How do you create an ongoing win/loss analysis?

I haven't seen a method per se at my previous companies, but going forward, ideally a internal dashboard, collaborative wiki which has the details of why we won, why we lost would help everyone. I have not seen a good internal collaboration tool which also has a website/wiki kind of look / feel for editing/posts etc. Slack not so good, I am realizing. Linking this to SFDC would also be helpful. Ability to research by segment, region, competition etc. Remember that every region, Win/loss might be for different reasons. 

I recommend a weekly cadence of reaching out to prospects that have completed deal cycles in the prior week. It's okay to skip a week if priorities or holidays intervene.

Interview those who respond. Ask consistent questions and don't hesitate to go "off-script" if you are learning something interesting. Report in a way that makes sense to your organization.

Twice a year, launch a broader win-loss survey to the prospects that never responded to weekly outreach. Collect the data from the survey and all your interviews into a presentation you can deliver internally. Be careful to understand your company's culture and don't offer advice to other teams if they will react negatively to it.

NEVER let sales reps get involved in a win-loss process, but make sure they know they can trust you. I do this by taking positive quotes from any win-loss call and sharing them by email with the sales people who earned the praise, along with their managers up to the CEO. Everyone appreciates this. Otherwise, all win-loss reporting is totally anonymous and I will not identify companies or reps internally with anyone other than C-level executives.

First, don't think of Win/Loss as a project to be done at certain times of the year. It's like a lifestyle change that has be worked into your organization's priorities (like exercise or losing weight). Second, salespeople should never conduct W/L interviews. Never. The purpose of W/L is to figure out how buyers make a decision (in the aggregate) and salespeople are not the best resource in this regard. To get a sustainable W/L program you need to bring something to the table: reasons why you lose deals and recomendations to fix it. Once your organization experiences the benefits of W/L it will stick. I wouldn't worry so much about the infrastructure as much as collectng the insights. --D

W/L is a market research tool. It's not a sales performance tool. The goal of W/L is to understand - over a set of sales engagements - why you win, why you lose, who is involved in a buying decision, and how they make that decision. 

W/L interviews should occur as quickly after the win or loss as possible, or you begin to lose important details. Salespeople are not the target of a W/L interview. Customers are. 

W/L questions are open-ended and designed to flush out behaviors, biases, preferences, and methods. The analysis reveals patterns that are used to improve content, sales tools, messages, and sales enablement. 

For continuous win/loss insights, consider combining a once-per-year formal win/loss analysis (eg interviews and scorecarding with decision makers) with quarterly win/loss reviews. During the quarterly reviews you're with the sales team, debriefiing on each deal to find win or loss causes. To those reviews, bring as much deal data (prospect demographics, competitive, etc) as you can from your CRM to identify patterns. You act as the voice of the buyer (VOB), providing a counterpoint to the internal perspective, leveraging what you learned during the once/year buyer interviews.

Creating an ongoing w/l analysis program can be exciting. There are many things to consider when building a program. I have outlined three below to get you started. 

1. Gain stakeholder buy-in (leaders in marketing, sales, product, competitive)—Reach out to each leader to ask them what they would like to learn through the program. By doing this, you're gaining their buy-in and they become that much more interested in the outcome.

2. Craft an interview guide and online survey—Using the stakeholder input, you can build a few data collection tools that align to their needs. It's important to have a guide for the interviews. With that said, don't be worried about going off script to probe into areas of interest. After all, we're looking for the buyer to tell their story.

3. Build you target list—Set some general criteria for your target list so that you can zero in on those companies that are most qualified to participate. At a minimum, we recommend interviewing people within 90 days of the decision, those that went through each of your sales stages, and competitive scenarios.

4. Leverage tools—Consider using tools such as SurveyMonkey or Qualtrics to collect data via an online survey, Fuze or GoToMeeting for your conference call bridge and call recorder, and find a transcription service that works well for you such a Chorus.ai. 

Best of luck! Happy to chat if you have more questions.