How to Build Your AI Chief of Staff

Roisin Bennett

AI Strategist & Digital Workforce Lead

Anish M.

AI Solutions Architect & Copilot Expert

Stop using AI like Google. Build an assistant that actually knows you.

You're the CEO, the COO, the marketing lead and half the sales team. Your calendar is full, your inbox is louder, and the strategic work that actually grows the business keeps slipping to "next week."

Most owners reach for AI and end up using it like Google - type a question, get an answer, close the tab. Useful, but it never adds up to real capacity. The owners pulling ahead this year aren't using AI more often. They've set it up properly so it works for them in the background, every single day.

In three hours, with Roisin Bennett and Anish M walking you through every step, you'll build a personal AI Chief of Staff that knows your role, your priorities, your voice and your people. It reads your calendar and email each morning and writes you a short, personalised brief, what's on today, what genuinely needs a reply, where to focus. Each evening it quietly captures your meetings and gets sharper overnight.

No coding. No jargon. You leave with a working assistant delivering its first brief to you tomorrow morning and a system that compounds in value every week you use it!

What you’ll learn

Go from AI curiosity to a working AI Chief of Staff that reads your day, surfaces what matters, and helps you run your business with focus.

Create four simple “about me” files covering your role, priorities, and what good work looks like for you.
Capture how you actually think and decide, so the assistant can mirror your judgment instead of giving generic advice.
Calibrate tone and style using real emails and messages, so every suggestion sounds like it came from your desk.

Configure a routine that reads your calendar, scans email, and checks your priorities list before you open your laptop
Receive a focused brief highlighting today’s key meetings, must‑reply emails, and one clear recommendation for your best work block.
Stop starting each day in your inbox and instead act from a one‑page overview of what truly matters.

Automatically turn meeting notes and transcripts into clear decision summaries and action lists, filed where you can find them.
Build lightweight people files as you go, so your assistant remembers who everyone is, what they care about, and what you promised.
Wake up knowing yesterday’s conversations are captured, organised, and ready to feed into today’s brief.

Follow a step‑by‑step walkthrough to connect Gmail, Google Calendar, and Drive in a secure, read‑only way.
Use a simple online “filing cabinet” so your assistant can write briefs and notes without touching your main systems.
Leave with everything wired up and tested, so your assistant keeps working even when you close the browser.

Turn vague reminders like “follow up with Dan” into clear, context‑rich priorities your assistant can act on.
See how better‑written priorities change the quality of your Morning Brief and End‑of‑Day suggestions in practice.
Build a simple, living priorities file that becomes the backbone of how you plan weeks and months.

Use a short checklist to spot whether weak output is caused by missing context, unclear priorities, or a routine issue.
Practise “rescuing” a bad response live, so you know exactly what to tweak when it happens in your own setup.
Leave confident that you can keep improving your Chief of Staff instead of abandoning it after the first mistake.

Workshop agenda

See it live: a real morning brief in action
Open with a real Chief of Staff brief landing in the vault - what's on today, which emails actually need a reply, and where to focus. The target you're building toward in the next three hours.
Teach the AI who you are
The AI interviews you, one question at a time, to build your "About Me" files - your role, how you make decisions, your voice, and how you like to be challenged. The single mo
Connect everything together - Anish walks every click
Set up the secure online filing cabinet, the reading app, and the cloud sync that lets your assistant work in the background. No coding. If anything stalls, Anish gets it working in the room.
Write priorities the AI can actually act on
Build your live priorities list - urgent today, important this week, on the back burner with the real context that turns vague reminders into sharp, useful suggestions.
Switch on your daily Morning Brief
Schedule the routine that reads your calendar, scans your email, cross-references your priorities, and writes you a personalised brief before you open your laptop tomorrow morning
Switch on your End-of-Day catch-up
Set up the second routine that runs while you're at dinner -capturing today's meetings, updating your people files, and triaging tomorrow's actions so the system gets smarter overnight.
The honest mirror: where your time really goes
Close by surfacing the gap between your stated priorities and what your calendar actually shows. The kind of insight an executive coach takes months to reach.

Learn directly from Roisin & Anish

Roisin Bennett

Contact

Roisin Bennett is an AI Engineer, AI Strategist, and Chief AI Officer for SMEs.

Anish M.

Contact

AI Solutions Architect & Copilot Expert

See all products from Roisin

Who this workshop is for

SME CEO/COO juggling growth and operations, needing a safe, practical way to make AI part of the daily workflow.
Solopreneur / founder doing it all, wanting AI to take real work off their plate, not add another tool to manage
Ops, Marketing, or GTM lead in a small team who wants hands‑on AI help with real tasks, not another theory session.

What's included

Live sessions

Learn directly from Roisin Bennett & Anish M. in a real-time, interactive format.

Lifetime access

Go back to course content and recordings whenever you need to.

Community of peers

Stay accountable and share insights with like-minded professionals.

Certificate of completion

Share your new skills with your employer or on LinkedIn.

Maven Guarantee

Your purchase is backed by the Maven Guarantee.

Testimonials

Roisin delivered a series of highly engaging, practical AI workshops for our business clients on using AI in marketing and sales. The sessions were well structured, full of real examples, and focused on tools people could start using straight away. She made complex ideas easy to grasp and participant feedback was exceptionally positive. We’d happily recommend her to any organisation looking for high‑quality AI training for SMEs.
Carrie O’Donoghue
Development Officer, Ballyhoura Development CLG
Roisin ran a full‑day AI training for our Destination Lough Derg tourism businesses, followed by one‑to‑one sessions with individual operators. She showed very clearly how AI can support marketing and customer engagement, in a way that felt practical and unintimidating even for those with only basic computer skills. Many participants implemented ideas immediately afterwards. I’d strongly recommend Roisin for any tourism or SME group starting their AI journey.
Carmel Ormonde
Destination Lough Derg Tourism Officer
Roisin’s session for our Women’s Rural Entrepreneurial Network was exactly what our founders needed. She showed how female entrepreneurs can rethink their marketing and move their businesses forward with AI, using live, hands‑on examples. Rather than talking about AI in the abstract, she walked participants through how to apply it to their own content and customer outreach. Even those who were nervous about tech left feeling confident and excited to put AI to work in their business
Donna Cleary
Programme Lead SECAD Partnership