Watch the full video: How to Increase Meetings Booked Per Positive Response
The Two Things You Need to Do
When someone positively responds to a cold email and says "Hey, I'm interested," there are two objectives:
- Get back to them as fast as possible and give them times to book a meeting
- Raise the stakes of the offer and give them more reasons to hop on a call
Most people nail the first one and completely fumble the second. Here's how to do both.
The Initial Reply: Two Times Plus a Calendar Link
The first response should always include two specific times you're available and a calendar link. Not just one or the other.
Here's why: some people love calendar links. They'd rather click a link than go back and forth on availability. Other people get offended when you send them a calendar link -- they think it's impersonal or presumptuous.
Since you don't know which type of person you're dealing with, cover both bases:
"Hey Katie, thanks so much for the response. Are you available Tuesday at 10 or Thursday at 2? If it's easier, here's my calendar link."
The mistake: Replying with just "Thanks so much for the response. Book a time here." That feels transactional and rubs a lot of people the wrong way.
Beyond that first email, also reach out on LinkedIn and call them if you can. Multi-thread the touchpoints.
When They Don't Book: Raise the Stakes
If that first reply doesn't convert into a meeting, this is where most people blow it. They send follow-ups like "Hey, following up on this -- are you still interested in booking a meeting?"
That's lazy. Here's the escalation framework instead:
Step 1: Match Them to a Case Study
Do manual research on the prospect. Figure out how they map to a customer you've already helped. Then spell it out:
"Hey, just to keep in mind why we were so interested in meeting -- you fit this criteria, and I found this about your company. We worked with another wholesaling company and took them through this process. I'd love to explain how we could get a similar result."
The key is specificity. Don't just say "we've helped companies like yours." Name the industry, the process, the result.
Step 2: Do Free Work
Give them a taste of your product or service right in the email. Whatever you sell, find a way to deliver a small piece of value for free:
- List building company? "I saw you're targeting CEOs in Tampa, Florida. Here's a list I already pulled. Want to hop on a call to expand on that?"
- Website optimization? Do a quick competitor audit and share the findings.
- Marketing agency? Pull some data on their current campaigns and surface an insight.
This triggers the law of reciprocity. They already said they were interested, and now you're giving them free value. The likelihood of booking goes way up.
Step 3: Combine Everything
Iterate between case study showcasing and free work. Each follow-up should include one or both, plus two new available times and the calendar link.
The Status Alignment Trick
Oren Klaff talks a lot about status alignment, and there's a specific follow-up tactic that works extremely well.
Let's say on Wednesday you offered Tuesday at 10 and Thursday at 2. They didn't respond. On Friday, instead of "just checking in," say:
"Hey, I lost Tuesday at 10 to another person and a meeting popped up on Thursday -- those times are gone."
This reframes you from a hungry salesperson badgering for time to a busy professional coordinating schedules. You're signaling that other people are booking your time, which changes the dynamic entirely.
The Bold Move: Send a Calendar Invitation
Another strategy that works well -- but requires some comfort level -- is to send a calendar invitation directly without the back and forth.
The messaging:
"Instead of all the back and forth, I put some time on your calendar for 10 AM on Tuesday. I marked it as not busy so it won't block your calendar and someone could schedule over it if needed. I usually find this is easier than going back and forth. Let me know if something else works."
The important details:
- Mark it as "available" so it doesn't block their calendar
- Explain that all they have to do is accept it and you'll mark it as busy
- They can also move it or propose a new time right from their calendar app
This eliminates the friction of switching tabs to Calendly. They're already looking at their calendar.
Key Takeaways
- Always reply as fast as possible with two manual times plus a calendar link
- Multi-thread: email, LinkedIn, phone call
- Never send "just checking in" follow-ups -- raise the stakes instead
- Match the prospect to a specific case study and explain how the result would apply to them
- Do free work to trigger reciprocity
- Use the "I lost those times" technique for status alignment
- Consider sending a calendar invite directly, marked as available, to reduce friction