Executive Assistant Training

My two most effective AI consulting moves have nothing to do with data or tech. Here’s why they work: And they're NOT what you'd expect from someone at the executive level. After hundreds of enterprise engagements, I've distilled my approach down to two signature moves. 𝗙𝗶𝗿𝘀𝘁: 𝗜 𝗰𝗼𝗻𝗻𝗲𝗰𝘁 𝘄𝗶𝘁𝗵 𝗲𝘃𝗲𝗿𝘆 𝗲𝘅𝗲𝗰𝘂𝘁𝗶𝘃𝗲 𝗮𝘀𝘀𝗶𝘀𝘁𝗮𝗻𝘁. Before I even start an engagement, I reach out to all the EAs. I send thank-you notes in advance. I host a call with them. And I tell them: "I see the magic you do with calendars and emails. I know your work is hard and often thankless." Why? - Because they're the power behind the power. - They're the ones who make room on impossible calendars. - They get you in front of the right people at the right time. And on EA Day, I make sure every single one gets treated,not just mine, but ALL of them. 𝗦𝗲𝗰𝗼𝗻𝗱: 𝗜 𝗴𝗼 𝘁𝗼 𝘁𝗵𝗲 𝗴𝗿𝗮𝘀𝘀𝗿𝗼𝗼𝘁𝘀. When I establish a strategy, I dedicate the first four months to one-on-ones,not just with executives and stakeholders. I go all the way down to analysts and junior analysts. People are often surprised when they see an EVP or SVP talking to an analyst or a manger. They ask, "Why are you doing that?" My answer is, "Because they're the ones doing the actual work, they are the closest to the issues." They know where the inefficiencies are, where the systems don't talk to each other, and where the manual workarounds happen that executives never see. This lets me bridge the gap between what executives THINK is happening in steering committees and what's ACTUALLY happening on the ground. Those two things together? Creates clarity on the real issues (not the symptoms felt) AND time to talk to the people I need to talk too when I haven’t built up my credibility or reputation yet. Because strategy without relationships is just PowerPoint. And executive perception without ground truth is just wishful thinking. What are YOUR signature moves that others might overlook?

When communicating with executives, it's important to use small words... Okay, that's not true, but executives don’t need fancy vocabulary. They need the information. Here is how I write executive summaries (as an executive!): Over the years, I've learned that writing an effective executive summary is both an art and a science. It takes time and practice to refine your communication so that it’s both concise and compelling. Here are some of the strategies that have helped me along the way: What Matters? Executives are inundated with information daily. They don't have the luxury of wading through multiple paragraphs to extract the key points. An executive summary must cut through the noise and present the core message in a few short, impactful sentences. 2. Simplicity is Your Friend Avoid jargon and unnecessary details. Focus on “what,” “why,” and “what’s next.” This ensures that your update can be read and acted upon. 3. Details Attached A good trick is to include a line that offers additional detail for those who want it. For example, you might end your summary with “Attached is additional detail” or “More details are provided below.” This signals to the executive that the main points have been covered, but there’s a deeper dive available if they want more information. 4. Mentorship Early in my career, I was fortunate to have a manager who pushed me to perfect my executive summaries. Every update I wrote was reviewed and refined until it truly communicated the essential information. That hands-on mentorship was invaluable. It taught me that the process of drafting and revising is crucial to developing a clear, effective communication style. If you don’t have a boss who’s willing to invest that time, look for a senior stakeholder, mentor, or coach who can provide honest feedback on your communication. The right guidance will help you communicate more quickly. 5. AI We’re living in an age of technological breakthroughs. That includes the way we communicate. I frequently use AI to help summarize and distill complex information into clear insights. It can also be useful for drafting the first version of your executive summary or double-checking that you've captured all the critical points. A strong executive summary requires clarity, brevity, and practice. It’s about cutting through the clutter and presenting a concise snapshot of the most important information. Focus on what truly matters, seek constructive feedback, and don’t use too much jargon, and your updates will surely stand out and drive action. Leaders, how do you like to receive executive summaries?

Taking on executive communications or supporting a new executive? Communicators should: 👀 Read previous communications from the leader to get a sense of how their writing was worded. It’s especially helpful when you can read non-official-comms emails so you can get a sense of how they write when they put their own fingers to the keyboard. 👂 Listen to recordings of the leader speaking to get a pulse on their speaking style and cadence, and pay special attention to how they speak and what they say when you have conversations with them. Are they more formal or casual? Do they speak plainly, use certain crutch-phrases or have certain ways they address groups (like “hello, team”)? Incorporate those into your writing and talking points for that leader. 🗣️ Read what you’ve written out loud. Can you hear the executive saying the words in their own voice? Or have you inserted your own personality and ways of speaking into their material? Leaders should: 👉 Be consistent with your voice. Deciding on a whim to use fancy expressions or Execuspeak when you typically speak in easy-to-understand terms can sound stilted, make it hard for the audience to connect because it doesn’t sound authentically you, and disrupt the communicator’s understanding of your voice. 🤔 Be receptive to conversations with your executive communicator where we ask questions about how you like to say things so we can establish a better understanding of your voice. We understand you’re busy, but 15 minutes today can save you hours in editing later.

If I'm an EA starting a new job, here's one thing I would do immediately. I'd have my Executive answer a simple yet insightful question: "What is going well?" Based on that answer, I'd double down on those things before jumping in to solve, optimize, enhance, or implement. Here's why: 👓 Minimizes working from a lens of scrutiny. It's never a good idea to go into a new place looking to find faults or problems immediately. If someone was doing the role before you, regardless of whether they're still there (but especially if they are), starting with what they did well and understanding how they did it signals character on your end and is a sure way to build trust. 🪜 Ensures you maintain the standard the Executive is used to. Yes, you intend to come in and eventually make things better, but at a minimum, you don't want to fall below the standard already in place. Having a clear understanding of what currently works and ensuring it stays that way is essential and a trust-builder with the Executive. 🔨 Builds a habit of respecting the Executive's preferences. As an EA, your job is not to come in and do things your way. Executives are often particular, and no two are exactly alike. Listening intently to what they like about the current systems/processes should only be done to enhance them, not change them, to make them "your way." 🔍 Helps you focus on what is missing. This is where you can clarify what you can do more of, less of, or start altogether. If you jump in with the mindset that everything needs "doing," you'll get it wrong. Once you've understood what's already firing on all cylinders, you can move on to solving and implementing. Remember, trust isn't built only on what you do but what you don't do: → Don't be overly scrutinizing. → Don't bad-mouth the EA who did the role before you. → Don't belabor the point of what wasn't being done that should've. Now, keep in mind that this will look different depending on a few factors: 1. Are you the Executive's first EA? 2. Are you backfilling an EA who has left? 3. Are you backfilling an EA who has been internally promoted? 4. Is this your first time as an EA, or is it a new role? Regardless, the principle remains the same. Find out what's working well and double down. #executiveassistant #administrativeprofessionals

today marks 21 years since i started in pr. feeling nostalgic, i realized i've built countless playbooks over the years that have elevated my career. so i present to you 21 years in pr. 21 playbooks to share. playbook 1: working with executives it's not that executives are busier than you. they're just juggling more high-stakes elements at the same time that directly impact revenue, team performance, and business continuity. every minute you waste becomes exponentially expensive. 1 anticipate questions before they're asked. set up an AI prompt that includes the types of questions they usually ask or create one that tells you to "think like an executive" 2 document everything in their preferred format (not yours). some want bullet points, others want narrative 3 label folders and documents, then hyperlink and add an emoji. i am not kidding, create custom folder and document names in their email, slack for immediate retrieval. "ces 2025 client name press release" is faster than scrolling 4 respect calendar boundaries religiously. if they block focus time, it's sacred 5 prepare one-pagers and briefs for complex topics. busy executives scan before deep diving. you do this and you are golden 6 workbacks mean you can kick back. think about all of the steps, outline them. again, use AI to help and work with their EA to time block as needed 7 be notetaker to the AI notetaker and provide post meeting recaps and next steps (no matter your role in the organization). those with the knowledge have the power 8 establish a communication hierarchy. texts for urgency, emails for record, calls for complexity 9 create templates for recurring requests to ensure consistency 10 filter information ruthlessly. your job is to present the signal, not the noise 11 update them, then update them again. until it's done and you tell them, it's not done 12 create "if/then" scenarios for contingency planning before they ask 13 perfect the "elegantly interrupted meeting" technique to extract them from conversations that have outlived their time 14 when invited to exclusive events, your first thought should be "would my executive benefit from being here?" gatekeeping the right opportunities makes you valuable beyond measure 15 translate technical jargon into business impact language. not "server down" but "customer portal inaccessible, estimated revenue impact $x" 16 never deliver problems without solutions. present "options a, b, c with my recommendation being b because of x" 17 make professional development part of your routine. i still read at least 3 industry newsletters daily after 21 years 18 master your executive's schedule patterns. know when they're sharpest for complex decisions 19 own your mistakes quickly, fix them even faster. nothing builds trust like radical accountability 20 talk to them about your growth, when they know where you want to go, the good ones will help you get there 21 be agile. learn the rules and know when to break them

As EAs, we’ve all faced it: an overbooked calendar, meeting invites flying in from every direction, and very little space for actual thinking time. Sometimes we’re told to protect our Exec’s time, only to watch it fill up before our eyes. So, how do we really figure out what’s going on? Why is the calendar so packed? And more importantly, does your Exec even want to change it? Some Executives love the pace. They thrive on back-to-back meetings and feel energised by it. Others don’t realise how much it’s costing them until they hit burnout. Or maybe they know it’s not working but genuinely don’t know how to fix it. Before we suggest new processes or rework the diary structure, we need insight. And the best way to get that insight? Ask smart, subtle questions. Not all at once, and not in a formal way. These are prompts to weave into your 1:1s, chats between meetings, or reflections after a particularly intense day. 1️⃣ "How are you feeling about the pace of your week right now?" - This opens up space for them to reflect without judgment. Are they energised or overwhelmed? 2️⃣ "Which meetings this week felt really valuable to you?" - This helps you spot patterns and see what they actually care about versus what just takes up space. 3️⃣ "Is there a type of meeting you’d love to have fewer of?" - This frames things proactively without sounding like you’re trying to cancel meetings behind their back. 4️⃣ "Do you get enough time for strategic thinking or planning?" - If not, this is your cue to start building in focus time. 5️⃣ "Are there meetings you feel you attend out of obligation more than necessity?" - This helps uncover status-based meetings or ones that no longer serve a purpose. 6️⃣ "Do you ever feel like your days are being shaped more by other people’s priorities than your own?" - This can be a lightbulb moment. It also gives you permission to get protective of their time. 7️⃣ "When do you feel most productive during the week?" - This tells you where to start protecting focus time, or schedule the big stuff. 8️⃣ "If we could free up even 2–3 hours a week, what would you love to spend that time on?" - This shows the why behind protecting their time. 9️⃣ "Are there any meetings you think could be replaced with a summary, a Slack update, or a quick check-in instead?" - This starts the conversation around meeting alternatives without proposing drastic change. 🔟 "Is the way your week is currently structured helping you get closer to your big goals this quarter?" - Bringing it back to the bigger picture can spark real change. You’re not trying to overhaul their calendar overnight. But with curiosity, empathy and a bit of tact, you’ll start to uncover what’s really driving the schedule, and where you can make a difference. And remember, you don’t need to wait for permission to start the conversation. Asking thoughtful questions is one of the most strategic things we can do.

I asked 50+ EAs one question: “What’s the one thing you wish your exec understood about your role?” Here’s what they told me (anonymised): “I’m not just moving meetings. I’m quietly removing multiple decisions a day from your plate so you can think.” “If you loop me into the context, I can protect your time before the chaos hits, not just clean it up afterwards.” “When you cancel our 1:1, I lose the only protected space we have to align. That’s when I start guessing priorities.” “I see patterns you don’t, because I’m across your calendar, inbox, team and home life. Ask what I’m noticing more often.” “Trust isn’t just about confidentiality. It’s you backing me in front of others when I make the tough call on your behalf.” For founders/execs, the message is pretty simple: Your EA is often already thinking at a higher level than the job description. The more context, trust and space you give them, the more leverage you’ll get back. If you’re an EA or a Leader, I’m curious: What’s the one thing you wish your exec / EA understood about your role or partnership? Drop it in the comments. #ExecutiveAssistant #FounderLife #LeadershipSupport #SecondBrainTalent #EALife #CEO #Hiring #EAhiring

I’m going to throw a wrench into what it looks like to onboard an executive assistant successfully. Some may hate it. You do not need a structured onboarding plan with agendas, SOP’s, 30/60/90 day plans, KPI’s, or tutorials. All of that is useless w/out one thing. Time👈🏻That’s the thing. After coaching 175+ exec and EA partnerships (and being in the role many times myself), I’ve seen what makes the biggest impact. Again and again, the execs who gave their EAs their time received the greatest return on their investment. Ironically, it’s the hardest thing for an exec to give, especially when they are literally hiring someone to free up time. So how does an executive give time when they have none? ✅ Open up your calendar to your EA. Let them join every meeting you’re on. They’ll begin absorbing info like a sponge as they experience the day instead of being told about the day. ✅ Ditch the manual and give your EA time to ask questions. I promise they have a gazillion. ✅ Give your EA time to adjust to how you operate. Don’t expect them to immediately understand your voice, cadence, & preferences. ✅ Give your EA time and space to make mistakes. If the threat of messing up is so severe, perfectionism will hold them back from confidently executing. ✅ Give them time to learn your business. Eventually, they’ll start to notice core KPIs, priorities, risks, challenges, & even bring solutions. ✅ Prioritize your syncs. Just show up even if you have nothing to discuss. They do. Assistants - this is where I’m going to push you a bit. If your exec does the above (plus full access and trust), you have everything you need to create your own onboarding plan. Don’t wait for someone to give it to you. Here’s what you can do: 👉🏻 Schedule a sync w/ each of your execs direct reports. Ask them how you can support their communication flow. Ask where they see your exec as a bottleneck. 👉🏻 Write down the questions you need your exec to answer to do your job well. Organize it into categories like inbox, calendar, travel, and priorities. Spend each sync focusing on one category. 👉🏻 Draft your own 30/60/90 day plan. What do you need? Go after it. 👉🏻 You be the one to schedule regular syncs at the frequency you need to operate well. If 1x per week isn’t enough, adjust the calendar. 👉🏻 Learn the biz model. Write down every word you don’t know. Research. Watch product trainings. Meet w/ the product team for a customer demo. 👉🏻 Write down every wish, idea, and frustration your exec has. This is low hanging fruit if you can proactively execute and bring solutions. Hopefully it’s clear that it takes two to tango. — Hi, I’m Megan. I’ve been in the EA world for 16+ years. I’ve trained EAs, matched 175+ EA/exec partnerships, & spent years in the role myself. Feel free to follow along for all things relating to EA’s. ***Every word of this post was written by me, not AI. Yes, I love AI, but I miss humans. So, it’s just me. Welcome 🫶🏻

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.

If your Executive Assistant (EA) is only supporting you... they’re a bottleneck, not a bridge. Founders, the power of an EA isn’t just in handling your inbox or scheduling meetings. It’s in embedding them as a true extension of your operating system... empowering your team, streamlining workflows, and multiplying your leverage. Here’s how you can transform your EA from isolated to integrated: 1. Connect Your EA to Your Core Tools - Don’t let your EA dwell in your inbox. Grant access to project management, CRM, and messaging platforms. This empowers them to coordinate directly with your team and stay aligned with organizational priorities 2. Standardize Workflows, Not Just Tasks - Build out SOPs for recurring processes (from recruiting to onboarding to weekly reporting). Enable your EA to manage these flows, catching issues early and proactively nudging teammates instead of waiting for you to delegate. 3. Make Them a Team Resource, Not Just a Personal One - A top-performing EA answers team questions, handles cross-department handoffs, and acts as a communication conduit. Encourage your team to go to your EA for updates, approvals, and routine decisions. 4. Use Automation, Data, and Communication Platforms - Leverage tools that allow your EA to automate calendar bookings, manage internal dashboards, or set up internal briefings using Slack, Notion, or Asana. This magnifies their impact and reduces your dependency as the center point. When your EA is integrated into your company’s operating system, they boost efficiency across the board, keeping you free to focus on strategic moves, not task triage. Start by mapping your critical workflows and identify anywhere an EA could slot in as the operator, not just the admin. Empower, automate, and embed... don’t just delegate. How are you using your EA today? Where could they add more value for your whole team? Let’s share best practices in the comments below.