10 Questions Every Services Founder Should Answer Before Scaling Past $10M
- Sahil Harwani
- August 1, 2026
- Blog
- 0 Comments
Before we start working with a services founder, there are a few questions I always ask. Not a formal framework, just things I’ve learned to check over a few hundred conversations. They’re not trick questions. Most founders have thought about at least some of them. But the pattern I keep seeing is this: the founders who’ve actually broken past $10M in revenue can answer all ten, even messily. The ones stuck below it usually have solid answers for two or three and blank stares for the rest.
Here they are, roughly in the order I ask them.
On positioning
- Does a Fortune 500 client see you as an advisor, or just the team that executes their tickets?
- Someone lands on your site cold – what do they actually remember after?
- Are you a services company, a dev shop, a SaaS business, or an AI product company? You have to pick. Buyers won’t do it for you.
These three usually get answered fast, but the answers rarely hold up under a follow-up question. A lot of founders think they’ve picked a lane, then describe their business in a way that sounds like three different companies.
On growth and knowledge
- When a new product idea comes up internally, is there an actual process, or does it just depend on who’s excited that quarter?
- How do you go about picking up expertise in a new domain?
This is where the improvisation shows. Most services businesses grow by accident, someone gets excited about a client problem, builds something, and it becomes a capability. That’s fine early on. It stops being fine once you’re trying to scale past a founder-led sales motion.
On visibility
- Who’s selling for you when you’re not in the room?
- Who talks about your work besides your own team?
If the honest answer to both is “nobody,” that’s not a marketing problem. It’s a business model problem. It means every deal depends on your direct involvement, which is a ceiling with your name on it.
On concentration risk
- What share of revenue comes from your single biggest client and what happens to the business if they leave?
- When you lose a deal, do you actually know why, or do you just move on to the next one?
- If your best engineer or salesperson quit tomorrow, would clients notice within a month?
These three are the ones people least want to sit with. They point at fragility, client fragility, feedback, loop fragility, people fragility and fragility is uncomfortable to name out loud, especially when the business looks healthy on paper.
Most people can answer three or four of these without much thought. The ones who actually break past $10M usually have an answer, even a messy one, for all ten.
Which one made you stop and not want to answer honestly? That’s usually the real one.
