Someone finds customers. Someone builds the thing. Someone answers the email at 11 p.m., someone reconciles the bank account, someone decides what the company is for. Every business has the same boxes, and in a solo company your name is in every one of them by accident. The chart is where you put it there on purpose. Draw it before you buy the tools.
Fill each box by consequence of error. How boring the work is doesn't enter into it. Boring, low-consequence work goes to an agent. Skilled work where a mistake is recoverable goes to a contractor, or to an agent with a reviewer. Work where a mistake ends the company, a relationship or your legal standing stays with you until you have a human you trust with the keys. Easy to say. Hard to follow at 11 p.m.
The three tiers
| Tier | Who does it | Test for putting work here | Typical examples |
|---|---|---|---|
| Agent | An AI model, an automation, or an agent with tools | Output can be checked faster than it can be produced; errors are cheap to catch and cheap to reverse | First-draft support replies, meeting notes, lead research, data cleanup, test writing, changelog drafts, invoice reminders |
| Contractor | A human you pay by the project or hour | Needs judgment or taste you lack, or a license you don't hold; errors are costly but recoverable | Design, bookkeeping close, tax filing, security review, specialized code, legal drafting, video editing |
| Founder-only | You | Errors are irreversible, or the work is the company's judgment | Pricing, hiring and firing, what to build next, signing contracts, moving money above a threshold, apologizing to a customer you wronged, anything with your name as the person responsible |
A fourth category hides inside the first two: agent, with a human gate. The agent does the work, and nothing leaves the building until a person approves it. Most early delegation starts here and earns its way to "agent, unsupervised" on a track record. Chapter 8.3 covers how to build the gate, and Chapter 8.9 gives the step ladder for loosening it.
What never gets delegated
Some things stay with you however good the models get. An agent could produce a plausible version of each. You're the one legally, financially or morally on the hook, and plausible is the dangerous kind.
- Deciding what the company is for. Strategy, the one bet (Vol 1), what you will not do. An agent can argue options. It doesn't live with the result.
- Pricing and discounts above a floor you set. Price is a strategic statement (Vol 3, Ch 3.6). Let an agent quote from a price sheet. Don't let it improvise.
- Moving money. Paying bills can be automated inside hard limits (a named payee list, a dollar cap per transaction). Opening accounts, wiring to a new payee and approving anything off the list stay with you. Wire fraud against small businesses runs on exactly the gap an unsupervised payment agent creates.
- Signing. Contracts, tax filings, loan documents, anything with a signature line. Your signature is a legal act (Vol 4).
- Hiring, firing and paying people. A contractor's livelihood is on the other end.
- First contact after you've hurt someone. Outage apologies, refund disputes that got ugly, a customer who's angry for a good reason. Draft with help. Send as yourself.
- Credentials and access. Who can log into what. The password manager's recovery kit. Admin roles on the domain, the bank and the code host.
- Public statements under your name that make claims of fact. The FTC does not care that a model wrote your testimonial page (Vol 4, Ch 4.6).
- Final review of anything irreversible: deleting data, sending to the whole list, pushing a database migration to production, filing with a government agency.
Put this list in your business wiki (Chapter 8.3) as the "founder-only" page. It's there for the tired evening when you want to hand one off.
Mapping every function
Assign each task below a tier. Most functions split. "Marketing" is a dozen tasks with a dozen different risks.
| Function | Agent | Contractor | Founder-only |
|---|---|---|---|
| Strategy | Market scans, competitor summaries, first-draft memos | Occasional advisor or coach | The bet, the no-list, what to kill |
| Product | Spec drafts, code, tests, docs, bug triage | Senior engineer for review; designer | Roadmap priority, what ships, final approval of risky changes |
| Sales | Lead research, CRM hygiene, follow-up drafts, call summaries | Appointment setter (later) | Discovery calls, pricing conversations, closing, key relationships |
| Marketing | Drafts, repurposing, SEO research, scheduling | Designer, video editor, copy editor | Positioning, voice, anything that makes a factual claim |
| Support | Triage, first drafts, help-doc answers, tagging | Part-time support person (later) | Escalations, refunds above a threshold, angry customers |
| Finance | Categorizing transactions, invoice reminders, reports | Bookkeeper for month-end close; CPA for taxes | Approving spend, moving money, signing returns |
| Legal | Summarizing contracts, flagging clauses | Attorney for anything binding | Signing, deciding to sue or settle |
| Ops/admin | Scheduling, inbox sorting, data entry, file naming | Virtual assistant | Access control, vendor selection over a dollar threshold |
| Security | Monitoring alerts, dependency updates | Periodic security review | Who has access to what, incident decisions |
| People | Drafting job posts, screening for hard requirements | Recruiter (rarely, at this stage) | Selecting, offering, managing, ending |
The agent column is long because that's where the volume is. The founder-only column is short. That column is where the company gets decided.
Worked example: solo SaaS
About 140 paying physical therapy clinics, one founder, no employees, a scheduling tool. Eighteen months in, the chart looks like this:
Founder (roughly 30 hours a week):
- Customer calls: discovery, onboarding for clinics over a size threshold, renewals at risk
- Roadmap and weekly prioritization
- Review and merge of every change touching billing, auth or patient data
- Pricing, contracts, and the business associate agreements that come with health data (see Vol 4, Ch 4.7 on HIPAA)
- Weekly ops review (Chapter 8.8)
- Escalated support tickets
Agents:
- Coding agent working from specs, in branches, on a staging environment. Opens pull requests; never merges to main.
- Support agent answering from the help center, with an escalation rule for anything mentioning billing, data, cancellation or a legal word.
- A research agent that prepares a one-page brief before each sales call from the CRM, the clinic's website and past tickets.
- Bookkeeping categorization inside the accounting software, reviewed monthly by the bookkeeper.
- Scheduled jobs: failed-payment emails, weekly usage digest to the founder, dependency update PRs.
Contractors:
- A senior engineer, 6–10 hours a month, reviewing architecture decisions and any change the founder flags as risky.
- Bookkeeper, monthly close.
- CPA, quarterly and annual.
- A healthcare-privacy attorney on call, used twice last year.
- A designer, one project per quarter.
What changed over time: the support agent started with every reply held for approval, step 0 on the Chapter 8.9 ladder. Password resets and "how do I" questions stepped down as clean reads accumulated: 30 consecutive clean reads before review dropped to half, 60 more before a fifth, 150 more before a tenth, 300 more before one in twenty. Over the first six weeks their unedited-approval rate ran 95%-plus; that number is watched as a signal that something changed, never as the threshold for loosening. One critical defect sends a category back one step. A new model, prompt, SOP or input source sends it back to step 0. Billing never left step 0.
Worked example: solo services firm
Eight retainer clients, one founder, a fractional-marketing practice for regional credit unions.
Founder:
- Every client relationship. The clients bought her judgment; that's the product.
- Strategy sessions, quarterly plans, and anything presented to a client's board
- Final edit on every deliverable before it goes out
- New business: all sales calls, all proposals
- Compliance judgment calls (financial marketing has regulators; see Vol 4)
Agents:
- Meeting notes and action items from every client call, filed to the client's folder
- First drafts of monthly reports from analytics exports
- Content first drafts from her outlines, in each client's documented voice
- Research briefs on a client's market before quarterly planning
- Invoice generation and reminders
Contractors:
- Two freelance writers who edit agent drafts into client-ready copy (she found the drafts needed a human pass for voice and regulatory care)
- A designer on retainer
- A paid-media specialist for the two clients who run ads
- Bookkeeper and CPA
In a services firm the founder's time is the inventory. Agents free hours. Those hours can go to more clients (revenue), better work for existing clients (retention and price), or productizing (Vol 3). Decide where, on purpose. Undirected hours get eaten by email.
Building your own chart
- List every recurring task you did in the past four weeks. Pull from your calendar, sent mail and task list. Expect 40–80 items.
- For each, write the worst realistic consequence of it being done wrong and not caught for a week.
- Assign a tier from that consequence. Ignore how much you enjoy or hate the task.
- For every agent-tier task, write who or what checks the output and how often.
- For every contractor-tier task, write whether you have the contractor, or the gap.
- Circle the three tasks eating the most founder hours that could move down a tier. Those are next month's delegation projects.
Revisit the chart every quarter. It's supposed to change.
Field exercises
- Inventory your work. Done when you have a list of every recurring task from the last four weeks with an estimated weekly hours figure for each.
- Tier it. Done when every task on the list has a tier and a written worst-case consequence.
- Write the founder-only page. Done when a page titled "Never delegate" exists in your wiki with at least eight items specific to your business.
- Pick one delegation. Done when one task has moved from founder to agent-with-gate, with the gate described in writing.
- Set limits on money. Done when any automated payment runs against a named payee list and a per-transaction cap, or you've confirmed none does.