The Journey: #58 Context is King

The worst thing I’ve done in my Customer Success career is take something at face value.

Early on, I wanted to believe that what a customer said was the whole story. I would think that what I read in a note or ticket was all I needed. That a single piece of feedback represented reality. But here’s the truth. Most of the time, it doesn’t.

I was leading a team a few years back and a customer had submitted a feature idea into our idea bank, but never mentioned it to their CSM. So it sat there. Quietly. For a few weeks. Eventually, we reached out. On the next call, the CSM casually mentioned she saw the request and said something along the lines of, “Our product team will take a look at this.”

She asked if it was important or impactful. The customer said, “Yeah, we need it to finish an integration.”

Okay. Helpful. But still surface level. She added that note to the ticket and moved on.

When the product team started working through the roadmap, the item didn’t make the cut. It wasn’t prioritized for that sprint. So the CSM followed up with the customer and let them know.

That’s when everything blew up.

The customer started rattling off implications. This was a blocker. This impacted their timeline. Their leadership team was involved. Their launch date would shift. There were dependencies across teams. Now, executives were paying attention. Escalations started flying.

Let’s just say things got bad. Fast.

And we were caught completely off guard. Why? Because we didn’t have the context.

We didn’t know this integration was tied to a major organizational priority.

We didn’t know it was a hard blocker.

We didn’t know the timeline had executive visibility.

We didn’t know missing this would delay a launch.

We only knew what we were told at face value. “No context” turned into “big issues” for the business.

That moment stuck with me because it was avoidable. Not because we didn’t care. Not because we weren’t trying. But because we didn’t ask enough questions. We didn’t zoom out. We didn’t dig deeper to understand the full picture.

That’s what happens when you skip context.

This is why I always say, “It depends.” Because it does.

If someone gives you an answer without asking follow-up questions, be careful. Without context, they’re just guessing. And those guesses can cost you trust, customers, and revenue.

Context is king. Without it, we’re flying blind.

So how do you make sure you actually have it?

Here are five habits that have saved me more times than I can count.

First, ask more questions. Don’t stop at the first answer. The first answer is usually the surface. Ask what this impacts. Ask who else cares. Ask what happens if this doesn’t get done.

Second, listen beyond the words. Tone matters. Urgency matters. Hesitation matters. Sometimes customers understate risk. Sometimes, they don’t even realize the implications themselves until you ask.

Third, validate assumptions. Repeat back what you heard. “Just to confirm, if this isn’t completed by X date, what happens?” You’d be surprised how often this uncovers the real stakes.

Fourth, zoom out. One ticket. One comment. One request. None of these live in isolation. Tie it back to goals, timelines, initiatives, and business priorities.

Fifth, gather perspectives. Talk to multiple stakeholders. Check the data. Loop in product. Loop in leadership if needed. Context gets clearer when you triangulate.

In Customer Success, context isn’t a nice-to-have; it’s the difference between reacting and leading, being surprised and being prepared. It's what shifts things from a manageable situation to a full-blown escalation.

Every time I’ve been burned in this career, I can trace it back to a moment where I accepted something too quickly, where I didn’t ask one more question, or where I didn’t pause to zoom out.

Context would have changed the outcome, and let's face it, it almost always does.

So this week, here’s the challenge.

Before you take something at face value, pause and ask yourself: What am I missing?