Key Takeaways
- Great mentors ask questions that expand your thinking rather than give answers that contract it.
- The best mentorship happens around real decisions with real stakes.
- A mentor who has been where you are going is more useful than one who is simply successful.
Saim Abbasi has been mentored by people who changed his trajectory and has mentored hundreds of founders over his career. The difference between mentors who transform and mentors who simply advise is consistent enough to describe clearly.
Questions Over Answers
The mentors who changed how Saim thinks did not primarily give him answers. They gave him better questions. The answer to a specific decision is useful once. A question that changes how you frame a category of decisions is useful for the rest of your career.
The specific questions that have stayed with Saim from influential mentors: What would have to be true for the opposite approach to be correct? Who has the most to lose from this decision and have you heard their perspective? What does the person who is skeptical of this know that you do not?
Real Stakes Create Real Learning
Mentorship conversations about hypothetical decisions are less valuable than conversations about decisions you are actually making right now. The stakes of a real decision make you more honest about your reasoning, more willing to hear uncomfortable feedback, and more likely to apply what you learn. Saim makes it a practice when mentoring to ask what specific decision the founder is currently wrestling with rather than what they want to learn about generally.
The Proximity Principle
Mentors who have been where you are going are more useful than mentors who have simply achieved success in a different context. A founder raising their first institutional round benefits more from advice from someone who raised their first round five years ago than from advice from someone who has been an executive in a large company their whole career. The specific experience of having been in the same situation, with the same uncertainty, makes the advice grounded in a way that general success cannot replicate.
"The mentor who tells you what to do is useful for one decision. The one who changes how you think is useful for the rest of your career."