Hitler was right up to the point where he defeated France.
Hitler owned Stalin on the Non-Aggression Pact. Stalin thought there would be a long war in the West, but France fell in six weeks, meaning Hitler could turn his attention towards Russia that much sooner....it was all there for the taking. It would have been very easy to plunge Russia itself into another Civil War and divide and conquer, just as in the First World War. Certainly amongst the generals there was no love lost for Stalin after the Purges, and I think most would have willingly defected, like Vlasov did.
Both of these decisions were based on political whim rather than sound strategy. Both resulted in avoidable debacles. Worse decisions followed. A shrewder man than Hitler could have easily destroyed the Soviets. But by 1941 Hitler was unable to construct an effective plan against them. He defeated himself.