Win or Lose: Implementing a Post-Deal Review Process

Last verified Apr 26, 2021

One of my favorite activities to work on as a product marketer is win/loss reviews. Every time an Account Executive closes an opportunity in Salesforce—either Closed Won 🥳 or Closed Lost 😔—we ask them to introduce one of our product marketing managers (PMMs) to their main point of contact to do a win or loss review. It’s a chance to get unfiltered feedback from prospects and future customers about our messaging and positioning, sales process, product offerings, and more to help us learn and grow as an organization.

These conversations are easily some of the most interesting and informative ones that I have as a product marketer. In a lot of cases, they’re so interesting to the prospect that they ask for a copy of our questions to share with their own teams internally!

So, to make it easy for other product marketing teams to implement a win/loss review process, I thought I’d share how we do it at Guru, including some templates to copy:


What is a win/loss review?

Essentially, a win/loss review is a candid conversation between a prospect and a product marketer about the evaluation process, with the goal of obtaining honest and actionable feedback. These conversations are opportunities to speak directly with customers that most organizations don’t usually get.

Such a review might sound like a one-sided ask to make of new customers or uninterested prospects, but there is value in these conversations for both parties. Your prospect has just spent weeks (if not months) evaluating your software; even if they have decided not to sign on with you, engaging in a loss review helps give all their hard work meaning. They might have strong feelings about certain aspects of the process that they want to bring to your attention.

If they are buying your software solution, then they likely had a good sales experience and want to share that feedback as well. Or, maybe they have a feature request and want a fast track to the product roadmap. People like to feel heard, so providing the opportunity for a prospect to be the expert and share their opinion can end up feeling more like a give than a get.

It’s worth noting that not every opportunity makes a good candidate for a win/loss review. The goal of these conversations is to learn what made the difference for a prospect so you can use that information to learn and grow. In cut-and-dry wins and losses, there’s not much to learn. For example, if an AE qualified out an opp because they didn’t fit in your ICP, it’s safe to say you don’t need a loss review. Or conversely, if a deal was a slam dunk and closed in record time because the champion used your product at a previous company, you probably don’t need a win review. Your AEs should know better than anyone if a given opportunity will present actionable learnings, so have them use their discretion in scheduling win/loss reviews.

We’ve documented the purpose of win/loss reviews at Guru for all employees to better understand why this is a critical step in our sales process and what to expect from these conversations:

Why win/loss reviews are valuable

It’s also important to prove why win/loss reviews are valuable. Sales reps are not going to be as inclined to introduce their champions to PMMs (especially in the case of a loss) if they don’t believe that there is value in it for them. That’s why it’s crucial to outline not only the things your PMM team expects to learn in a review, but what they mean to do with that information. Sales teams, product teams, and marketing teams can all learn and evolve thanks to prospects’ evaluation experiences, so it’s critical that the PMM team share insights with those teams and close the loop when those insights make a difference on internal processes.

Win/loss review process

Once your organization understands the purpose and value of win/loss reviews, the next step is to build this exercise into your sales process. A good way to do this is to make it a part of reps’ Salesforce workflow. At Guru, when a rep updates the opportunity stage in Salesforce to Closed Won or Closed Lost, one of the Guidance for Success tasks instructs them to “Connect your champion with the appropriate PMM team member to schedule a win/loss review.”

Making the introduction

It also helps to make the process as easy as possible for reps to execute on. To that end, we have win and loss review introduction email templates easily accessible in Guru. Reps can copy and paste product marketing-approved language into an email to their champions to get the ball rolling. From there, the PMM who is copied on the email can chime in to provide additional context and schedule the review. Here’s the language we use at Guru:

It’s important to note that after the intro email, the sales rep’s involvement with the review process ends. Prospects provide the most candid feedback when speaking to someone who wasn’t directly involved in the sales process, so make sure your reps are clear on why it’s imperative that they not join the call.

👋To be excruciatingly clear: you are not leaving sales reps off these calls to get the dirt on their sales skills. This is not an exposé! You are simply bringing in an objective team member to capture unfiltered feedback.

Setting internal expectations

To make sure that everyone is clear on their individual responsibilities and expectations during the win/loss review process, (sales reps and PMMs alike) we have created the following Card:

Interview questions

Once everyone knows what’s expected of them, it’s time to get to the meat of the matter: the interview questions. These conversations are always going to be fluid and PMMs should never feel like they need to stick to a set script, but it helps to have a list to refer to. Check out our full win/loss review questions template below:

We use the same list of questions for both win and loss reviews because we want to hear all prospects’ thoughts on these key topics, regardless of the outcome of the evaluation. However, based on whether it’s a win or loss review, PMMs may focus more intently on some categories and not others.

Focus on the conversation

The final key element to our win/loss review process at Guru is a conversational intelligence component. The insights shared by prospects and customers can be as good as liquid gold, and we don’t want to miss a single drop. By recording calls with a conversational intelligence tool like Chorus or Gong, your PMMs can focus on the conversation instead of furiously scribbling notes. Our PMM team at Guru listens back to every review and pulls out high-level insights to share with the organization, along with the call recording itself so that others can get a first-hand experience.

Sharing knowledge from win/loss reviews

After you’ve completed a win/loss review, share those insights far and wide! Remember, it’s important for the sales team to see what came out of that intro they made. Especially in Closed Won opportunities, sales reps may be wary of making too many “asks” of a new customer, so being able to show the outcomes of these conversations (for both your organization and the prospect’s!) is key.

We house all of our win/loss reviews in Guru so that the entire team can access them at any given time. Sales reps can revisit their own opportunities to learn and improve, sales managers can get a feel for trends in recently closed opportunities, product teams can better understand which features are making or breaking deals... The list goes on! By making the recordings and any high-level notes from win/loss reviews widely available, the insights the PMM team gleans can serve the greater good.

Our PMM team also proactively shares key insights with the appropriate stakeholders. Here’s how we relay critical information internally:

#Winning, even when we lose

In an ideal world, every prospect your sales team engages with would convert into a paying customer and have nothing but positive feedback about your messaging, sales process, and product. In the real world, that won’t always be the case. But for the opportunities that don’t go your way, getting the prospect to do a loss review can still end up feeling like a win.

We hope you use these templates to spin up a win/loss review process at your organization. We rely on Guru to help us capture and share the knowledge we glean from these conversations, and encourage you to do the same! Get your own win/loss process spun up in Guru with our free Starter plan.