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.