Executive Assistant Insights

Doing your job won’t get you promoted; managing up will. There are 6 key parts of managing up to executives: 1. "Be bright, be quick, be gone." Executives are busy. Come to your conversations prepared with well-thought-out ideas, and then express them quickly and clearly. Then move on. 2. Avoid bad surprises. Managing up before a crisis is way easier than doing it after the crisis begins. Stay on top of worrying signals and keep the executives informed before things blow up. 3. Build trust before you need to rely on it. Trust is built through consistent delivery. Deliver consistently, frequently give brief updates on your work, and build trust before you need it. You will need this trust when you are trying to influence outcomes, create change, or recover from a crisis. Also, when you make a big mistake, you lose some trust. This is natural. The more trust you have built up to draw from, the less likely you will be fired or blocked from a promotion when some trust is lost. 4. Executives cannot operate at your level of detail. Executives need to be in a million mental places at once. Don’t be upset when they don’t know the details as well as you do. Instead, anticipate this and communicate the key points. Then, say you can give more detail where necessary. 5. Provide options and solutions. Let executives know what you recommend and why, what you do not recommend and why, what you have considered, what support you need, and when you will follow up. Bring solutions, not problems. Give them answers to the questions they didn't ask. 6. Do not go around your management chain. If you absolutely must talk to an executive without your manager present, or if the executive comes to you, loop your manager in as soon as possible. This is common courtesy. You don’t want to gain a reputation for going over your manager’s head.

I haven't read my emails in 3 years. That's when I hired my first Executive Assistant and completely changed how I operate. That single hire freed up 25+ hours weekly. Here's the system we use (so you can replicate it for yourself): Step 1: Master the twice-daily inbox protocol Goal: Inbox zero by 10 AM and 4 PM every day. • We sort every email into 4 buckets: "Action needed," "Review required," "Waiting on response," "Archive" • The EA handles 80% immediately with templates: "This is [Name], Dan's assistant. I got your email before he did and thought you'd appreciate a speedy reply..." • They flag only emails that need strategic thinking (usually 3-5 daily) • Everything else gets archived with proper labels (Receipts, Newsletters, Investment, etc.) Step 2: Build the 10-minute daily sync agenda This eliminates random interruptions all day. • Yesterday's meeting action items and follow-ups • Today's calendar review with missing details filled in • Emails flagged that need my input (pre-sorted and prioritized) • Current projects requiring decisions (with 3 solution options each) • Tomorrow's priority planning Same agenda every single day. Takes exactly 10 minutes. Step 3: Create the perfect calendar system Every meeting gets color-coded and audited. • Red: Client work (never moved) • Yellow: Team meetings (flexible timing) • Blue: Protected time blocks (workouts, family, deep work) • Green: Travel and logistics Plus every invite requires: clear agenda, contact phone numbers, 20-minute default timing. Step 4: Create meeting preparation standards Walk into every conversation fully briefed. • Background research on all attendees • Previous conversation history and notes • Relevant documents organized and accessible • Clear agenda with desired outcomes defined • Contact information for backup communication Never get caught off guard again. The transformation: Email time: 2+ hours daily → 15 minutes daily Calendar chaos: Constant stress → Smooth operations Meeting prep: Scrambling → Always ready Those reclaimed hours became business strategy, family time, and actual growth work. Whether you implement these systems yourself or delegate them, the frameworks remain the same. Most entrepreneurs think they can't afford this level of support. The math is backwards: every hour you spend on $25/hour work costs you 20x in missed opportunities. Stop trying to get better at work you shouldn't be doing. Start investing in people who can do it better than you ever will. -DM P.S. Want my complete 23-page EA implementation playbook with every template, system, and process my EA uses daily? Message me "EA" and I'll send you the full guide that shows exactly how to set this up step-by-step. My gift to you 👊

I was asked the difference between an Executive Assistant and an Administrative Assistant the other day. And I drowned in the answer. Me! The one who, you know, helps turn Admins into Assets?? As I waffled through the answer, I just had to stop because I wasn't doing either role justice. I do much better when I have time to think through an answer, so now that I've had a day, I'm going to try to articulate it better now. Administrative Assistants are the operational backbone. They support teams or departments, managing schedules, correspondence, travel coordination, and systems. They're often the ones that keep things running smoothly. They're amazing at tactical work. Executive Assistants are strategic partners to senior leadership. They support C-suite executives or VPs, often working best with one executive rather than supporting an entire team. EAs are representatives of their executives and can speak and make decisions on their behalf. Here are a few differences: 👩🦰 Autonomy – EAs speak for their executive, declining meetings, reprioritizing schedules, and communicating decisions. AAs work within established protocols with less independent decision-making authority. ⏲️ Focus – EAs think strategically about how their executive's time serves business priorities. AAs focus on tactical execution and operational excellence for the company. ✒️ Scope – EAs manage sensitive projects, prepare executive briefings, and coordinate cross-functionally at senior levels. AAs handle essential day-to-day tasks that keep departments functioning. The pay scale is often 20-40% higher for an EA than an AA. If you're thinking about whether you need an Administrative Assistant or an Executive Assistant, ask yourself this: "Do I need someone to think strategically on my behalf and be my representative, or do I need someone to execute the tasks I don't have time for?" That will be a good indicator.

Ever wonder why your EAs are always swamped but can’t seem to explain why? Here’s the real reasons: 💡Countless “it’ll only take a minute” interruptions. All. Day. Long. Tally up all those “just a minute” requests and you’ll see why their time disappears into a black hole of everyone else’s priorities. 💡The myth that if the boss isn’t there, there’s nothing to do. Wrong. If the boss is away (even momentarily), that’s the only time they have a clear runway to focus without interruption. It’s not an open invitation to pile on extra work because they “must have extra capacity.” 💡Being the safety net for many creates complacency. When there’s an oracle of all wisdom in the room, it's astonishing how suddenly everyone forgets how to be self-sufficient. Instead of looking for answers themselves or referencing what they’ve already been provided, they just… go to the EA. Every. Single. Time. 💡The boss contributes just a fraction of an EA’s workload. Surprised? The rest comes from managing organisational interdependencies, serving as a trusted advisor, anticipating needs before they’re voiced, and finding solutions when no one else has a clue what to do. Being an oracle is a full time job in itself.   💡 They can’t run, and they can’t hide. EAs are like tagged animals in the wild—everyone needs to know where they are at all times because things fall apart the second they’re out of sight. They’re expected to be ever-present, always visible, and a perpetually green dot on Teams. And here’s the kicker: When you’re constantly on, there’s no space left for deep focus or strategic work—the very things that make an EA invaluable. It’s a relentless cycle that keeps them reactive instead of proactive. This is the reality no one talks about. An EA’s role isn’t just misunderstood—it’s wildly underestimated. They’re not just “keeping things running”; they’re navigating the chaos, steering priorities, and creating order where there would otherwise be none. Next time you wonder what’s keeping them so busy, remember this: They’re not overwhelmed because they’re inefficient—they’re swamped because the entire organisation leans on them. ➡️ EAs: what did I miss?  📢 What do you wish others would understand about the complexity of your role, balancing many competing demands and doing it all with the requisite smile and can-do attitude? 💌 And because it's Valentine's Day - how about tagging the superstar in your team that your organisation cannot do without?

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?

Your career gets decided when you're not there. (and you're never invited) The promotion conversations happen in closed-door meetings. Your raise gets discussed over executive dinners you're not invited to. 9 Ways to Get Advocated For in Rooms You're Not In: 1/ Make Your Boss Look Like a Talent Developer → Send weekly wins that highlight their coaching → Credit them publicly for your growth moments → Give them stories to tell about developing you 2/ Document Quantifiable Business Impact → Keep a monthly scorecard of your contributions → Connect your work directly to revenue/savings → Make your value undeniable with hard numbers 3/ Build Relationships with Your Boss's Peers → Attend cross-functional meetings when possible → Offer to help other departments solve problems → Become known beyond your immediate team 4/ Share Your Wins in Writing Before 1:1s → Email key accomplishments 24 hours prior → Include metrics and stakeholder feedback → Give your boss ammunition to defend you 5/ Volunteer for High-Visibility Strategic Projects → Raise your hand for CEO or board initiatives → Lead cross-departmental problem-solving efforts → Get exposure to decision-makers naturally 6/ Create Systems That Run Without You → Build processes that outlast your presence → Train others to execute your methodologies → Show executive readiness through scalability 7/ Become the Go-To Person for Critical Issues → Develop deep expertise in company-critical areas → Be the first call when urgent problems arise → Position yourself as indispensable to operations 8/ Communicate Up with Executive-Level Thinking → Frame updates around strategic business impact → Speak in terms of market opportunities and risks → Show you think like the next level up 9/ Plant Seeds About Your Next-Level Readiness → Mention stretch assignments you're interested in → Ask about skills needed for VP-level roles → Express strategic vision during planning sessions Most people wait for others to notice their potential. Smart operators make sure the right people can't ignore it.

I filled notebooks for twenty years. Every meeting, every idea, every commitment — written down, then shelved. Here is the uncomfortable truth: almost none of it ever came back to me at the moment I needed it. A notebook cannot re-read itself. Today, I don't lose a single word. Every meeting and discussion I hold is scribed and fed into my AI assistant — so before any decision, I can ask: what have we said about this before, and what did we promise? Running a hospital means holding thousands of moving details across hundreds of people. The job was never remembering them. The job is bringing them together. In my new newsletter piece, I share the exact system — the tools I use, how the transcripts flow into my assistant, and the governance rules I hold myself to. The discipline came first. The technology only recently caught up to it. #ConnectedCare #DigitalHealth #ExecutiveLeadership

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?

That VP who barely knows your work just vetoed your promotion. "Not enough strategic presence," they said. After coaching Fortune 100 leaders, here's what I've discovered: ➟ Strong team results ➟ Outstanding metrics ➟ Top performance reviews Yet when promotion time arrives, someone in the leadership room says: "I'm not sure they're ready." What's really happening? The Executive Trust Gap. Take Sarah, a Senior Engineering Manager who led a $14M product launch. Despite stellar metrics (98% team retention, 42% faster delivery), her CPO said: "Great execution, but I need to see more strategic leadership." Three months later, using what I'm about to share, she got promoted and now leads high impact meetings which opens doors to career-defining opportunities. The truth? Trust influences promotion decisions more than performance metrics alone. Here are 7 strategic moves that turn skeptical executives into your biggest champions: 1. Master the executive language shift ↳ Junior leaders talk about activities ("I completed the project") ↳ Senior leaders talk about outcomes ("This delivered 20% growth") ↳ Top leaders talk about strategic implications ("This positions us to...") ↳ Frame your updates at the highest appropriate level 2. Volunteer for cross-functional initiatives ↳ Creates visibility with multiple decision-makers ↳ Shows your impact beyond your immediate role ↳ Proves you think about the broader business 3. The "Preview" Strategy ↳ Brief key stakeholders before big meetings ↳ "I want to share our approach first and get your input" ↳ Eliminates surprise (which executives hate) 4. Create "Trust Deposits" before needing withdrawals ↳ Share relevant industry insights without asking for anything ↳ Congratulate executives on company wins ↳ Build the relationship when stakes are low 5. The 10-minute rule for executive meetings ↳ Practice delivering your message in 10 minutes ↳ Then practice delivering it in 5 minutes ↳ Then practice delivering it in 2 minutes ↳ Be ready for any time constraint 6. Demonstrate intellectual honesty ↳ Address problems before they're mentioned ↳ Acknowledge limitations in your recommendations ↳ Shows judgment and builds confidence in your thinking 7. The "Proxy Champion" technique ↳ Identify who already has the executive's trust ↳ Build strong relationships with these proxies ↳ Their endorsement becomes your shortcut to trust The most qualified person rarely gets the promotion. The most trusted one does. Which of these 7 moves will you implement this week? ♻ Repost to help someone bridge their trust gap. ➕ Follow me for more proven leadership strategies that create real career momentum.

After years working as an Executive Assistant I’ve noticed something about the job that rarely gets talked about... There are actually two versions of the role. The one people can see and the one that quietly keeps things running. The visible version is the obvious stuff; Meetings Travel & Events Inboxes Coordination But there’s another layer most people never really notice... It’s spotting when a conversation is about to go sideways It’s knowing when a decision needs a pause before it’s made It’s connecting the right people before something escalates It’s reading the room before the room realises it needs reading None of that sits neatly in a job description. But it’s often the difference between things working… and things quietly falling apart. Most experienced assistants learn this layer of the role over time. The tricky part is recognising that it IS a skill. Not just “being helpful”. And once you see it that way, the role starts to look very, very different. Curious... when did you first realise the job was bigger than the description you were hired for? #ExecutiveAssistant