I've solved this in the past by asking the person if they want a comforting lie or an honest truth. I still provide feedback in both ways but the honest truth path is what is taken by most people who are able to take negative feedback correctly.
The more you trust somebody the more leeway you will give them in how they can express themselves to you, because you expect them to be honest and you assume that they mean well. You are more willing to interpret ambiguity favorably. From experience this seems to be a rather universal phenomenon. I often determine how I should express myself to people based on how much I think they trust me, and this approach seems to work well enough.
Which is long term self sabotage imo, but it is what it is.
I didn't call it a lie, but yes, that's what I was requesting.
In that circumstance, I believed things would ultimately work out, but my confidence was faltering. I needed to hear my own belief in an outside voice whether that person believed it or not.
I didn't actually need his belief. I already had my own. I just needed him to voice it.
I've met people who treat any investor as a part owner and will listen to them as best they can. Then there are those who treat any investor as someone who is graciously being tolerated.