How to hire your first contractor

You run a one-person agency with one or two clients, and either the client work is eating your selling hours or a client wants something you cannot do well. Here is how to hire your first contractor: check you really need one, set the most you can pay before you talk to anyone, and pay three freelancers for the same small trial before you trust one with a client. Most people do it the other way round: they hire the first person who replies in their busiest week, then spend more time fixing the work than it saved.

Do these three things

About 1.5 hours today and 5 hours this week. The trial costs 3 pieces at each person's price. Sign the agreement and get a W-9 before the first payment.

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1. 1Today: add up your client hours for the last two weeks. If they passed 24 a week both times, or a client has paid for work you cannot do well, write that one task as a checklist and set the most you can pay: half of what the client pays for that work, worked out from your lowest price per hour.
2. 2This week: send a short brief to 30 freelancers who already do that task, starting with people you know and then on Upwork. Pay 3 of them for the same trial piece, and keep the one whose work meets every "Done when" line with under 10 minutes of fixes.
3. 3Every Sunday: count the contractor's pieces, your minutes fixing them, and the hours you got back. Put those hours into 100 personal messages a day, and pay every piece within 7 days of your approval.

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1. Check you need a contractor: 24 client hours a week, or work you cannot do

You need your first contractor when client work passes 24 hours a week on two Sundays in a row, or when a client has paid for a piece of work you cannot do to the standard they expect. If neither is true, do not hire yet. A contractor costs money every month, and with one or two clients the hours you need are usually selling hours, not more hands.

Add up your hours. Open your calendar or time sheet and look at the last two weeks. For each week, write down the hours you spent on client work and the hours you spent finding clients. Count only real hours, not how busy it felt.

Apply the rule:

• Client work over 24 hours a week, two Sundays in a row: hire for the task that takes you the most hours, such as client posts or drafting the monthly report. 24 hours a week is about 96 a month, the hours one person can really sell when they also find clients, as in how to go from freelancer to agency. Above it, your 4 hours a day of selling is what stops first.
• A client has paid, or signed, for work you cannot do well: hire for that piece only. Examples: designing ad creatives, editing short videos, or running ads on a platform you have never used. Hire after the client signs, never before.
• Neither: do not hire. Write one piece of client work down as a checklist each day, and keep sending 100 personal messages a day to win your next client. Check again next Sunday.

Check the price before you hire. Divide what each client paid last month by the hours they took. If a client pays less than your lowest price per hour, a contractor does not fix it. You would pay someone to do work that already loses money. Raise that client's price at renewal, or cut the work to what the price pays for, before you hire.

Last, write the task down in one line, with the client and the hours a month: "8 LinkedIn posts for [client], 4 hours a month." That line is what you hand over. If the work is a whole service you do not want to run, such as SEO, white-label work may fit better than a contractor.

• Tool: Google Sheets or your calendar. No paid tool needed.
• Time: 20 minutes.
• You will have: a yes or no with the reason, and one task with its client and hours a month.
• It worked if: you can say which rule applies in one sentence, with two weeks of real hours behind it.
• Common mistake: hiring after one busy week, or hiring because clients pay too little. Both turn into a monthly cost you cannot cover in a quiet month.

2. Write the task as a checklist and work out how much to pay

Write the task as a numbered checklist someone else could follow without asking you, and work out the most you can pay for each piece before you talk to anyone. The checklist is the contractor's brief. The top price stops you agreeing to a quote that leaves you nothing.

Write the checklist. Do the task once as normal, timing each piece, and type each step into a Google Doc in one line as you go. Paste your notes into ChatGPT or Claude and ask: "Turn these notes into a numbered checklist. Under each step, add a 'Done when' line someone can check." Fix what it gets wrong. If you already write one checklist a day, use the one for this task.

Add the client sheet. The checklist says how the work is done. The client sheet says what is true for that client: who they sell to, how they sound, the words they never use, and who approves. It is how you keep each client's voice separate when someone else drafts the work, and most of it comes from how you onboarded the client.

Task: [name] · Client: [client] · Pieces a month: [ ] · Time per piece: [minutes]
You get: the client sheet, [files], [access]
[Step, starting with a verb]
Done when: [what someone can check]
[Step]
Done when: [check]
[Step]
Done when: [check]
Send it to [your name] by [day and time]. Nothing goes to the client without [your name]'s check.

Work out the most you can pay. Use the sum from pricing your services: the task's hours a month × your lowest price per hour ÷ 0.65. That is what the client pays for this piece of your package. Pay the contractor at most half of it. About 15% pays for your time checking, and 35% is the margin you keep for slow months. Divide by the pieces a month to get the most you pay per piece, then write down the monthly cap.

• If you hire for hours: use the sum above.
• If you hire for work you cannot do: the most you pay is half of what the client pays for that piece. If the client pays $600 for a set of ad designs, the most you pay is $300.

If you cannot find good work at half, keep the task, or price that piece higher at the client's next renewal.

• Tool: Google Docs, and ChatGPT or Claude to tidy the notes.
• Time: about 1 hour.
• You will have: one checklist, one client sheet, the most you pay per piece and the monthly cap.
• It worked if: you paste the checklist into ChatGPT or Claude, ask it to read it as a new hire and list every question it would need answered, and no answer changes the work.
• Common mistake: a step like "write in the client's voice" with nothing else. Say where the voice is written down. The other mistake is working out the price after the first quote, so the quote sets it for you.

3. Send a short brief to 30 freelancers who already do the task

Send the same short brief to 30 freelancers who already do this task for other people: about 10 you know or are pointed to, and about 20 through one platform. Thirty feels like a lot for one small job. It is how you find three good people in a week instead of waiting a month on one job post.

Start with people you know. Write to freelancers you have worked beside, other freelancers in your niche, past colleagues, and people whose work you have seen in your online communities. Ask other freelancers and your LinkedIn connections who they would hire for this task. Someone whose work you have already seen is the safest first contractor.

Then use one platform for the rest. Use Upwork: you may already find clients there, and posting a job is free. Post one job with the brief below, then invite freelancers who show this exact task in their portfolio. Know these rules before you start:

• Invites: a standard Upwork job post comes with 30 free invites. On the free Basic plan you can message only 5 new freelancers a day directly, so use the job's invites, not messages, to reach 20 people.
• Fees: on the Basic plan, Upwork adds a client marketplace fee of up to 7.99% on every payment (3% for eligible US clients who pay by bank account), plus a one-time contract fee of $0.99 to $14.99 for each new contract. Add these to the contractor's price before you compare it with your top price.
• Staying on Upwork: for 24 months after you meet a freelancer there, you must pay them through Upwork, unless you pay a conversion fee of at least $1,000. Plan to keep paying through Upwork.
• The other option: Contra charges freelancers no commission. If the freelancer is on Contra's free plan, you pay a $15 or $29 fee on each payment over $500.

Let AI draft, then make each one true. As with any AI-drafted writing, paste 10 names at a time into ChatGPT or Claude, each with one thing you noticed in their work, plus the template. Ask for one message per person. Read each draft and fix the first line so it is true. That is about a minute a message. Follow up once after 3 days with anyone who has not answered, then stop.

Subject: paid trial: [task] for a [kind of business]Hi [first name],[One true line about their work: a post, a portfolio piece, a project you saw.]I run [agency name]. I do [service] for [kind of business]. I'm looking for one person to do [task], about [pieces] a month, from a written checklist.To start, I'd pay you for one trial piece at your normal price. You'd get the checklist, a short sheet about the client and a deadline of [3] days.If you're interested, reply with:
Your price per piece
Two samples of this kind of work
[Your name], [agency name]

Log every reply in a sheet, the way you would build a lead list: name, price per piece, samples, and where you found them. Anyone above your top price per piece, after platform fees, is out.

• Tool: Google Sheets, Gmail or LinkedIn, Upwork's free Basic plan, and ChatGPT or Claude to draft.
• Time: about 2 hours to find 30 people and send the brief, plus 15 minutes for follow-ups.
• You will have: 30 briefs sent, and a sheet of replies with a price and two samples each.
• It worked if: at least 6 people reply with good samples at or under your top price. Fewer than 6 after 30 briefs: send it to 30 more. If most prices are above your top, your top is too low for this task, so go back to the rule in step 2.
• Common mistake: posting one vague job ad and waiting. The other is hiring the first person who replies, before you have seen anyone else's work.

4. Pay 3 freelancers for the same trial task and keep the best one

Pick the 3 best replies at or under your top price, and pay each one to do the same real piece of work from the same checklist, with the same deadline. A paid trial on real work shows you what an interview cannot: how they follow a checklist, keep a deadline and take a correction.

Send the trial. Give each of the 3 the checklist, the client sheet, any files, the deadline and the agreed price. Use a real piece from the client's next month on the content calendar, not a made-up test, so the trial is work you would pay for anyway. If you would rather not name the client yet, take the name off the client sheet. Pay every trial, pass or fail: it is the same small paid first job a founder should ask for when they hire an agency.

Score each piece the same way. When a piece comes in, fix it until you would send it to the client, and time how long that takes. Write down three things:

• Did it meet every "Done when" line?
• Did it arrive by the deadline?
• How many minutes did you spend fixing it?

Pick one. A trial passes if it meets every "Done when" line, arrives on time and needs under 10 minutes of fixes. If two pass, keep the one with the lower price, and save the other as your backup. If nobody passes and all three made the same mistake, the checklist is unclear: fix that line and send it to the next 3 on your sheet. If they made different mistakes, send the same trial to the next 3.

The honest cost: three pieces at each person's price, plus any platform fees. For a $25 post, that is about $75 to find someone you can trust with a client. A bad hire costs far more. One agency owner who skipped a trial wrote that he spent "3-4 hours per day reviewing and fixing" a new hire's work, and lost about $6,000 before he let him go.

• Tool: Google Sheets for the scores. Pay from your business bank account, or through the platform if you found them there.
• Time: 30 minutes to send the three trials, and about 30 minutes to check and score each piece.
• You will have: one freelancer who passed, a score sheet, and one backup.
• It worked if: the person you keep met every "Done when" line, on time, with under 10 minutes of fixes, at or under your top price.
• Common mistake: an unpaid test or a long interview instead of real work. Good freelancers skip unpaid tests, and an interview tells you how someone talks, not how they follow a checklist.

5. Sign a contractor agreement and get a W-9 before the first payment

Before you pay for anything past the trial, sign a short written agreement and get the contractor's tax form. In the US that is Form W-9, which gives you their taxpayer number. Then set up their access so they never need your password.

Sign the agreement. Write it in Google Docs from the template, with only the task, price and dates changed. Ask a lawyer in your state to read it once. Send it for signature with Dropbox Sign: the free plan gives 3 signature requests a month, and signing your own documents does not count. In New York City, the law requires a written contract with the work, the pay and the pay date for any freelance work of $800 or more, counting all work for the same person over 120 days. The template covers all three.

[Agency name] and [contractor name] agree:
Work: [task], following the checklist "[checklist name]". A piece is done when every "Done when" line is met.
Price: $[ ] per piece, paid within 7 days of [agency name]'s approval. Most per month: $[ ] ([ ] pieces).
Deadline: [day and time] for each piece.
The contractor chooses their own hours, place and tools, and may work for others.
Once paid for, the work and all rights in it belong to [agency name].
Client information stays private. The contractor does not contact [agency name]'s clients directly, and names any AI tool they use on client work.
Either side can stop with 14 days' written notice. Approved work is paid.
The contractor gives a Form W-9 (or W-8BEN outside the US) before the first payment, and pays their own taxes.
Signed: [name, agency name, date] · [contractor name, date]

Get the tax form. In the US, ask for Form W-9, from the IRS website, before the first payment. If the contractor lives outside the US, ask for Form W-8BEN instead: the IRS says a valid Form W-8 "should be required before any payment is made" to a new foreign vendor. Ask an accountant about your own country's rules if you are not in the US.

Know the 1099 line. For payments made in 2026, you send a Form 1099-NEC to each contractor you paid $2,000 or more in the year, and file it with the IRS, by the end of January. The line was $600 until the end of 2025, and many guides still say $600. You can file for free on the IRS's IRIS portal, but it needs a Transmitter Control Code that can take up to 45 days, so apply in December if you might reach $2,000.

Keep them a contractor. The IRS looks at three things: who controls how and when the work is done, who controls the money side (how they are paid, whose tools they use), and what the relationship looks like (benefits, how permanent it is). Pay by the piece, let them choose their hours and tools, and judge the result against the checklist. Do not set their working hours or tell them how to do each step beyond the checklist. Some states use a stricter test: California uses the "ABC test". If you or the contractor are in one of them, ask a lawyer there before the first payment.

Give access the right way. Add the contractor through each platform's own team roles, such as a LinkedIn page admin role or a shared folder, and never share your password. Remove the access the day the work stops. If the work is posting, set it up the way you manage your clients' social accounts.

Tell your clients the rule, not the name. If your client agreement already says you may use contractors and check all work first, as the agency agreement does, you do not need a new conversation. If it does not, add that line to your scope of work at the client's next renewal, and tell them before the contractor starts.

• Tool: Google Docs, Dropbox Sign's free plan, the IRS website for Forms W-9 and W-8BEN, and IRIS for the 1099-NEC.
• Time: about 1 hour, plus the IRIS code once a year.
• You will have: a signed agreement, a W-9 or W-8BEN, access set up by role, and a reminder for January.
• It worked if: both documents are saved before the first payment, and the contractor can do the task without your login.
• Common mistake: treating the contractor like an employee: fixed hours, daily check-ins, your laptop. The other is sending your own login in a message.

6. Check every piece before your client sees it, and count the hours you got back every Sunday

Every piece the contractor makes comes to you first. You check it against the checklist, then the client approves it before anything goes live. Every Sunday, count what the contractor did and where your freed hours went, because the reason you hired was to sell more.

Check every piece. Check it against each "Done when" line and the client sheet, and log the minutes you spent fixing it. Then send it through your client approval as normal. Pay each approved piece within 7 days, from money already in your business account. A drop in quality that the client sees first is one of the fastest ways to lose a client.

Move the freed hours to selling. Every hour the contractor saves you goes into your 100 messages a day, your follow-ups, your discovery calls and your proposals. If the hours drift into more client work, you have paid for help and still not grown.

Week | Pieces done | Fix minutes (average) | Cost this week | Most you pay | Your client hours | Your sales hours | Messages sent | Calls booked

Then use these rules:

• Average fixes over 10 minutes, two Sundays in a row: send the contractor the 3 most common fixes and add them to the checklist. If it happens again, give the next piece to your backup.
• Cost above your most-you-pay line: stop and check why. Usually it is extra pieces outside the client's package, which is scope creep. Never pay less than you agreed.
• Sales hours under 21 (3 a day): the freed hours went to client work. Put them back into selling before you take on more work.
• Client hours over 24 again, two Sundays in a row: hand over your next biggest task from step 1, to the same contractor if they have room.

Once a month, add the contractor's cost to each client's row in your monthly review, so you can see what each client really leaves you after contractors. That number also tells you what you can spend to win the next client. When you have three or more contractors and steady clients, the next job is to scale the agency.

• Tool: Google Sheets, and your client approval sheet.
• Time: about 10 minutes to check each piece, and 20 minutes each Sunday.
• You will have: one row a week, every piece checked before a client saw it, and every contractor paid on time.
• It worked if: after 4 Sundays, your client hours have fallen by about the task's hours, your sales hours have risen by the same, and the average fix time is under 10 minutes.
• Common mistake: sending the contractor's work straight to the client to save time. The other is letting the freed hours fill up with more client work instead of selling.

Your first contractor checklist

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Step 1 · Check you need a contractor

• Add up your client hours for the last two Sundays and apply the rule.
• Write down the one task to hand over, with its client and hours a month.

Step 2 · Write the checklist and work out the pay

• Write the task as a numbered checklist with a client sheet.
• Work out the most you can pay per piece and the monthly cap.

Step 3 · Send a brief to 30 freelancers

• List 30 freelancers who already do this task.
• Send the brief to all 30 and follow up once.

Step 4 · Pay 3 freelancers for the same trial

• Send the same paid trial piece to 3 freelancers.
• Score the three trials and keep the one that passed.

Step 5 · Sign the agreement and get the W-9

• Sign the contractor agreement and get a Form W-9 or W-8BEN.
• Give the contractor access through each platform's own roles.
• Set a reminder to send a 1099-NEC if you pay them $2,000 or more this year.

Step 6 · Check every piece and count every Sunday

• Every dayCheck each new piece before the client sees it, and pay approved pieces.
• Every SundayFill in the Sunday contractor sheet and apply its rules.

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