How to trigger Drift conversations based on user behavior in real time

If you want to talk to your website visitors at the right moment—say, after they’ve spent a while on your pricing page or look lost on the checkout—this guide’s for you. Triggering live chat in response to real user behavior isn’t magic, but it’s not always plug-and-play either. Here’s how you can actually set up Drift to do this without losing your mind (or your lunch).

Step 1: Understand What Drift Can (and Can’t) Do

Let’s get something straight before you start: Drift’s strength is in targeting chat messages and bots based on a mix of visitor data and on-site behavior. But it’s not an all-seeing eye. You’re mostly working with:

  • Page URLs: What page are they on?
  • Time on page/site: How long have they been hanging around?
  • Scroll depth: Have they actually read, or are they just bouncing?
  • Custom attributes: Data you send in (think: logged-in status, account tier, etc.).
  • Events: Actions like clicking a button, filling a form, etc.—if you wire these up.

What doesn’t work? - Tracking anything super granular without your dev team (e.g. hovering over a specific image, partial form fills). - Real-time triggers for complex in-app behaviors out of the box. You’ll need the API for that.

Pro tip: Don’t try to boil the ocean. Start with obvious triggers—like time on page, or repeat visits—before obsessing over micro-events.

Step 2: Map Out the Behaviors That Actually Matter

Don’t just set up chat triggers because you can. Before you log into Drift, ask yourself:

  • Who do you want to talk to? New visitors, returning users, trial subscribers?
  • Where are they on your site? Pricing, docs, checkout, blog?
  • What do you want them to do? Book a demo, ask a question, finish signing up?

Make a quick list. Here’s a simple example:

  • Pricing page, 45+ seconds: Offer help or answer pricing questions.
  • Checkout page, stuck for 2+ minutes: Nudge to see if they need help.
  • Logged-in users on dashboard: Offer onboarding resources.

Skip the “chat everywhere, all the time” approach. You’ll annoy people and overload your team.

Step 3: Set Up Basic Behavioral Targeting in Drift

Now, let’s get hands-on.

  1. Log in to Drift and go to Playbooks.

  2. Playbooks are where you set up targeted chat messages and bots.

  3. Create a new Playbook.

  4. Pick Chatbot or Live Chat, depending on if you want a bot to start or a human to jump in.

  5. Set audience filters.

  6. Here’s where the magic happens. You can target by:

    • URL: Show only on /pricing, /checkout, etc.
    • Device type: Desktop or mobile.
    • Visitor type: New, returning, or known user (if identified).
    • Time on page: E.g., “Show after 30 seconds.”

  7. Add custom attributes (optional).

  8. If you’re passing in user info—like plan type or account status—you can target based on that too.

  9. This requires adding Drift’s JavaScript API to your site. If you don’t have a dev handy, stick to out-of-the-box filters for now.

  10. Draft your message.

  11. Keep it short and specific: “Need help comparing plans?” works better than “Hi, can I help you?”

What works well:
- Time on page and URL targeting. Easy wins, no code required. - Using “if visitor is known user” to avoid pestering logged-in customers with sales pitches.

What to ignore:
- Overly broad triggers (“Show chat on all pages after 5 seconds”). You’ll annoy more people than you help. - Trying to get too clever with emojis or “personalized” greetings if you don’t have real data to back it up.

Step 4: Trigger Messages Based on Real-Time Events (Advanced)

If you want to get fancier—like triggering chat when someone clicks a specific button or completes a certain action—you’ll need to set up custom events. This is where most folks get stuck because it requires a bit of JavaScript and possibly help from your dev team.

How to do it:

  1. Add Drift’s JavaScript snippet to your site.

  2. You probably did this during setup, but double-check.

  3. Use the Drift API to identify users and send custom events.

  4. For example, when a user clicks “Request Demo,” fire a Drift event:

    js drift.api.track('Requested Demo');

  5. You can now use this event as a trigger for Playbooks.

  6. Set up Playbooks to respond to these custom events.

  7. In the Playbook audience filters, select “Triggered by event” and pick your custom event (“Requested Demo” in this case).

Honest take:
Custom events are powerful, but they’re fiddly. You need someone comfortable with code, and you’ll need to test thoroughly. If you’re not technical, stick with URL and time-based triggers until you can get help.

Step 5: Test Like a Real User (Not Just in Preview)

You’d be surprised how easy it is to mess this up—like messages never firing, or firing too often. Here’s how to avoid embarrassing yourself:

  • Test in incognito mode. Make sure you’re seeing what actual visitors see.
  • Try on mobile and desktop. Triggers can behave differently.
  • Check for “creepiness.” If your message is too specific (“I see you’re stuck on the pricing page for 2 minutes…”), people get weirded out.
  • Watch for chat overload. If users get hit with 3 different chatbots in one visit, you’ve overdone it.

Pro tip: Ask a friend or colleague to try your site and give you honest feedback.

Step 6: Measure and Tune—Don’t Set and Forget

You’ll want to keep an eye on what’s actually working. In Drift’s analytics, look at:

  • Open rates: Are people actually opening your chat messages?
  • Response rates: Do they reply, or just close it?
  • Conversions: Did chats turn into booked demos, purchases, etc.?

If something’s getting ignored or closed, change it up. Shorten your message, move the trigger later, or try a different page. And don’t be afraid to turn off what isn’t working.

Step 7: Keep It Simple, Then Iterate

It’s tempting to build a web of triggers, bots, and logic—especially if you’re technical. Resist the urge. Here’s what actually works:

  • Start with 1–2 targeted, helpful messages on high-intent pages.
  • Use clear, human language.
  • Tune based on real results, not wishful thinking.
  • Don’t assume more automation = more sales.

You can always add complexity later. But if you annoy people or drown your team in pointless chats, you’ll just end up turning it all off.

Summary

Triggering Drift conversations based on user behavior isn’t rocket science, but it does take some thought (and a little discipline). Focus on the moments where a real human touch can help—like when someone’s stuck, curious, or about to buy. Set up your first couple of triggers, see what works, and tweak as you go. Keep it simple. Iterate. And ignore anyone who says you need a “holistic conversational engagement strategy” on day one. Just help your visitors, one real-time chat at a time.