Harder to find this than I expected. Google gives me a lot of bullshit interview questions like what’s the culture. Or it gives me financial metrics I probably can’t ask for.
What can I ask a startup in order to assess its health, future, founder competency, and so on?
I found some good questions like asking about Runway, and I have a lot of specific questions that are relevant to the role. But what’s the other “must know” info you need before working at a very early stage startup?
I normally ask:
I used to ask how much runway they had, but everywhere I asked would either lie or not answer properly unless they were Series B or beyond. So, I look for external news about their funding/etc. and compare to staff numbers. If they’re UK based and are a Ltd you can look up their accounts on gov.uk too, or any country’s govt sites.
Few thoughts… Understand the founder/founders’ or CEO’s knowledge or experience of product management in general e.g., have they worked with someone in this function before?
Ask about traction and whether they have trials or paying customers etc. - the numbers could look great but it’s useful to understand where the revenue is coming from at a certain stage.
Suss out their level of bullshit e.g., are they focused on chasing awards more than building a great product? You could also ask about team processes in the org to date and how they’re used day to day - some startups never get past messy undocumented chaos and that’s going to make your job even tougher.
Final thought is, be honest with yourself on your risk tolerance for different stages of a startup, and some of my above thoughts will depend on where they’re at. Good luck (and I’m looking forward to others’ comments on this one too).
I see you mentioned “very early stage” - if there is more than one founder ask how they resolve conflict. I’ve found out too late in previous roles that the founders weren’t on the same page regularly and it can get ugly.
The first one is super important because that’s exactly how you can get yourself a shitty culture.
I’ve gone through this a couple times. Some things to dig into:
Where are they in terms of raising? What’s the hiring plan and how does that project runway?
How have they developed product so far? How will those people’s roles change to accommodate adding you?
Who are their investors? More credible ones make them more credible.
Ask about the founders history. You should also think about the product. Are they building / selling a good product? Does it fit a need? Is it something you know about and are passionate about?
I wouldn’t change industries to take a product job at a startup in an area I didn’t know.
When’s the last time you’ve spoken to customers / users?
What’s the last product / feature you killed? Why?
Understand the business / product value and how has it adapted. Why?
Depending on what stage you’re talking about, you want to understand the ability for the company to actually do discovery, learn, and adapt and eventually pivot if needed.
If it’s growth stage, then you should be able to gauge the potential a lot easier. I think it’s more do you want to work in that product environment and help scale up. The org design of the product org and the company’s practices and philosophy matter a lot as far as enjoying the role (and learning).
There are already some great answers in the comments. Only thing I can add is that I’d consider asking questions startups like a VC would, pursuing that structure would allow you to understand the startup itself better. If you would invest in that yourself, then maybe you can consider working there.
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.
One good way to also assess a startup would be to look at their alumni, as in where the folks do who worked here earlier ended up going next. This could potentially tell you a lot more about where you might also set yourself up for success someday.
I’d ask about scaling the product teams, to suss out if they understand when it’s time to get an implementation team, support team etc.
Extremely relevant thread recently posted by Shreyas Doshi
PS: Highly recommend him a follow.
@RobMartin, Thanks for sharing this. This guy (Shreyas Doshi) is a freaking gold mine, holy shit. I wish he wrote a blog or something easier to follow.
He’s smart actually. He knows the value of twitter distribution and how it works. Blogs people follow but they don’t have that level of distribution.
Also, blogs take much more commitment/time than a thread.
He’s evaluating the option to enable super follow-on twitter
@RobMartin, Yeah, I know what you mean, it’s great when you stumble upon it to read concise points quickly. But now I want to read much more of his stuff and it’s really hard to go find it.
You can start here
Warning: It’s a deep rabbit hole 
Yep I’ve been going through that, it’s just super hard to navigate. I actually just downloaded this cool app called threader which helps save his “articles “
Adding to the others:
Also, checkout this list of breakout startup companies, it evaluates them on multiple factors (high growth, impact potential, good team, recent funding, etc.) https://breakoutlist.com/
Thank you so much everyone for the replies, I found a lot of it to be helpful. I’ve also realized that despite having this knowledge, the amount of uncertainty is still overwhelming. I think that’s just the nature of the beast.