Sometimes it can be a challenge to get the data maps to work properly, but using the “Automatic” map is almost foolproof. Follow these basic steps:
1. Create an advanced find with all of the entity’s “custom columns” (ignore CRM columns like created by, status, etc)
2. Export the results to Excel and remove the hidden GUID column (Column A)
3. Using the exported data as a guide for picklist values, insert the new data
4. Run the Import wizard. You should see “Automatic” in the Data Map