Context is a Strategy: How Smart CS Teams Use Headwinds and Tailwinds

Two of the most powerful things to report on as a Customer Success Leader?

Headwinds. Tailwinds.

If you're not talking about them, you're not leading.

Too many teams operate in a vacuum, executing against goals without stopping to ask why things are easier or harder right now.

But high-performing teams?

They build context into the conversation. Always.

⚠️ Headwinds give us friction:

Market saturation

Budget freezes

New competitors

Internal turnover

Shifting buyer behavior

✅ Tailwinds give us momentum:

Category growth

Regulatory shifts

AI innovation

Strategic hires

A new use case gaining traction

It’s not enough to say “we hit target” or “we missed it.”

👉 What were the environmental factors?

👉 How did you respond?

👉 And what did you learn?

The best teams don’t just report results. They understand the forces behind them and plan accordingly.

So how do you uncover your headwinds and tailwinds? Ask these 5 questions every month (or at least every quarter):

1️⃣ What’s happening in our customer’s world?

Industry changes, new priorities, leadership turnover, funding rounds, those shifts show up in your numbers.

2️⃣ What’s changing in our pipeline?

Faster closes? Slower onboarding? More ghosting? Trends in sales velocity and conversion tell a story.

3️⃣ What are customers saying directly or indirectly?

Support tickets, product feedback, QBRs, NPS comments, sales recordings, it’s all signal.

4️⃣ What macro trends are helping or hurting us?

AI, privacy laws, labor costs, inflation, tech layoffs, zoom out to zoom in.

5️⃣ What plays are suddenly working (or not)?

If an approach stopped converting or started winning big, that’s not luck, it’s likely a trend.

The smartest companies I’ve worked with make headwinds and tailwinds part of their operating rhythm and discuss these in leadership meetings, planning sessions, board meetings and collaborative syncs.

Because when you understand the why, you can change the how.

If you’re not having these conversations yet, start now. Your goals will thank you later.