Want to send a bunch of emails and actually get replies? You're in the right place. This guide is for anyone who needs to reach a lot of people—cold outreach, sales, recruiting, event invites, whatever—but doesn't want their messages to go straight to the trash. If you use Gmail and have heard about Boomerang but aren't sure how to make your emails sound less like spam and more like a real person, keep reading. No hype, just practical advice.
Why personalize mass emails anyway?
People can smell a generic email a mile away. If your message feels like you sent the same thing to 500 other people, most folks will ignore it—or worse, hit "Report Spam." Personalization helps you:
- Stand out in packed inboxes
- Sound like a human, not a bot
- Get real replies, not just opens
But, there's a catch: You don't have time to hand-craft every single message. That's where smart tools and a bit of planning come in.
Step 1: Know Boomerang’s strengths (and limits)
Boomerang is best known for scheduling emails and reminders, but it also has a feature called "Respondable" to help tweak your writing. It isn’t a full-on mail merge tool like Mailchimp or GMass—so if you’re trying to send 10,000 emails with auto-filled fields, look elsewhere.
What Boomerang does well:
- Scheduling emails to send later (so you look like you’re working normal hours)
- Reminding you to follow up if people don’t reply
- Nudging you about emails you still need to answer
- Some help with writing better, friendlier emails
What it won’t do:
- Bulk send hundreds of personalized emails at once
- Automatically fill in custom fields from a spreadsheet
- Track opens or clicks in the same way as traditional marketing tools
Bottom line:
Boomerang is great for sending a manageable number of emails (say, 10–50) where you can spend a minute or two personalizing each one. If you want to blast out thousands, use a real mail merge tool.
Step 2: Build a targeted list (don’t just copy-paste your contacts)
Before you write anything, make a real list. Who actually needs to hear from you? Take a few minutes to:
- Pull together a spreadsheet (Name, Email, Company, maybe one “fun fact”)
- Ditch anyone who’s totally irrelevant. You’re not doing yourself any favors by emailing everyone you know.
- Add a “hook” column—something specific you could mention to each person (e.g., “met at the conference,” “loves hiking,” “just changed jobs”)
Pro tip:
A small, well-targeted list will get you way more replies than a giant, random one.
Step 3: Write a flexible template (but avoid sounding like a template)
Draft your core message in Gmail, but leave spots for real details. Here’s how to do it:
- Start with a subject line that’s specific. “Quick question about [project]” works better than “Hello.”
- In your greeting, use their actual name. No “Dear Sir or Madam.”
- In the first line, reference something specific to them: “Saw your recent post on LinkedIn about remote work—great points.”
- Get to the point fast. Nobody wants to read a novel.
- End with a simple, direct ask. Don’t be vague.
What to avoid:
- Overused phrases (“I hope this email finds you well…”)
- Faking personalization (“I noticed you work at [Company Name]…” if you know nothing else about them)
- Gimmicky tricks (“Just circling back!” as your opener)
Example skeleton:
Subject: Quick question about [topic they care about]
Hi [Name],
I saw [specific thing about them]. [One-sentence genuine comment.]
I’m reaching out because [honest reason]. Would you be open to [your ask]?
Thanks, [Your Name]
Step 4: Use Boomerang to schedule and space out your emails
Here’s where Boomerang shines: you can send each email individually, but schedule them to go out over time. This keeps you from looking like you just mail-merged everyone at once.
How to do it: 1. Open Gmail and compose your email. 2. Personalize each one—copy your template, then fill in the real details for that person. 3. Click Boomerang’s “Send Later” button and pick a time (spread them out, so if someone forwards your email to a colleague, it’s less obvious you sent the same thing to both). 4. Repeat for each contact.
Why bother? - You avoid Gmail’s sending limits (which are lower than you think) - You don’t look like a spammer - You give yourself a chance to tweak as you go (and not batch-send a mistake to everyone)
Step 5: Actually personalize—don’t just swap a name
Here’s the part most people skip. Real personalization is more than just “Hi [Name].” Take a minute per email to:
- Mention something specific from your “hook” column
- Reference their recent work, a mutual connection, or a shared interest
- Change your tone slightly based on who they are (formal to a CEO, casual to a peer)
If you can’t find anything personal to say, ask yourself: should you really be emailing this person?
It takes extra effort, but even a short, specific line (“Congrats on the product launch last month!”) can double your chances of a reply.
Step 6: Use Respondable to check your tone (but don’t rely on it blindly)
Boomerang’s “Respondable” analyzes your email for things like subject line length, politeness, and readability. It’ll give you suggestions like “Try to sound more positive” or “Make your email shorter.”
Here’s the truth: - Respondable can help you spot obvious problems (emails that are too long or too vague) - Sometimes it just nags you for the sake of it—don’t feel you have to hit 100% - Trust your gut. If it sounds like something you’d reply to, you’re probably fine.
Step 7: Set reminders to follow up (but don’t be a pest)
The real magic of Boomerang is its follow-up reminders. If someone doesn’t reply, Boomerang can move the email back to your inbox after a set time.
How to use it: - When sending, check “Boomerang this message if no reply” and set a time (e.g., 3 days, 1 week) - If you get no response, the email pops back up so you can follow up - Keep your follow-up short, polite, and even more personal if possible
What NOT to do: - Don’t send a follow-up every day - Don’t guilt-trip people (“Just bumping this to the top of your inbox…” gets old fast) - If they haven’t replied after two tries, let it go
What to ignore (or watch out for)
- Tracking opens: Boomerang doesn’t do this natively. Don’t get obsessed with who opened your email—focus on real replies.
- Attachments: Sending the same attachment to lots of people can trigger spam filters. Link to a file instead.
- “Hi {FirstName}” mail merges: Tools that let you send hundreds of emails by swapping in people’s names are tempting, but the results are usually underwhelming. People can tell when you’re faking it.
Pro tips for getting real replies
- Keep your emails under 100 words. Shorter emails get more replies, period.
- Use plain language. Big words and fancy sentences just sound fake.
- Don’t bury the ask. If you want a reply, make it obvious what you want them to do.
- Avoid sending at weird hours. Boomerang’s scheduling lets you look like a normal person.
- Treat everyone like a human, not a lead. If you wouldn’t say it in person, don’t write it.
Wrapping up
You don’t need fancy automation or AI to get more replies. If you use Boomerang to help you space out and track your emails, and actually put in the effort to personalize, you’ll stand out from the noise. Start small, tweak as you go, and remember: a handful of real conversations beats a thousand ignored emails any day.