Ask HN: What should I ask a successful startup CTO?

[samovar_booth]

I'm a software engineer who's casual acquaintances with the CTO of a growth-stage startup, a successful person with multiple exits. We often have coffee, informal chats, etc. I have aspirations to be a founder myself so I feel like I could learn a lot from this person, but I'm not sure I know the right questions to ask. I'm senior-level with solid experience, yet it's hard for me to figure out how to best learn from someone at a much higher level of experience/accomplishment. Advice appreciated!

[solipsism]

I think successful mentorship works in the other direction. The mentor analyzes the mentee, matches the mentee's experiences against his/her own, and guides the mentee in the right direction.

I think the best question you can ask is "what do you think I should do to meet my goal X" for whatever value of X.

I guess it can't hurt to ask questions like "what books influenced you," as someone else answered. Except that it wastes your valuable time with this person. If this person thinks a book was instrumental enough to make a difference for you, they'll certainly mention it.

[auslegung]

These might sound simple but it’s what I would ask (and have asked) people that I aspire to be like.

1) What people, books, events, experiences, etc have most influenced you? 2) What’s your daily schedule like, from waking to sleeping? 3) What are some things that may help me get from where I am to where you are? 4) What are the foundational skills necessary to achieve at your level, and how to you practice them? 5) Do you ever regret your career choice or path? Or what are some of the worst parts of your career?

Hope these help at least a little!

[cimmanom]

1. Ask them for advice about specific problems you’re facing

2. Ask what the most difficult situation was that they had to deal with lately in $area; how they approached it; how that worked out; what advice they’d give someone in a similar situation

[xjia]

Why not invite him to join you?