14 ways to make proposal decisions based on too little information

Our instincts betray us. Playing it safe will lower your chances of winning. In our regular life, sometimes playing it safe is necessary for continued survival. But in order to have a superior, winning proposal, it must first be different. Different in a way that no one else can match. You don’t get there playing it safe.

1. Anticipation and research. What professionals do is try to anticipate the issues, conduct research, and start the proposal already informed with your mitigations and strategies. Yeah, doing your homework is always best. The strategies below are mainly for procrastinators, outsiders, and underdogs.
2. Make assumptions and document them. This is a classic engineering response. It’s not very accommodating and inflexible. Those traits can lower your chances of winning. If you had an extended amount of time you could try experimenting with different sets of assumptions. But the challenge here is to make winning decisions with the information you have now.
3. Avoid rules. As humans, we like the simple certainty of rules. We like to know exactly what to do and what will happen. But this requires knowledge in full. We may not like it when things are uncertain, but we often live in an uncertain world. The problems caused by rules being applied to circumstances they didn’t anticipate can be major problems. When you don’t know what you need to know, look for solutions based on criteria and incentives over hard inflexible rules. But keep them simple because people crave certainty, even when it's irrational.
4. Identify your risks and prioritize mitigation based on severity. If an analytic approach is the way to go, you can itemize your issues so they can be tracked and resolved. Otherwise, you’re just frantically reacting instead of moving forward deliberately.
5. Seek options. If you can do it more than one way, then offer the options. Explain the pros and cons and let the customer choose. Better yet, arrange the options to increase efficiency and effectiveness. Start with the foundation and build on it. 
6. Manage decisions over time. The reason Agile and Spiral methodologies caught on was that customers recognized that they often don’t know all the details on day one. For projects where decisions get made over time, your approach to managing those decisions can be as important as the technical details for implementation. Under some circumstances, a quick decision that might be wrong but can be corrected is better than waiting for certainty. Let the circumstances of the customer’s environment and the nature of the project determine how you will manage those decisions, and use your proposal to demonstrate your insight regarding how to make them. 
7. Incentivize the customer. If you have a preference, or concerns like scalability, offer a business and pricing model that incentivizes the outcome you desire while giving the customer flexibility. This is only possible when the customer gives you flexibility in how you construct your pricing model. But for some bids, offering a superior pricing model can matter more than the technical details of your offering. 
8. Positioning. Position your approach against the possible customer preferences and concerns so that you show insight into the possibilities while covering them all. Many offerings can be applied in different ways, with different outcomes and characteristics. If it’s all the same to you, then offer the customer choices and help them make those choices. Along the way, you’ll not only be showing flexibility, but also insight. 
9. Profiling. If you don’t know the customer or what they prefer, perhaps you can envision what someone like the customer might prefer. You might create multiple possible profiles. And then design your offering and pitch to appeal to each of them. It’s bad when profiling is used in a restrictive way. But if you can use it to enhance the support you offer to someone new, it can be beneficial to them.
10. Empathy. What would you care about if you were the customer? If all else fails, write to that. What would matter to you if you were in their shoes and dealing with their issues? What kind of help and support would you find beneficial?
11. Alternative visions. What do you think should matter to the customer? If you really, really don’t know what the customer cares about, offer them your own vision and see if they go for it. It’s a high-risk strategy, but it can work. Think about how often you are indecisive or under what circumstances you might appreciate a suggestion for a completely different approach. If your vision is that good, it might just be worth ignoring the customer.
12. Avoid muddying the waters. Overlapping issues and unknown variables compound the problem. Try to achieve clarity on as many as possible so you only have to guess about one unknown at a time. For example, if you are dealing with uncertain staffing, aren’t sure about your priorities, don’t know what the customer wants, and haven’t given any thought to what your win strategies should be, you’re going to have difficulty untangling all that. If you had answers to all of it except knowing what the customer wants you’d have a fighting chance at coming up with an approach that has a chance of working.
13. Differentiate. Get out of the box. Be a contrarian. Go where the other competitors won’t. If there is something better, it will be hiding there.
14. Don’t fear what you don’t know. Don’t retreat into your comfort zone because you are afraid of getting things wrong. What you don’t know might be an opportunity to come up with something better than what those who think they do know will put on the table. They might be more in the dark than they realize. A solution that addresses the challenges you face has a good chance of being a better solution than one that didn’t recognize the challenges at all. 

The last thing you want to do is to defer to authority. This is replacing strategy with CYA. The real problem with it is that the only authority that matters is the customer. They will decide whether you win or lose. So they are who you need to appeal to. And if you don’t know what will appeal to them the most, you need a strategy to maximize your chances. 

And if you do lose, it’s better to have given the customer a strong proposal that made them think about it than it is to have given the customer an ordinary, forgettable proposal that took no risks and held back because of what you didn’t know.