[brlewis]

Did you follow the advice of this article and describe why the old way won't continue to work? Did you point to winners who have already gone in the direction you want to move? Did you dissect the pros and cons, acknowledging what's true on their side and being specific about what's false? (Disclaimer: my current project is about doing that last one)

[LaundroMat]

Only this week I had a discussion about a client we worked with 2 years ago (large retailer). Their IT infrastructure was and is a mess and seriously hampers the development of their business. We spent a lot of time back them telling them about it and showing them the way forward. (Mind that our proposals were not all beneficial to us even).

Their request today? "You were absolutely right two years ago. Nothing has changed in the mean time and things have become even more complex now. But could you develop X for us, knowing that you can't touch or change any of the architecture?"

We did dissect the pros and cons, pointed to winners, showed the opportunities ahead etc etc. We were discussing everything at C-level too. But sometimes it just doesnt work.