Blog Series: Making Software Work for Growing Businesses

Software Project Kickoff Checklist

Use this checklist before you start your next software project to avoid wasted time, money, and frustration.

Align on Goals and Outcomes

What business problem are we solving?
What does success look like in measurable terms?
Who are the end users, and how will this help them?
What’s the “must have” vs. “nice to have” scope for version 1?

Define Roles and Responsibilities

Who is the single point of contact on your side?
Who owns delivery on the development team?
How will questions, blockers, or changes be communicated?
Who signs off on milestones and releases?

Establish Communication Cadence

How often will we meet (daily standups, weekly demos)?
What tools will we use (Slack, Teams, email, project tracker)?
How do we handle urgent issues after hours?
What’s the escalation path if something goes wrong?

Agree on Transparency and Deliverables

Will I see working software weekly?
How will progress be tracked (boards, burndown charts, checklists)?
What’s the definition of “done” for each feature?
How do we document decisions along the way?

Manage Risk and Budget

What’s the realistic timeline (not just the optimistic one)? (actual vs elapsed)
How are payments tied to deliverables or milestones?
What’s the fallback plan if deadlines slip?
How will scope changes be estimated, approved, and tracked?

Plan for Deployment and Support

Who handles hosting, infrastructure, and environment setup?
How will testing and quality assurance be done?
What’s the rollout strategy (pilot group, phased launch, big bang - don’t do big bang rollouts)?
Who supports the system after go-live?

Ensure Long-Term Scalability

How is the system designed to scale with business growth?
Are we documenting architecture, APIs, and integrations?
How do we avoid lock-in (can another team pick this up later)?
What’s the plan for future updates and maintenance?

Pro Tip: If your development partner can’t answer these questions clearly, you’re heading for trouble. Use this checklist as a litmus test. Good partners will welcome it, bad ones will resist it.