Initiative is a tough thing to breed ...
Getting people to take more of the lead
You can give them more rope
But still they say “nope”
So it takes more than just planting the seed
Some people take a responsibility and run with it. Others want to do a good job, but feel the need to get approval for each step along the way.
If you want people around you to take more initiative, you may need to be more explicit in how you'd like to see them act:
"Chris, I want you to know I have a lot of confidence in your abilities and trust your judgment. When you're assigned a project, I'd like you to really take the lead on it. You don't need to get my approval for each step along the way. Instead you can just report routinely on how things are going and turn to me for my thoughts on only the most significant decisions."
And perhaps even more importantly, check your own behavior for how you respond to your colleagues' initiative. It's pretty easy to send someone back into follower mode if we question each of their decisions or unnecessarily countermand some of the choices they make.