7 Questions I’d Ask Every Founder

Marcus Smith
5 min readFeb 1, 2023

Why do I ask Questions? Whether I’m working with a founder to develop an estimate for their MVP or advising on a strategic next step, I always ask a few of the same questions to explore how to build product priorities. Hopefully these questions can help you refine where to start or even where to take your product next.

Photo by Ana Municio on Unsplash

Priority Questions for Building an MVP Feature Set

How do you develop a product feature set that is useful, usable, and will help you achieve growth and revenue goals? I suggest these guiding questions to help you get to the root of: the problems to be solved, how to solve them, and how to focus your efforts.

Questions are key to refined learnings. Do you need to do a root cause analysis? Use the 5 Whys. Are you trying to find truth in the midst of disagreement? Use the Socratic Method (a form of dialogue based learning built around questions). Do you want to find the most important focus of your startup? Ask these strategic prioritization questions.

What are you already doing without technology? Would some basic automation/application feature allow you to scale those efforts? Could technology bring higher value elsewhere before building fancy customer features?

In honor of the Lean Startup I always like to ask this question. Often founders think they need a whole digital product to validate their business. But finding a path to money forged through your blood, sweat, and tears, with a little boost from extra automation, will help you grow revenue & traction along with the necessary confidence to build the right thing. For example, my old consultancy built a custom data importer tool that allowed a platform admin to bulk add/update user information. This greatly increased their velocity, freeing them up to focus on other priorities.

Can you “white-glove” parts that require complexity?

In a similar vein founders often think a product should be totally self serve, but even at scale many smart companies don’t follow this trap. If you have a handful of users that touch a certain feature, it may be better to manually onboard them with a “personalized” experience, just so you can fudge the data on the backend without needing to make a fool-proof portal for those select few to use. This will save you money in the early stage when you already want to be closest to the user. It’s easy to get distracted by “urgent” product requests. Being able to identify when a request fits into the roadmap is essential.

What do you think is the ONE most important capability you want to build?

Seems straight forward? It’s not. So many founders will say “x is most important but we also really need y”. I won’t stop asking until you’ve only given me one. Maybe you’ve read The ONE Thing… I haven’t yet but I can still tell you focus is vital, especially starting out. This question, augmented with the others, quickly shows founders that their priorities are too divided, killing their focus, and keeping them from accomplishing anything.

What feature differentiates you from the “similar things” (competitors) out there?

If there’s nothing that differentiates you, your business will probably fail. If you think there’s nothing similar, you haven’t done enough research or been creative enough looking at the alternatives. Consider building your differentiated feature first, potentially even by itself. If it’s compelling enough: you will have a following before you do anything else… or you will learn no one actually cared.

What part of the business makes the money (when do people start paying, who)?

There’s an obvious fad with startups offering something awesome for free and subsidizing it with Venture Capital. But cash flow is never optional in the end and, if you can put a lot of focus on just that money maker, you will give yourself a lot more runway on borrowed money and time. Consider this answer when you think back to your “most important capability”. Even if your only money maker is selling user data still consider this. Maybe your data collection and data + cloud engineering/ management are actually what you should put a bit more focus on from the beginning and get your buyers paying before you even have an app.

What data or external systems need integrated? Can you find links to the documentation or an example of the data?

Having a clear understanding of data access is vital for preventing technical blockers. Often founders will build their whole concept around access to specific data, say for instance LinkedIn contact info. Sadly, sometimes those integrations don’t exist or are completely restricted. If you can do the research beforehand you may save yourself a world of pain. Plus when you’re prioritizing features and setting timelines, certain integrations can end up dominating your time and blowing up your release plan. Better be considering that beforehand.

How much is this worth to you? How will you pay for it?

How does this help you prioritize features? I love the statement “You can build a house for $50, $5,000 or $5,000,000 the only difference is what it’s made of”. Trite, but seriously… with a budget that only covers a portion of the features, which ones have the strongest chance together to make more money. Your goal is to build a useful and usable product that marketers, salespeople, developers, and ultimately customers will love. Whether you are VC financed, bootstrapping your venture, raising a community round, or exploring alternative forms of financing, you must align product development costs to your financial model.

Never Stop Asking Questions!

I’m sure there are dozens of other questions to ask, but hopefully these help you create an MVP feature set that people will love. When it comes down to it, the moment you stop asking yourself questions about your product is the day you stop innovating. No one creates the perfect product the first time, and even if they do… the market will change out from under them. If you take nothing else from this, just remember: good questions are the key to good innovation. If you never ask yourself the questions your customers ask, you’ll only be “their answer” if you get lucky.

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Marcus Smith

— Entrepreneur | Engineer | Ecosystem Curator | (Ed)venturer — Owner: The Smith Team, LLC— https://twitter.com/marcus_thesmith