We've made a 'Post-holiday follow-up toolkit' For how to reopen conversations when prospects have been away on their vacay.
Whilst summer’s great for recharging, it's just not great for your pipeline. Conversations go on pause. Prospects disappear for summer climates and deals stall somewhere between “Looping in legal” and “Heading to Majorca 🏝️.”
But August is already halfway over, (cry) which means inboxes are being reopened… and so are your opportunities...
You don't want to just follow up. It’s following up with ✨relevance.✨ Think about it: they’ve just returned to a full inbox. Why should your email be the one they actually read and reply to?
Here are our tips on how to re-engage your prospects the right way.
❌ 1. Do NOT use 'Just checking in' and 'Just following up' ❌
Open with value, not just “checking in” try this instead...
“Hope you had a great break - here’s a quick recap of where we left off” works way better than “Just bubbling this to the top of your inbox.”
Bonus: If you're using a Digital Sales Room like our trumpet Pods
✅ Update the Mutual Action Plan
✅ Fresh ROI proof points
✅ Personalise video with next steps
It lets them jump straight back in. Digital Sales Rooms > long, endless email chains.
🆕 2. What’s new? Share it. 👀
Use the post-holiday moment to introduce something genuinely new:
- A feature that launched while they were away
- A recent customer win
- A stat or proof point you’ve been waiting to share
Template:
“Quick heads-up: since we last spoke, [feature/integration] went live. Thought this could really support [their specific goal]. Added a short walkthrough here if helpful.”
⏳ 3. Reset the timeline
Don’t rush the close. Instead, co-create a refreshed timeline based on what’s changed.
Try this:
“Let’s realign on next steps - has anything changed on your side since we last spoke?”
- Reconfirming internal stakeholders
- Updating the Mutual Action Plan
- Asking what’s changed during the break
🕵️ 4. Check in before you check in
If you are using a Digital Sales Room (like our trumpet Pods) - check in before you check in.
This means check your Pod analytics.
What pages did they view before going OOO? Did they watch your video? Did they share it with anyone?
Use those signals to personalise your message:
“Saw you’d checked out the case study section - here’s a recent one we just added that I think fits your use case even better.”
Relevance > reminders.
A good all rounder
💬 Here's a good template to steal
Welcome back - here’s where we left off
Hope you had a great break! I’ve put together a quick recap of our last chat (plus some new updates that dropped while you were away).
Final sign-off
Your follow-up isn’t just a reminder - it’s a second chance to re-engage with context and confidence. Instead of a generic “just checking in,” use timely insights, a clear recap, and something new to spark interest.
And if you're using a Digital Sales Room (like trumpet Pods), make it even easier for buyers to jump back in - no endless threads or re-explaining needed, see their insights on what they've last been engaging on, what they last viewed and just update a Mutual Action Plan or drop them a Pod message.
🎺 trumpet makes the follow-up part easy.
For all things Digital Sales Rooms, book a quick call with our awesome Account Executives:
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