[zunzun]

I worked at a large natural gas company in the US where the MS sales reps had accurately analysed the IT director to have Imposter Syndrome causing professional insecurity. By taking the IT director out to lunches - away from everyone else - and letting this person know what a smart choice they were making, how wonderful the .NET platform was, etc. they were able to persuade the company via this person to redesign all internal software from scratch using MS's UML design and coding tools. You might be in a similar situation, where the kickbacks are social and emotional rather than financial.

[gesman]

Separating decision maker away from distracting and legacy-invested lieutenants is wise approach and a win by itself to have a focused conversation.