8 Common Challenges When Writing Proposals

Proposal writing is a critical skill for organizations responding to RFPs (Requests for Proposals), government contracts, and other competitive funding or project opportunities. The success of every proposal depends on careful planning, collaboration across internal team members, and a deep understanding of the proposal development process. While writing proposals, teams often face common challenges that can affect overall win rate and the effectiveness of proposal content. Addressing these challenges early ensures every proposal has a higher chance of success.

Industry data shows that the average RFP win rate across sectors is around 45%, highlighting the importance of overcoming proposal writing challenges¹. With growing competition, organizations are increasingly adopting AI tools to streamline proposal development, improve coherence, and save time while maintaining compliance and quality.

For proposal development teams, creating winning proposals requires strategic planning, meticulous attention to detail, and strong coordination among team members. Even with strong procedures, roadblocks in the proposal process are inevitable. Understanding these challenges for proposal writing and knowing how to overcome them strengthens the entire proposal development process.

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1. To Bid, or Not to Bid?

One of the most frequent proposal challenges is deciding whether to pursue a specific RFP. Not all RFPs align with your team’s scope, resources, or strategic objectives. Business development stakeholders must evaluate opportunities carefully to ensure compliance with internal goals and procurement standards.

Key evaluation criteria include:

• Is this feasible for our proposal development team?
• Does this RFP match our product or service capabilities?
• Will pursuing this opportunity require extensive outsourcing or extra resources?
• Does it align with our organizational mission and unique value?
• How much profitability is tied to this project proposal?
• Are the chances of success realistic given our team’s current workload?

Careful planning and a pre-RFP review process improve success rates. For example, a software company might decline an RFP for a highly specialized government contract because the proposal requires expertise outside their proposal development team, saving time and resources. Focusing on well-aligned RFPs increases win rates and reduces wasted effort.

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2. Overlooking Accountability in Proposal Writing

Time constraints are a constant roadblock in proposal writing. According to recent statistics, 41% of organizations submit between 51–250 RFPs per year², placing heavy pressure on internal team members to meet deadlines. Accountability across the proposal team is crucial.

Best practices include:

• Clearly define each stakeholder’s role in the proposal development process.
• Assign deadlines and track progress using project management tools.
• Hold team members accountable for providing compliant content, client references, or budget input.

Even under a tight deadline, ensuring accountability enables teams to deliver winning proposals efficiently. For example, a nonprofit preparing a grant application can designate a single senior proposal manager to oversee all content, reducing delays and maintaining quality.

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3. Tracking Proposal Content

Managing proposal content is a frequent challenge. Content libraries help centralize reusable material, but without proper organization, boilerplate content can be misplaced. Teams often find themselves asking, “Where did that document go?” during the review process.

Tips for managing content:

• Maintain a centralized, version-controlled content library.
• Keep templates and attachments cross-referenced for easy retrieval.
• Regularly audit the library to ensure content is up-to-date, especially for recurring RFPs or grant applications.

Proper content management saves time, reduces errors, and ensures every proposal maintains consistency and coherence.

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4. Content Overload from SMEs

Subject Matter Experts (SMEs) provide technical insights, but too much jargon or multiple writing styles can compromise readability. This can result in the “Frankenstein effect,” where content reads as patchwork rather than a cohesive narrative.

Proposal writers can:

• Consolidate and edit SME contributions to maintain a single, persuasive voice.
• Translate technical language into plain language that reviewers can understand.
• Prioritize clarity while retaining essential technical accuracy.

A deep understanding of the target audience and evaluation criteria ensures the proposal is compelling and easy to navigate.

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5. Document Style and Formatting

Formatting issues are a common challenge for proposal teams. Misaligned text boxes, inconsistent fonts, or improper use of templates can undermine professionalism. Many RFPs specify exact formats for tables, graphics, or charts, making formatting critical.

Best practices:

• Use standardized templates for the entire proposal development process.
• Check alignment, headings, and page numbers before submission.
• Ensure the table of contents accurately reflects sections.

Consistent formatting conveys professionalism and improves readability for reviewers, enhancing the chances of success.

6. Updating the Table of Contents

As project proposals grow and evolve, updating the table of contents is essential. This ensures reviewers can quickly locate sections and confirm compliance with request for proposals requirements.

Tips:

• Automate table of contents updates when possible.
• Conduct a manual check to verify headings match content.
• Maintain cross-references for all attachments and exhibits.

This attention to detail reinforces meticulous attention to detail, a key factor in winning proposals.

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7. Changes in Pricing

Pricing is often dynamic, especially in proposals for government contracts or highly customized products or services. Stakeholders in finance or sales must collaborate to determine competitive pricing, track changes, and ensure alignment with the proposal strategy.

Strategies to manage pricing changes:

• Maintain version-controlled pricing spreadsheets.
• Communicate updates immediately to internal team members.
• Include contingency plans for last-minute adjustments in project scope.

Teams that manage pricing changes effectively improve compliance and increase chances of success.

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8. Continuous Editing

Editing is an ongoing part of writing the proposal. Every proposal writer may review content multiple times to ensure clarity, compliance, and formatting. The review process must account for pricing, content, graphics, and submission requirements.

Tips for effective editing:

• Use a checklist for proposal development tasks.
• Conduct peer reviews and cross-functional checks.
• Emphasize clarity, conciseness, and coherence in responses.

Integrating AI tools into editing can speed up the process, highlight inconsistencies, and ensure content aligns with evaluation criteria.

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Integrating AI for Proposal Development

Modern proposal development teams are increasingly adopting AI tools to streamline drafting, enhance coherence, and organize proposal content. AI can:

• Suggest improvements in language and tone.
• Cross-reference previous submissions for boilerplate content.
• Ensure deadlines are met by tracking progress across internal team members.

AI adoption is particularly useful for organizations handling high-volume RFPS, saving time and improving win rates.

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Conclusion

Proposal writing challenges are inevitable, but careful planning, collaboration, and adherence to best practices in proposal development help teams overcome them. By addressing common challenges, teams can deliver compliant, cohesive, and competitive proposals that increase win rates and maximize opportunities for growth.

Effective proposal development teams leverage strategic planning, proper content management, accountability, and AI tools to create winning proposals. Overcoming challenges for proposal writing not only increases chances of success but also strengthens organizational capacity for grant funding, government contracts, and other strategic opportunities.

With meticulous attention to detail, strong stakeholder collaboration, and careful review processes, your team can ensure every proposal submitted is compliant, professional, and impactful, giving your organization the best chance to succeed.

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