A founder asking an investor about their biggest blind spot during evaluation is a disarming and intelligent question. As shared by Maytha Agarwal of Defy, it forces the VC to self-audit their decision-making process in real-time, revealing their introspection and leading to a more honest, transparent conversation.
LPs have a binary focus: cash-on-cash returns. As long as a VC fund is consistently distributing multiples back to them (high DPI), they are less likely to question the fund's strategy. This "what have you done for me lately" attitude is key to securing re-investment in future funds.
Proactively asking a potential investor how they navigate disagreements reveals their philosophy on board governance and CEO autonomy. Investor Alex Nihanky of Scale notes the CEO is the "runner" and the tie should go to them, but not all investors share this view. This question helps founders vet investor fit before a conflict arises.