Investors should view a founder's desire to learn skills like etiquette not as a weakness, but as a strong positive signal. It demonstrates humility, introspection, and a drive for self-improvement—key traits for a coachable and successful leader. The capacity for growth can be more valuable than pre-existing polish, identifying them as better long-term partners.

Instead of being discouraged by over 100 rejections, Canva's founder treated each one as a data point. She added new slides to her pitch deck to pre-emptively address every objection—such as market size or competition—making the pitch stronger and more compelling with each "no."

Founders can use AI pitch deck analyzers as a "sparring partner" to receive objective feedback and iteratively improve their narrative. This allows them to identify weaknesses and strengthen their pitch without burning valuable relationships with real VCs on a premature version.

Founders should press VCs on how they specifically envision working together. A strong investor can articulate a nuanced plan tailored to the team's unique needs and the founder's working style, moving beyond a generic menu of services to show true alignment and understanding of the business's goals.

Instead of walking into a pitch unprepared, Reid Hoffman advises founders to use large language models to pre-emptively critique their business idea. Prompting an AI to act as a skeptical VC helps founders anticipate tough questions and strengthen their narrative before meeting real investors.

When a client offers harsh, fundamental criticism during a pitch, the best response is not to defend the work but to acknowledge the miss. One CEO won a pitch by immediately conceding the point and offering to re-pitch, demonstrating humility and confidence.

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.

In initial meetings with enterprise prospects, Nexla's founder didn't pitch a solution. He focused entirely on validating the problem. By asking, "Do you see this problem as well?" he framed the conversation as a collaborative exploration, which disarmed prospects and led to more honest, insightful discussions.

To get candid early-stage feedback, founder Janice Omadeke disarmed potential advisors by explicitly asking them to tell her if her "baby is ugly" and why. This framing signaled a thick skin and a genuine desire for constructive criticism, leading to more valuable insights instead of polite encouragement.