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5 Ways to Nail “The Ask” at Work |
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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 the win, not the want
Frame your request around outcomes, not just the thing you want.
Instead of: “Can I buy Copilot?”
Try: “I’ve found a way to save us 3 hours a week in meeting prep — Copilot will handle summaries and drafts so you get cleaner inputs faster.”
Bullet-point the business case
Keep it tight: Cost + Time + Return.
- Cost: £450 course / £X licence
- Time: Self-paced, no disruption
- Return: 2–3 hrs saved weekly, faster decisions, smoother workflows
Pre-answer the “No’s”
- Budget? “Online = no travel costs.”
- Time? “I’ll fit it around BAU.”
- Priority? “Training me means multiplying your productivity.”
Offer a give-back
Show how others benefit. “I’ll create a 1-page playbook for the team” or “I’ll run a 15-minute lunch and learn with my key takeaways.”
Make it a two-option ask
Executives love clarity. End with:
“Option A: Approve [training/course] now (£450).
Option B: Approve [AI tool] 60-day trial, then I’ll report hours saved.”
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In this article, we’ll explore why it’s historically been difficult for Assistants to access training, why we often don’t ask for it, and how to ask for training in a way that sets us up for success. We’ll also break down exactly how to make the request, with a template you can adapt for your own Executive.
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The most successful Assistants commit to personal growth, embrace change, and view learning as an ongoing journey. Understanding why Assistants should never stop learning is crucial for maintaining effectiveness in an ever-changing professional landscape.
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Advanced EA Communications Masterclass
5th September, 10:00AM ET | 3:00PM BST
In this masterclass, you’ll gain the knowledge, tools, and confidence to leverage the latest technology and AI solutions in your role. Our interactive training will empower you to harness the power of AI and other tools specifically for EAs.
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Landing Your Message
This webinar will provide practical strategies to help you communicate effectively across all levels of your organization—whether you’re collaborating with colleagues, engaging with clients, or briefing busy executives.
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This week, your challenge is simple: take the first step toward making the ask for training, tech, or resources that will make your role easier (and more impactful).
Step 1: Research what you want
Is there a course, masterclass, or tool (like Copilot or Gemini) that would make a measurable difference to your workload? Spend 15 minutes this week looking into one option.
Step 2: Start building your case
Write down:
- Cost (be specific!)
- Time commitment (e.g., 3 hours self-paced, no travel)
- Return (e.g., hours saved weekly, smoother workflows, better support for your Exec)
Step 3: Practice your ask
Draft the first sentence of your request. Don’t send it yet if you’re not ready — just practice framing it around outcomes, not the want.
That’s it. One step closer to a confident, clear ask. The point isn’t to secure budget this week. The point is to normalize putting your own development on the agenda.
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September 5th, 2025 @ 10.00am ET | 3:00pm GMT
EA Communications Masterclass
Led by award-winning facilitator Laura Thomson-Staveley, this session will equip you with practical tools to influence without authority, handle challenging conversations with calm clarity, and show up as a trusted partner at the highest level. Book now>>>
September 16th, 2025 @ 10.00am ET | 3:00pm GMT
Collaborative Assistant Masterclass
In this masterclass, you will explore the intricacies of effective collaboration, strategic thinking, and proactive support, all designed specifically for the unique challenges of Executive Assistant roles. Book now>>>
September 18th, 2025 @ 11.00am ET | 4:00pm GMT
Free Webinar: Landing Your Message
This webinar will provide practical strategies to help you communicate effectively across all levels of your organization - whether you’re collaborating with colleagues, engaging with clients, or briefing busy executives. Book now>>>
September 26th, 2025 @ Live over 24 hours
Lead Virtual Summit
This Summit will empower Assistants with the skills to become influential leaders and strategic partners. Learn how to lead projects, manage up, influence decision-making, and work more strategically with your Executive. Book now>>>
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Refresh your skills with our 20% discount.
Throughout September, we’re offering 20% off all EA Campus online courses with the code BTS20 — but hurry, this offer is only available until September 30th!
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