This happens all the time. You have a design and it could go in several directions. All directions have pros and cons. What do you do?
My technique is to mockup (quickly) as many of the alternatives as possible. Give them all a chance to survive the bright light of day. You will find (quickly) that some alternatives just wilt and die as soon as you mock them up. They didn’t make enough sense. Keep going.
Soon, the choices will naturally winnow down to 2-5 possible directions. Now, you need to categorize them. Specifically, group them based on which use cases they emphasize. Designs naturally emphasize one use case over another. Do they emphasize ease of use or flexibility? Power or obviousness? Simplicity or explicitness? You need to break down the choices into 1-3 groups. At this point, the leadership of the project has to make a decision about the values. Look at the group names and NOT the designs. Which group names resonate most strongly with the values you are trying to stick to?
By grouping and suppressing the design, it makes it easier to decide what the direction should be. The direction should stay true to your ideals and goals at a higher level.
Once you decide that, usually the decision becomes much easier (or finished completely). If left with two alternatives within one category, then you probably are fine either way and you can make a gut call. Gut call is a technical term meaning, “Don’t over-think it, go with your emotional mind. Use the force.”
It’s hard to design because the choices are limitless. Hopefully, this technique will help you hone in on some good decisions.