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Great article! I have a question, however.

In your theoretical example of the exec asking the designer for the subscription opt-in, what is the best way for the designer to talk to them if the exec had spent a week in round table discussions that resulted in the request? Then, even the recommended solution of suggesting a different way of speaking to the exec is a problem for the exec, as the exec had already done significant work to identify this solution.

For example, the exec needs a way to increase ARR this week, or very soon, and this is the solution identified from their roundtable/workshop as the quickest solution. When the designer says, "you're looking to increase subscriptions?" The exec stops and thinks negatively, "Does this designer think I'm short-sighted? I spent a week finding this solution... this is a waste of time!"

How should the designer handle this situation? What if the designer doesn't even know that the exec spent a week identifying this solution?

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It'll probably depend...

You can always try to ask more clarifying questions up front or (if the org has open calendars) check and see where the idea may have come from. I'd approach it differently knowing there was a roundtable vs. it being out of nowhere.

If this is a pretty consistent pattern, it sounds like "you aren't in the room" - and if that's where the real work gets done, that's a different issue. There's a likelihood that won't change in this role.

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