Remember that conversations can be like rivers: they meander.
Be prepared for the conversation to happen organically and not necessarily in a preplanned, expertly facilitated way.
You might see an opening here, a window there. It might go slowly here, and swiftly there.
Don’t gird yourself for conflict with anyone, not even Soandso – they might surprise you.
Your conversation will, eventually, lead to a certain point: the point where your organization articulates the need to develop its own digital capacity.