How I Passed My CFI Checkride on the First Attempt

Looking at my paper Temporary Airman Certificate and seeing ‘FLIGHT INSTRUCTOR’ in Box ix, my main reaction was relief.

I did it! The DPE gave me a grin, shook my hand, and said, “Congratulations!” That was the moment I became a Certificated Flight Instructor.

The Reality of the CFI Initial Checkride

The FAA’s initial CFI checkride has a reputation for being one of the toughest. When I took mine in 2021, the national first-attempt pass rate was about 77 percent. It has since dropped to 73.7% in 2025, according to the U.S. Civil Airmen Statistics. That means one applicant in four walks away disappointed on the first try.

The FAA treats this checkride differently. Under Order 8000.95, Designee Management Policy, DPEs may conduct up to three checkrides in a day — but only one CFI initial in any 24-hour period.

So why take it on?

I wasn’t pursuing a job in the airlines or even as a professional pilot. By this point, I was (and still am) a mid-career software engineer who flew on the weekends for fun and stress relief, occasionally flying to the beach or to college football games.

During instrument training, my CFI/I was first to suggest that I become an instructor. I’d never even considered it before.

When I passed the commercial checkride, the DPE said he hoped I’d continue to CFI and that I was almost there.

An instructor who’s highly respected in the Huntsville aerospace community called and left a voice message in response to my question about how much flying it would take to prepare for the commercial checkride. I still have it in my phone, where it has survived a couple of phone upgrades since 2018.

“Hey Greg, this is my encouragement call back to you… I think you’d make a great instructor. You’ve got a lot of practical experience. Owning an airplane gives a lot of knowledge… So my encouragement is: plot it out, budget it out, execute it, and you would be a great asset to the flying community.”

That message stuck with me.

Then I heard Jason Blair on Max Trescott’s Aviation News Talk podcast describe a CFI candidate who said he wanted to “make safer pilots.” That flipped a switch for me. I began thinking of ways I’d train primary students differently. I realized becoming a CFI wasn’t just another rating. I could make a difference in ground instruction and in the right seat. I could be a positive mentor. I could see myself in the role of CFI.

Now how would I get there?

My Unusual System That Actually Worked

I didn’t follow the typical “fly good, don’t suck, and hope for the best” path that pilots commonly take. Instead, I borrowed a systematic, repeatable studying system that medical students have used for years to ingest huge volumes of new material to pass their brutal board exams and adapted it to flight training.

At the core is spaced repetition with Anki combined with active recall, deep FAA handbook work, and constantly thinking from the examiner’s (and future student’s) perspective from day one.

Thanks to this hybrid approach, the DPE said “You really know your stuff!” after my oral exam. Acing the oral puts the DPE on your side by showing you took your preparation seriously. Drilling the facts in a smart, efficient way took pressure off to help me fly a solid flight test and pass the CFI initial checkride — all on the first attempt.

In this post, I’ll show you how I built my Anki deck, the exact preparation strategies that mattered most, what surprised me on checkride day, and the tools and resources I actually used (and still recommend).

If you’re preparing for your own CFI initial, this isn’t theory. It’s what worked under real pressure.

The Knowledge or “Written” Tests: FOI and FIA

The FAA calls them Knowledge Tests. Pilots just say “writtens,” even though they’ve been computer-based for decades.

Download the Flight Instructor for Airplane Category ACS (FAA-S-ACS-25) and know it cold. You’ll soon be teaching your own students how to use the Private and Commercial ACS guides. They’re legal cheat sheets for FAA tests.

The CFI ACS lists two required (outside the exceptions in FAR 61.183) knowledge tests for the CFI initial: Fundamentals of Instructing and Flight Instructor – Airplane.

Passing the writtens is a solved problem. Go directly to Sheppard Air. If you purchase their FIA study course first, Sheppard will give you a healthy discount on the FOI course down the road. I happened to do them in the other order. Prepare for the writtens one at a time.

Sheppard’s software is straightforward with no frills. Nothing fancy is needed. Follow their Study Strategy exactly. I used their iOS version on my iPad. There’s a lot of material, so buckle down and knock them out.

For further reading, see my experience report about passing the FOI.

Key Mindset Shift: Instructor, Not Student

The DPE wants you to pass — but is evaluating you as an instructor, not just a pilot. On both the oral and flight test, you’re being graded on whether you deliver safe, effective instruction.

Remember, the standard is not perfection. A minor mistake will not bust you. “Consistently exceeding tolerances” or the DPE having to take the flight controls will bust you.

Being tested as an instructor gives you another tool. When checkride nerves get to you and you mess up a maneuver, teach your way out of it. “I should have added more power, correcting now.” “Got distracted, pitching forward for airspeed.” “That’s what happens when you don’t use enough trim.”

Just like on the private and commercial checkrides, don’t make the examiner read your mind. Keep communicating because that’s how we teach in the cockpit. The CFI ACS specifically lists “Failure to take prompt corrective action when tolerances are exceeded” and “Failure to provide effective instruction while demonstrating a procedure or maneuver” as grounds for failure. That’s what the ACS is really looking for: effective instruction, even when things don’t go perfectly.

Tools and Routine: My CFI Preparation System

Here’s the system I actually used.

Study Buddy with Active Recall

Get a study buddy who is also working toward CFI. Each of you will pick up on different aspects of the material and strengthen each other’s overall depth of knowledge. Not wanting to let your study buddy down is also great for when motivation is low.

Practice teaching lessons to each other. Cal Newport in his book How to Become a Straight-A Student (paid link) is a strong proponent of active recall, a technique that is much more effective than reading and rereading the same material. You may have heard the saying that the best way to learn is to prepare to teach someone else.

A form of the above advice is to grind out your own lesson plans while working on your commercial. I did not do this and instead purchased my own professionally created lesson plans to take to the checkride for occasional referral. The volume of the lesson plans is so large that the temptation to copy-and-paste, or these days outsource to an LLM, is strong. Neither one of these creates understanding in the way that active recall forces. Active recall is possible with your study buddy or by yourself. Even when you’re alone, practice teaching your lessons out loud. It will feel strange at first but is an essential part of the process.

Get a “Gouge” on Your DPE

Every DPE is unique with different personalities, preferences, idiosyncrasies, and quirks.

Your recommending instructor likely has a DPE in mind. Find one or more checkride write ups or gouges on that DPE’s checkride. This will help minimize surprises and avoid the DPE’s hot buttons. Each DPE will tend to emphasize different subjects. One of the DPEs in my area is an attorney and expects to see familiarity with the FAR and application of the FOI. Another has an A&P certificate and wants CFI candidates to demonstrate significant systems knowledge. Your DPE may expect you to be able to calculate density altitude using an E6B flight computer (paid link).

Know your DPE. You may be weak in some areas and strong in others that your DPE will ask about. You want to know what they are to fill in any gaps in your own knowledge.

Once you know what to study, the real challenge is getting all of it into long-term memory. The way to do that is not reading the same handbooks and guides over and over.

Anki

I first learned about Anki from a medical student’s guide on efficiently loading large volumes of information into long-term memory.

Anki is a spaced-repetition system. Think of that as smart automated flashcards. For the cards you have an easier time recalling, Anki shows them less often. The harder ones you see more frequently. In each study session, Anki shows you one card at a time, and you self-rate your ability to recall the correct answer on a scale of Again, Hard, Good, or Easy, where Again means you got it incorrect.

This system was a game changer for me.

At the beginning, you’ll have to plow through lots of cards. Over time they separate themselves into low-frequency maintenance and high-frequency topics being learned. Establish a daily Anki routine. Once you’re in the groove, your study sessions will take about 20 minutes each day. I liked doing mine first thing in the morning, but I’m a morning person. Evenings after work may be better for you.

Missing study sessions means they stack up on you. It will happen. Keep skips to a minimum to keep your study sessions quick and efficient.

Download Anki. I used the desktop application that defaults to showing you only a few cards per day. Borrowing from med students, I made the following settings changes.

Options > New Cards
- Steps (in minutes): 1 360
- Order: Show new cards in random order
- New cards/day: 9999
- Graduating interval: 1 day
- Easy interval: 2 days
- Starting ease: 250%
- Bury related new cards until the next day: UNCHECKED ☐
Options > Reviews
- Maximum reviews/day: 9999
- Easy bonus: 130
- Interval modifier: 100
- Maximum interval: 36500
- Bury related new cards until the next day: CHECKED ☑

These aggressive settings let me tackle more information and front-loaded my learning. The defaults would never allow you to get through everything.

Anki supports Windows, Mac, Linux, iOS, and Android. The Android and desktop versions are free. The iOS Anki app costs money. I used the desktop version most frequently at home on my laptop. AnkiWeb is a free companion webapp that allows you to upload your cards and study over the web. On the go on my iPhone and iPad, I studied for free with Safari and AnkiWeb.

I mostly used cloze deletion cards. An example cloze template is

{{c1::Commercial}} Steep Turns:

Altitude: +/- {{c2::100}} feet

Airspeed: +/- {{c3::10}} knots

Bank: {{c4::50}} +/- {{c5::5}} degrees

Heading: +/- {{c6::10}} degrees

At study time, that becomes 6 cards to study, one each for c1 through c6. One of those will be

Commercial Steep Turns:

Altitude: +/- 100 feet

Airspeed: +/- 10 knots

Bank: […] +/- 5 degrees

Heading: +/- 10 degrees

which tests your recall of commercial steep turns being at 50±5 degrees.

Cloze cards are great for testing your recall of associations in both directions. For example, you might use a template of

Memory aid for {{c1::Levels of Learning}} is {{c2::RUAC}}.

to quiz yourself on both “What is the memory aid for levels of learning? and “What is RUAC the memory aid for?”

Memorizing sets and enumerations are known difficulties, and unfortunately aviation is full of them. Think of the awful ATOMATOFLAMES alleged memory aid for required day VFR equipment. Good luck keeping all the different A, O, and T words straight. Similarly for defense mechanisms we have DR DR FCPR, F-RADAR-CP, or FARRPRCD. Even emergency checklists for power on or power off can be tough to memorize. I recommend creating overlapping cloze templates of no more than 3 items each and also a cloze template with the full enumeration.

Refer to my CFI study deck for examples to follow. It is important to make your own cards. Mine may or may not match your situation and your DPE. The process of building your own deck will solidify the concepts in your mind, so don’t skip this crucial step.

Anki and Levels of Learning

All of the facts in your Anki deck are at the Rote and Understanding levels. The DPE will want to see you demonstrate Application and Correlation of these facts, which you will learn during your CFI training. Having facts available for quick recall in the stressful environments of the oral exam and during the flight test will improve your confidence, keep you from stumbling, and avoid having to look up every bit of information the DPE asks about.

With my knowledge solid, it was time to prepare for the oral.

Oral Exam

Remember that the oral is an open book, open note exam. Refer to FAA sources. The ASA Flight Instructor Oral Exam Guide (paid link) is a fine resource for preparation and mock orals, but I do not recommend taking it to your checkride.

Never try to bluff the DPE. The DPE’s questions are not idle curiosity. The DPE knows the answers. Different DPEs will have their own pet questions, such as where are high-performance and complex airplanes defined in the FAR. (It turns out they’re in separate sections.) Admitting when you don’t know and searching the FAR has an important application for flight instruction. Remember the P in REEPIR: the Law of Primacy. The first time we learn something, it tends to be really sticky, so never ever teach your students incorrect information. Admitting when you don’t know and when you make mistakes will build trust with your students.

“I don’t know, but I know where to look it up.” That’s the pat answer you may have learned for your private checkride. Thanks to Anki, you will know where to look them up: e.g., Part 61 for certification or Part 91 for rules of the air. Know them a level deeper: 61.87 for student pilot solo rules, 61.103 for private pilot eligibility, 61.123 for commercial pilot eligibility, 61.183 for CFI eligibility, 91.205 for required equipment, 91.213 for inoperative equipment, and so on.

Be able to talk through all the logbook endorsements from first solo through being ready for the private checkride.

You should have practiced the expected ground lesson until you can almost recite it, but don’t memorize it. Know the key points and be able to talk through it extemporaneously. Your DPE will probably throw out a few unexpected questions, so you’ll need to be able to adapt to those. Your DPE may also toss you a few helpful hints. Teaching an Eights on Pylons ground lesson during my checkride, I drew the maneuver entry on the upwind leg rather than the downwind, and my “confused student” said he thought he remembered reading that part differently. Unless you know otherwise, assume that your DPE will not ask trick questions. If a question seems leading, take a hint.

Materials I Took to the Oral

As much as possible, bring electronic searchable copies of documents with you to the checkride. You do not want to be thumbing through a paper book under pressure.

I brought my laptop. Remember your power cord. A larger screen and keyboard will be easier to read, get more information on a single screen, and allow you to type more quickly than a tablet or your phone.

Documents on my laptop were

ACS (Private, Commercial, and CFI)
- My CFI initial was under the CFI PTS, no longer relevant.
Advisory Circulars
- AC 61-65, Endorsements
- AC 68-1, BasicMed
- AC 91-73, Runway Incursions
FAA Handbooks
- Airplane Flying Handbook
- Pilots Handbook of Aeronautical Knowledge
- BasicMed FAQ
Knowledge Test Reports (AGI, FIA, FOI)
Runway Safety
- FAA Order 7050.1
- Airport Sign and Marking Quick Reference Guide
- Runway Incursions and Severity Categories
Lesson Plans
My 61.183 CFI Qualifications (Excel spreadsheet)
Airworthiness summary for the airplane I brought to the checkride
Copy of my IACRA application
Weight & Balance spreadsheet for that day

My kneeboard had paper notes with quick reminders for the laws and levels of learning, Maslow’s hierarchy, defense mechanisms, etc.

The summaries of my qualifications and the airplane’s airworthiness were to make the DPE’s job easy. Annoying or frustrating the DPE will hurt and never help your cause.

Flight Test

If you can get to the ramp, you’re probably in great shape. The FAA doesn’t report statistics, but the common belief is most CFI initial failures happen during the oral exam, not the flight portion.

Remember your training. Let your muscle memory carry you through. Fly like you trained. Start maneuvers on cardinal headings and altitudes that are even multiples of 500 or 1,000 feet. Remember to perform clearing turns. Teach the whole way through the flight. Teach your way out of imperfections. Never scare the examiner.

If you are mentally exhausted from the stress of the oral and the long day, you have the option to request a discontinuance at any point. A discontinuance is a pause, not a failure. You get credit for everything you’ve done up to that point but do have to complete the rest of the checkride within 60 days. You will be at the mercy of the DPE’s schedule, so be diligent and get it done if you have to exercise this option.

The specific tools I actually used and still recommend follow.

My aviation equipment and accessories went in my FlightGear duffel bag (paid link).

My ASA Trifold Kneeboard (paid link) had some quick paper notes clipped into the binder that I used during the oral and flight portions.

My laptop and power cord went into my professional leather messenger bag (paid link).

My Bose ANR headset (paid link) kept communication with the DPE and ATC solid and reliable.

Conclusion & Next Steps

I logged my first landings from the right seat on July 4, 2020. Ten months later on April 26, 2021, I passed the oral and on April 30 I passed the flight portion — all on the first attempt.

The system that got me there was simple: Anki for spaced repetition and active recall, a study buddy for teaching practice, deep familiarity with the ACS and FAA handbooks, and the constant mindset of “I am the instructor now.” None of it was flashy. It was just consistent, daily work that turned dense material into something I could digest and then use later under pressure.

If you’re preparing for your own CFI initial, start today with two things:

Download Anki and set it up with the aggressive settings I showed.
Grab my CFI study deck as a starting point but make it your own.

You don’t need endless hours of reading and highlighting. You need a system that gets the knowledge into long-term memory so you can focus on teaching when the DPE is sitting beside you.

Becoming a CFI is one of the best decisions I’ve made in aviation. It changed how I fly and how I think about safety. If you put in the work with the right tools, passing the CFI initial on your first attempt is absolutely within reach.

See you in the traffic pattern.