This is a discussion, not an argument so nobody wins, nobody loses and nobody needs to give up or continue for that matter.
What I'd really do is size up the runner vs. the catcher and pitcher and if I were certain he was going to get the steal I'd let him go. If there was any doubt then I wouldn't give the steal sign. Hard to say if a runner is 95% or 90% against a given battery and I really have no idea what the probability of hitting into a double play or having the force at second be a much easier play than the force at first is. It is a judgement call as a coach.
The situation I hate is a slow runner on first and a slow runner at the plate, where you're darned if you do and darned if you don't.