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How to create a win strategy cheat sheet

If you want proposals that reflect strong bid strategies, a little inspiration can help!

Instead of reinventing the wheel every time and having every team start from scratch figuring out what their win strategies should be, you can create a cheat sheet that helps them figure it out faster.

The goal is not to identify the wording or control future responses. The goal is to help people more quickly identify the strategy, the approach, or the positioning that fits their particular circumstances. They’ll have to come up with the wording based on the specific issues they need to resolve.

See also:


  • Management plan. What management structures and procedures do you typically respond with for different types of projects?
  • Offering features and benefits. What features do you typically include and what benefits do they typically deliver? You can always expand them later and tailor them for a specific bid.
  • Pricing. How do you typically try to position on pricing, and what strategies do you typically follow in various circumstances?
  • Terms and conditions. When the customer requires a certain term or condition, how do you typically respond?
  • Staffing. Like your offering, what are the features and benefits of your staffing? What are your typical approaches to staffing?
  • Schedule. Too short, too long, or just right? What strategies do you typically employ for various scheduling contingencies?


Circumstances and contingencies related to:

  • Customer attributes, preferences, and issues. While each customer is different, they often share some similarities. Which customer attributes, preferences, and issues can you anticipate and how do you typically respond?
  • RFP requirements and evaluation criteria. Some RFP requirements appear frequently. Sometimes the evaluation criteria emphasize this or that, but you can anticipate both. Sometimes RFPs have problems, like when they lack detail or are ambiguous. What do you typically do in response to the things you often see in RFPs?
  • Competitive environment. You may not know the names of the competitors on your next pursuit, but you may know the types. You may not know whether you’ll be on top or the underdog, but you can anticipate being both at some point. How do you position or what do you typically do in each competitive circumstance?
  • Team composition. Sometimes you want a big team. Sometimes you want a little team. And sometimes you go it alone. In each circumstance, you need to explain why and ghost your competitors. And many of the circumstances you can anticipate.
  • External issues and trends. Things go up and things come down. The pendulum swings. People react. Things change. What should you do when faced with things you can anticipate coming up sooner or later?
  • Other. Sometimes things are unpredictable or something completely new comes up. By its very nature it can’t be anticipated. And yet what you do when faced with something new, both good and bad, might be anticipated.

Within each topic and circumstance, identify the things you can anticipate coming up and what strategies to employ or ways to position your company and offering in each. Many things come in pairs (big/small, centralized/decentralized, fixed/variable, positive/negative, etc.), so remember to address both possibilities. Basically you’re trying to help people out by telling them that you’ve seen something before or thought something might happen and here are some approaches that may or may not fit. Even when they don’t fit, they can help people zero in on something that does more quickly.

One way to approach this is to make it an attachment to your company's Strategic Plan and update it annually. While a Strategic Plan normally deals with positioning at a fairly high level, a Win Strategy Cheat Sheet can show how to connect the high level positioning to what people will face on a day-to-day basis.

A little bit of inspiration goes a long way. And since we’re talking about win strategies, anything we do that strengthens them increases your win rate.


Let's discuss your challenges with preparing proposals and winning new business...

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Carl Dickson

Carl is the Founder and President of CapturePlanning.com and PropLIBRARY

Carl is an expert at winning in writing, with more than 30 year's experience. He's written multiple books and published over a thousand articles that have helped millions of people develop business and write better proposals. Carl is also a frequent speaker, trainer, and consultant and can be reached at carl.dickson@captureplanning.com. To find out more about him, you can also connect with Carl on LinkedIn.

Click here to learn how to engage Carl as a consultant.

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