A version of this article originally appeared in the Fast Company Executive Board.

Many organizations view custom software as a way to gain a competitive advantage and unlock new opportunities. Yet, convincing stakeholders to commit to such a significant investment—in time, resources, and cost—can be challenging.

When executive leaders plan for an innovative software product, securing internal approval is often the first hurdle. We advocate for an iterative approach, where exploration and learning guide the journey—ensuring you make appropriately sized bets instead of assuming guaranteed success.

Stakeholders want to be confident in the project’s value, which is often best determined by exploring these key questions:

• How does the project align with the company's core goals and strategy?

• What essential tasks will this software allow users to accomplish?

• How do the costs, timeline, and expected ROI compare to other initiatives?

• What are the project’s risks, and how will they be mitigated?

Stakeholders want to know: Is the project worth pursuing and is it the right solution?

The decision often lies along a spectrum—including whether to build custom, buy off-the-shelf, or opt for a hybrid approach. Digital products rarely operate in isolation; they typically need to integrate with existing systems to deliver maximum value.

Since Michigan Software Labs frequently supports clients through this process, we’ve outlined a framework to help you evaluate your project and get approval.

1. Lean business case

The process usually starts with a lean business case to determine whether the project warrants further investment—specifically a paid product strategy phase.

This high-level document outlines project goals, scope, and financial impact. Importantly, it focuses on identifying where value might be found and pain points that could be solved, without trying to answer everything prematurely.

We often help clients by identifying key questions they might explore during product strategy. We combine our software expertise with executives’ deep industry knowledge to ensure they are on the right path.

We recommend using a simple template, including:

1. Project summary

   1. What are the project’s goals? What does success look like?

   2. What is the background of the project? What have we already tried, and why is this different?

   3. How does this project align with our company’s core values?

2. Timeline

   1. What are the key milestones?

   2. When might we see initial signs of success?

   3. What risks and assumptions need to be considered?

3. Next steps

   1. Who will be accountable for the project? Who else will be impacted or involved?

   2. What vendors or partners should be consulted?

   3. How will change management be handled?

2. Presenting a cohesive story across the organization

Securing approval requires clear communication. You’ll want to engage in internal discussions and gather input from various departments—call it a ‘listening tour’—to build support.

1. Economic considerations (Learning from your CFO or finance leaders):

As you begin to gather details about the digital product you are considering to build, you’ll want to have a discussion around strategic financial outcomes for the business. While you might be able to provide an insightful analysis that goes beyond basic numbers, you really want to understand how this new digital product will impact the organization positively in an economic way.

Engage in a dialogue with your financial team members about how the project supports long-term financial objectives, and consider discussing how it positions the company in the market from a financial perspective. My experience shows that you will often need to engage your finance team early on in your research to ensure your analysis makes sense and aligns with your company strategy.

Key takeaway: View your CFO as a strategic partner. Listen to their concerns and demonstrate how the project supports the company’s growth plans.

2. User and operational considerations (Learning from your COO and operations leaders):

Engage those closest to your users and operations to understand how the project impacts daily workflows. Some questions to explore include:

• How could this software enhance operational efficiency?

• What is the long-term operational impact, including maintenance and scalability?

• How will you manage risks to ensure a smooth implementation?

This will be a good spot to learn about your approach to change management and how you will engage the various stakeholders throughout the roll-out.

Key takeaway: Focus on how the project integrates with existing processes and drives long-term value.

3. Technical considerations (e.g., the CTO, CIO, or VP of IT):

Engage with your IT team to evaluate technical feasibility. Ensure the project aligns with the company’s technology strategy and supports its innovation goals. You might ask the following:

• How does this project fit within our existing technology stack and future technology roadmap?

• What are the technical risks, and how will they be mitigated?

• How does the project support our innovation goals and technological leadership?

Engage in a discussion about the strategic technical benefits of your project but don’t try and speak for IT. Listen to how the technology will enhance the company’s competitive edge and discuss any technical challenges with a clear plan for resolution.

Key takeaway: Learn how the project fits within the existing tech stack and roadmap, and how it will enhance the company’s competitive edge.

Embrace the learning process

You’ll likely have many opportunities to create value-adding projects throughout your career. Pursuing custom software is about exploration and making educated decisions—not having all the answers upfront. Each project offers a new opportunity to learn and discover hidden value.

A common mistake is focusing solely on the most obvious questions while overlooking deeper issues that emerge through discussion and collaboration. Be open to gathering feedback, adapting your approach, and refining your pitch over time.

Remember, successful digital products aren’t built on certainty but on curiosity, learning, and strategic decision-making. Approach each initiative with a mindset of exploration and growth. As you build your case, consider where to explore further and when external guidance—like a product strategy phase—might provide clarity.

I'd love to support you as you build buy-in with your team! Start a conversation by completing our simple contact form or reaching out to me on LinkedIn.