· 7 min read
What to
delegate
first.
Most delegation fails in week two, and almost always for the same reason: the founder handed over the wrong work first. Here's the afternoon exercise we run with every new client.
The instinct is to delegate what you hate. It's the wrong filter. What you hate is often what only you can do — the difficult client conversation, the pricing decision, the hiring call. Handing that over is how you end up doing it twice.
The better filter is repeatability, then cost of a mistake. Here's how to find it in about ninety minutes.
Step one: track a week, badly
Don't buy a time-tracking tool. Open a note on your phone and log what you're doing every time you switch context. Rough is fine — "45m, inbox", "20m, chasing invoice", "1h, deck". A week of scruffy data beats a month of nothing.
Founders who do this honestly are usually shocked by two categories: email, and re-doing something that should have been written down the first time.
Step two: split it into five lists
- Rules. Work with a clear right answer that you could describe in a paragraph. Booking travel, chasing an unpaid invoice, entering a lead, sending the day-three follow-up.
- Reps. Work with no single right answer but a repeatable shape — first-draft replies, ticket triage, content repurposing, research briefs.
- Reviews. Work someone else can prepare but you must approve — proposals, client reports, anything with a number in it going outside the company.
- Relationships. Work that is the relationship. Sales conversations with your top ten accounts, team feedback, partnership calls.
- Rare. One-offs. Genuinely infrequent work that costs more to document than to just do.
Delegate list one immediately, list two in month two, list three in month four. Never delegate list four. Ignore list five.
Step three: start with Rules, not with volume
The temptation is to hand over the biggest time sink on day one — usually the inbox. Don't. The inbox is a Reps task wearing a Rules costume: it requires context about your business, your clients and your tone that a new assistant doesn't have in week one.
Start narrower. Give them invoice chasing, calendar management, receipt filing and CRM entry. Small blast radius, obvious right answers, and — this matters — a fast feedback loop. You'll know within three days whether they're careful.
Then expand into the inbox with training wheels: they draft, you approve, for two weeks. By week three most assistants are sending 70% of routine replies unsupervised.
Step four: write the SOP by narrating, not typing
Nobody has ever finished the SOP document they promised to write on Sunday. So don't write it. Record your screen while you do the task once, talking through the decisions out loud, and hand the recording over. Your assistant writes the SOP from the recording — that's part of their job, not yours.
The SOP they write will be better than yours, because they'll document the steps you've stopped noticing you do.
Step five: define "done" and "escalate"
Two sentences per task, and delegation stops being scary:
- Done looks like: "Invoice marked paid in Xero, client thanked, note logged in the CRM."
- Escalate when: "Payment is more than 30 days late, or the client disputes the amount."
Most delegation anxiety is really uncertainty about the edges. Name the edges and it goes away.
The order, in one line
Rules first, Reps second, Reviews third, Relationships never, Rare ignored. If you do nothing else from this piece, do the five lists. It takes an afternoon and it's the difference between an assistant who saves you two hours a week and one who saves you fifteen.