How to Win More Sales by Running a Proper a Win / Loss Analysis

As a sales leader, it’s important to reflect on the wins and the losses. It’s fun to rehash victory stories and overcoming resistance to win a new customer logo. And while it can sometimes be discouraging to rehash a loss – especially if it’s fresh and still hurts – there’s a lot that can be learned from understanding why the deal went south. This is why running a regular win/loss can truly be a “win-win” for your sales team.

The benefits of these win/loss reviews are more powerful than they may appear. For customer wins, you understand the value the customer saw, the red flags you overcame, the relationships you built, and so on. And for losses, you can take a deeper look at objections and where they went wrong, relationships that perhaps weren’t strong enough, competitor’s value, and etc. And because you’ll run them in cooperation with your sales team, it’s the ultimate way to build buy-in on executing new sales strategies so you can put more deals up in the win column.

But the true value of win/loss reviews and deep analysis isn’t only understanding the sales process and what went right or wrong. There’s also value in that you’ll better understand the buying process and putting yourself in your customer’s shoes to grasp all of their interactions with your company and team. This “buyer centric” approach of evaluating the buying process from a recent set of wins and losses via a workshop discussion can prove to be incredibly valuable.

The Buyer Centric Win/Loss Approach

Preparing for the Meeting

Here’s a detailed look at the process that your team can essentially copy and paste into your own buyer centric win/loss analysis:

  • Schedule a 90-min meeting with a group of your sales team to perform a “win / loss analysis”.
  • Ask each salesperson to come to the meeting with 3 recent wins, and 3 recent losses.
  • At the start of the meeting, explain the purpose, which is to help everyone understand why we win and why we lose so everyone can get better together (together is the key word – this shouldn’t feel like a threatening meeting).
  • Stress that although we all love talking about our wins, it’s important to talk about losses so we can learn what happened and come up with ways to win more in the future. It’s important for your team to know this is a safe environment to objectively discuss the losses – not a meeting to criticize. It’s key that you let the salesperson who worked the deal do most of the talking on the losses – it should NOT be the sales leader explaining what they did wrong.

Reviewing the Wins

Go around the table with each rep one-by-one. First each rep should cover their 3 recent wins. Ask them these questions:

  • Where did this lead come from?
  • Why did they buy? What was going on in the business to motivate them to make an investment? Note: Coach people away from why they bought from YOU, and towards what business problem the client was trying to solve and realized they needed to address.
  • Who was involved in the decision that we spoke with? Who was involved in the decision that we didn’t speak with?
  • Walk us through the steps the customer went through from your initial call to close. What decisions and key steps occurred internally? For this one, be prepared to probe and ask clarifying questions. Reps will tend to give some generic answers, but you want to really dig in and ask 2 to 3 clarifying questions. So when someone says “they saw our demo and liked it”, ask follow up questions such as: What stood out to them? How did they explain it to people internally to get buy-in?
  • The above steps will give you a sense of what the customer was going through along their buying process.

Reviewing the Losses

Now switch to losses and ask:

  • Where did this lead come from?
  • What did they end up deciding – did they go with a competitor, or was it a no-decision?
  • Reflecting back, was there a point in the process that signaled to you the deal was going south?
  • Did you get any signals that you wish you would have listed to or trusted your gut so you could have gotten out earlier?
  • Looking back, what could we have done differently that may have turned this into a win?

Adopting a Buyer Centric Win/Loss Analysis

Did you notice a trend in the questions above? The questions don’t revolve around the faults or successes of the sales team. Instead, the idea here is to understand what the customer was going through in their buying process as well as helping reps learn from each other about the wins and the losses. This process should help you define your sales stages in a way that aligns with that process, and also includes steps to help minimize the losses.

For example, let’s say that you learned from the deals that you won there was always a VP involved in the discussion somewhere. And let’s say in the deals that you lost there was a common theme that there wasn’t a clear ROI discussion. You can use these to add steps in your sales process such as “ROI Discussion Completed” or “VP Agreement”. These are very different than the old school sales steps like, Qualified Opp or Proposal Sent, and are more specific and helpful for the sales team to remember the steps they need to take to win more business.

The value that can result from buyer centric win/loss analysis discussions can be incredibly eye opening, and can help your sales team know where to focus (and know what to avoid)! So often, sales team members feel like they’re reacting to circumstances that seem out of their control. But by drawing parallels and understanding past trends and how they relate to future deals can save your team significant time, help them focus on what matters most, and avoid wasting time on areas that have failed multiple times over in the past.

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