England in 400BC was a broadly Celtic culture with Pictish remnants in the North; 1600 years later it had gained a lot of influence from Roman, German, French, and Norse invasions. Language, food, architecture, laws, and so on were much different. These are the obvious changes.
Your middle age Englander transported to Iron Age England would perhaps guess he was in the land of the vikings. The Celts of the time were warlike, tribal, proud and primitive people that practiced a pagan religion, all of which would have looked barbaric in comparison to the medieval commoner. While the Celts had urban settlements and hillfort citadels, neither would come close to comparison with the vibrant self-governed towns and stone castles of the Middle Ages.
Celts had a hierarchical society with nobles, commoners and slaves, but the middle ages saw more political stratification and legally stronger ties to the land. The Celt's lord would have been a king who directly controlled his land and was directly related to most of the people he ruled, whereas the Englishman's lord could have been a mere knight or baron who held the land in the name of a superior noble, ultimately traced to the king, and often was a foreigner given the manor or territory with no particular relationship to the people he ruled.
The Celts had trade networks and practiced agriculture, but the average Celt would be more oriented towards cattle raising, whereas the typical Englishman would be more focused on cultivating his farm. Yet farming is farming; animals need fed and slaughtered, crops planted and harvested, and tools mended. Assuming the Englishman was a typical farmer, he could easily have slipped into a similar role in 400BC.
In 1100-1200 A.D. farming technology had made some significant advances. The Englishman would have been able to improve the yield of his farm through the new 3-field rotation system, the heavy plow, and use of draught animals. He could have demonstrated cheese making to take advantage of the Celts' huge cattle herds. Crops and domesticated animals in Celtic times were less diverse and farm plots generally smaller in size. Farming practices in Celtic times also included religious practices which our Englishman would find odd. Yet he might have things to learn from the Celtic farmer. Pliny noted that the Celtic plough superior to the Roman type, and remarked at their use of chalk fertilizer.