If your inbox is a graveyard of ignored outreach, you're not alone. Following up is the real work—and most folks drop the ball after the first email. If you're using Derrick-app (more on that here), automating follow-ups can help you get more replies without nagging people or drowning in busywork. This guide walks you through how to set it up, what to watch out for, and how to avoid common traps.
Whether you're in sales, recruiting, fundraising, or just trying to herd cats for a project, this is for anyone who wants more responses with less hassle.
Why automate follow-ups at all?
Let’s be honest: most people don’t respond to the first email. They’re busy, they forget, or your message just gets lost in the shuffle. Following up—politely and persistently—increases your chances of getting a reply. But doing it by hand gets old fast, and almost nobody keeps up with it for long.
Automating follow-ups isn't about spamming people. It’s about giving yourself a fair shot and reclaiming your time. Done right, it’s the difference between a full pipeline and a pile of “just checking in” drafts you never send.
Step 1: Decide if Derrickapp is a good fit
Before you dive in, make sure Derrick-app is worth your time:
- It’s good for: Simple, honest outreach sequences—think sales, recruiting, event invites, or partnership requests.
- It’s not for: Complicated nurture drips, heavy design, or mass marketing. Derrickapp keeps things lightweight and to-the-point.
- What it actually does: Lets you schedule, send, and track personalized follow-up emails right from your inbox or their web app.
If you want flashy graphics, dynamic content, or a CRM that cooks breakfast, look elsewhere. If you want to keep your outreach human and organized, you’re in the right place.
Step 2: Map your follow-up sequence (before you touch the tool)
Don’t just start clicking around. A little planning saves a lot of headaches later.
Here’s what to figure out up front:
- How many follow-ups? 1–3 is the sweet spot. More starts to feel desperate (and annoying).
- Timing: Typical gaps are 2–5 days between touches. Don’t send three emails in 48 hours, but don’t wait two weeks either.
- Message content: Each follow-up should add value or at least feel like a human wrote it. Avoid "just bumping this up" unless you really have nothing else to say.
- When to stop: Decide if you’ll send a final “last try” email or just let it go quietly.
Pro tip: Write your follow-up drafts before you set up automation. It’s easier to tweak messages in a doc than in a clunky email editor.
Step 3: Connect Derrickapp to your email
This part usually trips people up, but it’s not rocket science.
- Sign up or log in to Derrickapp.
- Go to settings and find the spot to connect your email account.
- Most folks use Gmail or Outlook. Derrickapp uses standard authentication, so you don’t need to hand over your password.
- If you use something weird (self-hosted, custom SMTP), be ready for a little extra fiddling. Their help docs aren’t bad, but support is hit-or-miss.
- Authorize the connection. You’ll get bounced to your email provider—just follow the prompts.
Heads up: Make sure you’re connecting the right email account. If you use multiple addresses, double-check which one you’re about to automate. Cleaning up automation mistakes is a pain.
Step 4: Build your follow-up sequence
Here’s where the magic happens. Derrickapp’s interface is pretty bare-bones, but that’s not a bad thing.
- Create a new sequence (sometimes called a “campaign”).
- Add your first email—this is your initial outreach.
- Add follow-up steps.
- For each step, set:
- Delay: How many days after the last email should this one go out?
- Message: Paste in your pre-written copy. Personalize with placeholders (like
{first_name}) if needed.
- Repeat for each follow-up you want.
- For each step, set:
- Set stop conditions.
- Decide if you want Derrickapp to stop the sequence automatically when someone replies. (You probably do.)
- You can also set manual stops for bounces or opt-outs.
Things to skip: Don’t waste time on optional bells and whistles (like A/B tests) unless you’re sending hundreds of emails. Focus on getting your core sequence solid first.
Step 5: Add your contacts
You can add people one by one, but nobody’s got time for that. Use Derrickapp’s import feature:
- CSV upload: Download your contacts from wherever (CRM, spreadsheet), then upload. Make sure your columns match Derrickapp’s required fields (
email,first_name, etc.). - Manual add: Works in a pinch, but you’ll hate yourself after the fifth entry.
- Double-check mapping: Sometimes the import tool guesses wrong. Verify that names, emails, and any custom fields line up.
Pro tip: Don’t blast everyone at once. Start with a small batch so you can spot mistakes before they go wide.
Step 6: Preview, test, and launch
Don’t just hit “Send” and hope for the best. Automation mistakes are embarrassing and hard to undo.
- Preview every step for at least one contact. Make sure personalization works and nothing looks off.
- Send test emails to yourself. Read them on your phone—real people do.
- Check for triggers: Make sure a reply actually stops the sequence. This is non-negotiable. Nobody wants to get a follow-up after they’ve already responded.
If something feels clunky, fix it now. Automation amplifies whatever you put in—good or bad.
Step 7: Monitor and tweak
Automation isn’t “set it and forget it.” Keep an eye on what’s working and what’s not.
- Track open and reply rates. If nobody’s replying, your message (or your list) probably needs work.
- Watch for deliverability issues. If lots of emails bounce, your list is dirty or your sending reputation is in the gutter.
- Edit on the fly: Derrickapp lets you pause sequences, edit copy, or remove contacts mid-stream.
What to ignore: Don’t obsess over vanity stats (like click rates) unless you’re sending links that matter. Focus on replies.
What actually works (and what doesn’t)
What works
- Short, clear emails: Nobody reads long blocks of text from strangers.
- Personalization: Even just a first name and a relevant reference make a huge difference.
- Polite persistence: 2–3 follow-ups, spaced out, is enough for most people.
What doesn’t
- Spammy templates: If your email sounds like a robot wrote it, it’ll get ignored (or worse, marked as spam).
- Too many touches: More isn’t better. You’re not winning any friends with a 7-email sequence.
- Forgetting to stop: If someone replies and you keep following up, you look clueless.
Common mistakes to avoid
- Sending to the wrong list: Double-check your import. Automation mistakes happen fast.
- Messy merge fields: “Hi {first_name},” looks dumb when it goes out as “Hi ,”.
- Testing only on desktop: Mobile previews catch a lot of formatting mistakes.
- Ignoring replies: Automation doesn’t replace reading your inbox. People still expect a human on the other end.
Wrapping up
Automating follow-ups in Derrickapp is about working smarter, not just faster. Start small, keep it simple, and don’t overthink it. The real win isn’t blasting more emails—it’s getting more real replies, from real people, with less hassle. Try it, tweak it, and adjust as you learn. The best system is the one you’ll actually use.