Recent reviews
Write a reviewDescribes the CFI ride as a "how test" — can you teach a concept, not just recite it. Wants endorsements derived from 14 CFR Part 61, not read from the AC. Long, thorough oral (5+ hours). Flight to the Ramona practice area with emergency work over Lake Wolford.
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Same teaching-first philosophy for the CFII. Expect to actually instruct him through instrument concepts and approaches. Very knowledgeable, patient, and consistent.
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Starts from the aircraft logs — prove the airplane is IFR-legal and how you know. Detailed flight-planning discussion (file above the MEA, DP routing from MZB), lost-com specifics, chart symbology. Fair but exacting.
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Checkrides conducted
31st-time pass rates
First-attempt only — rechecks excluded.
AI study guide
David William Leonard (DPE #334493, San Diego, CA area) conducts the CFI-ASEL initial as what he himself calls a "how test." Based on the single detailed gouge available, he is far less interested in applicants reciting memorized definitions than in watching them actually teach — deriving answers from the FARs live, building analogies, and using a chalk-talk/ground-lesson style. The oral moves through foundational instructional theory (levels of learning) into a long, FAR-based discussion of student pilot privileges/limitations (medical validity, endorsements), then aircraft airworthiness paperwork (AROW, ADs), and a slow-flight ground lesson before flying. The flight (SEE–Ramona area) is a compact but thorough sampling of short-field, slow flight/stalls, an emergency descent/landing over Lake Wolford, and soft-field touch-and-goes at Ramona, where he has been known to pull a light/switch to force a go-around decision — testing instructional judgment under a simulated student scenario as much as stick-and-rudder skill. Overall tone from the one gouge available: professional, methodical, and focused on your ability to instruct, not just perform.
- Typical start: Not specified in available material
- Locations: KSEE (Gillespie Field, El Cajon/San Diego), Ramona Airport (KRNM) area, Lake Wolford area for emergency descent/landing practice
- Duration: Not explicitly stated, but oral covers multiple deep topics (levels of learning, student pilot regs, airworthiness, slow-flight lesson) before a full flight profile from SEE to Ramona and back — plan for a long day combining a substantial oral and a multi-task flight.
- Fees: Not specified in available material
Oral appears to open with instructional-theory topics (levels of learning with practical examples), then transitions into a long, discussion-style session on student pilot regulations built around deriving answers from Part 61 rather than quoting them, followed by aircraft documentation/airworthiness (AROW, ADs), and finally a ground lesson on slow flight delivered by the applicant as if teaching a student — setting up the same maneuver to be flown later.
Clear understanding of each level of learning with your own practical, relatable examples rather than textbook recitation.
- Explain the levels of learning and give real examples of each from your own instructing/training experience
Ability to derive answers directly from Part 61 (and related medical/endorsement rules) in real time rather than reciting memorized answers — showing you know how to find and apply the regs.
- Scenarios about student pilot medical validity/currency
- Scenarios about which endorsements are required/valid for various student pilot operations
Solid working knowledge of required documents (AROW) and how ADs/maintenance inspections affect airworthiness, explained in instructional terms.
- Walk through what documents/inspections are required for the aircraft to be airworthy
- Discuss how to determine AD compliance
A clear, well-organized teaching presentation on slow flight (aerodynamics, procedure, common errors) delivered in instructor mode.
- Deliver a short ground lesson on slow flight as if teaching a student pilot
- Departure from SEE toward the Ramona area
- Short-field takeoff/landing operations
- Slow flight and stall series (tied back to the ground lesson topic)
- Simulated emergency descent/landing over the Lake Wolford area
- Transition to Ramona airport for soft-field touch-and-goes
- Possible simulated system/light failure during pattern work at Ramona to prompt a go-around decision
- Treating the oral as a recitation exercise instead of demonstrating actual teaching ability
- Being unable to derive/explain student pilot medical and endorsement rules directly from the FARs when asked to reason through them live
- Ground lesson on slow flight not matching how the maneuver is actually flown/corrected in the air
- Slow reaction or unclear instructional narration when the examiner introduces an unexpected prompt (e.g., a simulated light failure) during pattern work at Ramona
- Weak or memorized-only knowledge of AROW/airworthiness and AD requirements without being able to teach it
- Prepare to teach every topic and maneuver as if instructing a real student — this examiner explicitly frames the ride as a "how test," not a recitation test
- Practice deriving answers live from the FAR/AIM (especially student pilot medical/endorsement questions) rather than memorizing canned answers
- Rehearse a tight, teachable slow-flight ground lesson and make sure your in-flight demonstration matches it exactly
- Be mentally ready for an unbriefed abnormality (e.g., a light being killed) during touch-and-goes at Ramona, and narrate your instructional decision-making through it
- Know AROW and AD/maintenance requirements well enough to teach them, not just list them
- Expect a genuine cross-country-style flight segment (SEE to Ramona area) with short-field, slow flight/stalls, an emergency landing scenario near Lake Wolford, and soft-field work — pace yourself for a full flight profile
Aggregated from 1 gouges (2026). Derived “what to expect,” not verbatim test items.
Checkride FAQ — David William Leonard
What is David William Leonard's first-time pass rate?
Based on 3 pilot reviews, David William Leonard's first-time checkride pass rate is 100%. First attempts only — rechecks are excluded.
What checkrides does David William Leonard conduct?
Pilots have reviewed David William Leonard for CFI, CFII, IR checkrides.
Where is David William Leonard based?
David William Leonard is based in San Diego, CA and assigned to the San Diego FSDO.
Where can I find the gouge for a checkride with David William Leonard?
The reviews on this page are applicant-written checkride debriefs (gouge) for David William Leonard, covering the oral and the flight. The study guide aggregates approved gouges into what to expect on your ride.
Flew with David William Leonard? Add your gouge to improve the study guide.