In this episode, we take a practical look at how to assess the true health of your sales pipeline. It’s a topic that frequently arises in client conversations, especially during due diligence, forecasting, or periods of commercial strain. Yet, many businesses still rely on surface-level metrics or default CRM settings. So we share the tools and thinking we use to dig deeper into: what's really driving pipeline performance?

By exploring concepts like data hygiene, deal velocity, and the importance of accurate forecasting, we highlight where typical sales metrics fall short and what to use instead. Whether you're managing a small sales team or scaling a more complex operation, we offer a set of insights and calculations that will help you understand your pipeline more clearly, act more deliberately, and forecast with greater confidence.

Chapters:

00:00:00 – Intro & Rotisserie Chickens

00:04:10 – Episode Focus: How Healthy Is Your Sales Pipeline?00:06:30 – Data Hygiene: The Foundation of Pipeline Health

00:09:10 – What Should You Measure First?

00:11:30 – The Problem with the “3x Pipeline” Rule

00:14:20 – The Correct Pipeline Cover Formula Explained

00:17:05 – Forecast Accuracy and Probability Weighting

00:20:10 – Sales Velocity vs. Value Added

00:23:00 – Stalled Deals & Activity Flags

00:26:40 – Redesigning Pipeline Stages Around the Customer

00:29:00 – Win Rates by Segment and Deal Type

00:32:00 – Deal Concentration Risk

00:34:00 – Front-of-Pipeline Health & New Logo Acquisition

00:35:30 – Final Thoughts: Continuous Measurement & Improvement

00:36:50 – Outro: Future Topics & Podcast Wrap-Up

Key Topics Discussed:

• Why data hygiene is the foundation of any meaningful pipeline metric

• The problem with universal “3x pipeline” rules, and what to do instead

• How to calculate true pipeline cover using weighted values and sales cycle length

• The importance of forecast accuracy and how to spot over-optimism

• Reframing your pipeline from the customer's perspective to identify bottlenecks

Who This Podcast Is For:

This episode is designed for business owners, sales leaders, and commercial managers in growing SMEs. If you're responsible for driving revenue and making decisions based on pipeline data, this is a must-listen.

Quotes to Remember:

“You’ve got to measure the health of your pipeline in the context of the health of your system.”

“Know your data intimately, the goal is to be able to talk about it almost fluently.”

“If you’re just selling what’s already in your pipeline and not replacing it, it’s not been a good month.”

Top Takeaways:

1. Audit your CRM for data hygiene- make sure every deal has a value, an expected close date, and is linked to a contact and company.
2. Calculate weighted pipeline value and average deal length to assess whether you have enough activity to hit your annual sales target.

Find the Formula Here:

Pipeline Coverage (%) = (Weighted Pipeline Value × Churn Rate) ÷ Annual Sales Target × 100

3. Review forecast accuracy and correct optimism bias- compare forecasted win probabilities to actual results.
4. Reframe pipeline stages based on what the customer is doing, i.e., reviewing, considering, deciding, to better align with their journey.
5. Segment win rates across deal size, salespeople, sectors, and customer types, to spot patterns, allocate effort more effectively, and refine targeting.

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If you are interested in what Wellmeadow does, head to our website: We deliver board support and HubSpot consultancy & implementation

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