The Customer Success Café Newsletter

The Customer Success Café Newsletter

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Stop Dreading Sales Talks: Easy Tips Inside
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Stop Dreading Sales Talks: Easy Tips Inside

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The CS Café Newsletter
May 04, 2025
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The Customer Success Café Newsletter
The Customer Success Café Newsletter
Stop Dreading Sales Talks: Easy Tips Inside
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Do you love helping customers but hate selling to them?

Many Customer Success pros feel their stomach tighten when they have to bring up new products during calls.

In today’s edition, I’ll share simple and easy ways that will help you turn these awkward selling moments into natural, helpful conversations that boost your confidence and results.

All without losing your trusted advisor status.

Did you know expanding existing customers costs companies 3x less than finding new ones? And Customer Success teams with strong expansion skills see up to 91% ROI over three years.

Here’s what CS pros say about selling in their role:

“I used to dread talking about upgrades, but now I see it as helping customers solve real problems.” – Jamie, Financial Services CSM

“Tracking customer pain points changed everything. My customers actually thank me for recommendations.” – Annie, SaaS CSM

Tracking the right metrics is key—learn which ones matter most in my Stop Building Systems Your Customers Don’t Care About article.

Meet Annie: A CS Pro Who Hated "Selling"

Annie was great at solving problems and building relationships.

But when her manager talked about "expansion opportunities," she thought, "I didn’t sign up to be a salesperson."

Then she shifted her mindset from selling to solving problems:

She started tracking customer pain points with a clear process.

She noted down their challenges and goals during every call, and soon, started talking about new products that felt like a natural part of helping her customers.

Results: her customers even thanked her for the recommendations instead of seeing them as sales pitches.

If you’re new to Customer Success or coming from sales, check out my Top Tips for Transitioning from Sales to Customer Success for practical advice on building strong customer bonds.

Before vs. After: How This Mindset Shift Changes Conversations

Before:
“By the way, we have this new feature I wanted to tell you about...”

After:
“Last week you mentioned struggling with reporting. We have a tool that could cut that work in half. Would you like to see how it works?”

See the difference?

The second way focuses on a real problem, making the conversation feel helpful instead of pushy.

If you feel sales anxiety, this simple change can calm your nerves and make customers more open.

The Problem-Solver Mindset: Your Key to Natural Conversations

The biggest change happens in your mind.

Stop thinking about "selling" and start thinking about "solving."

When you track customer challenges in every call, you realize recommending new features isn’t selling—it’s helping.

This mindset shift changes how you feel about expansion talks and how customers receive your suggestions.

A problem-solver mindset means:

  • Listening more than talking

  • Writing down specific pain points

  • Connecting solutions to those problems

  • Timing recommendations when they matter most

  • Measuring success with customer outcomes, not just revenue

Three Simple Steps: Make Product Conversations Feel Natural

Here’s how you can recommend products in a helpful, not pushy, way:

  1. Ask first: "What’s your biggest challenge with our platform right now?"

  2. Listen carefully: Note their exact words about what’s frustrating them

  3. Connect the dots: Show how a specific feature solves their problem

This puts the customer’s needs first.

You’re not pushing products—you’re offering real solutions.

So the conversation flows naturally from their needs to your recommendations.

For more on building deep customer relationships and engagement tactics, see my post on Customer Engagement Tactics.

Real Example: Jamie in Financial Services

Jamie works with banking clients.

Instead of pushing new security features, he asks about their compliance concerns first.

When clients mention audit challenges, he shows how the premium security package solves those exact problems.

“I used to dread talking about our premium offerings,” Jamie says. “Now I get excited when I hear a problem I know we can solve. My expansion rate jumped by 34% in three months using this approach.”

Quick Win: Try This on Your Next Call

Before your next customer call, write down 3 problems your customer has mentioned before.

For each, note which product might help.

You can also boost your prep with data-driven insights using my proprietary CS Calculators to quantify impact and ROI.

During the call, listen for these issues and bring up the right solution in a natural way.

This simple prep makes product talks feel more natural and helps you focus on solving, not selling.

The CS pros I coach say they feel more confident right away using this technique.

Give it a try and let me know how it goes!

To prepare for expansion conversations, use the proven frameworks outlined in my 4 Traits of Top-Performing CSMs post.


From Reluctant Seller to Trusted Advisor

The steps above will help you start.

But top CS professionals ($120K+) use specific frameworks that make these conversations even more natural and effective.

Upgrade to premium now and get my complete toolkit:

  1. The simple "Pain-to-Gain" conversation framework enterprise CSMs use

  2. Word-for-word scripts that make upsell talks feel helpful, not sales-y

  3. The 5-step checklist CS leaders use at growing SaaS companies

  4. Visual templates that make upgrade opportunities clear to customers

Mastering your communication is essential—see my Customer Success Communication Skills guide for more.

Upgrade To Premium

🔐The Complete Toolkit for Natural Expansion Conversations

1. The Pain-to-Gain Framework: Turn Problems into Solutions

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