My boss of 16 years was about the same as yours - not very knowledgeable on photography. When I bought my A550 last year and was looking to sell my A300 body, he asked about buying it. I ended up selling him my A300 plus 18-55 kit lens, and then helped him look up and order a used 70-210 Minolta lens. He decided last minute to attend a photography meet-up at Disney World that I've been helping with for 4 years, learning the basics of photography and camera control. Since then, he's been addicted to it, is planning on coming up to Disney World again in December for the 5th photo meet, and has traveled to Poland, Czech Republic, Peru, and Dominican Republic with the camera.
It's nice having a shared interest with your boss, and it's great to still see my old camera body getting some good use! Usually you sell your old camera and never see it again - I still see mine all the time.
Sony DSLR-A580 / Sony 18-250mm / Minolta 50mm F1.7 / Sigma 30mm F1.4 / Tamron 10-24mm / Tamron 150-600mm / Tamron 90mm F2.8 macro / Minolta 300mm F4 APO
Sony A6000 / 18-55mm F3.5-5.6 / 55-210mm F4-6.3 / 10-18mm F4 / 35mm F1.8 / 16mm F2.8 / via manual adapter, lots of Pentax K mount, Konica K/AR mount, and Leica M mount manual lenses