The Proactive Play: Initiating a Valuable Dialogue
Most brands wait.
They wait for users to visit the site. To click the chat bubble. To ask for help.
But great brands don’t just wait — they start the conversation.
Proactive conversation marketing is about initiating contact at the right moment, in the right context, and with the right message — to add value, not pressure.
Done well, it builds trust, improves engagement, and opens doors that wouldn’t otherwise be knocked on.
What Is a Proactive Conversation?
A proactive conversation is brand-initiated, context-aware, and helpful. It might:
- Greet a returning visitor
- Offer support when someone appears stuck
- Recommend content based on browsing behaviour
- Follow up after a purchase or abandoned cart
- Trigger outreach based on lifecycle or sentiment
It’s not cold outreach. It’s smart timing.
The Golden Rule of Proactive Messaging
Don’t interrupt. Assist.
A proactive message should feel like help, not a hook.
Examples of Proactive Triggers
| Trigger Type | Example Message |
|---|---|
| Behaviour-based | “Need help deciding between these two?” |
| Time-based | “Still thinking it over? Let’s book a quick call.” |
| Location/context | “Chat available while you browse” |
| Lifecycle event | “Welcome back! Want a refresher?” |
| Sentiment signal | “Looks like something went wrong — can we help?” |
| Cart/browse intent | “Still thinking about this product? Here’s a review.” |
Tools That Enable Proactive Dialogue
Proactive messaging depends on data, timing, and automation. The right tools help you sense intent and act fast.
| Tool / Platform | Proactive Use Case |
|---|---|
| Intercom, Drift | Website-based live prompts |
| Klaviyo, HubSpot | Triggered email and SMS outreach |
| Braze, Customer.io | In-app and mobile notifications |
| Segment, GA4 | Behavioural triggers and custom events |
| AI engines (ChatGPT, Claude) | Dynamic message generation and variation |
Integrating your data layer ensures messages are relevant — not random.
Real-World Example: Booking.com
Booking.com doesn’t wait for questions. It sends helpful nudges throughout the booking journey: price alerts, weather reminders, transport info, cancellation policies — all before the user even asks. The tone is helpful, timely, and always relevant.
This creates value, not noise — and builds customer confidence.
How to Start Proactive Conversations Without Being Pushy
- Use behavioural signals: Only trigger messages when there’s clear intent or hesitation
- Be useful: Offer help, not hype
- Be personal: Use name, context, and tone where possible
- Give control: Always offer a way to exit or mute the conversation
- Test and optimise: Use A/B testing to refine timing, wording, and frequency
Proactive Doesn’t Mean Pushy
The best proactive messages feel like great service — not marketing.
It’s the digital version of a helpful store assistant who shows up just when you need them, but never lingers too long.
Right: “Need help checking out? I’m here.”
Wrong: “Only 3 left! Don’t miss out!” (on every page)
What This Chapter Really Means
You don’t have to wait for customers to make the first move.
With the right timing, tools, and tone, you can initiate conversations that create value, reduce friction, and build stronger relationships — without ever feeling intrusive.
“The brands that engage in relevant conversations are the brands people come back to.”
— Jonny Bowker