5 questions to ask while you're building..

I met with a leadership team last week to chat about the future of an internal tool we built. It’s a strong internal platform and they’re now weighing whether or not they should take it to market. They’ve got clear workflows and have put real thought into the experience and features/functionality.

That said, they’ve put a lot less thought into how they would actually commercialize this and take it to market. I asked them some questions like, “Who exactly is the first ideal customer? How big is the addressable market? What portion is truly serviceable versus attainable in year 1 and beyond? What price and packaging will create healthy margin while matching what buyers need and expect?”

I keep seeing this pattern across companies. Teams jump straight to building because execution has gotten a lot easier. They skip the hard questions about who they’ll sell to, whether there’s a real market they can reach, and how to price it in a way that’s profitable without breaking trust.

The result is a solid product without a commercial backbone. The fix is to really spend some time/effort answering the following questions first and letting those decisions shape what you build/launch.

Questions to answer:
How big is the opportunity? Who buys first and why? Which role in which type of company feels the pain now? What triggers action? Who owns the budget?

How to answer:
Do a top-down analysis of your target market (AI can help you with this). Pair it with a bottom-up count from your existing customers that match the profile. Land on ranges for what the total addressable market is (i.e., how big is the possible market you could sell to, aka “TAM”), serviceable addressable market (i.e., of that addressable market, how much of it could you reasonably service, aka “SAM”) , and attainable market (i.e., of what’s serviceable, how much you you reasonably attain?).

Define your ICP with a simple formula:

Here’s a quick example:

Write yours down and come up with a few ways you can actually validate if you’re on the right track. A few tried and true ways are things like:

If the signals are weak, tighten the ICP sentence and rerun the tests. Side note, I went deep on this in my 2026 Growth Strategy Playbook newsletter from a few weeks ago.

Questions to answer:
How does value turn into dollars, margin, and break-even? What do you charge? What’s the term? What do you think your profit margin will be? What’s the payback period? When do you break even?

How to answer:
A value meter is the one thing your price moves with as customers get more value. Think number of people using it, number of jobs processed, or amount of data handled.

Choose one meter and create three tiers (e.g., light, core, plus). Set a clear price for each and guess a simple mix to estimate average monthly revenue per customer. List the monthly costs to serve one customer so you know your monthly profit. Estimate what it costs you to win a customer, then count how many months of profit it takes to earn that back.

Sketch out a 12-24 month view of new customers, customers who leave, and upgrades to see when the line turns positive. Test your plan by changing price, customer churn, and cost to win a customer by ~20% to see what breaks. Put your biggest benefits in the higher tiers so the price steps feel fair. Finish with simple rules for discounts, when customers move up a tier, and how a trial becomes a paid plan.

Questions to answer:
Are all customers worth the same (e.g., Is LinkedIn better than YouTube)? How does volume/usage by different customer segments differ (will some use/buy more than others)? Which channels will consistently put you in front of your target buyers?

How to answer:
Think through ways to tier customers by volume or usage so that one big, high-volume customer isn’t modeled like ten little ones. Pick a few key go-to-market moves for the first 90 days. For example:

Put names/dates next to each one and set up a way to measure each channel for things like # of meetings, customer acquisition cost (CAC), etc.

Questions to answer:
What proves this should scale? How do we make paying a one-step action?

How to answer:
Use a pilot scorecard with three proofs:

Define measurement and a decision date before launching. Start with a standard pilot agreement and a single monthly bill that shows usage and human support. Move to a master agreement (MSA) after value is proven. Customers buy outcomes, not overhead.

Questions to answer:
Can your org sell and support this? If you’ve never built/launched a digital product or SaaS, what changes will you need to make to actually sustain this long term? Who will you need to hire? What functions/departments will need to exist?

How to answer:
Map today’s capabilities against tomorrow’s needs. This could be things like product management, customer success, support, and marketing/growth. Decide what to add, what to pause, and what to automate. Assign owners, expectations, and start dates. Set a weekly operating rhythm to measure things like pipeline, product adoption, and churn/expansion. Ideally, you’ve got some sort of dashboard that ties it all together so everyone can see how you’re tracking.

If you build it, they will NOT come. The Field of Dreams is a lie (sorry Kevin Costner). Said differently, just because you build it, DOESN’T mean you’ll get any customers or make any money.

In an era where execution is fast and inexpensive, the real leadership work is to slow down long enough to answer these questions with clarity. Do that first and you’re much more likely to have a real market with a real buyer at a price that makes sense and a path to profit that everyone can believe in.

Onward & upward,
Drew

P.s. If you missed it, I launched 2 free tools (AI Sanity Check & AI Impact Analyzer) to help leaders at mid-sized companies accelerate with AI this January based on 18 months of trial and error at StealthX. Check them out and let me know what you think 😊