one thing that we do is when you find someone that you think has the capabulity of being a descent operator, we slowly work them into situations where they are running the equipment more and more often, we also use this method to work people into the office and into management possitions.

I haven't seen a guy in the trades that doesn't love hard hat stickers. You could try to incorporate them into your program. There are some training videos out there, but hands on is always best.
We did some training on weekends and after work, but it kinda went south as we grew and didn't have the time. I really wish we focused on it more now though.
I think at a minimum it needs to be enjoyable. Maybe training through the year and then contest based at a company picnic, i.e.: who can burn a steel beam the fastest, cut concrete the straightest, who can drive a truck the longest without the radio dying .
It all seems like a lot of work, but definitley worth the investment.
Now you got me thinking!!

Thanks for the suggestions guys. I still welcome anymore on this topic. Another thing that has made me think about this is the fact today companies and industries look to create "communities". Whether it's online, like this forum, or monthly gatherings etc. A community that people can feel welcome, appreciated and feel that they get value from. This could help develop a solid team to help alleviate the "personnel" issue. I'm thinking that even if we offer the training to prospective employees then we can have a pool of guys available on an as need basis and start to create value within our local contractors community. I'm not sure exactly how to put together, but I obviously want to do this to give us an advantage and not to shoot ourselves in the foot.

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I think what does work best is a on the job training program also. Maybe it's done on the weekends or right after work.

We used to have a dealer come in also and teach everyone how to operate, let's say a Bobcat. The dealer would go through everything, how to check the fluid levels, greasing the grease points, etc. The guys enjoyed it and appreciated it.

On top of the hard hat stickers, which is a great idea, You need to come up with a program that states to move up in the ranks of your company, including raises they need to complete these courses.

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I agree with all of the above, but i would get your top guys together and have them write some important ideas down and incorporate into some kind of written plan of what you expect from your employees. This way your can work into it over time.