When you decide you’d like to build a Win/Loss program, two things will happen with your teammates. First, many of them will have specific questions they’d like you to ask customers during your interviews. And second, they’re all going to want to see the results, and what customers are saying about their worlds. The head of product will want to see product feedback. The Head of Sales will want to see sales feedback. The Executives will want to see anything related to increasing revenue, so insights around “why we lose” will be especially important.
Win/Loss programs should be built and managed by a single person.
A Win/Loss program functions best when there is a single internal champion building and running the program. That’s probably you, or someone who works for you. When a Win/Loss program doesn’t have a single, well defined champion, it tends to break down. If that individual isn’t well defined as the leader of the program, there tends to be a lot of interesting ideas thrown around, and then a lot of strange energy and lack of accountability. Stuff just doesn’t get done.
A Win/Loss program is a complicated beast, and it needs a single architect to function well. Think about a time when you’ve built a big complicated project on your own, and after it was built it was complex enough that anytime you tried to bring anyone else in at the decision making level it just broke stuff. Win/Loss programs are like that. There are too many moving parts and too many things happening to share decision making responsibility across more than 1 person. There should be one general. You can have soldiers, and issue orders (maybe you want to train someone to help you with interviewing). And you can answer to superiors who might say things like “let’s do more or less interviews”, but almost everything else should be your call and under your control (when the interviews are conducted, how much the incentive is, what questions get asked, who transcribes them, who analyzes them, how and when reporting occurs, and on and on). Don’t let others get too close to the decision making in how your program runs.
Your teammates will want you to ask participants specific questions.
As you think about the list of questions you’d like to ask participants, inevitably different people will chime and and say things like “hey, could you ask customers about this new feature we launched”, or “could you ask about this pricing change we’re thinking of making”. In our experience, the majority of the questions your colleagues will want to add are going to be bad questions. In customer interviews there are a lot of bad questions. The two examples above are both bad questions. Asking people’s opinions about a perceived pricing change is usually pretty useless feedback. You need to be asking about people’s experiences, not about their opinions. And asking about a certain feature misses the huge point that if you interview 10 people, you’ll be lucky if one of them has deep experience with that feature. It’s very hard to ask about specific features because interviews are expensive, and it’s hard to get a big enough dataset to see real trends on a single feature. Use your product analytics for that type of insight. On the flip side, you can ask general questions about product like “what are your favorite 3 features”, or “what’s missing from the product” and you can see whether trends start emerging there - that type of feedback comes directly from the well of their experience. Whereas asking them about a certain feature will pressure people to provide you with feedback even when they’ve never used the feature.
The point I’m making here is that, as you can see, you have to be careful with what questions you decide to ask. At one level you want to be open to the contributions your teammates are trying to make, and at another level you need to be discriminating about whether they questions they’re proposing will yield any fruit.
One complicated aspect of this dynamic is when an executive or your boss comes to you with a specific question they’d like to you ask. There’s a good possibility that the question they’re proposing isn’t a fruitful question. So you’ll have to use your own best judgment about how to navigate that situation. We sometimes run into this issue with our clients. If it feels right, we’ll try to explain that the question is unlikely to yield much fruit, based on our experience with that type of question. But if it doesn’t feel like we have that kind of wiggle room, we’ll sometimes ask the question and then use that experience to explain that it was indeed an unfruitful question. As a rule of thumb try to carefully consider each question people ask you to include, and prune the question guide very carefully. Because if you’re not careful, you can end up with a lot of bad questions which not only yields weak data, but makes the interview feel pretty awkward for both people.
Presenting the findings to your teammates.
Everyone is going to be keen to hear the insights and results. And as you’re working through the analysis process, the main question you’re going to face is how to present this data to the different teams. Do you present to everyone at once? Do you present to individual teams? Do you present to individual heads of teams one at a time?
Present to the executives all at once
We generally recommend presenting to the executives all at the same time. The executive presentation may feel a little intimidating, but it’s also a huge opportunity to shine. You’ll be in possession of many of the most impactful company insights, and you’ll be seen as the key person within the company to deliver those insights to the executives. There’s a huge amount of value that flows to the person running the Win/Loss program in these meetings. Mainly because the insights you share with them tend to have big impacts on revenue, and many of the insights will be new to the team, so the novelty factor is exciting and tends to stimulate conversation and action at the executive level. There’s also usually an interesting power dynamic as long as the most senior executive signs off on the findings, all the other executives see it as a cue to view the Win/Loss program as highly valuable. So in a single meeting you can really change your own profile and visibility within your organization. When it comes to executives, present to everyone at once if you can.
Present to the individual teams one at a time.
In your Win/Loss data you’ll have different buckets of feedback for different teams. Get the head of product together with a few other product leaders and share some of the high-level findings, but then dive deep into the product feedback. When it comes to sales, share your findings directly with the head of sales, preferably in a one on one setting. Sales feedback contains criticism about specific individuals on the sales team, and oftentimes individuals will be part of the story of why a deal was lost. If you present this feedback in a group setting, sales people will get very defensive very quickly, and you’ll unintentionally create a hostile dynamic in the meeting. Instead, share the findings with the sales leader and let them decide how they want to share the critical feedback with each individual sales person.
As you think about all the different buckets of data you have, you’ll be best served to share the appropriate data with the appropriate team. Share growth insights with marketing, share onboarding insights with your account managers, and share retention insights with customer success. The better organized your data, the more opportunities you’ll have to present, disseminate the insights, and build rich relationships with your teammates.
Beware of group dynamics.
When you’re presenting your findings to teammates, the more people you’re presenting to at once, the more dead the conversation will be. Ideally you want to present to small groups of 3-4 people where the individuals involved feel comfortable asking questions and sharing their opinions. If you can create that type of dynamic Win/Loss conversations tend to be very rich and exciting for everyone involved. If you give a big Win/Loss presentation to 100 people at the same time, which we’ve done many times, all of your exciting insights will be met with silence. Big groups like that make people fearful to ask questions, and they stifle conversation. If you can, think about group sizes that will maximize the free-flow of conversation about the data. If you do, you’ll have exciting conversations with pretty much everyone, and you’ll also start building valuable relationships with people across the company.
