56 examples of how combining the power of inquiry and perspective can help you win your proposals

People working on a proposal often ask themselves what they should do when instead they should be asking other questions. Asking the right questions will tell you what you need to do, what you should say, and how you should present It. 

It’s important to realize that working around the questions you can’t answer informs your bid strategies just as much as the questions you can answer.

One of the secrets to asking good questions is to have a sense of perspective. Questions can help you see things from other points of view. Winning proposals requires being able to see things from the customer’s perspective. But there are always other stakeholders who matter as well. Their perspective can impact the customer’s decisions.

The following list of questions is a combination of inquiry to get the information needed to write a great proposal, and perspective to account for the impact other people’s perceptions, motivations, and needs might have on whether you win or lose. 

1. What matters to the customer?
2. Do they realize everything that should matter regarding what you are proposing?
3. What matters to the customer’s stakeholders?
4. Do the stakeholders’ goals and the customer’s goals align?
5. How much accommodation does the customer give to the needs of its stakeholders?
6. How does what you’re proposing align with the customer’s goals?
7. How does the customer make decisions?
8. Who will be involved in making the customer’s decision?
9. What challenges does the customer face?
10. What challenges will you face if you win?
11. What assumptions has the customer made?
12. What does the customer not know?
13. What other alternatives does the customer have?
14. What would I do if I was the customer?
15. What would the customer do differently if they could?
16. What makes the customer feel comfortable?
17. What level of detail do they need?
18. What information does the customer need to make their decision?
19. What do their stakeholders want from their decision?
20. How would you make the decision if you were them?
21. What is driving the customer’s schedule?
22. Is the schedule realistic?
23. How does that impact what you propose?
24. Should you be concerned about schedule risk and how can you mitigate it?
25. What do you want to know about the customer, opportunity, and competitive environment?
26. What do you already know?
27. What can you find out?
28. How do you work around the things you don’t know?
29. How does that impact what you recommend to the customer?
30. How will the customer perceive what you are proposing?
31. Are there any conflicts between what the customer does and what they say?
32. Can you believe what the customer has said, even (especially?) if it was with good intentions?
33. Are there any conflicts between what you do and what you say?
34. Can the customer believe what you say, even (especially?) if it is with good intentions?
35. Can the customer believe what your competitors say, even (especially?) if it is with good intentions?
36. How should the conflicts impact what you are proposing?
37. What are the various opinions about each feature that you are proposing?
38. What is the customer’s opinion about the features you are proposing?
39. What are the customer’s limits?
40. What are your limits?
41. What is the price to win?
42. How does the customer perceive value?
43. What does the customer consider to be strengths and weaknesses?
44. How does what you are planning to propose align with their perception of strengths and weaknesses?
45. How many different ways are there to interpret the RFP requirements?
46. Which one is the customer’s interpretation?
47. What is the customer’s tolerance for risk?
48. How many different voices and agendas does the customer have?
49. What will it take for the customer to trust you?
50. What are you saying or proposing that could work against the customer trusting you?
51. How could you change what you are proposing to make it more trustworthy?
52. Do you trust the customer?
53. Which does the customer rely on more, people, processes, or tools?
54. What do you rely on more, people, processes, or tools?
55. What would Chat GPT say?
56. What will your competitors say?

Inquiry gathers information. Perspective ensures you gather all of the relevant information. To fully engage both you must integrate them into your proposal efforts. Proposal writing isn’t a simple process of picking words. Or even about picking the right words. Proposal writing is a process of understanding other perspectives so well that you can fulfill someone else’s needs through your words well enough for them to make a decision in favor of what you are recommending.