Running a Win/Loss Program Will Get You Promoted

Good Win/Loss data is both scarce and valuable. Everyone in leadership wants to to see the insights. As the person managing the program, your profile within the company tends to rapidly elevate.
by: 
Brennon Garrett
Kaptify Founder
Brennon has conducted thousands (and thousands) of Win/Loss interviews. If he doesn't hold the world record for most Win/Loss interviews ever conducted, he's at least a contender.
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The Big Opportunity (for your career)

When I ask people why Win/Loss programs are valuable they say things like "we'll gain key insights into why we're losing" or "we'll increase our win-rate and revenue". And yes, those things are true. But there’s another really valuable that often happens, but it doesn’t happen to the company, it happens to the person running the program. I almost never hear anyone talking about this, but we’ve observed this phenomenon over and over again amongst our clients:

The person who builds and runs the Win/Loss program usually starts shining pretty brightly within the company, and eventually gets promoted.

If you’re like most people, the idea of running a Win/Loss program sounds like a lot of work. And if you’re running the entire program by yourself, it is a lot of work. But what most people overlook is the impact it can have on your career if you do a good job. A well run program elevates your visibility within the company, it increases your status, and it makes you “in demand” across most teams. Here's a list of the valuable things that flow to the person running a Win/Loss program:  

More interactions with Executives

These interactions increase because executives start realizing that you’re the only person at the company who has a deep understanding of key revenue questions like “why we’re losing deals”. Usually it’s the sales team who tries to answer that question, but as soon as you start doing Win/Loss interviews at scale, you quickly realize that the answers provided by the sales team are incomplete at best, and often just wrong altogether. And as soon as you start sharing your data with the executive team, they start realizing it too. And that's when some interesting things start happening to you, namely:

You start getting regular invites to join executive meetings. And your opinion really starts to matter.

And because your Win/Loss data is both new and highly impactful to revenue, executives tend to be pretty engaged with you during meetings. They start viewing you as the owner and distributor of these insights, and they start asking for more of your time. As you spend more time in meetings with executives, your visibility and status naturally start rising within the company.

More interactions with team leads

Win/Loss data generates insights for a lot of different teams. In addition to the C-suite, the insights directly impact Product, Sales, Support, Customer Success and Growth/Marketing. As the person who runs the Win/Loss program, you become the go-to person for the leaders of all of these different teams. The Head of Product wants to know what people are saying about certain product features. The Head of Sales wants to know what people are saying about the sales experience. And the Head of Marketing wants to know how to attract more customers.

As people across the company start relying on you for insights about their departments, your communication with senior leaders increases and your relationships deepen.

And since you’re the person running the Win/Loss program, everyone has to go through you to watch the interviews or see the insights . You're suddenly sitting in a new and really valuable position within the company.

You hold the keys that unlock new revenue

By running the Win/Loss program, you become the resident expert on the most valuable questions facing your company. When the executives are making company level decisions trying to drive more revenue, you’ll often have a much deeper understanding of the decision than the executives themselves do. When the product team is considering whether to build a new feature you’ll be able to make a real contribution to the decision making process because your perspective is uniquely rich and data-driven. Your opinion on any number of issues can help nudge teams in the direction of revenue growth, and people start to notice.

Running a Win/Loss program is like have a machine that prints maps to where new revenue can be found. If you’re involved enough in the interviews and analysis, the machine produces lots of these little maps (and you own them).   

Most companies regularly make high-stakes decisions without great data (“should we decrease pricing?”, “should we build X feature?”, “should we change the length of our free trial?”). With enough Win/Loss data, you’ll quickly become an authority on all kinds of important questions. And over time it becomes apparent to most teams that they should get your advice before making key decisions.

Win/Loss data is really valuable (and you own it)

Most teams have mountains of quantitative data (analytics, business intelligence, etc).  But well-structured qualitative data (customer interviews) is pretty scarce. To understand why Win/Loss data can be so valuable, we need to clarify the fundamental difference between quantitative data and qualitative data in general:

What vs. Why
Most data-sources at your company are quantitative and tell you “what happened”. Conversely, Win/Loss data is qualitative and tells you “why it happened”. Understanding “what” happened points out the problem while understanding “why” it happened leads you to the solution.

Revenue growth happens when you figure out the right solution. That's why a single Win/Loss insight can sometimes be worth millions of dollars.
Win/Loss data is really persuasive (and you own it)

Quantitative data (bar charts, graphs, statistics) engage with the analytical parts of our brain and tend to take a lot of executive function and reasoning skills to interpret. Win/Loss data on the other hand is qualitative and engages directly with the story-telling part of our brains.  That's important because us humans are story-telling creatures. We're energized by stories, we remember stories, and we use stories to make sense of the world around us. Seeing and hearing a real people talk about your product in "story" form is incredibly impactful.

If someone on your team tells you that customers don't like a certain feature, that conversation does create a certain kind of "knowledge" in your mind. But if you see and hear actual customers on video, expressing their emotions and frustration about the feature, that's a very different experience. What you now have now have is a deep, emotive, and visceral kind of KNOWLEDGE. It's a qualitatively different thing, and it's the type of knowledge that motivates people to take action.

Once you see a customer’s experience close-up, you can’t unsee it. The experience tends to burrow deep into your mind, and those memories become the mental material you use to understand the customer experience. The stories that get captured in Win/Loss interviews contain this special magic that motivates people to take action, that’s what makes them so valuable. But incidentally, it’s also why you need to conduct a lot of interviews to make sure you stay balanced. Win/Loss interviews done in small numbers can almost be too potent. There’s a famous quote I’ll paraphrase that says you should be more wary of the person who has read 1 book than the person who’s read no books. Reading a single book makes a person over-confident about their version of reality, and thus vulnerable to making big mistakes. And watching a single Win/Loss interview can do the same. To grasp the whole picture a person should read a lot of books, just like you should conduct a lot of interviews. And as the person managing the Win/Loss program, you need to manage your teammates experiences on this topic as well. If the CEO wants to watch a single Win/Loss interview, make sure and emphasize that it's just a single interview.

Win/Loss data is brand new (and you own it)

Win/Loss data is usually a brand new data-set that the company hasn't had before, and that makes it both novel and interesting. Anytime a meaningful new data-source comes into the company most people are interested in checking it out. And if you gather enough Win/Loss data, you’ll be sitting on top of a very large data-set that no one has ever seen before. People are going to be interested.

You own it - but don't be a gatekeeper

This is one of the most important things about running a successful Win/Loss program. Most programs have a single internal champion, and that person does have ownership of almost everything Win/Loss. But if you want your program to succeed, and if you want to build strong relationships with all of the leaders throughout the company, you need to share as much data with them as often as possibe. Make them stakeholders in the program. Invite them to watch the interviews, sit down with them are share the insights on a regular basis, and encourage them to explore the data on their own.

If you show up one day without warning and present a list of Win/Loss insights , and your teammates don't feel like stakeholders, some of them may get overly defensive because the insights will feel like a criticism of their work. Avoid this by making them stakeholders in Win/Loss. Share data early and often with as many people as possible.

In closing, If you're thinking about building a Win/Loss program at your company it’s important to remember that it's a lot of work (though... if you hire a 3rd party firm you can reduce the workload by a lot). But if you create the time and budget to build a successful program, the rewards can be incredible. Not only will you single-handedly start driving new revenue for your company, you'll also probably catapult your career upward.