The Journey: #61 Be Ready, Or Not

There is something I tell every CSM I've ever led or coached, and I say it often enough that they can probably hear it in their sleep.

Be prepared.

Be prepared for your customer to tell you they’re evaluating competitive solutions.

Be prepared for your customer to tell you the product isn't meeting their needs.

Be prepared for your champion to share that they’ve been promoted and are moving into a different role.

Be prepared to learn about a recent acquisition that could present a massive expansion opportunity… or quietly put your entire partnership at risk.

This is real life for Customer Success Managers.

And the GREAT CSMs, the ones who consistently protect revenue and expand accounts, are prepared for the agenda they planned so carefully to get tossed out the window in the first five minutes.

The best leaders? They don’t just tell their teams to “be proactive.” They enable this level of preparation. They role-play. They debrief. They normalize hard conversations. They make it safe to talk about what went wrong so it can go better next time.

Because here’s what happens if you don’t prepare.

You get emotionally hijacked.

I remember very clearly the first time a customer (The Limited, I'll never forget) told me they were churning. I can still feel it in my body when I think about it. I was shocked. I was upset. I was confused. I was embarrassed. I was trying to process what they were saying while also trying to sound composed and professional.

All of those feelings prevented me from managing the conversation effectively.

I left that call with almost no additional information. No real understanding of what changed, no clarity around timing, and no insight into whether this was salvageable or already decided months ago.

Thankfully, I had a strong leader at the time. I was able to debrief, get support, and get the customer back on another call.

But let’s be honest. That is not always a likely outcome.

When a customer delivers bad news and tells you they’re “done” with the partnership, they are not usually eager to give you more of their time. You might not get another shot. You cannot assume you’ll get a redo.

You have to make the most of the time you have in that exact moment and assume you may never speak to them again and ask the questions you need to move forward effectively, whether that means trying to save the deal, learning from the loss, or protecting the rest of your book of business from the same outcome.

I had a bit of déjà vu today.

I was on a call with one of my consulting customers, and their CSM ran into this exact situation. A customer communicated their intent to churn and move to a competitive solution, and they were completely caught off guard. They wrapped up the conversation professionally, but they walked away knowing nothing more than the customer’s intent to move.

No depth. No timeline. No underlying driver.

I coached them through the next steps, which started with getting that customer back on a call. But the bigger conversation was this: preparation isn’t about scripting every word you’re going to say. It’s about being emotionally ready and strategically curious when the conversation shifts unexpectedly.

Since there are a lot of different things that can surface in any customer conversation, here are three questions I would ask in some of the most common high-stakes scenarios.

Not because they’re perfect questions. But because they force clarity.

Customer Churning

“What specific outcomes were you hoping to achieve that you feel we didn’t deliver on?”

“When did you first start considering alternatives?”

“If nothing changed on your end, what would have needed to be different on ours for you to stay?”

These questions help you understand expectation gaps, timeline, and whether this decision was reactive or building quietly for months. They also give you insight you can use to prevent the next churn.

New Executive Stakeholder

“What does success look like for you in your first 6-12 months in this role?”

“Have you used a similar solution in the past, and how does that compare to what you see here?”

“What would make this partnership a clear win in your eyes?”

This aligns you to their definition of value, surfaces competitive bias early, and gives you a chance to anchor the relationship at the executive level before someone else controls the narrative.

Upcoming M&A

“How do you anticipate this acquisition impacting your current tech stack?”

“Who will ultimately be involved in decisions about which systems stay or go?”

“What would integration success look like from your perspective?”

These questions help you understand decision power, consolidation risk, and whether you need to reposition yourself as essential infrastructure versus a replaceable tool.

Product Gaps

“How is this gap impacting your team’s daily workflow?”

“What workaround are you currently using?”

“If this were solved tomorrow, what would that enable for your team?”

This shifts the conversation from feature request to business impact and helps you quantify urgency.

Lack of ROI

“What metrics are you currently using to evaluate success?”

“Were these the same metrics we aligned on at the beginning of the partnership?”

“What would need to happen in the next 90 days for you to feel confident in the investment?”

This uncovers misalignment, adoption issues, and whether expectations were ever clearly defined in the first place.

Preparation is not paranoia, it’s professionalism.

It’s assuming that at some point, a conversation will not go the way you planned and deciding in advance that you will stay calm, stay curious, and stay in control of the moment.

The best CSMs aren’t the ones who never get surprised. They’re the ones who are steady when they are.

And the best leaders don’t just hope their teams will “handle it.” They actively coach for these moments before they happen. Because ready or not… the conversation is coming. The only question is whether you’ll be prepared when it does.