Companies that excel at win-loss do one thing really well: they get busy buyers to open up and share exactly why they made their decision – month after month. 

Their edge? A systematic approach to interview sourcing – one that consistently engages the right decision-makers from the right deals. If you want your win-loss program to move the needle, building and maintaining this interview pipeline is critical. 

In this guide, we’ll show you how to master both sides of effective interview sourcing. This includes:

  • 1. How to target the right interview candidates by:
    • Creating research cohorts
    • Prioritizing deals within those cohorts
    • Partnering with Sales to identify – and recruit – prime interviewees
  • 2. How to boost your interview acceptance rates by:
    • Using the right outreach method
    • Building a consistent outreach cadence
    • Using proven tactics to secure more “yeses”

Let’s get started.

📌 New to all this? Check out our guide on how to get started with win-loss, or download our free win-loss interview guide below 👇

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Define Your Research Cohorts

The key to sourcing great win-loss interviews isn’t casting a wide net –  it’s knowing exactly who to target and from what deals. That’s where research cohorts come in.

Research cohorts are groups of similar deals that share key characteristics. By organizing your deals into cohorts, you’ll bring focus to your program and make it easier to spot meaningful patterns in your feedback.

Here are the three main dimensions to consider when building them:

  • Product Line: Different products mean different buyer personas and competitive dynamics. The insights you need from someone evaluating your enterprise security solution will be vastly different from someone considering your SMB analytics tool.
  • Deal Size: A $500K enterprise opportunity requires different interview targeting than a $50K mid-market deal. Each brings unique stakeholders and decision processes worth investigating.
  • Region: Market dynamics shift across geographies. Your EMEA buyers might obsess over data privacy compliance while APAC prospects care more about localized support options.

Strike the Right Balance Between Wins and Losses

Within each cohort, aim for a 50/50 split between wins and losses. While it might be tempting to focus heavily on losses to understand what went wrong, wins yield equally rich insights, especially when it comes to competitive intelligence. 

Think about it – customers who chose your solution want to see you succeed and improve, making them naturally more forthcoming about your competitors. This candid competitive feedback from satisfied customers can be gold for your program.

💡 Advice Straight from the Klue Win-Loss Team: Target at least 10 interviews per cohort. This sweet spot provides enough variety to identify reliable patterns while keeping your outreach efforts focused and manageable.

Filter for the Right Deals


Once you have well-defined cohorts, you still need a way to prioritize specific deals within those cohorts – especially if your closed-won/closed-lost pipeline is large. Here are three things to focus on when narrowing things down:

Late-Stage Deals

Target buyers who went deep into your sales process. These candidates provide the most comprehensive feedback because they:

  • Interacted with multiple teams, from sales to customer success
  • Engaged directly with pricing and may have gone through negotiations
  • Formed complete impressions of your product and process

Competitive Deals

Deals where you went head-to-head with key competitors should be high on your target list. These interviews often reveal:

  • Critical differentiation points
  • Specific feature or capability gaps
  • Ankle-biter competitors that weren’t on your radar

Closed Approximately 90 Days Ago

Timing can make or break your interview insights. Wait too long (6-12 months), and crucial details fade from memory. Move too quickly, and you might interrupt active vendor evaluations or ongoing negotiations.

Ryan Sorley, VP of Klue Win-Loss, recommends waiting exactly 90 days after a deal closes to reach out. He calls this timing the “Goldilocks Zone” – that sweet spot where everything is just right.

  • Buyers have had enough time to process and reflect on their decision
  • Details remain fresh in their minds, from specific feature comparisons to key decision factors
  • Key stakeholders are typically still in their roles and are accessible
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Collaborating with Sales & Other Stakeholders

You can’t build a strong interview pipeline alone. While your CRM and marketing automation tools help, they’re only one part of the equation. To consistently source high-value interviews, you need cross-functional support – especially from Sales, Product, and Marketing leaders, who can help you identify high-value deals. 

In a recent Coffee & Compete podcast episode, Alexis Yeh, Manager of Win-Loss Program Associates at Klue, broke down exactly how to build these critical partnerships. Here’s her playbook for success 👇

First, Win Over Sales

For many sellers, “win-loss” triggers immediate alarm bells – Is this a witch hunt to find out why I lost deals?

That’s why your first priority is making it clear that win-loss interviews aim to help the entire organization improve, not to blame individual reps.

Alexis recommends emphasizing these direct benefits to sales:

  • It can help them win more deals – win-loss interviews uncover what top-performing reps do differently so others can replicate their success.
  • It will arm them with better competitive intelligence – if you keep losing to Competitor A, these insights will help refine their objection-handling tactics.
  • It can even revive lost deals – some “closed-lost” deals are actually stuck in no-decision limbo. Hearing why the buyer hesitated could reignite the opportunity.

Next, Make It Easy for Sales to Actually Help You

Set up simple repeatable systems to get deal recommendations flowing:

  • Add an “Interview Candidate” checkbox in your CRM when opportunities close. 
  • Create a quick nomination form for high-priority deals
  • Host short enablement sessions to explain the program’s value
  • Share initial win-loss reports to demonstrate the insights they’ll receive

As Alexis puts it: “When you have sellers championing your program, they’ll route the best interviews your way without you having to chase them.”

Finally, Don’t Forget Product and Marketing

While Sales plays the most active role in sourcing interviews, Product and Marketing leaders can help refine your targeting:

  • Product Leaders: Can help identify deals where feature gaps or competitive differentiation played a key role
  • Marketing Leaders: Can flag opportunities where messaging didn’t resonate or campaigns underperformed

By involving stakeholders across the organization, you’ll secure high-value interviews that deliver meaningful insights for every team.

Outreach Methods and Best Practices

Once you’ve identified who you want to interview, the next big question is how to reach out. Below are three outreach methods, each with its pros and cons.

Direct Outreach

The straightforward approach: someone from your win-loss team or product marketing reaches out directly to the buyer, introducing themselves and requesting feedback.

Pros:

  • Simple to execute – just a list of emails and go
  • No complex coordination with Sales needed
  • Quick to get started

Cons:

  • Feels like cold outreach with no existing relationship
  • CRM contact data isn’t always accurate
  • Might accidentally interfere with deals that aren’t truly closed

Warm Intro Through Sales

Here, your account executive sends a short note to the buyer, introducing you and explaining the purpose of the interview. This personal touch can significantly boost your acceptance rates.

Pros:

  • Higher acceptance rates due to warm relationships
  • Sales can identify the right decision-makers
  • Reps can flag if deals are still active
  • Access to valuable context about the deal

Cons:

  • Some sellers might “gatekeep,” especially if they’re wary of negative feedback
  • More time-intensive than direct outreach
  • Sales bandwidth issues, especially at quarter-end

The Assisted (Hybrid) Approach

Think of this as a best-of-both-worlds solution. You start by pulling potential candidates from your CRM, then share the list with relevant account reps for validation. They’ll flag any live deals, confirm the best contacts to reach out to, and often provide valuable context for personalization. Once validated, you handle the actual outreach yourself, but copy the sales reps on emails to keep them in the loop.

Pros

  • Sales can verify contact info and deal status
  • You maintain control of the outreach process
  • You’ll get valuable context for personalization
  • Builds sales trust without over-relying on them

Cons

  • Initial coordination takes time
  • Need buy-in from multiple reps
  • Requires clear process documentation
  • Can get bottlenecked waiting for Sales validation

💡 Note: Most successful win-loss programs use a blend of these approaches, adapting their strategy based on the deal type and buyer relationship.

Choosing the Right Outreach Cadence: Weekly, Monthly, or Quarterly?

You’ve got your outreach method(s) down – now it’s time to establish when and how often you’ll reach out. 

This isn’t just about picking arbitrary timeframes, however. Your outreach cadence sets the rhythm for your entire win-loss program. Pick the wrong tempo, and you’ll either overwhelm your team or miss critical insights.

Alexis Yeh breaks down two effective approaches here – and one common cadence to avoid:

Weekly Outreach

Perfect for high-volume sales organizations that need a constant pulse on buyer feedback. You’ll spot emerging trends faster and respond quickly to market changes – but you’ll need dedicated resources to manage the steady flow of deal validation, outreach, and follow-ups.

Alexis warns that this approach does demand significant coordination and a well-oiled process. Without dedicated resources to manage consistent deal validation, outreach, and follow-up cycles, weekly outreach can quickly become overwhelming.

Monthly Outreach (Recommended for Most Companies)

There’s a reason monthly outreach is the go-to cadence for most successful win-loss programs. It strikes that perfect balance between keeping insights fresh and your workload manageable. Your sales team has enough breathing room to validate deals properly, while your win-loss team can maintain quality in their outreach efforts. This rhythm also aligns naturally with most organizations’ reporting cycles. 

Quarterly Outreach (Not Recommended)

While it might seem like an efficient use of resources, quarterly outreach can create more problems than it solves. By the end of the quarter, your left with a massive backlog of deals to sort through, making deal validation feel like an overwhelming task.

Alexis is particularly adamant about avoiding this approach: “I do try to encourage folks to stay away from the quarterly approach because by the end of the quarter there’s so many things that have happened that it becomes this massive task that a program leader has to review all of the opportunities and vet them with stakeholders… and you’re not getting all of your feedback on a continuous flow.”

Setting Up a Repeatable Process

Once you’ve chosen your cadence, you need to make it sustainable. Building a structured process that aligns with your deal flow is crucial for maintaining a healthy win-loss pipeline. Here are some tips for getting this right:

  • Set up automated reminders in your CRM for follow-ups at the 30-, 60-, and 90-day marks to ensure consistent tracking
  • Focus resources on high-value deals, recognizing that not every closed opportunity requires an in-depth interview
  • Engage Sales teams early in the process to verify that deals are fully closed before initiating outreach

By timing your outreach strategically and maintaining a consistent cadence, you can maximize interview participation and ensure your win-loss program delivers reliable, actionable insights.

Final Tips For Improving Your Interview Acceptance Rates

No matter your approach, some buyers simply won’t have the time or inclination to chat. Below are proven tactics to nudge them to a “yes” 👇

  • Lead with Sales: Start your outreach through the account’s salesperson. Alexis strongly advocates for this approach since a familiar face dramatically increases acceptance rates and adds immediate credibility.
  • Personalize Your Outreach: Reference specific details about their evaluation in your outreach. Something as simple as “I know your team was particularly interested in our reporting features” shows you’ve done your homework.
  • Use Strategic Incentives: A $50-100 gift card works well for most loss interviews. For senior executives, consider offering to donate that amount to their preferred charity instead.
  • Take a Multi-Channel Approach: Don’t stick to just email. A quick LinkedIn message or phone call can catch attention when inboxes are full. Two or three gentle follow-ups across different channels is perfectly acceptable.

What Interview Acceptance Rates Should You Expect?

What does a good acceptance rate even look like?

Alexis has found that acceptance rates vary significantly by deal type. For most win-loss programs, you can expect:

  • Win interviews: ~60% acceptance rate
  • Loss interviews: ~30% acceptance rate
  • Inbound opportunities: ~25% acceptance rate

Keep in mind these numbers aren’t set in stone. As Alexis notes, industry context matters – cybersecurity buyers, for instance, tend to be more cautious about sharing feedback, leading to lower conversion rates.

If you’re seeing substantially lower acceptance rates, consider implementing the tactics above to boost your numbers.

📌 Looking to ramp up your program? We wrote a guide on how to scale win-loss data collection. It walks you through everything from automation to survey design

Time to Start Generating Pipeline!

Behind every game-changing win-loss insight is a carefully crafted pipeline of conversations. It’s your job to keep that pipeline flowing with the right stories from the right buyers.

Luckily, if you’ve followed this guide, you should now:

  • Have your research cohorts clearly defined
  • Know exactly which deals to prioritize for outreach
  • Have a plan for engaging Sales in the process
  • Understand which outreach method(s) fits your organization
  • Be ready to implement a consistent outreach cadence

You’ve got the blueprint. Now it’s time to build.

Good luck!

Want to jump straight into conducting win-loss interviews? Check out our free guide below 👇

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