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Five Questions to Ask Before Starting a Software Project
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Five Questions to Ask Before Starting a Software Project

Russ AlexanderMay 15, 20242 min read

Most projects fail before they start

The majority of software projects that go sideways don't fail because of bad code. They fail because the wrong questions were asked — or weren't asked at all — before work began.

Here are five questions that should have clear answers before you commit time or money to any software initiative.

1. What problem are we actually solving?

Not "what do we want to build" — what problem exists today? If you can't describe the pain in concrete terms, you're not ready to build. "We need a portal" is a solution. "Clients can't access their assessment results without calling us" is a problem.

2. Who is this for?

Every project needs a primary user. Not "everyone." Not "the team." A specific person with a specific workflow. If you're building for case workers, sit with a case worker. Watch how they do their job today. The best requirements come from observation, not imagination.

3. What does success look like in six months?

Define a measurable outcome. "Reduce manual data entry by 50%" is measurable. "Improve efficiency" is not. If you don't define success upfront, you'll never know when you've achieved it — and the project will keep expanding.

4. What happens if we do nothing?

This question forces honesty. Sometimes the answer is "not much" — and that's a signal to deprioritize. Other times the answer is "we lose a contract" or "we can't scale past 200 clients." That urgency helps you scope appropriately.

5. Do we have the right people to support this after launch?

Software doesn't end at deployment. Someone needs to handle bugs, user questions, updates, and integrations. If you don't have a plan for ongoing support, you're building something that will decay the moment it ships.

The takeaway

These questions aren't revolutionary. But the discipline of answering them honestly and completely before starting saves more projects than any technology choice ever will.

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