The irony here is that you come across as a &quot;B Player&quot; CEO wanting to fire a &quot;B Player&quot; designer. Just sit him&#x2F;her down, tell him&#x2F;her it&#x27;s not working out and leave it at that. You seem to be romanticizing this by framing it as a conversation when your desired outcome is to let the person go. Just let them go. If you&#x27;re worried about the friendship, don&#x27;t hire your friends.