Why are CS Pros afraid of money?

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Hey CS Pro,

Ever had that moment where you see an expansion opportunity sitting right in front of you…and you just don't bring it up? Yeah, me too. Nearly half of all CSMs feel the exact same way. This week on the podcast, I am kicking off a two part series about moving from friendly to commercial. Part one is all about what is going on in your head, because if we do not fix the mindset first, no script is going to save you.

But first, today’s sponsor

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How Leading CS Teams Are Using Data to Build Trust

Retention comes down to trust. Check-ins and good intentions help, but consistently showing customers the value they’re getting, in their own data, is what drives renewals.

This ebook walks through the step-by-step process for using data-driven content across the customer lifecycle to earn and sustain customer trust. 

Inside, you will find:

• Why trust is the foundation of retention (especially in a downturn)

• How to map data-driven content to each stage of the customer journey

• The key components every piece of customer-facing content needs

• How Asana, Autodesk, Greenhouse, and Okta put this into practice

The Real Reason You Avoid Talking About Money

According to ChurnZero's CSM Confidential Report:

Not product knowledge. Not time management. The commercial side of the job.

And honestly, it makes sense. Psychology Today found that money conversations are one of the most universally avoided topics in human interaction. Combine that discomfort with a profession built on empathy and being the customer advocate and you get CS pros who are incredible at building trust but freeze the second it is time to talk commercially. That is not a personal failing. It is a systematic gap in how our industry was built.

The core problem is not that CSMs cannot sell. It is that most do not see themselves as someone who should sell. You spend months building an incredible relationship, then when the expansion moment shows up, you either pass it to sales, avoid it, or water it down to something like, "just a heads up, the renewal is coming up." That is not a commercial conversation. That is a throwaway comment.

The 5 Mistakes Keeping You in the Friend Zone

I have made every one of these myself, so no judgment. But naming them is how we fix them.

1️⃣ treating the word "commercial" like a dirty word. Being commercial just means you understand the business value of what you deliver and can articulate it. When a doctor tells you that you need surgery, you do not think they are being salesy. You think they are being direct and helpful.

2️⃣ waiting for permission to talk about money. If you are waiting for the customer to bring up the renewal or for sales to loop you in… you will always be too late.

3️⃣ leading with product instead of outcomes. Saying "we just launched this new module" is a product pitch. Tie it back to the business problem your customer is trying to solve instead.

4️⃣ apologizing before you start. "Sorry, I have to put my sales hat on for a second"… cringe. Research shows buyers are three times more likely to disengage from someone who avoids pricing discussions. The apology makes things worse.

5️⃣ separating value from revenue in your mind. When customers get value, they renew. When they get more, they expand. Revenue is not the opposite of value. Revenue is proof of value.

What to Do Instead

Redefine what commercial means to you. Stop associating it with pushy and start associating it with responsible. If you have all this knowledge about a customer's business and do not bring up opportunities that could help them… that is not being friendly. That is being negligent.

Detach your identity from the outcome. If a customer says no to an upsell, that is not a rejection of you. That is information. You are doing what a strategic advisor does, giving a recommendation.

Build commercial habits into everything you do. Every business review should include future growth opportunities. Every success plan should have a commercial milestone. When it is part of your rhythm, it stops feeling scary and starts feeling normal.

And learn the language of business. Your CFO does not care about health scores. They care about ROI, cost savings, and growth. When you connect product value to those conversations, talking about money is expected.

Your Weekly Challenge

Pick one customer this week. Just one. Write down the answers to these three questions.

1. What business outcome is this customer trying to achieve? Not features, the actual business goal.

2. Is there an opportunity for them to get more value from something they have not explored yet?

3. If you were going to bring this up in your next conversation, what would you say? Not a pitch. Just how would you naturally introduce it?

Write it down. Do not overthink it. You are building the muscle of connecting value to commercial opportunity.

Have a listen to the full episode on Spotify, Apple Podcasts, or YouTube and let me know what you think!

I hope you enjoyed this week’s newsletter.

If you have any questions or suggestions, please feel free to contact us.

Cheers to your CS success,

Anika