You've decided to build custom software. Before you sign anything or write any code, make sure you're ready.
This checklist will save you time, money, and frustration.
Business Readiness
✅ Clear Problem Definition
Can you explain in one sentence what problem you're solving?
- "Our order entry takes too long and has too many errors"
- "We can't get a unified view of our customer relationships"
- "We're losing sales because our inventory is never accurate"
If you can't articulate the problem clearly, you're not ready.
✅ Business Case Exists
Have you done the math?
- What's this problem costing you? (time, money, opportunity)
- What's a reasonable investment to solve it?
- What return do you expect?
- How will you measure success?
If you can't justify the investment, reconsider.
✅ Budget Allocated
Is there actual budget for this project?
- Development costs
- Ongoing hosting and maintenance
- Training and change management
- Contingency for the unexpected
If budget isn't real, don't start.
✅ Stakeholder Alignment
Do key stakeholders agree on:
- The problem to solve
- The general approach
- The budget
- The timeline expectations
- Who has decision authority
Misalignment now becomes conflict later.
✅ Realistic Timeline
Are expectations realistic?
- Custom software takes months, not weeks
- Good things take time
- Rushed projects fail
If someone expects it "in a few weeks," reset expectations first.
Requirements Readiness
✅ Core Requirements Identified
Do you know (at least at high level):
- Who will use this system?
- What will they do with it?
- What data is involved?
- What systems does it need to connect to?
You don't need perfect requirements, but you need a foundation.
✅ Must-Have vs. Nice-to-Have
Can you distinguish:
- Features essential for launch
- Features that can come later
- Features that would be nice but aren't necessary
If everything is "must have," you're not ready to prioritize.
✅ Key Stakeholders Identified
Who needs to be involved?
- Decision makers
- Subject matter experts
- End users
- IT (if applicable)
Missing stakeholders means missed requirements.
✅ Constraints Known
What are your constraints?
- Budget limits
- Timeline deadlines
- Technology requirements
- Integration requirements
- Compliance requirements
Knowing constraints early prevents surprises later.
Organizational Readiness
✅ Project Owner Designated
Who owns this project?
- Who makes final decisions?
- Who approves requirements?
- Who accepts deliverables?
- Who handles escalations?
No owner = no accountability = failure.
✅ Availability Committed
Will the right people be available?
- To answer questions
- To review work
- To attend demos
- To make decisions
Unavailable stakeholders slow everything down.
✅ Change Capacity Assessed
Can your organization absorb this change?
- Are people ready for new processes?
- Is there appetite for learning?
- Are there competing priorities?
- Is there change fatigue?
Great software fails if no one adopts it.
✅ Support Plan Considered
What happens after launch?
- Who handles issues?
- Who answers user questions?
- How will updates be managed?
- What's the ongoing budget?
Launch isn't the end.
Vendor Readiness
✅ Selection Criteria Defined
How will you choose a partner?
- Technical capability
- Relevant experience
- Communication style
- Cultural fit
- Price (but not only price)
Without criteria, you'll choose based on vibes.
✅ Multiple Options Evaluated
Have you talked to multiple vendors?
- At least 2-3 for comparison
- Understand the range of approaches
- Get different perspectives
One conversation isn't enough.
✅ References Checked
Have you talked to past clients?
- Were they happy?
- Did projects deliver value?
- How did problems get handled?
- Would they work with them again?
References reveal reality.
✅ Contract Understanding
Do you understand what you're signing?
- What's included
- What's excluded
- How changes are handled
- What happens if things go wrong
- IP ownership
Don't sign what you don't understand.
Ready to Go?
Green Light
All boxes checked? You're ready. Start the project.
Yellow Light
Most boxes checked, a few gaps? Address the gaps first. It's worth the delay.
Red Light
Many boxes unchecked? You're not ready. Starting now will waste money and time.
The Meta-Lesson
The discipline to answer these questions before starting is the discipline that makes projects succeed.
If you can't or won't answer them, that's a warning sign about project readiness.
Take the time. Get ready. Then build.
Ready to assess your project readiness? Let's have a conversation