Recently, I stayed at a hotel out of town. The overall experience was solid. Clean room, polite staff, and decent service. The included breakfast? Let’s just say it met the standard of “included hotel breakfast.” Overall, no complaints.

Then the marketing department got involved.

Exactly one hour after I checked out, I received an email asking me to leave a review.

Now, think about that.

Have you ever not been in the middle of something like traveling, navigating airport lines, wrangling bags, locating coffee, etc. an hour after hotel checkout?

Me neither.

At first, I thought I just forgot to leave a review. But then I realized I wasn’t going to just on principle. It felt like the brand didn’t understand me as a customer or as a human. That matters.

The Problem: Automation Without Empathy

This wasn’t just bad timing. It was a classic case of automating without thinking.

Yes, we’ve all heard “strike while the iron is hot,” but too many marketers interpret that as:

Strike while the iron is still in the fire.

Instead of reading the room (or the traveler), they fired off the request immediately, likely because that’s when their CRM or marketing automation system said to do it. No context. No empathy. Just a trigger and a template.

What Should Have Happened?

A smarter move? Wait 24–36 hours after checkout.

That’s the sweet spot. By then:

• The guest is home or back at work
• The travel stress has worn off
• They’ve had time to reflect on their experience
• They’re no longer reacting. They’re recalling

It’s a small change, but small timing tweaks often lead to big conversion lifts. Especially when you’re asking for something.

Human Behavior Isn’t Linear Your Funnel Shouldn’t Be Either

This whole situation reveals a deeper truth; customer behavior isn’t a checklist. People don’t move through funnels the way marketers draw them on whiteboards. Real human behavior is messy, emotional, and nonlinear.

At the moment I received the review request, I was trying to make a connecting flight. My attention was divided between gate changes, boarding announcements, and wondering if I had enough time to grab coffee. I wasn’t in a “reflect on my stay” mindset. I was in survival mode.

Understanding when people are mentally available is just as important as knowing what action you want them to take. Emotional state, context, and attention span all play into conversion. Miss those variables, and you’ll miss your window even if your copy is perfect.

The Customer Experience Is the Marketing

The hotel did everything else right. But that single poorly timed email left a bad taste in my mouth and that’s the moment I remember most.

That’s the irony. A decent stay. No complaints. But the follow-up is what I recall because it was off. That’s how powerful timing and relevance are in the customer journey.

Every interaction is a brand impression.
The ones that come after the sale are the ones that shape loyalty.

Marketing doesn’t end when the transaction is over. In fact, that’s when it starts building long-term trust. If your follow-up communication feels rushed, tone-deaf, or robotic, you’re sending the message that your business cares more about the metric than the memory.

Develop a Customer Avatar Then Think Like Them

Here’s a question: If the hotel marketing team had taken even five minutes to map out a customer persona; a real, thoughtful avatar of a typical traveler, would this email have gone out when it did?

Imagine the avatar:

• Business traveler
• Likely rushed in the morning
• Navigating airport logistics
• Possibly stressed, juggling meetings or family obligations
• Zero desire to answer surveys on the go

Now imagine stepping into that person’s shoes. Would you send a review request at that moment?

Of course not.

This is why developing customer avatars is not a marketing luxury, it’s a strategic necessity. If you don’t take time to understand your customer’s world, your timing, tone, and tactics will be off. Even if you have the best tools in the world.

Use Behavioral Insights to Inform Strategy

Let’s go a step deeper. Once you understand your customer’s behavior and emotional state, you can:

• Reorganize automation flows based on when people are likely to respond
• Adjust your messaging cadence to feel more like a conversation, less like a checklist
• Create trigger windows based on natural human downtime (evenings, post-trip, weekend mornings)
• Use conditional logic to delay certain emails based on travel time or location

This is how you move from tactics to strategy.

Most brands are playing checkers. They are trying to get the review, the referral, the upsell as soon as possible. Smart brands are playing chess. They’re thinking moves ahead and aligning their messaging with moments of maximum receptivity.

Timing Drives Trust. Trust Drives Results.

I didn’t ignore that email because I was mad. I ignored it because it reminded me that the business wasn’t thinking about me, it was thinking about metrics.

But customers don’t think in metrics. They think in moments.

Here’s what I believe:

If your brand respects my time, I’m more likely to give you mine.

That’s true for emails, ads, texts, popups or anything that asks for my attention. And it’s especially true for anything that asks for my feedback.

If this hotel had waited just one day, I probably would’ve given them a solid four-star review. Instead, they lost the moment and potentially, the marketing momentum.

The Takeaway: Think Human First, Martech Second

Don’t let tools dictate your timing. Let people do that.

Yes, use automation. Yes, build smart campaigns. But always, always anchor your strategy in human behavior. That’s the difference between forgettable campaigns and frictionless experiences.

Before launching your next campaign or setting up that next flow, ask:

• “What’s my customer doing when this message hits?”
• “What emotional state are they likely in?”
• “Does this feel helpful or intrusive?”
• “Would I respond to this if I were them?”

If the answer is “probably not,” then wait.

The best marketing isn’t loud. It’s timely.

Final Thought

The next time you’re mapping out a customer journey, don’t just focus on the steps. Focus on the timing. Ask not only “what do we want them to do?” but “when are they most likely to do it?”

And more importantly:
What would make them want to do it?

That’s the real difference between transactional marketing and transformational strategy.

Your conversions will thank you.
Your customers will notice.
And your brand will be remembered. Not for its automation, but for its understanding.

Let’s Discuss!

What’s the worst-timed email or notification you’ve ever gotten? Bonus points if it made you never want to engage with the brand again! Or, let’s chat on LinkedIn.

*This article originally appeared on Medium