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Improving your win rate by asking the right questions

With 8 examples of how it works

You need to do this, you need to do that. Everyone already seems to know what they should be doing to increase their win rates. But they have many excuses reasons for why they are not. Those reasons usually boil down to other people not doing what they should.

Improving your win rate requires changing other people’s behavior. Instead of creating a process based on steps and then using carrots and sticks to get other people to change, try building your process around asking questions. You can change people’s behavior simply through the questions you ask.

Pre-RFP examples

See also:
Information advantage
  • Instead of telling people to establish customer intimacy, try asking them, “What is your information advantage over your competitors?” If they don’t have customer intimacy, they’ll have difficulty answering. If they get caught unable to answer, they’ll have some incentive to gain customer intimacy on the next bid.
  • Instead of telling people to describe your win strategies or prepare some (usually watered down) themes, ask them, “What differentiates our offer?”  If they are struggling to identify your differentiators, they’ll start strategizing how to position your company on the next bid to have some real differentiators.
  • If people aren’t discovering pursuits early enough ask them, “What have you done to influence the RFP?” If they are finding pursuits by looking for RFP releases, they will not have done anything to influence the RFP.
  • If people are chasing any pursuit they find ask them, “How does the pursuit relate to the company’s strategic plans?” This is a double whammy. First, the company has to do some actual strategic planning. Then the folks chasing bids have to actually pay attention to it.

Proposal examples

  • Instead of telling people to plan their proposal, try asking them, “Has your Proposal Content Plan been reviewed?” It’s kind of hard to review something that doesn’t exist.
  • Instead of telling people to create an RFP compliant outline ask them, “Will your outline meet the customer’s expectations?” This subtly forces people to make their own opinion secondary to what they think the customer wants, such as what they itemized in the RFP instructions. It also can force the use of a compliance matrix. This is also a great example of how you can use questions to not only get people to do things, but to change their behavior.
  • Instead of telling people to follow the style guide that they usually ignore, try asking something like, “Is the proposal written from the customer’s perspective?” To answer this, they have to know what “writing from the customer’s perspective” means. You can do this with any writing style or preference that you feel strongly about. Getting people to change their writing style can be challenging. Telling them to do it has a low probability of success. But asking them a question that forces them to assess what they’ve done may just work.
  • Instead of talking about an opportunity at the kickoff meeting, try working through a script of questions. Anticipate what your proposal writers will need to know and turn it into a proposal input form. Then see what those pursuing the lead can answer. Correlate their answers with your win rate and you’ll be able to quantify the importance of starting proposals with an information advantage. By using the same script every time, you can train the business development function regarding what information you need to write a winning proposal. See if you can get them to give out a copy of your script at the beginning, when they decide to pursue a lead.


If nothing else, this approach will dramatically improve your company’s ability to weasel word around questions it can’t answer. If you win rate is really low, this alone might improve it! Seriously folks, I’ve seen how lots of companies weasel word things, and the quality of the weasel wording could be greatly improved. Of course, it might be easier just to find answers to the questions.

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More information about "Carl Dickson"

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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