When salespeople lose a deal, most prefer to move on rather than linger over the specifics of the loss. Similarly, when they win a deal, most are quick to celebrate. But very few take the time to assess why they won the business. In the authors’ experience leading and coaching sales teams, they see evidence that a brief, well-pointed sales retrospective, where you unpack the reasons behind a win or a loss, can significantly improve a team’s future win rate. Beyond the obvious benefits for the sales team — for whom the process can help identify the best messaging and behaviors to use going forward — unpacking wins and losses also provides valuable insights for product, marketing, and finance teams. Teams should ask three questions: 1) How would the customer articulate the value of their choice? 2) Who was the most influential voice in and out of the room? 3) Beyond price, what were the key deciding factors in the client’s decision?
When he read the email, “We’ve decided to go in another direction,” it was like a punch to the stomach. Brent hung his head trying to absorb the loss.
Brent, an account executive at a fintech company, had been so sure that this deal was going to go through that he’d put it on his forecast to close the quarter. He had even mentally spent his commission. As he sat with the reality that he’d lost the deal, he recognized there had been a few signs that the client wasn’t fully engaged. Now, they were going to use someone else.
Brent knew he was going to have to tell his boss. But the last thing he wanted to do was spend a meeting unpacking his own failure. Maybe he could get another deal cooking before they talked and avoid what he was sure would be a painful conversation.
When salespeople lose a deal, most prefer to move on rather than linger over the specifics of the loss. Similarly, when they win a deal, most are quick to celebrate. But very few take the time to assess why they won the business.
In our experience leading and coaching sales teams, we see evidence that a brief, well-pointed sales retrospective, where you unpack the reasons behind a win or a loss, can significantly improve a team’s future win rate. Beyond the obvious benefits for the sales team — for whom the process can help identify the best messaging and behaviors to use going forward — unpacking wins and losses also provides valuable insights for product, marketing, and finance teams.
The challenge is for leaders and sellers to dig beneath the traditional competitive analysis of pricing and features, to uncover the nuanced factors that played into the customer’s buying decision. While salespeople may groan at the thought of taking a magnifying glass to the rearview mirror, particularly on a loss that may still be stinging, we find that spending even as little as 10 minutes on a retrospective yields big dividends.
Below are three questions organizations and individuals can use in a sales retrospective. The questions work whether the team won or lost the deal. They are designed to help the team understand the real issues driving customers’ buying decisions.
How would the customer articulate the value of their choice?
Leaders can pose the questions to the team after a deal closes or falls through. The process starts by challenging the team to go beyond the solution itself. Instead, focus on how the customers would articulate the effects of implementing their chosen solution, be it yours or your competitor’s. For example, the solution may impact other departments at the client beyond the initial user group that sales traditionally talks to, or it may help the customer accomplish additional internal priorities. Looking beyond the obvious product users helps the team understand their larger impact.
If you lost the deal, digging deeper through this lens will help you frame your positioning to create more urgency next time. If you won the deal, this information will help you take actions to ensure a high-value implementation from the client’s perspective.
In the fintech firm described above, the sales retrospective revealed that the customer had placed a high value on a few product features, which they deemed must-haves for their internal team. The customer believed the competitor’s offering was more robust in these areas. Getting specific during the retrospective prompted the product team at Brent’s company to make some minor tweaks that put them at parity. Marketing also gleaned information about how to adjust their materials to highlight the changes.
Unpacking a loss typically helps identify opportunities. But there are also benefits to unpacking a win. Asking the salespeople involved how the customer would articulate the value of your solution creates a shared win for the entire team. In a tight economy, playing up the wins, versus exclusively unpacking losses, reminds your sales team that customers find your solution valuable and that many are still buying.
Who was the most influential voice in and out of the room?
Oftentimes, key decision makers, influencers, and subject matter experts aren’t revealed until after the deal has been decided. Knowing who these people are in a deal that you won prepares you for implementation. Knowing whose voices carried strong weight when you lost a deal helps the sales team address these influencers earlier in the sales process during future pursuits.
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’s worth noting that an environment of shame and blame rarely produces great insight. Instead focus on what they can do differently next time.
When the fintech firm looked more closely at the decision makers, it became clear that the CIO had made the final call. While most of the sales calls had been with the user group, it was the CIO who identified the must-have features that cost the team the deal. Knowing this prompted sales enablement to create additional training to help the sales team become more skilled at calling on CIOs. The marketing team developed a new deck showcasing how their offering addressed typical CIO challenges, and finance developed models to showcase their net-positive impact over time.
Beyond price, what were the key deciding factors in the client’s decision?
When a team loses a deal, it’s easy to blame it on pricing. Asking the team to think about why a client makes decisions for reasons other than price will allow them to reflect on the full value of the solution. It will also allow them to take a broader look at how their own offering stacks up in a competitive landscape. When you lose a deal, this question will help your team uplevel their skills by being more attuned to the nuances in the future. Conversely, when you win, unpacking why you won beyond pricing strengthens the team’s confidence, which helps you hold margin going forward.
It can also be helpful to ask the buyers themselves what other factors played into the decision. They may not even be aware of the subtle things that drove their thinking until they’re asked to unpack it.
After the loss, the fintech team went back to their client to ask why they choose the competitor, allowing the team to get more detailed information about the perceived product differences. Keeping the conversation neutral without trying to re-pitch the sale created an environment where the client was willing to share. The loss still hurt, but the deep insights they gained directly from a client helped the team adjust their offering going forward.
. . .
While the benefits of a sales retrospective are clear, the challenge is often in assessing when to use one. Organizations can have hundreds or thousands of deals in a quarter, and not all warrant introspection. The temptation is to limit retrospectives to large deals that didn’t close at the end of the quarter. However, in our experience, emotions are so high at that time that the utility of retrospectives is usually low.
Instead, we find it helpful for sales leaders to have at least one retrospective per account executive per quarter. That enables the team to gather information that is valuable for multiple functions in the company. Perhaps most importantly, this approach will train the sales team to think about why they actually won or lost independent of a retrospective.
Regardless of which deals a leader selects to discuss, going from no retrospectives to a few will be a considerable achievement and deliver insights that may change the go-to-market strategy. Through running deeper sales retrospectives, the fintech firm was able to tweak their offering, upskill their sales team, and create a stronger presence with a key set of buyers.
For most leaders, it will take time to drive an impact similar to what was achieved in the case study, but along the way, account executives will feel heard, sales will be more effective, and the go-to-market teams will be able to better support sales. Ultimately, this enables leaders to turn small losses into a big win.