Three Questions to Help You Discover the Right Problems to Solve

This One is for the Builders

Those of us who use legal technologies has been arguing about the “build vs buy” problem for decades. Recently, that has morphed into “build AND buy”. Now, we are also hearing some folks talk about “buy TO build” or “buy THEN build”. In all those scenarios where some element of building is involved, the same question comes up after the person tasked with building has been sitting in front of a blank canvas for a while: “where do we start?”

Conventional wisdom tells us to “start with the problem.”

That part of the answer is easy, but it doesn’t actually help much, because how do we discover the right problem?

This is exactly where many law firms and in-house legal teams find themselves today. The sheer scope of possibilities creates paralysis (especially with AI purporting to solve everything). We have the tools and the resources, but we're stuck asking: “What should we actually build?”

Three Questions to Clear the Road Blocks

After working with many organizations, we can share how we approach the exercise of “starting with the problem”. We have found that asking three questions can consistently yield breakthrough insights.

Q1. What's Frustrating You?

Look at your daily workflow. Ask your users about theirs. What creates the most emotional friction? What makes people groan, complain, or waste unnecessary energy?

This emotional response is the compass. Frustration points to genuine problems that, once solved, create disproportionate value.

Hypothetical: M&A Due Diligence

Imagine asking M&A associates what frustrates them most. They might describe spending 60-80 hours per deal manually reviewing hundreds of contracts for change-of-control clauses, assignment provisions, and consent requirements. But the real frustration isn't just the time — it's both the mind-numbing work and the terror of making a mistake.

The problem may be framed as the need to extract key provisions correctly from hundreds of contracts.

Q2. If You Had Two Extra Pairs of Hands, What Would You Make Them Do?

This is capacity-level thinking. It bypasses the "what's possible" question and gets straight to "what's needed".

When you remove resource constraints from the equation, people naturally gravitate toward their actual bottlenecks. The answers reveal where solutions can create the most leverage.

Hypothetical: Tax Advisory Practice

Imagine asking a tax partner: "If you had two extra pairs of hands, what would you make them do?"

Without hesitation, they might say: "I'd have them monitor every IRS ruling, tax court decision, and regulatory update that might affect my clients' positions. Then I'd have them draft personalized client alerts explaining what each change means for each specific client."

This reveals the hidden bottleneck. With 200+ corporate clients holding complex tax positions, the partner can only realistically track major changes. Smaller rulings and technical corrections, which can have huge impact, might slip through the cracks. Clients are getting reactive advice when they desire proactive strategy.

Here, the problem may be framed as the need to monitor, analyze, and communicate relevant changes to the law.

Q3. What Do Your Target Customers Want?

You can also ask your customers what their customers want from them.

Talk to your lawyers about what their clients demand. This creates a goal-driven framework that aligns your solutions with real market needs, not just internal assumptions.

Hypothetical: Litigation Discovery

Imagine a litigation partner asking corporate clients: "What do you actually want from us during discovery?"

The answer might be: "We want to know early whether we should settle. Discovery costs are huge, and we're often $300K deep before we know if we have a strong case."

The clients don't want exhaustive discovery — they want fast, accurate case assessment. They want to know within the first 5 days whether they have a weak position. Speed to insight is more valuable than comprehensive analysis.

So, the problem might be framed as "clients need early case assessment to make informed settlement decisions".

Discovering the Real Value

We have found that applying these three questions (emotional mapping, capacity thinking, and cascading goals) consistently surface the problems worth solving.

This is how we find our way out of analysis paralysis, and hopefully these are useful questions you can consider when you are next building a solution.