43 examples of questions that can drive proposal process success

See the companion article that describes how to build a goal-driven proposal process around questions like these.

To redefine roles
To encourage business development to play a larger role in writing the proposal, or to contribute more customer insight into the proposal: 

• Does the Executive Summary reflect what we discovered from talking to the customer?
• What should we say in the proposal based on our customer interactions?
• How can we translate our customer insights into differentiators for use in the proposal?

To encourage technical staff to improve their ability to write persuasively:

• What technical trade-offs are involved in doing this work?
• How is our approach to resolving them better than anyone else’s?
• What should the customer know about it?

To change assumptions
To encourage people to move away from an assumption that “Proposals always have a train wreck at the end,” during a proposal review ask:

• Is your section complete so the proposal can meet the deadline, or will it contribute to a train wreck at the end of the proposal?
• Has your review done everything possible to prevent a train wreck at the end of the proposal?

To change how people do things
When staff have a habit of not doing something they should, remind them:

• Did you address what differentiates our approach in what you wrote?
• Did you resolve all comments and issues related to your section?

When staff are submitting incomplete responses, ask questions like:

• Did you complete your section without leaving any holes?
• What impediments do you have to completing your section(s)?
• Did you get the help you needed to complete your section?
• If your proposal section is not complete, who is going to complete it and when?

To get people to show up prepared

In general:

• Have you read the RFP and the capture plan?
• Have you cleared your schedule to work on the proposal?
• Do you have any issues you need to raise at the beginning?

When reviewers are showing up unprepared at the start of a proposal review:

• What have you done to prepare for this review?
• Have you cleared your schedule to focus on the review?

When your reviewers are executives with competing priorities but outside your control:

• Can you clear your schedule sufficiently to thoroughly review the proposal?
• If you can't thoroughly perform the proposal review, who can?

To apply lessons learned
When the last proposal involved staff with competing priorities completing their assignments late, consider questions like:

• What is your plan for dealing with expected competing priorities?
• Who else might have relevant knowledge and be able to help with completing your section?

To meet expectationsWhen people aren't fulfilling expectations during the proposal, you should do everything possible to ensure that the expectations are clear. Questions like these can help:

• Have you discussed your expectations related to your proposal assignment?
• Do you have any exceptions or require any clarifications about the expectations for your proposal assignment?
• Are there any issues related to completing your proposal assignment?

To plan before they write

• When Proposal Content Planning is formalized, then it is an assignment of its own. But you can subtly remind people of its importance with questions like:
• Are your Proposal Content Plan contributions sufficient to prevent revisions later?
• Do your Proposal Content Plan contributions add up to the proposal the company would like to submit?
• Do your Proposal Content Plan contributions describe a proposal that is competitive enough to win?

When Proposal Content Planning is informal or new to a company, you can coach people through it by asking questions like:

• What do you plan to make your section about?
• What points do you plan to prove?
• What differentiators will you highlight?
• What options are you considering?
• What steps, details, or components do you plan to include?
• What do you need to say beyond RFP compliance to win?

To apply proposal quality criteria
To remind writers about the proposal quality criteria:

• Before writing, have you reviewed the proposal quality criteria?
• After drafting your section, have your reviewed the proposal quality criteria before submitting it and calling it complete?

To remind reviewers about the proposal quality criteria:

• Before reviewing the proposal, have you read the proposal quality criteria?
• Have you used the proposal quality criteria to ensure that nothing has been overlooked and that you achieve the goals of the review?

To change behavior

During proposal, people sometimes do, say, act, or behave in ways that are counterproductive. If this is showing up habitually in a lot of proposals, you can use the questions you ask to try to minimize the behavior by asking questions like:

• Are you bringing issues up at the proposal meetings quickly enough to prevent them from becoming major problems?
• Have you reviewed and discussed your expectations related to the proposal?
• Have you made sure that other people’s expectations related to the proposal are accurate?
• Are you fulfilling other people’s expectations during the proposal? 

Implementing this approach

In writing this, it occurred to me how many of these are conversational. Some are questions I would have asked in person. You can build those into your process. 

If you create before/during/after events for achieving each goal in your proposal process, you can pre-write emails with reminders and subsets of questions delivered at the moment of need. You can use them for conversational questions, or even to trigger real conversations. Smaller lists of highly relevant, just in time questions will get much better attention than large comprehensive lists delivered at the beginning of the proposal.