You can split a column with 'Analyst,Trainer' value, using XQuery methods(nodes, value) and then compare with the 'Workflow,Analyst,Tester,Trainer' value, using the LIKE operator.
SELECT t.col1, t.col2, MIN(CASE WHEN t.col2 LIKE '%' + o.col1 + '%'
THEN 1 ELSE 0 END) AS IsMatch
FROM YourTable t
CROSS APPLY
(
SELECT Split.a.value('.', 'nvarchar(100)')
FROM (
SELECT CAST('<M>'+REPLACE(t.col1,',','</M><M>')+'</M>' AS xml) AS col1
) AS a
CROSS APPLY col1.nodes('/M') AS Split(a)
) o(col1)
GROUP BY t.col1, t.col2
Demo on SQLFiddle
Also you can use option with dynamic management function sys.dm_fts_parser
Before script execution you need check full-text component is installed:
SELECT FULLTEXTSERVICEPROPERTY ('IsFulltextInstalled')
0 = Full-text is not installed. 1 = Full-text is installed. NULL = Invalid input, or error.
If 0 = Full-text is not installed then this post is necessary to you How to install fulltext on sql server 2008?
SELECT t.col1, t.col2, MIN(CASE WHEN t.col2 LIKE '%' + o.col1 + '%'
THEN 1 ELSE 0 END) AS IsMatch
FROM YourTable t
CROSS APPLY (
SELECT display_term
FROM sys.dm_fts_parser('"'+ 'nn,' + t.col1 + '"', 1033, NULL, 0)
WHERE display_term NOT LIKE 'nn%'
) o(col1)
GROUP BY t.col1, t.col2
For avoiding sorting operation, use index:
CREATE INDEX x ON YourTable(col1, col2)
FYI, The best performance will be with the sys.dm_fts_parser