Start the New Year Right

As the calendar flips to 2025, teams everywhere are aiming to improve on last year’s results. Sales kickoffs (SKOs) are in full swing, product roadmaps are being shaped, and ambitious goals are being set: increase win rates, retain more customers, grow deal sizes, and consistently beat the competition.

You could take the traditional approach—gather your leadership team, brainstorm strategies, and lean on a few charts from RevOps. Or, you could take a data-driven approach by leveraging win-loss insights to align your initiatives with what your buyers truly care about and respond to.

Here’s how to make 2025 your most successful year yet.

Tip #1: Set Up Your CRM to Track Win-Loss Reasons

Your CRM is the backbone of your sales data, but many teams fail to optimize it for win-loss tracking. Ensure your CRM has:

• A standardized picklist for win-loss reasons, allowing reps to tag deals with consistent categories.

• Detailed notes fields to capture nuances about each deal.

• Enforcement mechanisms to ensure this information is consistently filled out. Automate reminders or make it part of your sales process to guarantee compliance.

For more detailed guidance on how to set up your CRM effectively for win-loss tracking, check out our blog post here.

This foundational setup allows you to generate reliable data, providing insights into patterns across deals, teams, and segments.

Tip #2: Prioritize Win-Loss Interviews

The richest insights often come directly from the people involved in deals. Build win-loss interviews into your regular processes:

• Interview sellers after important wins and losses to capture their perspective on what worked and what didn’t.

• Interview buyers for deals that reach a certain stage. Whether it’s a competitive loss or a major win, understanding the buyer’s experience can reveal key themes about your product, messaging, and sales process.

For a comprehensive guide on running effective win-loss interviews, visit our blog post here.

A structured interview process will surface insights that numbers alone can’t provide, helping you refine your strategy.

Tip #3: Make Insights Accessible to Everyone

Even the best data is useless if it’s hidden or hard to access. Create systems to share win-loss insights with sales, product marketing, and product teams so everyone stays aligned on why you’re winning and losing. Options include:

• Dashboards: Interactive tools that let teams explore the data themselves.

• Periodic reports: Summaries delivered on a regular cadence to keep leadership informed.

• Email blasts or Slack updates: Quick insights shared in the tools your team already uses daily.

The more accessible and actionable your insights, the more effectively your teams can adapt.

Conclusion: Make 2025 the Year of Data-Driven Growth

Growing in 2025 is easier when you know exactly why you won and lost in 2024. Yet most teams struggle to track this information effectively. Make it a priority this year to:

1. Set up your CRM to capture meaningful win-loss data.

2. Conduct regular interviews to uncover deep insights.

3. Share findings widely to align all teams on what matters most.

These steps will help you make each dollar go further, maximize your efforts, and position your team for success.

If your team didn’t excel at tracking win-loss reasons last year or you’re looking to gather higher-quality feedback from buyers this year, Hindsight can help. With our win-loss analysis tools, you can turn feedback into actionable insights that drive growth.

Learn more about Hindsight.