---
title: What Broke When I Delegated the Contractors
description: "What happened when my assistant coordinated home contractors: the rules each mistake taught me, where the handoffs broke, and why some businesses want a person."
image: https://willcurran.com/hubfs/will-curran-brand/delegating-the-contractors-cover-nolane.png
---

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# What Broke When I Delegated the Contractors

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Will Curran Aug 28, 2026 · 8 min read

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![An abstract dark scene: a dotted orange line runs from a chat bubble toward a doorway glowing orange, broken by a small X partway down, with a silhouette standing in the doorway, next to the title What broke when I delegated the contractors.](https://willcurran.com/hs-fs/hubfs/will-curran-brand/delegating-the-contractors-cover-nolane.png?width=1600&height=900&name=delegating-the-contractors-cover-nolane.png)

This summer I handed my assistant the contractors: finding them, getting quotes, booking visits, following up. It had a phone line and a texting number through Twilio, a task list in Todoist and access to our calendars. The number had never been registered the way US carriers require for business texting, so carriers dropped messages while the sending service reported success. Seven texts to three contractors were logged, and I was told those people had been reached. None of the texts arrived.

The tools mostly did their jobs. What broke were the handoffs: between the tools, and between the tools and the people who show up at the house.

## Vendors are people you manage without employing

I came up in event production, where most of the people who make a show happen don't work for you. You manage them anyway, and trust is the whole job: built in person, lost over small things like a message that reads as an audit.

I wanted help with that at home. I didn't want to be on the phone; early on I told my assistant, "I don't want to talk to them - you're supposed to be managing the contractors." And I know my weak spot: "I always have a hard time remembering to really hold the contractors accountable."

## The stack was simple

- **Twilio** for calls and texts, on a dedicated callback number so my own cell stays mine.
- **Todoist**, one task per job. Every touch is logged on it, and it closes only when the work is confirmed done, not when someone replies.
- **Our calendars**, with every booked visit on them and a HOLD the moment a request for a date goes out. That rule exists because a visit got booked and never reached my calendar. I found out when the contractor mentioned it.

## Most rules came from a specific mistake

**Confirm first.** I started fully delegated. Then three vendor relationships were damaged in about 48 hours. I took every vendor message back, and two weeks later settled on confirm-first.

**One touch per vendor per day, across every channel.** I had already said, "Don't harass any of the vendors and be cognizant of their time and annoyance tolerance." That was a written convention, and one company still got seventeen calls and emails from us in a single day. Now a call, a voicemail and an email count as three touches, and after one we wait at least three business days.

**Warm all the way down.** The first follow-up playbook escalated its tone over time. I threw that out. Now every step is warm, ending in a warm goodbye. A vendor you part with warmly will answer the phone next year.

**Curiosity, not interrogation.** Every behaviour that cost us a vendor was a documented best practice: benchmarking, levelling bids, checking licences, a follow-up cadence. Stacked together they felt like an audit from a customer who hadn't paid anyone yet. One contractor withdrew a job he had already won after we reopened a price he had settled.

**Defer to the specialist you hired.** My assistant emailed a specialist we had just hired and asked them to justify their plan. Its research was defensible; the email was still wrong. I told it, "they're the experts, not you." Concerns now come to me.

**Get verification in writing.** Before booking anything that gets covered up, the contractor agrees by email to send photos before it is closed in. Writing it into the booking makes up for me being bad at asking in the moment.

![Diagram titled Where the handoffs break. A vertical chain runs from Me to my assistant, which keeps a task list and a calendar, then to text, voice and email, then to the business, and finally to the person on site, with a dotted return line from the site back toward the record. Seven orange markers flag failures: a job filled outside the system while follow-ups kept running; follow-up jobs that stopped quietly; a closed record that still said to contact someone who had said no; texts marked sent but never delivered; machine detection hanging up on a live person; a restart dropping a live call; and a deposit paid in person that the record read as unpaid. A note says every marker sits on our side of the handoff.](https://willcurran.com/hs-fs/hubfs/will-curran-brand/delegating-the-contractors-handoffs.png?width=1440&height=1266&name=delegating-the-contractors-handoffs.png)

## Where it fell apart

**Our broken channel looked like their silence.** My assistant was one status check away from recording a contractor as unresponsive when the fault was entirely ours.

**The phone system hung up on people.** Answering-machine detection decided a live contractor was a machine 31 seconds in, just after he had told us to go ahead, then hung up and redialled him. His anger got logged as hostility. He was owed an apology, and the same defect cut three other calls that morning.

**A restart cut a good call.** A contractor was mid-answer on pricing, four minutes and forty seconds in, when our own service restarted and dropped him.

**The silence was our price.** On one small job, a budget below what that work costs reached the vendors. Twelve businesses were contacted, and the only reply didn't answer the question. My assistant concluded the market didn't serve small jobs. We had told everyone we would pay less than their minimum.

**Follow-ups fell between systems.** I hired a service myself and never told the system, so a follow-up was still running a month later. Separately, a closed record still carried an instruction to email a contractor who had declined. The notes said he had gone silent. He had said no.

**The follow-up jobs stopped quietly.** The scheduled follow-ups stopped producing and nothing flagged it. I didn't restart them. I asked for a redesign: "Something that doesn't annoy them, something that is reliable."

**The real decisions happened on site.** I was uneasy taking a low bid from someone I had never met, and what I care about is who will actually be on the property. On one job I handed over my card in person and signed. With no emailed receipt, my assistant logged the deposit as probably unpaid. An empty inbox is not evidence.

## Some businesses want a person, and some don't mind

Eight times that summer, a business told us it wanted to deal with a person. They came from several kinds of home-service businesses. In the moment I said, "People's reluctance to talk to an AI and have to talk to me is super weird."

With some distance, I get it. My guess is that small businesses field a constant stream of automated calls, and someone coming to work at your house wants a person on the other end they can hold accountable. Saying no is a legitimate choice. The right response is to thank them and have me call.

Others didn't mind. One business kept working with my assistant and gave its own rates, the first real ones we had for that job. For one hire, I wanted a company willing to work with my assistant.

This part is my read, not something any business told me. Midway through the summer I wrote, "Man finding contractors who are AI friendly or have systems that an AI can use is really tough. I wonder if anyone is solving this or has already solved it." The marketplaces already own the relationships with the pros, and a marketplace built to expect agents routes around the refusal problem. So I asked my assistant to sign up for Angi's and Thumbtack's agent tools if they ship them. Businesses will keep the right to want a person, but I think that is where this is heading.

## Where I was the bottleneck

- I swung from full delegation to doing it all myself before landing on confirm-first. Each yes costs me seconds and protects the relationship.
- I resolve things by just hiring someone, and the system only knows if I tell it.

## If you are about to try this

- **Before you call a vendor hostile, check your side.** A dropped call or a hang-up looks exactly like a rude vendor.
- **Keep your budget to yourself.** Let them name the number.

## Build it yourself

Parts: a phone and texting service, a task manager, a shared calendar and email. The playbook:

1. **One task per job**, every touch logged, closed only when the work is done.
2. **One touch per vendor per day** across all channels, then wait three business days.
3. **Confirm first.** The assistant drafts; a human approves each outbound message.
4. **Never pretend to be a person.** Your assistant must never claim or imply it's a person. Decide up front how it identifies itself, and if anyone asks whether they're talking to an AI, it says yes, plainly, every time. Respect a no: if a business says they don't want to deal with an AI, stop and hand it to a human.
5. **Warm tone at every step**, ending in a warm goodbye.
6. **Check delivery, not "sent".** An undelivered message is an attempt, not a touch.
7. **A calendar hold** the moment you ask for a date.
8. **Written verification** before booking anything that gets covered up.
9. **Close the loop everywhere** when a job ends, and record why: declined, hired elsewhere or done.

Give this to your AIHelp me coordinate home contractors for \[jobs\]. Draft every outbound message for my approval; never send without my yes on that specific message. Track each job as one task in \[task app\] with a dated log of every contact, and close it only when I confirm the work is done. Contact each business at most once per day across all channels, then wait at least three business days, skipping weekends. Keep messages warm and short. Never claim or imply you are a person. We will decide up front how you identify yourself, and if anyone asks whether they're talking to an AI, say yes, plainly, every time. Respect a no: if a business says they don't want to deal with an AI, stop and hand it to me. Never escalate tone; if they go quiet after a few tries, draft a friendly goodbye. If they would rather talk to a person, thank them and tell me. Never share my budget. Confirm a message was delivered before logging "no response". Put a calendar hold on any date you ask for. When a job ends, remove every task, hold and follow-up for it.

If you have tried to get an assistant to work with the people who show up at your house, I would like to hear what held and what broke.

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Will Curran

I spent sixteen years building one company, and I have been in the event industry since 2007. These days I write about the technology I actually use — trucks, radios, home infrastructure, and the tools that survive past the first invoice.

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