When salespeople lose a deal, most prefer to move on rather than dwell on the details of the loss. Similarly, when they win a deal, most are quick to celebrate. But few take the time to evaluate Why they won the business. In the authors’ experience leading and coaching sales teams, they’ve seen evidence that a short, well-targeted sales retrospective, where you unpack the reasons behind a win or loss, can improve a team’s future win rate. Beyond the obvious benefits for the sales team – for whom the process helps identify the best message and behavior to use going forward – unpacking the wins and losses also provides valuable insights for the product, marketing, and finance teams. The groups should ask three questions: 1) How will the customer express the value of their choice? 2) Who is the most influential voice in and out of the room? 3) Beyond price, what are the deciding factors in the client’s decision?
When he read the email, “We’ve decided to go to another direction,” it felt like a punch in the stomach. Brent bowed his head to absorb the loss.
Brent, an account executive at a fintech company, was so sure this deal would go through that he put it in his forecast to close the quarter. He even spent his commission. As he sat in on the reality that he was missing out on the deal, he knew there were some signs that the client wasn’t fully engaged. Now, they use something else.
Brent knew he had to tell his boss. But the last thing he wants to do is spend a meeting unpacking his own failure. Maybe he could get another cooking deal before they talk and avoid his sure-to-be painful conversation.
When salespeople lose a deal, most prefer to move on rather than dwell on the details of the loss. Similarly, when they win a deal, most are quick to celebrate. But few take the time to evaluate Why they won the business.
In our experience leading and coaching sales teams, we’ve seen evidence that a short, well-taught sales retrospective, where you unpack the reasons behind a win or loss, can improve a team’s future win rate. Beyond the obvious benefits for the sales team – for whom the process helps identify the best message and behavior to use going forward – unpacking the wins and losses also provides valuable insights for the product, marketing, and finance teams.
The challenge for leaders and marketers is to dig beneath the traditional competitive analysis of pricing and features, to uncover the nuanced factors that play into a customer’s purchase decision. While salespeople may cringe at the thought of taking a magnifying glass to the rearview mirror, especially with a loss that could still hurt, we found that spending even 10 minutes on a retrospective can pay big dividends.
Below are three questions that organizations and individuals can use in a marketing retrospective. The questions work whether the team won or lost the deal. It is designed to help the team understand the real issues driving customers’ purchasing decisions.
How will the customer express the value of their choice?
Leaders can ask questions of the team after a deal is done or fails. The process begins by challenging the team to go beyond the solution itself. Instead, focus on how customers will express the effects of implementing their chosen solution, whether it’s yours or your competitor’s. For example, the solution may affect other client departments beyond the initial user group that traditionally communicates with sales, or it may help the customer achieve additional internal priorities. Looking beyond the obvious product user helps the team understand their larger impact.
If you lose the deal, digging deeper into this lens will help you frame your positioning to create more urgency next time. If you win the deal, this information will help you take actions to ensure a high-value execution from the client’s perspective.
In the fintech firm described above, the sales retrospective revealed that the customer placed a high value on certain product features, which they considered necessary for their internal team. The customer believes that the competitor’s offer is stronger in these areas. Being specific during the retrospective prompted Brent’s company’s product team to make some small tweaks that put them on par. Marketing also gets information on how to adjust their materials to highlight the changes.
Unpacking loss often helps identify opportunities. But there are also benefits to unpacking a victory. Asking the salespeople involved how the customer expresses the value of your solution creates a shared win for the entire team. In a tight economy, playing up the wins, versus exclusively unpacking the losses, reminds your sales team that customers find your solution valuable and that more are buying.
Who is the most influential voice in and out of the room?
Often, key decision makers, influencers, and subject matter experts are not revealed until after the deal has been decided. Knowing who these people are in a deal you win prepares you for execution. Knowing whose voices carry the most weight when you lose a deal helps the sales team address these influencers earlier in the sales process with future prospects.
Unpacking a loss more holistically by looking at the players and the value story can help a sales team move beyond the sting of rejection. It is worth remembering that an environment of shame and blame rarely produces good insight. Instead focus on what they can do differently next time.
When the fintech company takes a closer look at the decision makers, it becomes clear that the CIO makes the final call. While most sales calls are with the user team, the CIO identifies the must-have features that cost the deal team. Knowing this prompted sales enablement to create additional training to help the sales team become more adept at calling CIOs. The marketing team created a new deck that showed how their offering addressed common CIO challenges, and finance developed models to show their net-positive impact over time.
Beyond price, what are the deciding factors in the client’s decision?
When a team loses a deal, it’s easy to blame it on pricing. Asking the thinking team why a client makes decisions for reasons other than price will allow them to reflect on the full value of the solution. This will also allow them to get a broader view of how their own offering stacks up in a competitive landscape. If you lose a deal, this question will help your team increase their skills by becoming more attuned to the nuances of the future. Conversely, if you win, unpacking why you won beyond price will build trust with the team, which will help you maintain the margin.
It is also helpful to ask the buyers themselves what other factors played into the decision. They may not be aware of the subtle things that drive their thinking until they are asked to unpack it.
After the loss, the fintech team went back to their client to ask why they chose the competitor, which allowed the team to get more detailed information about the perceived product differences. Keeping the conversation neutral without trying to back the sale creates an environment where the client is willing to share. The loss still hurts, but the deep insights they gained directly from a client helped the team adjust their offering going forward.
. . .
While the benefits of a marketing retrospective are clear, the challenge is often in evaluating when to use one. Organizations may have hundreds or thousands of deals in a quarter, and not all require introspection. The temptation is to limit retrospectives to large deals that did not close at the end of the quarter. However, in our experience, emotions are so high at the time that the utility of retrospectives is often low.
Instead, we find it helpful for sales leaders to have at least one retrospective per account executive every quarter. That enables the team to gather information that is valuable for many functions of the company. Perhaps most importantly, this approach will train the sales team to think about why they won or lost independently of a retrospective.
Regardless of which deals a leader chooses to discuss, going from no retrospectives to a few is a huge success and will provide insights that can change the go-to-market strategy. By running deeper sales retrospectives, the fintech company was able to tweak their offering, improve their sales team, and create a stronger presence with a significant set of buyers.
For most leaders, it will take time to drive an impact similar to what was achieved in the case study, but in the long run, account executives will feel heard, sales will be more effective, and go-to-market teams will be able to better support sales. Ultimately, it enables leaders to turn small losses into big wins.
