At a high level, a few questions I would like answered drives my conversations. I don’t necessarily ask these questions, but I keep writing and asking other questions around them until I could answer them myself.
What problem does your product solve, and how do you make money from that? I’m looking for clarity and simplicity where value, product and pricing all make sense.
How much longer can you keep doing what you’re doing without raising more funding? If they don’t have a year’s runway at current revenue, I’m pretty wary. I’ve heard some say 1yr is not enough, but in my experience if it’s more than that they’re not ambitiously hiring or developing.
How do you grow your revenue, how fast is it growing, and what are your revenue goals this year? I’m looking for 2x year of year as a minimum, and solid sales or marketing plans, people, resources, etc. put towards growth goals. I tend to prefer B2B products so these are relevant measures of structures driving growth, in other contexts this may be a different kind of question, but you do want growth.
What is the development process like today? I’m looking for understanding of design-focused product work with a priority for user research, flexibility towards their current process, and understanding on what it would feel like to get into their flow. In this I’m also often looking for a bit of a mess, and some fear on the part of the managers. I prefer helping rebuild these processes some, and most startups I’ve seen hiring a first product role should be wanting help in building this process. If they aren’t, it could be a fairly low impact role.
Is this executive team well respected in this industry? This can be hard to “ask” for, but I think it comes more from research and feel/vibe from that stakeholder. Is their demeanor as impressive as their background? Do they have proven accomplishments in the space or a related one? Is this someone you could see taking as a role model for multiple years of your life? What do you think not getting along with this person would be like?
What does the roadmap look like now, how was it arrived at, and how married to it is the organization? I’m looking for a bit of a mess and open desire for change in this one too. I’m also judging different stakeholders’ level of care.
Good luck! I hope this helps some.