In a way.

Finland demonstrated many flaws in the soviet military system, above all extremely poor coordination between various units. While operations for sieging a fortified region demanded an artillery barrage first, then the tanks to move in, followed by infantry, often tanks would move in while the artillery barrage was still ongoing, and would retreat before the infantry moved in. Mannerheim described soviet operations as akin to a poorly coordinated orchestra, where every musician played out of tune and rhythm.

This was, of course, the extensive military purge taking its toll. By mid-39, 40,000 officers had been arrested, often with their untrained underlings immediately promoted, only to be arrested themselves soon after, be it for incompetence or simply because they ended up on an arbitrary list. Untrained officers mean poorly led units, poor communication, and poor coordination, of the nature I previously described.

The army suffered tactically as well. The arrest and political excommunication of Mikhail Tukhachevsky branded deep battle theory, possibly the most advanced form of military thought at the time, a taboo. Accepted military doctrine degenerated, and even from that unadvanced starting point, tactical innovation and deviation from the norm carried risks of arrest.

Alongside this (with occasional exceptions), the leadership of the Red Army was based primarily on political reliability. The People's Commissar for Defense at the time, Kliment Voroshilov, was a close friend of Stalin. He was also a notoriously bad commander. As an individual he was vain and careless, and more or less fucked around while the operations in Finland failed. It is also worth mentioning that later on, the tide of war turning was also brought about by a personal friend of Stalin being appointed defense commissar, to replace the incompetent Voroshilov.

All in all, the first months of the winter war were a tragic failure. So bad, in fact that Hitler put forward the offer of military assistance against Finland, in accordance with the secret clauses of the German-Soviet Nonaggression Pact (which had placed Finland firmly in the soviet sphere of influence). This offer was rejected, rather obviously due to a fear of exposing the degree of soviet military incompetence that dominated at the time.

Unfortunately I can't comment extensively on the thought processes that went into planning operation Barbarossa. It is, however, accepted that Finland being such a horrendous failure demonstrated the awful state of the soviet military to all the world which in turn played a part in cementing the nazis' belief that the USSR was in a disadvantaged-enough state to not be able to withstand German invasion.