... from most difficult to the least. If a conversation feels like it will be difficult, it means it's the most important one to stop avoiding.
Seek empathy and use as much tact as you can muster. You'll find that even if you disagree, you'll have a useful, productive conversation.
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The best way to determine that their product is useful is to put it in front of the people most likely to use it. This can mean market testing, or it can mean asking people on your own team--ideally, those in roles it's designed for--to give it a go.
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