We first got to know Richard through his work managing a Citation M2 which we acquired for a Pilatus client of ours. More recently, Richard helped acquire a Pilatus from us for a client living in Tennessee, but that’s just one of his many hats. At just 16 years old, Richard set his sights on becoming a missionary pilot, operating in a foreign country. This led him to the Amazon, where he resided for several years. After returning to the U.S., he expanded his aviation experience across multiple sectors—from corporate aviation and EMS helicopter operations to flight instruction. Today, Richard is the owner of CMA Aviation (short for Cimeria, the Portuguese word for “summit”)—a management, operations, and acquisition company.
In addition to running CMA, Richard is a Designated Pilot Examiner (DPE), a National Insurance Instructor for the 525 Series (CJ), a three-time Master Flight Instructor with the National Association of Flight Instructors, and most recently, he was recognized as the 2025 Flight Instructor of the Year by the National FSDO!
Needless to say, Richard was the perfect person for us to speak to regarding the topic of aircraft regulations and compliance. Let’s dive in!
What are some of the most common regulations pilots unintentionally violate during operations?
“Adequate weather planning and adequate weight and balance are just things that I unfortunately see on the intro level, and also really in the professional world.”
In the professional setting, airspeed and airspace violations have also become increasingly common. According to Richard, it’s 90% on pilots and 10% on controllers.
“I’ve been put in some really bad situations with controllers–not speaking badly about them at all, we are all humans. But one of my mottos is that when the pilot messes up, the pilot dies, and when the Controller messes up, the pilot dies.”
His advice: stay situationally aware and never let complacency replace good airmanship.
If a pilot realizes they may have violated a regulation, what is the best course of action to address it?
Richard suggests a three-step process.
- File a NASA report immediately.
“As soon as I land, I’m going to file a NASA report and explain what happened and why it happened.”
- Stay current with the FAA Safety Team.
“I am going to make sure that I’m current and I’m active in the FAA Safety Team–just as kind of a good cover for yourself…”
- Get to know the FAA.
“Find somebody that you like in the FAA and have them on the phone… They really moved away from the enforcement action to remedial training action.”
What is a common thing that people forget to do when flying?
“In my opinion, it starts on the ground… Let’s take the proper 10 or 15 minutes before hopping in the airplane and going.”
There is a lot of great technology like Foreflight and Garmin Pilot that gives you everything you need today. He also stressed the importance of checklists.
“The reality is, somebody’s got 2,000 hours in name it aircraft, they probably don’t need a checklist… until they do.” Use it to verify. And he says to practice!
Richard also stresses the importance of briefing approach plates and checking NOTAMs carefully.
“I’ve had to go miss three times in the past 12 months and every single one of them were due to a decision height that was higher on the NOTAM, which I checked and knew about. That’s why I had to go miss. It was 400 feet higher than normal, but the guy in front of me somehow made it… That’s the kind of stuff that trickles down to the FAA and becomes a problem.”
As an operator of now a PC-12, what are the key differences in compliance regulations for Part 91 operators versus Part 135 operators of Pilatus aircraft?
For the pilots, there are training requirements–initial, upgrade, line check, and you have to have your 6-month IFR checks.
For the airplane itself, you must ensure it meets all your maintenance requirements. There is also a lot of additional paperwork that needs to be kept, such as trip sheets and the weight-and-balance for 30 days. When Richard was a chief pilot for a Part 135 operation, the FAA would show up to his office for something called “No Docs.”
“You have to show them the last 30 days’ worth of flights. The helicopter base I was at, every now and then would get dinged because that’s on the PIC and he didn’t put the paper in like he was supposed to… For Part 91 operations, we don’t have to keep a record of the weight and balance.”
Let’s go back to private pilot check rides and someone is getting their first certificate. As a DPE, what is the most common mistake that applicants make when they fail a check ride?
“So, it happens often when I give them a diversion. We’re flying a Cessna 172, we’re out doing turns around a point, and I go hey, the engine is running rough. We need to get to the nearest airport… I am testing their ability to handle a situation. To find the nearest airport, and then find all the items about the airport… That one little question asks a lot of questions about their nautical decision-making.”
The mistake, he says, comes when pilots are rushing.
“Most of the time, they’ll scroll to ‘nearest’ on the GPS, which is fine—it’s a tool we use—but that nearest airport is often restricted or crossed out. They’ll start flying there and realize too late that they can’t actually land. By then, they’re 40 miles away from where they should’ve been.”
The second big mistake comes from short field landings.
“Flight schools like to save money on brakes and tires. People don’t know how to do short field landings anymore because they land, pull the stick back, and they go simulate max breaking, simulate max breaking, then they roll it out like 3,000 feet when we could’ve gotten the airplane stopped at 900.”
Bonus Story: A Good Student Kills You
We asked Richard if he had any crazy stories over the years that he would be willing to share. He shared a personal experience that taught him a lesson about complacency.
“I had an old instructor who, after I shared this experience with, gave me a phrase that I teach all my people now.”
Richard was teaching someone how to fly a helicopter.
“She was phenomenal–I mean, she flew this helicopter perfectly. She was going for her private and we were doing hoovering autos. For hoovering autos, you’re about 3 feet off the ground. I count it down 3…2…1… and I roll the throttle off. The aircraft starts to rotate, and it’s going to be on the ground in less than 2 seconds. If it goes bad, there’s really no time to fix it–you just have to stay on top of it all the way down.”
They had done six perfect autos in a row. Everything was smooth, controlled, precise.
“I always held my hand under the cyclic because you have a half second to fix it and keep the helicopter from rolling over. On the seventh one, I put my hand down and in my lap. I only had my left hand on the collective hoovering.”
3…2…1….
“For whatever reason, she pulled the cyclic backwards. That was all it took for us to get our tail rotor that close. We hit the back of the skids, dug in. I was able to push forward to keep from hitting the tail rotor, but we could’ve totaled a helicopter just because I moved my hand six inches.”
Later, when Richard told his old instructor about what happened, he received a piece of advice that would shape how he teaches to this day.
“A bad student will scare you, and a good student will kill you.”
Richard was reminded to always be ready for something to go wrong.
“I learned a lot and fortunately, it didn’t cost me anything but a little bit of humility.”
Richard Whittemore