Design work on the Skipper was begun in 1974 as the PD 285. The Skipper was Beechcraft's attempt to enter the two-place trainer market with an aircraft capable of competing with the popular Cessna 150/152 line of trainer aircraft. First flight of its prototype was in 1975. Though the aircraft first flew with a standard tail configuration, by the time it entered production, a T-tail configuration had been adopted, giving it an appearance very similar to its close competitor, the Piper PA-38 Tomahawk of 1978–82.
The Skipper wing utilizes a GA(W)-1 airfoil, especially engineered for general aviation applications, based on 1970s NASA research. The aircraft was certified for intentional spins. While it is an all-metal design, the Skipper incorporates a number of innovative construction techniques, including honeycomb bonding, tubular spars, and a hot-bonded wing structure.
The Skipper employed both a throttle quadrant and an instrument panel layout similar in design to the Sundowner, Sierra, and Duchess, with the intention of easing students' transitions to the more advanced trainers. Among its line of light aircraft, Beech only used the T-tail on the Skipper and on the four-place, twin-engine Duchess trainer.
Most of the production run was initially delivered to Beechcraft's flight school network, the Beech Aero Centers, where they were used as primary trainers. A handful of Skippers are still in use as trainers. Many others are in the hands of private owners who use them as touring aircraft.