The 5-Point Project Picker

Don’t build the wrong thing first.

Choosing the right first software project can make or break your digital strategy. The initial project sets the tone for everything that follows. If you build the wrong thing first, something too ambitious, or not valuable enough, you risk losing momentum and stakeholder support.

The right first build, on the other hand, will deliver a quick win, prove the value of custom software, and pave the way for bigger initiatives.

But how do you know which project to start with. Use a simple 5-point checklist to evaluate your options.

A winning first project should be Feasible, Impactful, Relevant, Small, and Timely. In other words, it should pass the FIRST test.

The 5-Point Project Picker Criteria

Feasible

Is the project realistically achievable with your current team and technology. As a first project, it’s crucial to pick something you know you can deliver.

Consider the technical complexity and the resources required. For example, integrating with ten legacy systems might not be feasible right out of the gate.

A feasible project is one that fits your team’s skills and can be built with available tools and budget. By choosing a project that’s comfortably within your capabilities, you set yourself up for a successful delivery.

Impactful

Will this project solve a real problem or offer significant benefit. The best first project addresses a pain point that people care about.

Look for an initiative that can deliver visible improvements, whether it’s saving time, cutting costs, increasing revenue, or improving customer experience.

An impactful project ensures that when you roll it out, everyone sees the value. This builds excitement and support for your software efforts.

If the project’s outcome wouldn’t matter much to the business, it’s not worth using as your flagship build.

Relevant

Does the project align with your organization’s current goals and priorities. A project might be feasible and useful, but if it’s not tied to a strategic objective, it may not get the support it needs.

The first project should be something leadership and stakeholders are already interested in or will readily endorse. Relevance also means the problem is timely for the business, for instance, addressing a recent issue or an operational gap that leadership has acknowledged.

When you pick a relevant project, you’ll have buy-in from day one, which is critical for smoothing the path ahead.

Small (Scoped)

Can the project be completed quickly and without excessive complexity. A common mistake is choosing a first project that is too large in scope.

Instead, aim for a project that is small or at least narrowly focused. The idea is to achieve a win in months, not years.

A smaller project is easier to manage and less likely to run into major delays or obstacles. Keeping scope tight reduces risk and allows the team to maintain momentum.

Remember, you’re not trying to boil the ocean with your first build. You just need a solid, demonstrable success.

Timely (Quick Win)

Will the project deliver value in the near term or address an urgent need. Timeliness is about picking a project that provides a quick win.

This could mean it has a short development cycle, or that it tackles a pressing problem that’s top of mind. When the results are timely, you validate the effort faster.

For instance, a project that can be launched in a quarter and immediately starts saving labor hours is ideal. Avoid first projects that will take a long time to show results.

An early win builds confidence and buy-in for the next projects on your list.

Mini Case Study. Smart First Project in Agriculture

An agricultural supply company had a list of software ideas to modernize their operations. They considered tackling a full end-to-end farm management system first, but that project would be massive and risky.

Instead, they applied the 5-point project picker and chose a more focused starting project. A custom irrigation scheduling app for their farming clients.

This irrigation app met all the FIRST criteria:

Feasible: It relied on readily available data (weather and soil info) and the company’s existing IT infrastructure. The in-house team had the skills to build it without needing new tech.
Impactful: Efficient water scheduling was a big pain point for clients. The app was projected to reduce water usage by 15%, a clear and valuable benefit for farms facing drought conditions.
Relevant: Water management was a top priority that year, with new regulations pressuring farms to improve efficiency. Company leadership had identified customer irrigation support as a strategic service goal.
Small: The app’s scope was limited to scheduling and alerts for irrigation. It wasn’t trying to solve every farming issue, so development was straightforward. The team planned a pilot rollout within three months.
Timely: Drought conditions made this solution urgent. By launching the app before the next planting season, the company could immediately help clients save water. The quick deployment meant faster feedback and early success stories.

The choice paid off. The irrigation app was delivered on time and widely adopted by the company’s clients. It generated measurable water savings and positive press for the business.

Internally, the successful first project built confidence in the IT team’s abilities. Armed with this win, the company secured executive support to take on larger, more complex software projects next.

By picking a first project that was feasible, high-impact, aligned to strategy, small in scope, and timely, they set themselves up for long-term transformation success.

Key Takeaways

Your first custom software project should be a high-impact, low-risk win. Aim for a project that is feasible to execute and delivers clear value.
Use the FIRST framework. Feasible, Impactful, Relevant, Small, Timely, as a checklist when evaluating potential projects.
Avoid choosing a project that is too large or misaligned as your first effort. Starting with a manageable, strategic project builds momentum.
A well-chosen first project will prove the worth of custom software to stakeholders and pave the way for bigger initiatives.

Next Step: Review your list of project ideas and apply these five criteria. Pick the project that checks all the boxes for your best chance at an early win.

How to Pick What Digital System to Create First