence. They act as a trusted partner in moments that require judgment, not just execution. Over time, something powerful happens: alignment becomes instinctive. Context doesn’t need to be explained. Decisions move faster. The executive operates at a higher level because someone is quietly protecting focus and flow. That kind of partnership cannot be duplicated with a handover document. You can fill a vacancy. You can redistribute tasks. But you cannot quickly replace: • Earned trust • Institutional memory • Political and cultural awareness • Nuanced decision-making • The rhythm built between two professionals working in sync Exceptional Executive Assistants are not administrative overhead. They are force multipliers. And when you find one, you don’t just value them — you invest in keeping them. #ExecutiveAssistant #Leadership #ChiefOfStaff #BusinessOperations #StrategicPartnership #WorkplaceCulture #OrganizationalExcellence #PeopleStrategy #OperationalExcellence #ProfessionalGrowth

One part of the Executive Assistant (EA) role that doesn’t get talked about enough? >>How much influence an EA has on a CEO’s reputation inside the organization. While the CEO sets the vision, the EA often shapes the experience people have when they interact with that leader. That experience matters because it directly impacts how employees perceive accessibility, reliability, and leadership style. Here’s where EAs quietly make a big difference: ✨ Responsiveness. When the EA keeps communication flowing, people feel heard. Quick follow-ups, clear answers, and organized coordination all reflect positively on the CEO. ✨ Professionalism with warmth. The EA often sets the tone for interactions before the CEO even enters the room. A respectful, friendly, organized approach helps build trust and humanizes leadership. ✨ Consistency. A CEO’s calendar, commitments, and expectations stay aligned because the EA keeps everything in sync. That consistency shows employees that their leader values time, people, and follow-through. ✨ Protecting focus. By filtering information, managing priorities, and creating space for meaningful work, the EA helps the CEO show up as prepared, present, and confident. That level of readiness builds credibility. ✨ Bridge-building. EAs connect people to leadership, clarify needs, and reduce friction across teams. Those smooth interactions contribute directly to how approachable and collaborative the CEO is perceived to be. The EA may work behind the scenes, but their impact is seen everywhere because the way a leader shows up every day is often a direct reflection of the partnership supporting them. A strong EA doesn’t JUST manage schedules. They help shape reputation, trust, and culture, and that influence reaches much further than most people realize. #executiveassistant #EA #trust #integrity #csuite #partnership #culture #CEO #influence #character

There’s something EAs don’t get enough credit for, and that’s managing the weight behind the work. Let me explain what I mean. Most people see an EA’s job as logistics... calendars, travel, inboxes, priorities. They see the visible tasks. What they don’t see is everything that sits underneath those tasks. The emotional load. The context management. The way EAs quietly track the pressure, mood, and pace of the people they support. An EA often knows an executive is overwhelmed before the executive says a word. They sense when something needs to slow down and when something needs to move faster. They notice who’s pulling their weight and who isn’t. They pick up on the tone shifts, the dynamics, the unspoken concerns, the things that influence decisions long before the decisions are made. That’s not admin work. That’s emotional intelligence in motion. It’s a level of awareness most people never realise they rely on. The tricky part is that EAs do this so naturally, most of it goes unnoticed. It looks effortless from the outside because they’ve learned how to read people, anticipate change, and smooth out the friction before anyone else even feels it. And I share this for two reasons... So EAs can recognise the leadership they bring, even when no one names it. You’re managing far more than logistics, you’re managing the environment your executive leads from. And for leaders because the partnership looks very different when you understand what’s actually happening beneath the surface. When you realise your EA isn’t just supporting you. They’re stabilising the conditions you make decisions in. This is about awareness, because awareness changes everything. #theeainstitute

You don’t hire an Executive Assistant to do more. You hire one so 𝘺𝘰𝘶 𝘤𝘢𝘯 𝘥𝘰 𝘭𝘦𝘴𝘴 — 𝘣𝘶𝘵 𝘢𝘤𝘩𝘪𝘦𝘷𝘦 𝘮𝘰𝘳𝘦. Because a strategic EA doesn’t just manage your calendar. They manage your capacity for greatness. Too many leaders see EAs as task-takers instead of growth accelerators. The result? Bottlenecks, burnout, and blind spots. A top-tier EA builds systems, shields focus, and drives execution. They multiply your impact by managing what drains your time and energy. Here’s how a strategic EA transforms a CEO’s bandwidth: 1. Protects time 2. Streamlines operations 3. Elevates communication 4. Anticipates needs 5. Enhances strategy 6. Drives execution 7. Multiplies focus An exceptional EA isn’t just behind the scenes — they’re behind the momentum. If you want to scale sustainably, start by scaling your support. Save this for when you’re ready to delegate with strategy. How are you leveraging your EA — as support, or as strategy? ------------------ Hi, I’m Colleen, an EA helping founders protect their most valuable asset: time. Because if your calendar isn’t strategic, neither is your business.

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.