One of the best pieces of advice I ever received during my days as a full-cycle salesperson came from a couple of great minds in sales and marketing: Jeffrey Gitomer and Perry Marshall. Gitomer, in his book Little Red Book of Sales, shared a simple yet game-changing tip:

Take your last 10 wins. Take your last 10 losses. Analyze them. What patterns emerge? What do your wins have in common? What about your losses? The goal is to identify replicable actions and behaviors that lead to success—and avoid the ones that lead to failure.

Marshall’s insights from 80/20 Sales and Marketing added an extra layer of brilliance. He emphasized the power of the Pareto Principle: 80% of your results come from 20% of your efforts. But he didn’t stop there. He introduced the concept of going deeper—finding the 20% of your 20% (the top 4% of actions) that drive 64% of results, as well as understanding the 80% of your 80% that holds you back.

Why This Matters in the Era of Data-Driven Sales

With tools like Salesforce, HubSpot, Tableau, and Looker, we no longer need to rely solely on memory or gut instincts. Instead, we can:

• Identify trends in customer behavior: For example, you might discover that 70% of your wins come from mid-sized companies in the healthcare sector, while 60% of your losses come from enterprise deals that stall during negotiations.
• Examine your sales process: Did you schedule follow-ups sooner for the wins? Was there a specific discovery question that led to deeper engagement?
• Evaluate the messaging: Were certain email templates, case studies, or value propositions more effective?

Applying the 80/20 Rule to Sales Wins

Here’s where Marshall’s principle kicks in. Once you’ve identified the patterns in your wins, look for the top 20% of actions or decisions that made those wins possible. Then, dig even deeper: What’s the 20% of that 20%? This is your goldmine—the activities, strategies, or customer profiles that consistently drive results.

For example:

• If your analysis shows that personalizing proposals leads to a 40% higher close rate, double down on this tactic.
• If certain lead sources, like LinkedIn ads, have a higher conversion rate, allocate more budget and resources there.

How to Analyze Your Wins and Losses

1. Gather Your Data: Start with the basics. Pull reports for your last 10 won opportunities and 10 lost opportunities. Make sure to include key metrics like deal size, timeline, lead source, industry, and sales stage.
2. Look for Patterns: Use your BI tools to create visualizations. For example, a heatmap might reveal that deals lost during Q4 correlate with a lack of follow-ups, while bar charts could highlight industries where you’re crushing it.
3. Validate with Your Team: Data doesn’t tell the whole story. Talk to your team to uncover nuances. Did a competitor’s feature set sway a prospect? Was pricing a deal-breaker?
4. Take Action: Build a playbook based on your findings. For instance:
   • If deals are lost due to pricing concerns, explore offering flexible payment terms.
   • If most wins include a demo within the first two weeks, tighten your timelines.

Examples of Insights You Can Uncover

• Deal Velocity: Deals won had a shorter average sales cycle (e.g., 45 days) compared to losses (e.g., 90 days). Focus on reducing bottlenecks in the pipeline.
• Lead Source Quality: Leads from webinars converted at 30%, while leads from purchased lists converted at just 5%. Invest more in high-performing channels.
• Sales Stage Drop-Off: 50% of losses happened after the proposal stage. This could indicate a need to refine your proposal templates or negotiation tactics.

Why This Still Resonates

The brilliance of this exercise lies in its simplicity. Whether you’re a solo rep or part of a data-driven sales organization, it’s scalable. Start with a qualitative review of your last 10 wins and losses, then supercharge it with data insights.

Sales isn’t just about working harder; it’s about working smarter. When you understand what’s driving your wins, you can double down on what works and avoid what doesn’t. And with the tools we have today, the depth of insight you can achieve is unparalleled.

So, what are your last 10 wins and 10 losses telling you—and how are you going to act on it?