Set alerts

Why This Works

Proactive outreach builds trust and loyalty. Reaching out to a user who is struggling *before* they complain to support or churn turns a moment of high friction into a moment of delight. It shows you're paying attention and you care about their success, creating a powerful positive experience that they'll remember and share.

These alerts are a powerful diagnostic tool for your product. They aren't just one-off support tickets; they are signals of where your UX is confusing, your onboarding is failing, or your features are broken. By tracking the frequency of different alerts, you gather quantitative data on your product's biggest friction points, which helps you prioritize the most important fixes.

Three real examples

Supercharge this playbook by integrating session replay tools (like LogRocket or Hotjar). When an alert for a stuck user fires, include a link to their latest session recording in the notification. This lets you see *exactly* what they were doing and where they got confused.

The step-by-step playbook

1. 1

   1. Identify Your 'Aha!' Moment

   What is the single key action a user must take to get value from your product? For Facebook, it's adding 7 friends. For Slack, it's sending 2000 messages. Define this clearly.

2. 2

   2. Define 'Stuck' Signals

   Brainstorm a list of behaviors that indicate a user is stuck. Think both in-app (e.g., visited pricing page 3 times but didn't upgrade) and 'negative' events (e.g., invited a teammate but teammate never accepted).

3. 3

   3. Choose Your Analytics Tool

   You need a tool that can track events and trigger notifications based on user cohorts. Product analytics tools like June.so, Mixpanel, or Amplitude are built for this. Start with the free plan.

4. 4

   4. Instrument Your Key Events

   Ensure you're tracking the events needed for your alerts. This includes signups, key feature usage, and 'negative' events like `payment_failed`. If you aren't tracking it, you can't alert on it.

5. 5

   5. Build Your First Alert

   Start with one simple, high-value alert. A great first one is: 'User signed up more than 3 days ago AND has not performed {Your Aha! Moment}'. This targets users who are slipping away.

6. 6

   6. Configure The Notification

   Send the alert to a place your team will see it instantly. A dedicated Slack channel (#user-alerts) is ideal. Make sure the alert message includes the user's name, email, and a link to their profile.

7. 7

   7. Reach Out Manually

   For the first few weeks, send every email manually. Use a template but personalize it. This helps you learn the exact pain points from user replies, which is incredibly valuable feedback.

Copy-Paste Outreach Template

When an alert fires, you need a simple, non-robotic way to offer help. This template works because it's personal and direct. Send it from your personal founder email address.

Subject: Quick question about {Your App Name}

Hi {FirstName},

I'm {Your Name}, one of the founders of {Your App Name}. I noticed you signed up and started to get things set up, but haven't had a chance to {Key Activation Event} yet.

Sometimes new users run into a small snag at this stage, and I wanted to see if I could help with anything. Happy to answer any questions or clarify how things work.

Let me know!

Cheers,
{Your Name}

Key Questions to Answer First

• What is the single most important action a new user must take to see value?
• What are 3-5 user behaviors that signal they are stuck, confused, or about to churn?
• Where should alerts go to be seen and acted on immediately (e.g., a specific Slack channel)?
• Who is responsible for monitoring the alerts and reaching out to the user?
• How will we measure success (e.g., reply rate, activation rate of helped users)?

Focus on defining specific, actionable 'stuck signals'. 'User logged in' is a weak signal. 'User attempted to connect their Google Calendar but the connection failed' is a strong signal.

Recommended tools

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Mistakes that kill this play

• ×Creating too many noisy alerts at once. Start with one, prove its value, then add more.
• ×Making alerts too generic. 'User was active for 5 minutes' is useless. 'User invited 3 teammates' is gold.
• ×Not including actionable data in the alert. Always include the user's email and a link to their profile.
• ×Automating the outreach too early. Send emails manually at first to learn from the replies.
• ×Forgetting about 'negative events' like `integration_failed` or `payment_declined`. These are often the most urgent and important alerts.
• ×Sending alerts to a black hole. Pipe them into a visible, dedicated Slack channel where they will be acted upon.
• ×Not having a plan to respond. If a user replies for help on a Saturday, you need to be ready to answer them quickly.

Your First 7 Days

• Day 1: Decide on your single most important 'aha!' moment. Then, brainstorm 3-5 specific 'stuck' signals related to that action.
• Day 2: Choose your analytics tool (e.g., June.so). Instrument the key events you need to track your chosen signals.
• Day 3: Build and enable your first alert in your tool. Target one specific 'stuck' signal like 'user signed up 3 days ago but has not completed activation event'.
• Day 4: Set up your notification destination (e.g., a new #user-alerts channel in Slack). Write the draft outreach email template in a separate doc.
• Day 5: Wait for the first alert to fire. When it does, copy your template, personalize it with the user's details, and send it from your own email account.
• Day 6-7: Monitor for replies and be ready to help. Every conversation is a learning opportunity. Note down the user's problem - it's a roadmap for improving your product.

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