A checklist for owners hiring contract pilots for the first time

You own or manage an airplane, your full-time pilot is on vacation or you do not have one, and someone recommended a contract pilot. Good contract pilots are the most flexible crew you will ever use, and the relationship goes wrong for only a few, predictable reasons. This checklist covers them. It is written for owners, assistants and new flight departments, and it is not legal advice: your aviation attorney and your insurance broker get the final word on the items that mention them.

Before you call anyone

• Call your insurance broker first. Most policies require named pilots or an "open pilot warranty" with minimum experience in make and model. Get the requirements in writing and give them to the pilot before the trip. A pilot who does not meet the warranty may not be covered on your airplane, however good they are. Your broker decides, in writing.
• Know your operating basis. Part 91 owner flying with a contract crew is normal. If anyone is paying you for the flight, or the airplane is on a charter certificate, different rules apply and the pilot generally has to be on that certificate. Ask your attorney before the trip, not after. If you are not sure which you are, ask your attorney before the trip, not after.
• Decide who is responsible for what. The contract pilot is pilot-in-command, with everything that entails. You remain responsible for maintenance, airworthiness, records and insurance. Write it down in a short agreement if you plan to use them more than once.

Qualifications, verified by you

No software verifies a pilot, including ours. Ask for and look at:

• Pilot certificate and medical (class appropriate to the seat).
• Type rating for your aircraft, and date of last recurrent training.
• Logbook evidence of time in type and total time, against your insurance minimums.
• References from one or two owners or departments they fly for regularly. Contract pilots expect this call.
• For international trips: passport validity and experience with the destinations.

Agree the rate card, in writing

Experienced contract pilots have a written rate card. Ask for it. It should cover:

• Day rate for the seat (PIC or SIC) on your aircraft.
• Half-day, travel-day and standby rates, and the minimum days for an overnight trip.
• Per diem per day.
• What is reimbursable (hotel, airfare, rental car, rideshare, parking) and whether you book it or they do.
• Short-notice and cancellation terms.
• Payment terms (Net 15 is common) and how they want to be paid.

Reply "confirmed" to it. That single word saves more disputes than any contract clause. If you want context on what the numbers typically look like, this post is written for pilots but is equally useful to you.

The paperwork

• W-9 from the pilot (or their LLC) before the first payment. Ask your accountant whether a 1099-NEC is required at year end. n1099 does not file or prepare tax forms. n1099 does not file or prepare tax forms; your accountant does.
• Worker classification. Worker classification depends on the facts and on your state, and California's test is notably strict. A pilot who sets their own rate, flies for several owners and provides services per trip is often treated as an independent contractor, but have your attorney confirm before the arrangement becomes regular, and certainly before someone flies for you 20 days a month on your schedule.
• Short services agreement if you expect to use them regularly: scope, PIC authority, insurance representations, confidentiality about your travel, indemnity. One or two pages. Your attorney has a template.

Expenses: decide the policy once

The friction in contract crew relationships is almost always expenses. Pick one of two policies and tell the pilot:

1. You book everything. Your assistant books hotel, airline positioning and car on your accounts. The pilot's invoice has only fees and per diem. Cleanest for you; needs an assistant who answers at night.
2. The pilot books, you reimburse. The pilot books within guidelines you set (hotel cap, economy airfare), attaches receipts to the invoice, and you reimburse at cost. Flexible, and most contract pilots are used to it.

Either way, ask for receipts attached to the invoice, not emailed separately. Receipts attached is the difference between approving an invoice in a minute and chasing it for a week.

Invoice intake and approval

Decide where invoices go (one email address, not your personal inbox), who approves them (you, or your scheduler, or your controller), and how fast. Then tell every pilot the same thing. A standard invoice that you can approve from your phone, with every line and receipt visible, is the goal. If several contract pilots send you invoices in several formats, a tool that gives them all one format, and gives you one place to see them, is worth having. n1099's owner side does exactly that and is free, and you can approve any n1099 invoice from the link without an account.

Pay on time, and say when

If your controller runs payables on the 1st and the 15th, tell the pilot. They will time their invoice to it. Pilots carry your balance at their own expense; the ones you want to keep notice who pays in nine days and who pays in forty-five. If you cannot pay on time for a month, say so before the due date. That one message keeps a good pilot on your roster.

Build the roster

After the first good trip, keep that pilot's details, the types you use them on, their rate card and your notes in one place, and ask them for dates before you need them. Two or three trusted contract pilots who know your airplane and your passengers are a better department than most owners realize, and cheaper than a second full-time salary. That private roster is what the owner account in n1099 is for: invitations, availability requests, consolidated invoices. Nobody sees it but you.

The checklist

1. Insurance requirements in writing from your broker.
2. Operating basis confirmed (Part 91 owner flying, or on a certificate).
3. Certificate, medical, type rating, time in type checked against insurance minimums.
4. References called.
5. Rate card received and confirmed in writing.
6. W-9 collected; classification discussed with your attorney if usage will be heavy.
7. Expense policy chosen and communicated.
8. Invoice inbox, approver and payment schedule communicated.
9. First trip debriefed. Roster updated.

Print it, or create a free owner account and keep it where the invoices arrive.