I've been interviewing for jobs in software development over the past few months. My friends mentioned that they liked my rubric of questions to ask founders, engineering managers, and recruiters about their companies, so I thought I'd share it a bit more widely.

What are you building?

I like knowing what I'd be working on, and in my experience, most engineers relish the opportunity to talk about what they're building. For that reason, I find that these questions make for good ice-breakers. These questions are probably no brainers, but for the sake of completeness...

• Tell me about what you're working on right now.
• What's the biggest challenge (technical or otherwise) that your team is looking to tackle in the next 6 - 12 weeks?
• Who are your users?

How Are You Building It?

This is a good follow up to the previous section.

• How many engineers are on your team?
• Tell me about the tools you're using.

Where is the Money Coming From?

A great saying I heard once sums up the crux of what this set of questions drives at: if the service is free, you are the product. More concretely, consider Google Search: your attention and pageviews are the product that Google sells to advertisers for money. Your eyeballs are the monetization strategy.

I'm picky about what I want my time to be put towards. Even if my efforts won't be directly related to a money-making project, I like knowing that my time is spent on something I think is ultimately worthwhile (maybe for you Search is worth charging an eyeball tax!)

Ethics or personal morals around money sources aside, I also like knowing that the company has the potential to grow, and that there's a good chance I'd have job 6 months from now. In my experience, companies that do the best on these metrics tend to be B2B.

• How do you make money?
• How much VC funding have you taken? (Startups with a lot of VC money but no concrete money-making strategy are sometimes trouble. Consider running. Questionable counterpoint: Twitter)
• Are you currently profitable?

Who Am I Enriching?

For a publicly traded company, this is fairly straightforward -- the answer is (almost) always the shareholders. But for private companies, which most startups are, the only way to find this out is by asking the founders. For me, it's really important that employees are rewarded for their work. I don't have any great questions that I ask about this; if you have any that you like to ask I'd love to hear them.

The Role of Women In the Org

I love asking about this. The answer is important, but not in the way that you might think. Yes, I ask about women's role in an organization because I'm interested in what a company's representatives will say about it, but, more importantly, I'm using this conversation as an opportunity to gauge how comfortable it is. Gender representation is usually something companies are slightly embarrassed about. For that reason, it's a great topic to judge how well someone handles tough conversations, which is really good information to have when trying to decide where to work.

I'd love to hear how much mileage non-women engineers get out of these questions, too.

• How many women do you have in management roles, or are considered on the management track?
• ...on your board, or as advisors? (This is a good question for founders or CEOs, but asking a recruiter or engineering manager will probably get you a rough answer)
• ...working as engineers on the team that I'm interviewing for?

Interviews are Two-Ways

I really enjoy the opportunity to get to know more about how a company functions, where it sees itself growing, and how teams view their role in that growth. Interviews are a great chance to get an inside scoop on what's up with a company that you find interesting, or just better understand how they see themselves growing (or not...).

You may notice that I don't ask very many questions about their build process or particular languages that they use. I don't ask about their build pipeline, or how long it takes to compile their app (though after recent conversations around this, I'm strongly considering adding this to my list). In my experience, people who think deeply about their organization and their culture also tend to think deeply about what technologies they're using. If you really care about what ecosystem you work in, you should ask about it though.

Did I miss something? Do you have questions that you like to ask? I'd love to hear it (You can reach me on twitter).