4 Easy Ways to Add Empathy to Your CX and Retention

Hi Friends,

If you are reading this, thank you.

Thanks for taking time out of your busy day to read this newsie. I never take that for granted.

Next week, I will be cohosting the first-ever IRL meetup for the CX discord I started two years ago, which I am VERY excited about. It’s in NYC on May 7th, and I wanted to extend an invite to this crew too. 

What started as a fun idea to avoid leaving my house has turned into a community of more than 1250 members. 😊

Most of my career wins have been from a somewhat straightforward but alternate approach to the status quo.

It started in the CX world when I had this somewhat simple insight:

We should not come to expect sh!tty customer experiences as the status quo. If companies like Zappos and Chewy are making the news so often for doing what feels like the bare minimum (non-outsourced CX and giving a sh!t), we are doing something wrong.

I have done my best to continue pushing this narrative on both the CX and Retention side of the house and elevate the bar we’ve so lazily set.

If customers spend their hard-earned money, they deserve some basics. 

  1. Brands should meet the expectations they set within their ads

  2. Shipping and delivery should be as promised, with no bait and switch

  3. CX should feel like a personalized and human experience, not weird as hell

Overall, I think we need to add more empathy to the CX and Retention side of the business.

I know that sounds like fluff, so let me give you some real-life examples.

Let’s go. 

This week’s newsie is brought to you by Siena AI!

This week, we’re spotlighting Siena AI, the pioneer and category creator of Empathic Autonomous AI Agents.

What Makes Siena Stand Out:

  • Empathic Interactions and Brand Consistency: Siena AI excels in delivering empathic interactions that resonate deeply with customers, all while maintaining your brand's unique tone of voice. It ensures every interaction feels personal and on-brand, whether addressing complaints or celebrating customer milestones.

  • Seamless Integration and Human-Level Reasoning: Embedded directly into your helpdesk, Siena AI functions like a natural extension of your team. It applies human reasoning to understand and solve customer issues comprehensively and autonomously, from routine inquiries to complex problems requiring nuanced decisions like refunds in Shopify or subscription modifications in Recharge. 

  • Superior Conversational Capabilities: With Siena AI, conversations flow naturally, mirroring human dialogue. This isn’t your typical chatbot experience; it’s about engaging customers with interactions so fluid they feel like they’re conversing with a human, enhancing satisfaction and loyalty.

Spotlight on Success:

  • Douxds: “Unlike others, Siena is multi-channel. Others have just a chat bubble on your site, but Siena gives support across all my channels like social, email, and more.”

 – Damon Dixon, Founder of Douxds

  • Subtl Beauty: “Siena helped us change our hiring strategy. Now, we can retain our existing agents and level them up rather than having to hire a revolving door of talent to keep up with demand.”

—Rachel Reid, Founder and CEO of Subtl Beauty

  • Canopy: "Having a flexible resource like Siena means we can address a high percentage of tickets during our busy season without adding undue stress on our team.” 

- Lucas Lappe, Founder of Canopy

With Siena, you can amp up your CX without the hefty price tag. It keeps things smooth and consistent, making sure every customer interaction is spot-on with your brand. Plus, it turns your customer support into a well-oiled machine—everything from your operations to your communication runs on a single, streamlined playbook. This means you can expect steady enhancements and fewer surprises along the way.

Siena is offering my readers an exclusive 3-month free trial. Just hit up their team and drop my name, Eli Weiss. 

What is empathy in CX, and how we can create CX teams and processes that put empathy first?

1. The way you lead:

Truth be told, whether you put CX under Ops or under Marketing does not matter as much as putting it under someone who:

A. Gives a sh!t about the customer and has EQ
B. Has been in the weeds and knows what it’s like

“Doing CX” is not rocket science, but great CX teams are not just made of folks who “knock out tickets.”

They are groups of people who love making things right and turning an experience around. They love hospitality and treating people the way they would want to be treated.

Great CX teams are inspired by leaders who get that. When CX leadership gets it, the team feels it. 

They are 10x more productive and impactful with great leadership.

Yes, maybe you can get all of this and still be maniacally focused on quota and speed, but great CX is inspired by great CX leaders.

When the inspiration dies, so does the great CX.

Bonus: If you want to ensure the rest of the team has empathy for what CX does on a day-to-day basis, throw them in the water.

I’ve seen some great brands that have every single employee rotate through the CX team for a week or two a year, and it’s an idea I really like. 

2. The policies you create:


The policies you set across your businessneed to be in line with the brand you are trying to create.

Nordstrom is trying to build the most customer-centric company, and their return policy is there to back it up.

Now, if you are dropshipping cheap caps, feel free to have a “final-sale” return policy set up.

But if you are selling $85 tee shirts and then charge a $9.95 fee to exchange that shirt, it’s icky.

The policies you set for your customers should be created with empathy and thoughtfulness. It should feel “on-brand” to where you are at as a company, if that makes sense. 

3. The tools you use: 

I have been on the record for being “anti-AI” a few years back. Every experience I have had with the bots has not been nearly as great as talking to a human, and what should have been “self-service” was a bunch of brands deflecting tickets and frustrating customers.

As AI has evolved, I’ve actually tested the waters with AI tools and prefer them to outsourcing my CX to other humans who don’t get it.

Great AI tools are the ones built to enhance what you already have, and are built empathy-first. 

Tools like Siena (our sponsor) are focused on building an agent that deeply understands and adapts to the unique needs of each business, ensuring that every interaction is as human and helpful as possible. 

Here's how they do it:

  • Customization: Tailoring AI to meet the specific operational needs of each business, recognizing the uniqueness of every use case.

  • Human-Like Training: Their AI is trained to follow human principles, ensuring it responds with empathy and understanding.

  • Holistic Integration: Seamlessly integrating into teams and operations to support a unified approach to customer service.

  • Cultural Alignment: Embodying empathy as a core value within internal teams to ensure every stakeholder interaction is impactful and their engagement with AI is seamless.

  • Comprehensive Experience: Going beyond just customer-facing interactions, their AI provides an empathic UI/UX that benefits all stakeholders.

4. The messaging you use:

This one comes up for me almost weekly, and it drives me insane.

Messaging, both from the Retention side of the house (email and SMS) as well as the CX side, needs more empathy and thoughtfulness.

Just last week, I reached out to a brand that I order from often. The order was placed a full week before and I had not heard a single word about shipping.

Yes, I was getting emails to buy more. No, not a single word about the items I was waiting for. This happens every time I order from there.

Upon reaching out the the CX team, I was told my items were in the “final stages of processing.”

I replied, “Ugh, it feels like it always takes a full week to ship out.”

Instead of “So sorry, I can only imagine how frustrating this is; I will pass this feedback along…”

I got, “Unfortunately, we are not in control of the warehouse or the processing time frames; thank you for your patience.”

Something so simple and basic would have shifted my entire interaction.

Instead of validation, I got dismissiveness. Same character count.

Swap the canned response for a tiny bit of empathy. (Oh, and switch warehouses, they suck.)

That’s it for this week!

Any topics you'd like to see me cover in the future?

Just shoot me a DM or an email!

Cheers, 

Eli 💛

P.S. Looking for inspo on your next email/sms campaign?

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