If You Can’t Forecast Retention, You Can’t Lead Customer Success

Early in my Customer Success career, I made a huge mistake.

I thought forecasting was just another way to “surprise and delight.” My logic? If I forecasted lower than what I thought would actually happen, I could look like a hero when renewals came in higher.

That approach works great for building customer relationships.

It does not work for running a business.

What I didn’t realize at the time was that my “conservative” forecasting was actually creating blind spots. Leadership depends on accurate forecasts to make critical decisions, whether to hire, how to invest in product, where to allocate resources, and how to plan for growth. By forecasting low, I wasn’t protecting the business. I was hurting it.

Eventually, I had to learn to forecast like Sales, with rigor, discipline, and accuracy. Because in CS, just like in Sales, the number you put down isn’t just a guess, it drives real business decisions.

Why Retention Forecasting Matters

Forecasting isn’t about optimism, sandbagging, or looking good on paper. It’s about trust.

When leadership can trust your retention forecast, you earn credibility and a seat at the table. When they can’t, CS will always be fighting for relevance.

Five Ways to Get Forecasting Right

Here’s what helped me shift from “feel-good” forecasts to accurate, reliable ones:

1. Standardize Your Health Signals

Forecasting should not be based on gut instinct. Define clear, non-negotiable inputs like product adoption, usage frequency, customer engagement, and executive alignment. These signals create consistency and reduce bias.

2. Inspect What You Expect

Run weekly forecast calls. Challenge assumptions. Ask tough questions. CSMs should be able to defend their forecasts with evidence, not wishful thinking.

3. Time-Box Your Lens

Don’t just look at renewals 12 months away. Forecast at 30, 60, and 90 days out. This forces proactive action, surfaces risks earlier, and eliminates last-minute fire drills.

4. Incentivize Accuracy, Not Optimism

Reward the CSM who flags a risk early and gets it right not the one who paints a rosy picture or sandbags to “beat the number.” The goal is predictability, not surprise.

5. Make Predictability Cultural

Forecasting should be ingrained in how your team operates. It’s not about making yourself look good, it’s about giving the business confidence to grow.

The Bottom Line

Customer Success leaders can’t afford to treat forecasting as an afterthought. It’s not about under-promising and over-delivering, it’s about enabling the business to make smart, timely, and confident decisions.

If you can’t forecast retention, you can’t lead Customer Success.

It’s that simple.