How To Improve Client Retention and Boost Upselling in Sales

How To Improve Client Retention and Boost Upselling in Sales

Build Stronger Relationships, Not Just Pipelines

Client retention begins with creating a connection. The more your clients feel understood and supported, the more likely they are to stay and grow with you.

How to:

• Focus on understanding the client’s goals and objectives beyond your product or service.
• Express genuine curiosity, ask what’s changing in their world, and how you can support them in it.

Example:
A B2B account manager I coached stopped opening with product updates and instead started meetings with, “What’s been the biggest challenge in your role this quarter?” Within two conversations, she identified cross-departmental needs that resulted in an upsell worth £50,000, all without ever mentioning the word “upsell.”

Listen to Understand First, Then Tailor Your Support

Client retention improves when clients feel heard, acknowledged and valued, which means going beyond mere transactional listening.

How to:

• Summarise what your client shares before providing advice.
• Use the same language when discussing their needs or frustrations.

Example:
While coaching a tech sales rep during a client meeting, I watched him paraphrase the client’s frustration using their own words: “So, if I’m hearing you right, it’s not just about speed, it’s that the current system is holding your whole team back?” That simple act of reflective listening, combined with mirroring the client’s words, completely shifted the tone of the conversation. Instead of seeing the premium product as a luxury, the client began to view it as a necessary solution to a genuine operational problem.

Educate, Don’t Just Sell

Your existing clients may not be aware of everything you offer or how it can benefit them right now.

How to:

• Use quarterly reviews to showcase new features or services, ensuring they are directly aligned with their goals.
• Share brief case studies of similar clients who achieved excellent results.

Example:
One of my SaaS clients was having difficulty engaging existing customers with new features. During our coaching sessions, we developed a strategy to deliver short, focused update videos featuring results-driven headlines, such as: “How XYZ Media Reduced Manual Reporting by 40% with This Upgrade.” This slight shift in approach, which prioritised adding value instead of pushing for sales, led to a noticeable increase in engagement and a 22% rise in upsells within just six months.

Use Emotional Intelligence to Choose the Right Moment

Upselling too early, or when the client is facing unrelated pressures, can damage trust. Emotional intelligence allows you to notice unspoken cues.

How to:

• Pay attention to signals of satisfaction, curiosity, or frustration.
• Ask permission to explore: “Would you be open to looking at something that might help with that?”

Example:
While coaching an account manager during a client visit, we discussed how to read between the lines and lead with empathy. The client was clearly under pressure due to a staffing shortage. Instead of promoting a new service, the account manager said, “It sounds like now isn’t the right time to explore anything new. Can I check back in a month once things have settled down?” That simple, emotionally intelligent response built trust, and six weeks later, the client signed a significantly larger deal.

Track Progress, Celebrate Achievements, and Add Value

Retention isn’t just about solving problems; it’s also about acknowledging successes and showing that you genuinely care.

How to:

• Celebrate key milestones such as contract anniversaries or successful projects.
• Send personalised thank-you notes or messages without any specific agenda.

Example:
While working as an interim Sales Director with one client, we introduced a simple yet powerful practice: the client success team would send a short, personalised voice note every time a client hit a key KPI. It was quick, human, and meaningful, and it helped strengthen the emotional connection. That consistent recognition opened the door for deeper conversations and future expansion opportunities.

Why This Matters

When you prioritise retention and upselling with care and curiosity, clients stay longer, buy more, and become your best advocates. It’s not just a good business practice, it’s a smarter, more human approach to selling.

But here’s the truth: these skills are not developed by accident. They’re developed through intentional training, reflection, and coaching.

Are you ready to enhance your team’s relationships with clients?

My Selling with Integrity and Emotional Intelligence training workshop is designed to help account managers and sales professionals improve customer retention, build trust, and unlock new opportunities without ever sounding “salesy.”

Through practical interactive discussions, your team will learn to:

• Sell with self-awareness and emotional intelligence
• Ask better questions and listen with purpose
• Transform client conversations into long-term value

Let’s talk about what your team needs.
Because great selling starts with better relationships.

Please call me on 020 8337 5937 or send an email to gary@garymorgan.coach

Find out more about my sales training here.