Don't Automate Talking To Your Customers (When It Really Matters)

How I manually sent 100 emails to the people who tried, and failed to use, our product.


A few weeks ago we launched a new tool called Arrows Outreach, and let’s be honest… people didn’t use it like we expected. 😳 Even if usage had been higher, it’s unlikely we’d have launched a perfect product on day one.

We needed to figure out what was missing. ASAP.

I decided to email 100 of our users who dropped off after signing up. The responses have been extremely helpful so far, with more coming as I send follow-up emails. Here are a few of the responses I got:

Even your customers like getting personal emails!

People have been surprised to actually be hearing from the co-founder of an app they tried just once. They’re mostly replying because of the energy I put into writing them. They can tell I care.

Here’s the thing: a lot of people would send all these people the same bulk email, often with a link to a dull survey. But I’ll argue any day of the week that you should take the time to personally email each person. Especially if you’re the founder.

Most consumers can tell when an email is automated. Frankly, it’s pretty easy to sniff out when the “CEO” emails you seconds after signing up. People are quick to archive these messages, and why wouldn’t they? To confirm that people disliked automated emails from companies, I ran a poll with 50 random online participants who all resoundingly agreed that it’s “annoying” and they “HATE” to receive these emails.

You’re more likely to get useful responses when you make a human connection. Think about how much more often you go to coffee shops, stores, or restaurants when you get just the right amount of human attention. People notice when companies put a real human face on their communication without overstepping.

And I’ll always bet you get more valuable responses sending 100 targeted and personalized emails than sending 1,000 bulk messages.


Which customers should you email?

First you need to decide which type of user will likely to give you the most valuable responses given your situation. For us, this was the people who signed up and didn’t make it very far in our onboarding process.

With your product, it might be the users who cancel after a month, or who recently upgraded to a new plan (to figure out what’s causing them to upgrade). That said, you should run this process multiple times with different customer cohorts to get the most value. Just make sure you select a single, logically grouped batch and focus only on them for each cycle.

Once you’ve decided which group to email, go to your database, Intercom, Segment, Shopify, or wherever your general customer usage data is stored. You’ll want to filter and extract only these customers, but also the usage data relevant to why you’re emailing them and which will help you personalize the messages. Think: their website, twitter account, total orders, total payments, number of posts, total sessions, time since last X action, etc.


For us, I wrote a script to export this data directly from our database for each customer who didn’t complete setting up an Arrows Outreach list:

  • The customer’s email address
  • Signup date
  • Number of lists they created
  • Number of contacts they uploaded
  • Number of emails they’d sent from Arrows
  • Yes or No, if they’d created an email template

It’s best to have this data in a CSV format, so you can upload it to Google Sheets, Airtable, an email outreach tool, or ::cough:: our tool, Arrows Outreach. CSV gives you the most options for places to upload it.


What should you say?

Before sending emails to your list, write some boilerplate text to make each message easier to send. You should expect to tweak and personalize this text for each account based on the factors, so keep that in mind.

  1. Focus primarily on the #1 thing you want to learn or have happen from these emails. You don’t want to waste anybody’s time, and you’re hoping for the most valuable responses possible. That could be as easy as a simple Yes/No response, or as difficult as asking people to schedule a call. Either way, know your goal.
  2. Open your email with a personal greeting, and try to make it personal in a way that only a human could write. Find their twitter, or their recent blog posts, or draw on a personal connection might already have. It can be as simple as:
    “Hey Joel! Saw on twitter you launched a new album recently. Hope it’s going well!”
  3. Next, get to the point. Let them know why you’re emailing, and here you want to be specific as well. Don’t be creepy, but try to incorporate what you know about them as a user or customer. For example:
    “You’ve been a great customer of ours for over a year, but I noticed you stopped posting stories recently.”
  4. And finally, jump right to your ask. Keep it on one line and make it easy to understand what you’re asking.
    “Is there anything that’s changed recently to make you stop using X?”
Like I mentioned before, your #1 goal is to get a response. Hopefully you also get a useful initial response, but you mostly want to start a conversation. One simple question gives an opening to a back-and-forth where you can learn what you need to directly from your customers or schedule that call.


Sending the emails

Here we go. You have your email addresses. You have your email template. What’s next? Sending the damn emails, of course!

You have a few options: Some people like using a simple spreadsheet/Airtable and email (this was me in the past). Others prefer Trello to keep track of contact stage. If you have a CRM you like, then go for that. Since companies often already have a bulk email tool, you can even personalize the introduction line inside a spreadsheet and then use mail merge tags to insert the introduction.

If you have a tool that you feel comfortable with, where you can personalize each message, then go for it.

Otherwise, if you want to try something new and simple, we built Arrows Outreach specifically for this process. I’ve always hated jumping back-and-forth between a spreadsheet, my template file, and gmail… while always anxious that I was making a copy-and-paste mistake. (Also, it’s just smart to use the exact tool for which you’re getting feedback about. 🤣)

The other benefit of Arrows Outreach is that I didn’t have to send all 100 emails at once, or more likely: I’d send just a few and then bail. Instead, I scheduled it to prepare 25 contacts for me each day, across 4 days. This way I was able to spend about 20 minutes a few times to get it done.

Finally, because I was editing and sending each email one-by-one from my Gmail inbox, I was able to personalize the subject and structure of each email as it made sense.

For example, there were a few people I knew personally or who had tweeted about our launch. Since I knew that, I didn’t want to send the same exact boilerplate I’d started with. I wanted them to feel the same acknowledgement and attention that they’d previously given us.


Following-Up and Gathering Responses

Be sure you stay on top of responding to folks quickly. The more you do to be responsive, the more and better responses you’ll get! And it’s likely good practice to collect all the responses somewhere for your team to see.

As for the folks who didn’t respond? Set a reminder in your calendar or spreadsheet for 5–7 days later, and then follow-up. Always follow-up.

Try to be human again, and avoid phrases like “Just checking in.” 🤮 We’ve all done it, but it’s never good. Your best bet is a friendly reminder that they’re still important to you and you hope they can take a moment to respond.

That’s basically it! It takes practice, and a lot of people won’t respond. But it’s valuable, and you’ll get better as you do it more.


Let me know how it goes! dz@arrows.to

Get free tips to grow your business!

We'll send you occasional lessons about how to ask for feedback from your customers, find press to email, send cold emails that get replies, upsell existing customers, and a lot more.

You'll be able to unsubscribe at any time.