Instead of broad surveys, focus on your ideal customer—the one who got the best results. Asking what nearly prevented their purchase reveals the most significant friction points in your marketing and sales process, providing more valuable insights than any expert analysis.

The founders of billion-dollar companies like Wealthsimple and GoBolt demonstrated an insane level of focus on customer contact. This included calling every free user within 30 seconds and personally answering the 24/7 support line. This unscalable behavior generates deep customer understanding and powerful word-of-mouth.

Even after scaling past $10M ARR, Canary's founder gets back on the phone to cold call customers for every new product launch. This ensures the leadership team directly tests messaging, understands customer objections, and validates the new offering's value proposition before scaling the sales motion.

Systematically call every customer who has churned, not to win them back, but to thank them and understand why they left. This provides invaluable, unfiltered market research. By the 19th call, you'll have identified core product or service issues that data alone cannot reveal.

The most valuable question a VC can ask a founder is, "Why are customers churning?" According to G2's Godard Abel, investigating what's not working provides the most critical insights for improvement. While founders naturally market successes, the real opportunity for growth and learning comes from understanding and addressing failures.

To get high-quality feedback, founders should go beyond passive methods. Proactively emailing customers a scheduling link for a brief call, perhaps in exchange for a discount, creates a direct feedback loop that helps prioritize what loyal users actually want.

To revive its catering business, Dig In hired one person to call a list of lapsed customers from their ordering platform. Instead of a complex new campaign, this simple, low-cost effort to understand churn reasons successfully recaptured significant revenue.

Companies often diagnose slow growth as a top-of-funnel problem, demanding more leads. However, this is frequently a symptom of a deeper issue: high customer churn. The more effective growth strategy is to fix retention and upsell existing happy customers, which is far easier than new acquisition.

Even with a productive sales team, founders should periodically run sales conversations. Jack Altman continued doing sales calls to stay connected to the market. It's the most direct way to understand what resonates with customers, what feels hard, and what lights them up, providing an unfiltered view of product-market fit.