I originally wrote this as an answer to a question on Quora.

Full question:

“And, which kind of questions should I make to the initial founders?
I am not only talking about technical skills, all kind of knowledge matters.”

Knowledge

You should already know most of what you need to know to build version 1.0 of the product. You’ll learn the rest as you go.

You should also know how to deploy it, secure it, and manage it.

You should know how to document what you’re doing, at least enough that a smart person could pick up and maintain it later.

You should know enough to plan for disaster recovery. That’s not too hard at the early stage — just don’t keep everything on one computer in one building.

You should also know how to evaluate, onboard, and delegate tasks and projects to future hires.

You should be VERY good at estimating how long it will take to develop a new feature.

You should be comfortable with networking, presenting at user groups, and going out into the world to get to know other CTOs, developers, and people in your industry. If things work out you’ll be hiring these people someday.

You should be good at researching the competition and finding out what strategies they are using.

You should be good at the technical aspects of sales/marketing. A/B testing, mailing list management, promotional codes, etc. None of this is hard, but you should expect to do things that make it easier for the non-technical people to get the product tested and sold.

Questions to Ask

You should dig VERY deeply on what validation they’ve done and who they already have on the hook as potential users, investors, and beta testers.

You should find out whether they have the skills to do their job. Their main jobs are:

– Getting people to care about the product enough to buy. (selling).

– Getting people to the top of the sales funnel in the first place (marketing).

– Getting product-market fit (customer validation).

– Getting the resources the company needs (fundraising).

You need to find out whether they’ve done the work to validate their idea and whether they have people interested in at least trying (or better yet, buying) once it’s built.

You also need to find out how much of version 1.0 they’ve already designed. Find out what feature set they’ve designed, and be sure to ask how much they’ve validated each feature or aspect of the design.

You also need to find out what their expectations are and how rewards and equity are to be split up — what will your reward be for your efforts? What’s the existing equity split?