Detecting Customer Hesitation with AI and Converting That Into Sales

Customer Hesitation During Selling

One of the most overlooked hurdles when it comes to closing the sale is hesitation. It's not the case that people don't want to buy—it's just that something halts them at the last moment. It could be doubt, an element that is missing in their decision tree, or even just fear of making a poor choice.

But what if you were able to easily find those hesitation moments in the moment, and fix them? That is exactly what Generative AI in sales is allowing us to do today.

What Is Generative AI?

Generative AI is a form of artificial intelligence that can produce new content, insights, and data based on user interactions and behavioural patterns. It is currently being used in sales for helping teams to:

• Identify customer behaviour

• Detect hesitation signals/non-verbal signs

• Personalize solutions

• Improve conversion rates

Why Consider Customer Hesitation?

According to the Bayard Institute, over 67% of shopping carts in online retail are abandoned. That’s billions in lost sales due simply to hesitation on the part of the customer. Customer Hesitation can come in many forms like:

• Is this going to be the right product for me?

• Will it meet my needs?

• Is this brand trustworthy?

Addressing Customer hesitation, doesn't mean being overly aggressive. It means a little comfort and reassurance, when it's needed most.

Real World Examples of Brands Leveraging AI to Mitigate Customer Hesitation

1. Retail Brand Case Study

A major retailer found many of their users were spending tons of time on the sizing charts across their site but many were abandoning the cart without purchasing. We put together a little help for them by:

• Showing users a real customer picture - with size reference the same product was being displayed on the chart

• Offering live size expert chat

• Following up on product durability

Results:
✅ Conversions increased by 37%
✅ Returns went down 22%

2. Lululemon's Personalization Strategy

Lululemon is a brand that leverages AI to understand the intent of your visits:

They will:

• Personalize marketing messages based on new vs. returning consumers

• Track user behaviours relative to specific product pages they advocated

• Use Performance Max ad technology to dynamically adapt content in market in real-time

Results:
✅ Returns on total ad spend increased by 8%
✅ New customer revenue doubled
✅ Achieved an award from Google

3. B2B Sales with AI Understanding

B2B businesses face an additional challenge—buyers have teams and budgets. Using AI, they look for behaviours, such as utilizing multiple pricing tiers or downloading specifications without booking a demo.

They will respond with:

• ROI calculators

• Relevant case studies

• Direct access to a human expert

This is less about the hard sell and more about eliminating friction.

4. Microsoft’s Intelligent Ads

Microsoft modernized their advertising approach by utilizing AI.

• AI-generated ads were 25% more relevant

• Copilot Ads launched for 2024 with 1.3x conversions

• Almost half reported an improved experience

Instead of guessing, Microsoft allows AI to provide support at exactly the right time.

How to Leverage Customer Inertia into Conversions

Step 1: Identify "Pause Points"

Consider using:

• Heat maps to understand where users hover

• Session recording to identify abandonment

• Behaviour tracking to define hesitation patterns

• Pick up on common themes from sales call feedback

Step 2: Provide Reassuring Content

Reassurance = Trust = Sales

Some ideas:

• Reduce complicated ideas to comparisons or visuals

• Leverage customer reviews to overcome worry

• Be open about product limitations

• “And here's a tool to interactively understand "You vs. Them" charts

Step 3: Deploy AI Nudges at the Right Time

Not to be confused with annoying pop-ups—these are smart nudges.
AI can:

• Tailor up messages based on behaviours

• Suggest content that aligns with your user’s interests

• Launch a chat if someone is comparing prices

• Provide proof of success with other similar customers

Step 4: Test, Learn, Improve

You don’t have to throw the entire site in the bin and start again. You just need to test small changes.

• A/B test CTAs, eg, “See How It Works” vs “Get Started Now”

• Change your headlines to focus on speed, ROI or trust

• Republish your best-performing content in email, ads and blog.

How AI is Changing Sales?

More than 40% of sales teams are currently using AI tools to help with lead scoring, forecasts, and analysis, and those teams using AI report 1.3x better sales results.

Importantly, AI does not only automate activity, it enables sales teams to engage with the right customer, with the right message, at the right time.

Conclusion: Remove the Uncertainty, Get the Customer

Most visitors aren’t saying “no”, they are just saying “not now”. Your work is to shorten the time between uncertainty and confidence.

✔ Find the point of hesitation
✔ Provide them with valuable, authentic content
✔ Allow AI to guide them
✔ Document, test, and iterate

This way, you are not just growing sales; you are creating a longstanding trust. That is the victory.

But what if you were able to quickly discovery those hesitation moments in the moment, and resolve them? That is exactly what Generative AI in sales is enabling us to do today.

👉 Read more strategy in our blog posts about using AI to improve conversion rates.