8 Common Challenges When Writing Proposals

Win rates are a huge factor in measuring success for proposal teams. However, many teams experience challenges while writing proposals. If these challenges can’t be avoided, they should be planned for ahead of time. Success in this sense means analyzing factors where the proposal process fails or is disrupted.

For teams that want to generate proposals that win new business, it is essential to cultivate team synergy. No matter the type, scope, or size of a proposal, there will always be roadblocks on the road to its deadline. How various members choose to embrace them is all up to proposal planning.

Here are 8 challenges you can’t avoid when writing proposals, and ways to overcome these challenges.

1. To Bid, or Not to Bid?

This is a common challenge among all proposal teams. Not all proposals are a good fit. Even before the initial stages of writing proposals, you must decide whether this RFP is in the scope of your services, time, and effort. Relative stakeholders often meet this part of the decision-making process with opposition.

Forbes contributor, August Turak, summarizes the bidding dilemma succinctly:  “Every great plan or proposal must have teeth, and putting teeth into your plan or proposal means making projections.”

The argument over bidding or not bidding can be resolved by optimizing against evaluation criteria:  

• Is this feasible? Are we qualified?
• Does this RFP contain a requirement we can’t justify?
• Will this require extensive outsourcing?
• What benefits does this provide to our business?
• Does this opportunity align with our mission and corporate culture?
• Does this project fit our budget and schedule?
• How much profitability is tied to this RFP?
• Are we likely to win?

The answers to these questions weigh against bidding incentives and should align with the current state of organizational objectives and resources.

2. Overlooking Accountability When Writing Proposals

The amount of effort it takes to complete a proposal depends on the size and complexity of the RFP. However, time is nearly always the number one challenge in writing proposals.

New challenges crop up over time. This requires accountability from everyone involved in the proposal process. Even an ideal proposal team hinges on team member accountability.

When writing proposals, team members must be ready to carry out their responsibilities. Stakeholders are accountable for their input. Business development should have approval for client references. Support team members must prepare a realistic implementation schedule. Sales management should commit to finalized pricing.

Often, when the time comes to submit the proposal, the ball is dropped by someone. The planning behind every proposal should outline each proposal team member’s accountability and hold them to their responsibilities.

3. “Where did that ____ go?!”

Keeping tabs on content is cumbersome in the proposal process. RFPs mandate the size of answers and the types of proposal attachments. Content libraries prove helpful when writing proposals. There are numerous tools proposal teams use to keep their content organized.

Yet, often, team members are left asking, “Where did that _____ go?!”. The most up-to-date content can slip through the cracks if a proposal library is not updated regularly. Additionally, when not organized well, parsing through a stock answer repository takes up a large chunk of a proposal team’s time.

When writing proposals it is important to keep this content updated, keep stock of evergreen answers, and create an accessible folder of attachments frequently required in an RFP’s evaluation. These files often include the latest financial reports and security protocols.

4. Content Overload from SMEs

Jargon. Obscure abbreviations. Complex language. While the technical merit behind content from subject matter experts (SMEs) is undoubtedly true, it doesn’t mean the content is digestible for proposal reviewers. Esoteric terms and TLAs (three-letter) abbreviations also made HubSpot’s list of Bad Habits to Avoid When Writing Proposals.

Copying and pasting answers verbatim from SMEs creates a Frankenstein effect. The parts are connected, but there’s no cohesion. When a proposal lacks cohesiveness it reads like it was written by multiple, patchwork voices. While editing and writing proposals, ensure that a single persuasive voice is exhibited from start to finish.

5. Document Style Issues

Corrupted formatting is a proposal team’s worst nightmare. The content may be matched with the appropriate content, but when formatting goes askew, the proposal’s overall aesthetic value goes down. Overlayed text boxes in Adobe InDesign may cut off critical content. Faulty style settings in Microsoft Word can affect large sections of the proposal.

Frequently, an RFP will ask for a specific answer format for particular questions. For example, instead of just the list of people who make up an implementation team, the RFP may push for a graphical representation of the team. It’s especially important to pay attention to the wording of questions when writing proposals. Answer outlines will quickly change the formatting of a canned answer.

Some RFPs ask for the proposal to be submitted through an online portal or in a protected spreadsheet. For these more simple proposal submissions, teams must be careful to ensure they are filling out the appropriate answer to every question.

6. Table of Content Updates

During the process of writing proposals, elements are added and deleted. Doing so changes the flow of the entire proposal. A proposal is written into sections, depending on the complexity of the RFP.  As a result, the more heavily involved teams become in the writing process, the more significant the expansion of the original proposal outline.

The table of contents should be revisited to ensure that it accurately captures the major sections of the proposal. After all, this is one of the first proposal sections that reviewers see. The table of content’s function is to display the proposal’s content at a glance without confusion. Adobe InDesign and Microsoft Word provide the capability to automatically create a table of contents.

This section of the document should be reviewed and updated before submission, even if teams are relying on automation to update the table of contents.

7. Changes in Pricing

It’s abundantly clear that change is constant in writing proposals. Pricing is no exception. Depending on the product or service offering, updates on pricing can be straightforward. However, this section of a proposal greatly depends on a proposal team’s level of collaboration.

A proposal can be easily eliminated if the cost strategist or sales/finance team members are unable to determine competitive pricing for the RFP.

Pricing generally changes when stakeholders peel away the layers of the proposal and contrast it against the potential business volume. Pricing analysis changes dramatically for RFPs that outline highly customized contract requirements. As a result, it’s not uncommon for a proposal’s pricing to change numerous times–even in the final hours leading to its deadline.

8. Editing, editing, editing.

This is an unavoidable challenge in writing proposals. Nearly every proposal team member functions as an editor at some point in the process. Pricing, content, voice, technicalities, logistics, and graphics are never just cut and dried. Creating the proposal requires ongoing editing.

Ultimately, the review team provides the final go-ahead for a proposal’s submission. Nonetheless, every team member should embrace the continuing editing process.