20 Questions to Grade Your Personalized Customer Experience

The reason your human agents aren’t personalizing across channels the way they should be is probably because you’re asking them to be machines.

But they’re not. Nor should they be.

They’re likely tracking to volume-based goals. The data they have available to them is siloed and slow to be delivered. They have to bounce between 4 or 5 different tools just to interact with one prospect or customer…

They’re set up to be go-betweens, instead of just being set up to offer human support to humans who need it. It’s simply not sustainable.

For high-consideration industries like insurance, healthcare, education, and home services, delivering a personalized customer experience is no longer optional—it’s essential. But what does that really mean, and how can you do it at scale?

Here, we’ll define what it really means to personalize CX outreach in 2025, and highlight the 20 questions you can pose to yourself to score your own personalization efforts—helping identify how you can combine AI and human output to drive positive customer outcomes across every channel, all the time, at scale.

What is a Personalized Customer Experience?

We know “personalization” is a bit of a buzzword. Think of all the articles you’ve read telling you to, “tailor unique outreach based on customer behaviors and preferences,” or something similar.

Sure… But what does that actually mean? What does that actually look like?

From your viewpoint:

  1. Ingesting large amounts of first-party data, and utilizing the right tech to unify the data points that help build profiles for individual contacts—and update them in real time.
  2. Testing different paths of outreach (channels, timing, scripts, content, etc.) in real-time to know exactly when and how to connect with someone.
  3. Centralizing disparate outreach channels into as few tools as possible.
  4. Using AI to retrieve data, score interactions, and inform your agents of pertinent contact details.
  5. Blending in AI outreach and letting it continually learn and iterate, so you can personalize at any scale.

From your prospect/customers’ viewpoint:

They receive a message that acknowledges the precise stage of action they’re in:

  1. When they want it
  2. Through the right channel
  3. In a tone that matches their specific need
  4. With no lost context or redundancies across channels or messages

Perhaps most importantly in 2025, is that you’re able to do this at scale. That’s where your tech stack comes into play (more on that later).

Why Personalization Matters in High-Consideration Industries

According to Salesforce, 65% of customers expect companies to adapt to their changing needs and preferences, but 61% of customers say most companies treat them as a number.

80% of customers say the experience a company provides is as important as its products and services (and are more likely to make purchases from brands that deliver personalized interactions).

McKinsey even states that, “companies that grow faster drive 40 percent more of their revenue from personalization.”

Personalized CX matters for high-consideration industries because the decisions consumers make are more complex, and generally, more impactful.

In many, if not most cases, customer experience will be the sole decision point in a contact deciding to work with you.

There’s a lot that goes into each interaction:

Choosing a health plan, a new education program, pet insurance, life insurance… These are not easy decisions. People will have a lot of questions that are often delicate or very specific to their life.

There are also many events that play a part in every customer journey. For example…

How AI Powers a Personalized Customer Experience

Here’s the truth: AI agents (even phone agents) are getting really good at sounding and writing like humans.

That means you can build out your workflows so that your humans don’t have to try to be machines anymore.

Your people are extremely good at being human (go figure). AI agents are extremely good at being machines (also go figure). It’s kismet.

Humans can focus on being human and offering more hands-on support where needed, while AI acts as the machine—working through routine tasks and connecting dots between disparate workflows, data, and systems.

Using AI to Understand Customer Data

AI can process vast amounts of data to uncover patterns and preferences. For example, machine learning algorithms can analyze purchase histories, support tickets, and browsing behavior to predict future needs.

Automating Personalized Outreach with AI

AI enables businesses to send timely, relevant messages—e.g. an insurance company can use AI to remind a customer about policy renewal based on their engagement patterns.

Enhancing Human Agent Performance with AI Insights

AI tools like chatbots and recommendation engines can augment human agents’ ability to serve customers. Agents equipped with AI insights can offer more relevant solutions during interactions.

20 Questions to Answer to Grade Your Personalized Customer Experience

Maybe you’re not personalizing at all. Maybe your team is personalizing well, but you don’t have a great route to scaling. 

Whatever the case, the real answer to whether or not your CX is personalized depends on what your tech stack looks like, which we can’t prescribe from afar. It’s relative. The answer to that question—i.e. “How good is your tech?”—would answer how close you are to being able to personalize.

If you are personalizing successfully, but need to scale, the answer to a lot of these questions will be, “incorporate AI,” or “add new software (so you can incorporate AI).”

To give yourself a relative CX personalization score, answer the following 20 categorized questions.

Consolidating Customer Data into Unified Profiles

  • Have you gathered data from all key touchpoints (website, CRM, support logs)?
  • Are you currently able to integrate this data into a single, actionable profile for each customer?

Using AI to Segment Customers Dynamically

  • How well do you understand the different customer segments within your audience?
  • Are you using real-time behaviors and historical data to dynamically group and route customers? (For example: Grouping customers by their purchasing journey stage.

Mapping the Customer Journey to Identify Key Touchpoints

  • Have you visualized the complete customer journey from start to finish? Are you able to map this out for different customer paths?
  • Do you know which touchpoints have the most potential for personalized engagement?

Automating Timely, Contextual Outreach

  • Are you aware of the best times to reach your customers based on their preferences per channel?
  • Do you use automation to schedule and send messages when customers are most likely to engage?

Personalizing Messaging Based on Real-Time Insights

  • Are you adapting your communication to reflect the latest customer behavior, such as browsing patterns or purchase history?
  • How quickly can you react to live data to personalize your messaging?

Leveraging Predictive Analytics for Proactive Service

  • How effectively are you predicting your customers' future needs?
  • Are you proactively offering recommendations before your customers ask for them? (For example: Recommending additional home services after a recent booking.)

Training Agents on AI Insights for High-Quality Interactions

  • Are your agents equipped with AI-generated insights to improve interactions?
  • Do you train your agents on how to use the insights you’re providing them with?

Monitoring and Optimizing Campaigns Continuously

  • Are you continuously monitoring your campaigns, step-by-step, to understand their impact on CX?
  • How well are you using real-time data and AI dashboards to adjust and optimize your strategies?

Testing and Iterating Personalization Strategies

  • How often do you test new personalization approaches across phone, email, and SMS to identify more effective strategies?
  • Are you actively iterating and running new tests, step-by-step, based on connection rates, conversion rates, call times, and other performance indicators?

Measuring ROI and Refine Based on Metrics

  • Are you able to track the impact of your personalization efforts on customer experience, customer retention, and satisfaction?
  • Do you have the right metrics in place to connect specific customer journeys back to ROI and make necessary adjustments across phone, email, and SMS?

Real-World Examples of Personalized CX in High-Consideration Industries

Healthcare: AI-Driven Patient Engagement

Hospitals use AI to send appointment reminders and health tips tailored to patient histories, improving adherence and outcomes.

Insurance: Tailored Policies Based on Customer Profiles

Insurance companies leverage AI to recommend policies based on customer demographics, behavior, and previous claims.

Home Services: Automating Proactive Maintenance Reminders

Home service providers use AI to predict maintenance needs, scheduling reminders before issues arise.

Metrics to Track the Success of Your Personalization Strategy

Conversion Rates from Outreach

Across channels, keep track of your agents' success with connecting with contacts when they reach out. How many dials or messages does it take to have a meaningful interaction with a prospect or customer?

Conversion Rates from Outreach

More personalized interactions should move prospects through the journey more quickly. That might look vastly different per industry (could be a meeting booked, appointment made, payment scheduled, plan selected, etc.), but it’s important to keep an eye on these metrics as you iterate new personalizations.

Customer Retention Rates

For high-consideration industries, there are many regular actions being taken post-conversion. Are you treating your customers well when they ask for support, schedule follow-ups, or miss payments and appointments?

Meeting your customers where they want to be met will show directly in your retention rates. As you learn to excel with personalization, your retention rates will assuredly rise.

Net Promoter Score (NPS) / Customer Satisfaction Score (CSAT)

On a more macro-level, NPS and CSAT are the driving definers of your personalization efforts. If these scores are low or dropping, it means your customer experience needs to better connect with your customers.

These should be two anchor metrics you use to measure whether your personalization efforts are working.

The Future of Personalized Customer Experience

AI is revolutionizing how businesses approach personalization, especially in high-consideration industries, where every interaction matters. 

Hopefully the 20 questions above provided some insight into the next steps you need to seek to continue scaling your personalization efforts. 

Regal’s AI Agents and CX tools currently help companies across healthcare, insurance, local services, financial services, and legal better combine AI and human agents to personalize, scale, and continuously improve with every interaction.

Personalized Customer Experience using AI Phone Agents

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