I want to figure out if their team is strong in areas I won't be involved in. If they have crappy code at least I can fix it. But if their sales strategy sucks, I'm be stuck with the consequences without having much opportunity to improve matters.
There's not one specific question I'd ask to figure that out. Depending on how the conversation goes it might be asking about the background of the founders, or their plans for the coming months, or how they assess their threats.
I cannot stress this enough. Every single starup I worked with that has failed, has failed due to poor performance of the sales team, and/or leadership choosing the wrong path at critical points. Unless the product is highly technical, engineering mostly just needs to execute at a high level to do their part. They usually can't save or sink a company all on their own.
If your role is in engineering you may be at the mercy of failures which you have no control over. I've found those to be the most frustrating and stressful periods in my career.
Watching another department make bad choices or have poor skills/work ethic without being allowed to go in and correct it myself was very painful. Especially being in a small organization.
To be fair, this is true of all departments and all people. Sales can't be successful if engineering and product don't build a good product with product market fit.
The idea of going somewhere where the biggest blockers to success are under your control makes a lot of sense if you have confidence in your ability to execute.
The product matters little in some cases. Marketing can succeed with vaporware. Sales can succeed without an actual working product as long as they focus on the decision maker and have vender lockin. HR, c.level execs don't need a working product just a concept.
Product development rarely provides features that can be self fueling for marketing/sales. Brands rarely need killer product features they need a targeted story.
It is much easier to have a successful company without a product than it is to have a successful company that trys to use product features as a marketing department.
That's a great point. I should probably clarify a bit.
I was really talking about how frustrating the proximity of that failure I could not control was. In a larger or more stable organization, when a different department is failing of struggling, you can at least have confidence in the future. That eventually those people will either improve or move on to something that might be more appropriate for them. Or possibly be replaced with people that are better suited for the task at hand, and things will get back on track.
When I was involved in high stress early companies, where founders and early sales employees are often unlikely to be removed, it can be a especially difficult to deal with emotionally. At some point you are forced to chose between sinking with a ship you are not permitted to save, or bail on something you've poured so much work into.
There's not one specific question I'd ask to figure that out. Depending on how the conversation goes it might be asking about the background of the founders, or their plans for the coming months, or how they assess their threats.