TL;DR

• Successful win-loss programs require full company buy-in and a culture of continuous improvement.
• All companies face challenges when creating and implementing a win-loss analysis program.
• One of the best ways to navigate these challenges is to engage key stakeholders—including senior leadership—to support and promote the value of win-loss insights.
• Another way is to use win-loss feedback to drive cross-functional collaboration and implement solutions to improve customer experience.
• The goal of win-loss analysis is to drive positive change and increase revenue by aligning teams and adapting to buyer preferences.

_________________________________________________________________________

Let’s start with the facts. 

The most successful win-loss programs have full company buy-in. At these companies, everyone’s in the same boat rowing toward a common goal. Everyone—from the C-suite down to the newest sales reps—leverages feedback to better align themselves with their customers’ stated needs and priorities. They’ve cultivated a healthy culture of continuous improvement and transparent learning. 

And because of this, they win more deals.

Intuitively, it makes sense: The feedback comes directly from their customers, so give the people what they want! For many companies, however, developing their own impactful win-loss analysis program is a wish rather than a reality. What do those companies need to do to get to this Utopian state? 

Don’t let logistical bottlenecks slow you down

This is the point when we need to acknowledge a second fact: EVERY new win-loss analysis program will experience significant bottlenecks in both execution logistics and in the journey toward effectively consuming and acting on the insights they gather. On either side of that coin, win-loss practitioners will encounter hurdles—such as problems they can’t solve alone; detractors, nay-sayers, and people who won’t make time to help; conflicting company policies; and more. 

Some of the most common challenges include …

Logistical bottlenecks:

• Bad CRM hygiene or lack of buyer contact information
• Lack of permission to contact buyers
• The individuals necessary to creating outreach lists won’t help
• Difficulty managing outreach and scheduling
• Low participation rates

Feedback delivery bottlenecks:

• No executive engagement
• Win-loss program owners lack the bandwidth and/or tools to analyze the feedback
• The program goals are too narrow in scope
• Bureaucracy
• Insufficient strategic context

In short: CRM data is notoriously muddy, sales teams always have a reason why the timing is bad to reach out to a buyer,* and qualitative feedback is supremely difficult to parse and distribute effectively.

*This is usually a fear-based excuse.

Even after the interviews are flowing in, win-loss program owners often feel like the dog who caught up to the car, unsure about what to do next. The answer at every step of the way is to seek broader stakeholder engagement. 

Below are several steps you can take to engage key individuals throughout your organization.

Step 1: Set up your win-loss program & start getting useful feedback

The first nut to crack is the logistics problem. No win-loss program will succeed if you can’t actually get buyer feedback. 

So if you’re struggling, ask yourself: Where is your process breaking down between when a deal closes and when you’re conducting interviews? Is it due to any of the reasons outlined above? Is it something else? 

And then ask yourself: Who’s the best person to solve the problem? Sometimes it will be you, but in many cases, it’s a senior executive.

Senior leadership can mandate feedback for all closed deals, overruling individual rep concerns. And they can set policies requiring reps to actually add contact data into the CRM system when they create an opportunity. They can also message the value and importance of win-loss analysis to the company at large so people stop deprioritizing your requests. 

They can do all these things because people listen to them. They’re in charge!

This is why the best win-loss programs are top-down initiatives. If your win-loss program didn’t start out that way, however, you’ll need to win over your leadership team and start getting them involved first. Daunting? Perhaps. But certainly possible.

To gain their support, you should start by first identifying the specific individuals on your leadership team who can benefit most from powerful win-loss insights.

What are their names? How long have they been with the company? What key initiatives are they currently working on? Do you already know them personally? If not, do you know someone who does? Typically, you’re seeking: 

• Sales leaders
• Rev ops leaders
• Product leaders
• Customer success leaders
• Product marketing leaders
• Competitive intelligence leaders

Step 2: Make sure key stakeholders understand the benefits of win-loss insights

Next, you’ll need to find out if they’re already aware of the win-loss program. If so, how do they feel about it? Are they neutral, a promoter, or a detractor?

If they’re already aware and are a promoter, GREAT! Have them open doors to conversations with other department leaders or higher-ups, and ask them to support you in communicating the value of win-loss analysis. You’ve found someone who can punch harder than you can—let them fight the fight!

But if they’re neutral (or worse—a detractor) you’ve got some work to do. What matters here is finding a way to tie the individual to the outcome, making sure they can see how win-loss insights will benefit their team—and them personally.

If your program is already underway and you have some feedback in hand, leverage those previous efforts. Stakeholders respond more favorably to something tangible—qualitative data they can read and use—over abstract concepts of value. As a program builds momentum, proactively showcasing in-depth, impactful feedback can bring even the most resistant among them on board. 

Specifically, you should try to leverage any:

• Win-back opportunities
• Very strong loss reasons with constructive criticism attached

Win-back opportunities (interviews where buyers share that they’re still open to purchasing your product if certain conditions change) offer a particularly effective hook to gain a leader’s interest. Every leader wants to know where to find untapped revenue! 

This gives them a chance to look good! (Don’t worry, you’ll look good too.)

Feedback relating to strong, deal-breaking loss reasons is also effective—especially if the customer offers suggestions on how the outcome might have changed if specific things had been different during the evaluation. Such feedback is common, and if the loss reason is specific to the department or vertical your detractor oversees, all the better. 

Nobody likes egg on their face, and if buyers are telling them how to avoid that mess happening again, you’ll see ears start to perk up.

But even if you don’t have feedback yet, you can still get them involved. The goal is to help them feel like they have skin in the game. Ask them about their most pressing issues—the top three work-related things that keep them up at night. Find out what hypotheses they have for why they’re winning and losing, and then tell them you’ll find out if your buyers confirm their beliefs (or if they’re off the mark). 

You’re literally their conduit to a source of truth, so offer them answers! Once they see a path to real results, their interest will be piqued—and you’ll be on the path to winning a new champion.

Step 3: Don’t let yourself get stuck

If you don’t have a direct means of interacting with your company’s most senior leaders, you’ll have to rinse and repeat this process up the ladder. 

If you get stuck on your champion-building, try to move horizontally. People are generally most comfortable engaging at their own seniority level, or maybe one level up. By the time you get to C-suite conversations, hopefully you’ve caused a groundswell of people advocating for win-loss analysis!

Step 4: Use win-loss insights to connect departments, drive change

At this point, let’s imagine that you’ve succeeded in building cross-functional support for your company’s win-loss analysis program. Congratulations!

Broad stakeholder engagement is ultimately how you maximize ROI from your win-loss initiative. No single person has a monopoly on ideas and solutions. So while people need to use the data to meet their own needs and workflows, cross-functional engagement is how many of the best revenue-driving solutions get built. 

Consider this common scenario: Your customer didn’t feel like they could build a strong enough business case to convince their senior budget holder to buy your product.

Digging into the feedback, you discover that they wanted help from the sales team to understand the value prop more clearly. They admit that the sales team tried to explain it to them, but it sounded confusing, and they wished they had something visible to look at—or maybe a case study to reference—to make it make sense. Oh, and the pricing wasn’t very clear anyway. 

Let’s also imagine you’ve seen this same feedback across 15 different interviews.

A solid solution addressing these problems may require new marketing collateral, sales enablement training, and maybe even a new pricing model so your buyers can more easily tie cost to value. 

In short, it requires alignment from teams across your organization.

When you have stakeholders in each of these departments engage in consuming win-loss insights, your company can quickly and efficiently solve your challenges and adapt to buyer preferences.

After all, the purpose of win-loss analysis was never to simply collect feedback—and it certainly wasn’t to point fingers and play the blame game. Rather, it’s meant to drive timely, positive change and to help your company make more money.

Which is something every stakeholder should be willing to get behind.