The Roadmap

Every business climbs the same five steps with AI.

Five steps take a business from asking ChatGPT the occasional question to a company where AI does most of the daily work. Find your step in the first column, then read across to see what your week looks like, what slows you down, and how you climb.

The step AI workers What your week looks like What slows you down What we set up Safety rails
0: Dabbler You do it all by hand 0

You ask ChatGPT or Claude a question, copy the answer, and do the real work yourself.

In a bigger company: AI exists, but approvals keep it locked up, so most people never touch it.

The AI can't see your email, your calendar, your files, or your customers. It answers questions and stops there.

In corporate: security and legal haven't signed off yet, so nothing moves.

  • A safe starting point: Claude, with clear rules on what it can see and what it can spend
  • For corporate: the sign-offs that unlock it (who can use it, what data it touches, what it costs)
  • Company logins instead of personal ones
  • A monthly spending cap
  • Written rules on what data stays private
How you climb: connect AI to the tools you work in every day (email, calendar, files) so it can do real jobs for you.
1: One helper You review everything 1

You work with one AI assistant. It drafts your emails, preps your meetings, and updates your customer list while you watch.

You read every word before anything goes out. A task that used to eat an afternoon now fits between meetings.

Your attention. You don't trust it yet, so you check each draft line by line.

You sit with the AI while it works instead of moving on to the next thing.

  • Claude connected to your email, calendar, and files
  • Your first custom skills: email drafts in your voice, meeting prep, a customer list that updates when you ask
  • A plan-first mode, so you see what the AI intends to do before it does it
  • Nothing sends without your OK
  • A spending cap per person
  • A log of what the AI did and when
How you climb: give the AI a way to check its own work, then hand it more than one job at a time.
2: A small team You manage the work ~10

AI runs several jobs at once. It drafts your follow-ups, turns meetings into notes and action items, keeps the customer list current, and checks the books.

You review finished work instead of watching it happen. The backlog you never got to starts shrinking.

Reviewing. You produce less by hand and check more, and the checking now fills the hours the work used to.

  • Meetings that turn into notes, tasks, and follow-up drafts without you lifting a finger
  • A customer list that fills itself in
  • A drafts folder that's ready when you wake up
  • Access from your phone, so the office stops being a requirement
  • The AI checks its own work before you see it
  • Anything a customer will see (an email, an invoice, a post) still waits for your OK
  • AI work meets the same bar as human work
How you climb: turn the jobs that repeat every week into routines that run on a schedule, with no one asking.
3: The backbone You handle exceptions ~100

The routines run without you. The system sorts your inbox, debriefs your meetings, tracks your customers, and closes your books each month.

When something misses, you ask what the AI didn't know and fix it once. Cleanup work that used to wait for a free afternoon now runs in the background.

Trust and cost. You decide what to hand over next, and you keep an eye on what the growing system spends.

  • Routines on schedules: a morning briefing, weekly reports, a monthly books check
  • A playbook the AI reads before each job, so it works your way
  • AI that can start other AI for the big jobs
  • A watchdog on spending
  • A written playbook the AI follows on each job
  • A running record of what ran, what it did, and what it cost
How you climb: let the system spot work on its own and bring it to you, instead of waiting for you to ask.
4: AI-run company You set the direction 1,000+

The system starts most of the work itself. It watches your inbox, your pipeline, and your numbers, and it kicks off jobs the moment they come up.

You set direction and check results. A project that took a quarter becomes something you kick off on Monday and review on Friday.

Choosing what to automate next, and fitting the right guardrails to each kind of work.

  • Custom AI workers built for your specific business
  • Wired into the tools your team lives in, like Slack
  • Each one scheduled, supervised, and reporting back
  • Hard cost limits on anything that runs by itself
  • The right size of AI for each job, so simple work stays cheap

What step are you on?

Most owners land on step 0 or 1. I run my whole business at step 3 and take clients up the ladder one step at a time. On the first call we find your step and map the climb.

Find your step

Adapted from “Steps of AI Adoption” by Boris Cherny, creator of Claude Code at Anthropic. Translated from engineering language into plain business language.