Getting Started: What Does AI Know About You?

Two 120-minute sessions for founders who haven’t yet made AI part of how they run their business.

Everyone around you seems to have an AI story. Yours hasn’t landed yet, and you’re not sure whether that’s because it isn’t for you, or because you haven’t seen the right example.

What you want is one credible example, for a business like yours, not a tools tour, so you can decide whether this is worth your personal time, without looking foolish in front of your team if it turns out it isn’t.

Format

Live workshop

With Mark Littlewood

PRICE

$500

Per Participant

Schedule

11am UK

Two sessions, Tuesdays

SESSIONS

15 + 22 Sep

Doors close at 12 seats

Want to discuss fit before registering? Email mark@businessofsoftware.org


How we solve it

Session one is that example, live, on a real company in the room, not a demo reel. You watch it get built, and you watch it get corrected in front of you. What it gets wrong about a business tells you more than what it gets right.

Between sessions, you run the same thing on your own company. You build a first draft yourself, not a finished system handed to you, and a list of everything it missed. That list is what an agent working for you actually needs to know, and no public source can supply it.

Session two turns that list into something real: a working CLAUDE.md with your governance built in from the start, not bolted on after, and a North Star metric named in the room. You leave knowing exactly where you stand, and what a sensible next step looks like, if there is one.

This is for you if…


  • You’re a founder or CEO of a software business
  • You know there is leverage in AI but have not yet found the right starting point
  • You want the cohort curriculum built entirely around your specific business context
  • You are willing to do the prework and show up ready to build

Probably not for you if…


  • You want a tour of tools or prompt engineering tips
  • You’re looking for generic productivity wins rather than a system that compounds
  • You want to watch without doing the hands-on work between sessions
  • You’re already tinkering regularly and hit a ceiling, the four-week cohort is the right next step

What you get

Two 120-minute sessions, one week apart.

TUESDAY, 15 SEP

Live Build

Live build on a real business, and the reflection that shows you what a first draft always misses.

BETWEEN SESSIONS

Run it in your own company

You run the same build on your own company and write down everything it got wrong.

TUESDAY, 22 SEP

Turn it into a CLAUDE.md

Turn that into a CLAUDE.md that’s corrected and governed, a North Star metric named in the room, and a clear-eyed view of where to go next, continue alone, take one safe first step, or go deeper.

Maximum 12 participants.


What you’ll need

The setup is straightforward.

  • Claude Desktop
    The interface you’ll use for all workshop sessions and prework.
  • Cowork mode (Claude Pro or Team plan)
    Required for the agent workflow used throughout the workshop.

Who’s in the room

One facilitator, already running the system.

Mark Littlewood
Founder, Business of Software

Mark has run Business of Software for 19 years, two annual conferences, more than 400 practitioner talks, and a community of founders building software companies that last. He has spent that time working out what actually separates the businesses that make it from those that don’t. This workshop is built on the same principle as every BoS event: helping entrepreneurs build better businesses alongside other smart people.

Registration open now

Getting Started: What Does AI Know About You?

Two weekly two-hour sessions, starting 15 September 2026 11am UK

$500 per participant (excluding VAT where applicable)

The BoS No Quibble Guarantee: if you attend and feel you didn’t get value, we will refund your fee. No questions asked.  Questions about fit? Email Mark.

Common questions

What’s included in the workshop fee?
Two two-hour sessions – 15 + 22 September, 11am UK. Access to core systems and workshop materials.
You will leave with a working system you can run in your business right away.


What tools do I need before I start?
Claude Desktop, a Claude Pro or Team plan (required for Cowork mode), and to already be using Claude in some capacity in your business.


How is this different from an AI tools course?
This is not a tools course. It won’t teach you prompting basics or help you choose between platforms. It is about building the operating system underneath your tools, the documented rules, values, decision boundaries, and memory that allow anything you delegate to actually run without you holding it together. There are no paid speaker slots, no frameworks being sold, no sponsor content. The cohort is capped at 12 because peer quality and challenge are part of what you’re paying for, not a marketing tactic.