The Secret to Better Proposals: Know Which Question to Answer

There are two fundamental questions a prospect must answer for themselves before moving forward with a custom software project:

1. Do we even need custom software?
2. If we do, who will build it for us?

Some prospects know the answer to one question or the other. A sophisticated prospect may already understand they need custom software and are willing to invest the premium needed to develop it. A prospect from your close network may know they want you (and no one else) to build them a system, but they may not be prepared to spend what's necessary to build it.

The key to writing winning proposals is understanding which question your prospect needs answered—then delivering a clear, compelling case that addresses their specific concerns.

Understanding the Three Client Mindsets

Every custom software prospect falls into one of three categories.

The first group is asking themselves, "Do we really need custom software?" These prospects come in two flavors. Some are methodically comparing custom development against off-the-shelf solutions, focused on ROI and business case justification. Others are enthusiastic about the idea of custom software but have a fundamental misunderstanding of the investment required—they're thinking in terms of standard software license costs ($100s or $1,000s annually) when custom development typically requires investment in the $10,000s or $100,000s. Your proposal needs to address both the business case and set realistic price expectations.

The second group has already decided they need custom software and is asking, "Who should we get to build it?" These prospects are comparing you against other developers or agencies. They care about your experience, methodology, and track record. They want to know why they should choose you over your competitors. Crucially, these prospects already understand and accept the significant investment required for custom development.

The third group is asking both questions simultaneously. These prospects need help determining if custom software is right for them AND who should build it if it is. They're looking for a trusted advisor who can guide them through both decisions. This presents an opportunity to offer a paid software package analysis service—a systematic evaluation of existing solutions that could meet their needs. This approach demonstrates your commitment to finding the right solution (even if it's not custom development) while providing immediate value. If custom development proves to be the best path forward, you've already established yourself as a trusted partner who puts the client's interests first.

Recognizing Which Question Your Prospect is Asking

Identifying your prospect's mindset starts with active listening.

Prospects in the "Do we need it?" category often don't realize that's their question until they learn the true cost of custom development. They typically approach you confident they need custom software, but that confidence wavers when faced with realistic pricing. Listen for indirect signals about the scale of their operation: how many users will access the system, how many transactions they process, or the size of their current workflow bottlenecks. A solopreneur requesting an enterprise-grade ERP system might need help understanding that custom software isn't always the right answer—especially when the potential value generated can't justify the investment required.

Those asking "Who should build it?" focus their questions on your experience, process, and previous work. Listen for phrases like "We're evaluating several developers" or "What makes your team different?" These prospects often request detailed technical information and client references.

The hybrid prospects tend to be more thorough in their questioning, covering both areas equally. They're likely to say things like "We think we need custom software, but we'd like your opinion" or "We're trying to figure out the best path forward."

The Default Question is Always "Who?"

You should assume prospects are asking themselves, "Who should build it?" unless either of the following is true:

1. The client knows and trusts you or was directly referred to you by someone they trust
2. Your market positioning is so clear that you are essentially a category of one

Without an existing relationship or unique market position, you're competing against other developers in the prospect's mind—whether they tell you this explicitly or not.

The "Benefits" Section: Where Proposals Are Won or Lost

The key to winning more projects lies in crafting a compelling "Benefits" section that directly addresses your prospect's fundamental question.

Prospects often struggle to envision concrete, tangible benefits from a new software system. They might know their current process is inefficient, but they can't always connect the dots between their pain points and specific improvements. That's the purpose of your Benefits section—to make these connections explicit and memorable. Your goal, though, is to use these concrete benefits to answer their fundamental question of either "Do we need it?" or "Who should build it?"

Think of the Benefits section as your proposal's executive summary. It's the section decision-makers will focus on most, especially if they're not technical. This section should appear early in your proposal—ideally right after your Project Overview.

"Do we need it?"

For "Do we need it?" prospects, your Benefits section should focus on system value:

• Quantify time savings (e.g., "Reduce monthly reporting time from 3 days to 3 hours")
• Calculate direct cost reductions (e.g., "Eliminate $24,000 in annual data entry costs")
• Highlight competitive advantages (e.g., "Respond to customer inquiries 5x faster")
• Demonstrate scalability ("Support 3x growth without adding staff")
• Show risk reduction ("Eliminate costly data entry errors")

"Who should build it?"

For "Who should build it?" prospects, structure your Benefits section around partnership value:

• Emphasize relevant domain expertise ("10+ years building systems for manufacturers")
• Highlight risk management ("95% of projects delivered on-time and on-budget")
• Showcase support capabilities ("24/7 emergency support with 1-hour response time")
• Demonstrate longevity ("Average client relationship: 5+ years")
• Include social proof ("Trusted by industry leaders like...")

"Do we need it and who should build it?"

For hybrid prospects, your Benefits section should address both areas while emphasizing your role as a trusted advisor:

• Lead with strategic partnership benefits
• Include a software package analysis option
• Balance system benefits with agency capabilities
• Demonstrate value-focused decision making
• Show examples of saying "no" when appropriate

Remember: While other proposal sections focus on technical details and logistics, your Benefits section must be carefully crafted to match your prospect's mindset and answer their fundamental question.

The Psychology Behind Benefits: Speaking to Hidden Motivations

When crafting benefits, many developers make the mistake of focusing solely on system capabilities and ROI calculations. While these rational benefits matter, they often miss the deeper psychological motivations driving decision-makers.

Decision-makers are human beings first and business professionals second. They carry personal fears, ambitions, and biases that heavily influence their choices. Understanding and addressing these hidden motivations can make your Benefits section significantly more persuasive.

Here are common psychological factors to consider:

• Fear of failure ("This vendor has never failed to deliver a working system")
• Career advancement ("You'll be recognized as the driving force behind this transformation")
• Risk aversion ("Our staged delivery approach ensures early wins")
• Status preservation ("Your team maintains full control throughout the process")
• Peer perception ("Join other industry leaders who have modernized their systems")

Let's look at how to reframe typical benefits to address these psychological factors:

Instead of:
"Custom software will reduce processing time by 75%"

Write:
"The automated workflow ensures consistent, timely reporting to senior management"

Instead of:
"Following industry best practices, we include a design phase in every project"

Write:
"Every project starts with a comprehensive design blueprint, eliminating costly mid-project surprises"

Instead of:
"Our development team brings extensive technical expertise to every project"

Write:
"Our proven track record includes 200+ successful enterprise implementations, with zero project abandonment"

Instead of:
"We maintain a dedicated support desk with rapid response times"

Write:
"Our proactive monitoring and maintenance approach prevents system disruptions from impacting business operations"

Conclusion

A winning custom software proposal starts by identifying which fundamental questions your prospect is asking: whether they need custom software at all, whether you're the right person to build it, or both.

Understanding your prospect's mindset shapes how you present benefits. Technical decision-makers may already understand the need for custom software, making your track record and reliability the key selling points. Others may need convincing that custom software is worth the investment, requiring benefits that emphasize business impact and ROI. And those asking both questions need a balanced approach that establishes you as a trusted advisor while making the case for custom development.

By moving beyond generic feature lists to carefully crafted benefit statements, we address both the rational and emotional aspects of these decisions. This psychological approach transforms standard capabilities into compelling advantages that resonate with decision-makers.

Success lies in matching your message to your prospect's primary concerns.

Acknowledgements

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• Portions of this article's body generated with the help of Claude-3.5