AI Workshop: Building Your AI Chief of Staff
Get past the chatbot stage and into the operating layer.
Two half-day sessions. Twelve to fifteen executives. Every participant leaves with a working AI assistant for their actual job.
Most AI training shows your team a buffet of capabilities and sends them home with no working project. This workshop does the opposite.
Who this is for
You’re running an innovation function, a portfolio office, or an executive team inside a diversified business group, a family office, or a multi-business holding company. Your executives know AI is coming for their workflow. They’ve tried ChatGPT on the side for research and searches. None of it has touched the actual work.
You don’t want twelve people figuring it out in twelve different tools, with twelve different data postures. You want one common foundation, applied consistently, that you can build on.
That’s what this workshop is for.
What the cohort builds
Across two half-day sessions, every executive in the room builds a Claude project tailored to their actual function. Not a demo. Not a generic prompt template. A working configuration of instructions, files, and live data sources that they use the following week.
The curriculum covers:
- Projects, instructions, and files. The configured workspace that replaces the blank-chat starting point every executive currently lives with.
- Outputs. Artifacts, file creation (Word, Excel, PowerPoint, PDF), and writing styles that produce work you can ship, not chat you have to copy-paste.
- Live data via connectors. Reading from Google Drive, Gmail, Calendar, or Microsoft 365.
- Skills. Codifying internal processes as onboarding documents the AI follows. Your meeting minutes format. Your contract review playbook. Your vendor escalation protocol.
- Delegation via Cowork. Multi-step tasks running on a schedule, including the morning briefing every executive wishes they had.
Each cohort group also receives a tailored project pack mapped to their actual function in your business, built from a brief intake call before delivery.
Why this format works
The workshop begins with a demo of a finished product that closely matches what your teams already need in practice, then works backwards. Features are introduced as the answer to friction the room has just felt, not as a list of capabilities to memorise. Executives review each other’s work in groups so the facilitator can circulate and harvest patterns for plenary discussion. Each group’s project files are designed around their specific function before the day starts, so the work in the room is the work they’ll continue afterwards.
The result is a cohort that may arrive sceptical, but leaves with tools they can immediately apply to their work, and stays in touch about what they’re building next.
Format and logistics
Two half-day sessions
Scheduled one week apart, timed to fit your executives’ operating responsibilities.
In person delivery
At your office location or a venue of your choice, anywhere in Southeast Asia
Online support
Between each session via WhatsApp group, with mid-week check-in cadence
Claude Team plan included
So that chats and projects can be shared and referenced by all participants
Tailored project packs
Custom built for each cohort group to match their roles and responsibilities
Recently Conducted Sessions
A Southeast Asian business group asked me to conduct this workshop for thirteen executives across seven operating businesses, spanning industrial estate operations, agritech, agri-export, gaming and IP licensing, hyperscale data centre development, energy infrastructure, and venture support. Even with such a highly diverse group, each participant was able to produce a useful AI project to improve their day-to-day tasks.
About the facilitator
Alex Tan is the founder of Halfborg Software, a Singapore-based AI implementor and trainer. He’s a co-founder of Recommend.my (formerly Sejasa.com) and writes about practical applied AI at halfborg.com. LinkedIn
He designs and delivers every cohort personally.
Frequently asked
What if my team isn’t on Google Workspace?
We can also support Microsoft 365. For teams on Lark or other stack, we will switch to use an intermediary folder pattern. The workshop teaches this as a transferable technique, not a workaround.
Will participants still need their AI subscriptions after the workshop?
We include one month of Claude Team plan for every participant. After that, your team continues on whatever plan fits your organisation. We can advise on the right tier.
Do you deliver virtually?
The cohort coaching dynamics depend on people being in the room together. For organisations that genuinely can’t get the cohort in one place, it’s possible to deliver virtually and modify the sessions. We can discuss alternative formats by quote.
Can you tailor the curriculum further for our business?
Yes. The standard curriculum is the foundation. We can add modules for sector-specific work (legal, finance, ops, commercial) by quote.
How far in advance do you book?
Four to six weeks of lead time is typical. Intake calls, group assignment, and project pack design all happen before delivery.
Send me a brief
Find out whether this workshop format is a fit for your team and request a customised quote.