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That smug feeling when AI plans the trip faster than you ever could

Wednesday 17th September No: 036 The quiet satisfaction of letting AI handle travel How to look unbothered while juggling five itineraries This week, we’re talking about the quiet flex of AI-powered travel planning - the kind where you shave hours off bookings, look unbothered in Slack, and your exec thinks you cloned yourself. Here are four quick wins to make trips smoother, cheaper, and drama-free: 1) Build a clean itinerary in minutesExecs don’t want five confirmation emails; they want one...

CONNECT September 12th, 2025 | Issue 35 Latest Articles Asking Good Questions in the EA Role As Executive Assistants, we ask a lot of questions every single day. Whether it’s checking in with our Executive, following up with a colleague, or trying to pin down a supplier, so much of our role depends on the information we gather. What we sometimes forget is that the quality of our questions makes all the difference. Read more → How to Ask for Training as an Executive Assistant In this article,...

Wednesday 10th September No: 035 5 Ways to Nail “The Ask” at Work The EA’s Guide to Confident Questions This week, we’re talking about the nerves that come with asking questions - “Am I bothering them?” “Should I already know this?” - and how to ask in a way that feels smart, strategic, and genuinely helpful. It’s not fewer questions; it’s better ones. Here are five ways to set yourself up for a yes-and, fast decisions, and fewer back-and-forths: 1) Lead with context, then one clear question...

Wednesday 3rd September No: 034 5 Ways to Nail “The Ask” at Work The EA’s Guide to Confident Requests This week, we’re talking about the art of making the ask, whether that’s for training, new AI licenses like Copilot or Gemini, or simply the resources you need to do your best work. Asking can feel awkward (cue the inner monologue: “What if they say no?”), But done right, it’s one of the fastest ways to elevate your role and impact. Here are five ways to set yourself up for a yes: Lead with...

CONNECT August 29th, 2025 | Issue 33 Latest Articles Revolutionize Email Management It’s time to revolutionize email management and finally take control of the way we support our Executives through their inboxes. These days, we have the tools to revolutionize email management, and we’re here for it. Let’s walk through how things used to be done and what a modern approach looks like now. Read more → Mastering Every Important Conversation an EA Should Have In this guide, we’ll walk through...

Wednesday 27th August No: 033 5 AI Tools That Actually Do the Work for You The EA’s Guide to AI Inbox Assistants This week, we’re diving into five game-changing tools that can help you automate, organize, and speed up email management without losing your Executive’s voice (or your sanity). Superhuman Built for high-performing teams, Superhuman does more than just speed things up - it transforms your inbox into a finely tuned machine. Think automatic categorization, instant replies, email...

CONNECT August 22nd, 2025 | Issue 32 Latest Articles Mastering Every Important Conversation an EA Should Have In this guide, we’ll walk through every important conversation an EA should have, breaking each one down into what to say, how to say it, and how to prep – whether you’re writing an email or speaking face to face. Read more → Real Strategies When the Schedule Feels Unmanageable You know what a good schedule should look like – space to think, time to get work done, and meaningful...

Wednesday 20th August No: 032 Small Talk, Big Impact Because “So, how’s your week going?” Can Change Everything Whether you’re walking a client to your Exec’s office, stuck in a lift with the CEO, or making conversation at a networking event, small talk matters. Here’s how to turn those awkward silences into strategic moments: Prep 2–3 Go-To Topics in Advance. Think industry news, local events, or even a good restaurant rec. When you’re escorting a stakeholder from reception, having a neutral...

CONNECT August 15th, 2025 | Issue 31 Latest Articles Real Strategies When the Schedule Feels Unmanageable You know what a good schedule should look like – space to think, time to get work done, and meaningful priorities – but every time you try to help, the changes get swept aside. Read more → The Complete Guide to Working with Multiple Execs This guide is based on real experience. These are the tools, habits, and mindset shifts that genuinely help you stay in control, be proactive, and add...

Wednesday 13th August No: 031 When the Schedule’s Out of Control Because Carrying the Weight of the Calendar Wasn’t in Your Job Description 1. Your Executive’s Stress? Not Your Failure. When your Exec’s running on fumes, showing up late to their third back-to-back Zoom, and still hasn’t eaten lunch, it’s easy to internalise the chaos. But let’s make one thing clear: you didn’t create the system – you’re navigating it. The guilt hits because you care. You’re invested. That’s part of what makes...