21 June 2023 |

The secret to booking more meetings

By Gabrielle "GB" Blackwell

Hey y’all – I was missing you so much I couldn’t help but stop by in your email to share a bit about this super cool company you might have already heard about.

But before we get to the story, I have a question for you: what’s one piece of advice someone has shared with you that you can’t help but share with others?

For me, it used to be “like for like.”

I got this piece of advice from a VP of Sales who used to mentor me when I asked him about the best way to ask a prospective customer for a meeting. 

“Like for like,” he’d tell me. “You have to remember that people will answer your request similarly to how you ask them.” 

“If you’re concise in how you ask a question, people are more likely to be concise in responding back to you. Same thing goes for asking for a meeting – if you ask them a broad question like ‘when are you free next week?’ you’ll get a broad answer back like ‘sometime on Tuesday’. But if you ask them a specific question like ‘are you free tomorrow at 2 pm?’, they’re more likely to be specific in their response.”

Does ‘Like for Like’ work?

The short answer:

Even with the ‘like for like’ approach, I still ran into prospects asking me to suggest a few times over email. When I did follow up over email, the suggested times wouldn’t work or I wouldn’t hear back at all.

Now you see why it used to be my go-to piece of advice. 😫

It’s so frustrating to get so close to working towards a conversion, only to miss the mark because the prospect and I couldn’t figure out where our calendars matched up.

But this challenge of scheduling a meeting causes way more damage than most sales folks are aware of. Consider the following scenarios that happen all too often because of calendering challenges:

  • A prospect comes inbound, requesting a demo but passes on speaking with your team because they’re further along with a competitor
  • Sales reps lose momentum in their deals because next steps weren’t secured
  • Winnable deals are lost because a rep forgot to send timely follow up notes after a customer-facing meeting

If only there was a better way to get interested prospects in front of salespeople faster and keep them engaged throughout the sales cycle – wouldn’t that be great?

Thankfully for us, there is a better way with Calendly.

More than a scheduling link

You might be thinking to yourself, “isn’t Calendly just a scheduling link?”

You wouldn’t be totally wrong in thinking that, but you wouldn’t be right in thinking that’s all Calendly is good for. 

Stay with me.

Calendly’s platform goes way beyond being a scheduling link. It provides a much easier and less manual approach to:

  • Filling pipeline and booking more demos – Calendly customers tout a 70% conversion rate of meetings booked from a marketing form!
  • Improving your customer experience – no shows = no fun. A fun perk of being a Calendly customer is prospects show up to meetings more! 
  • Accelerating your sales cycles – tl;dr: 93% of sales team who use Calendly achieve faster sales cycles 🤯
  • Increasing your win rates — tl;dr part 2: 89% of sales teams close more deals using Calendly. Wowza!

These are real life results that Calendly is driving for companies like Signpost, Katalon, Lyft and more!

How magic is made

Some notable Calendly features that sales leaders should be thinking about (but likely aren’t) when looking to fill their pipeline, accelerate their deals, and increase their win rates:

  • Calendly Routing
  • Collective Scheduling
  • Workflows

Calendly Routing

While routing may be outside of the scope of responsibility for most sales managers, that doesn’t mean sales managers shouldn’t be aware of how lead routing impacts can help or hinder pipeline generation efforts.

Just know that trying to make lead routing work looks a little something like:

But with Calendly Routing, sales managers can rest assured that their reps will have more conversations with better qualified leads with less of a chance for great prospects to fall through the cracks. 

Collective Scheduling

Me whenever someone asks me to find time for the group to meet.

It’s hard enough trying to match schedules when there’s only two people involved. But as a sales cycle progresses forward and more people from your company need to get involved, trying to coordinate calendars can quickly become a scheduling nightmare. 

With Calendly’s collective scheduling capabilities, you can automatically see and offer up times that work for every member of your team who needs to be in attendance. 

Oh relief! Now you can stop waiting hours to hear back from teammates about their availability. 


Never have I ever heard someone say “sales reps are great at admin work.” 

In my now 8 years of being a sales professional, there’s one thing I know to be true – the best performing salespeople are the ones who have reliable processes for following up with prospective customers in meaningful ways.

Yet – deep sigh – the majority of sales reps don’t have a reliable process. 

Without a dependable approach to keeping prospects engaged in between conversations, sales reps open up the door to tons of unforced and easily avoidable errors. Think:

  • Forgetting to add conference details
  • Scheduling for wrong time zone
  • Forgetting to remind prospect of the meeting
  • Following up with prospect after the meeting
  • Not entering the meeting into the CRM

This is where Calendly’s Workflows – automation that triggers messages through the meeting lifecycle – helps sales teams big time!

With Workflows, sales teams can count on Calendly to automatically:

  • Eliminate human errors that get in the way of prospects showing up to the meeting
  • Keep ‘selling’ the prospect on showing to the meeting through event reminders and sending informative content
  • Send post meeting ‘thank you’ notes and mid-funnel collateral you know helps deals move forward
  • Log the meeting back to your CRM 

If you’re looking for ways to get your team better at the administrative work that helps drive sales velocity, Calendly’s Workflows are 🔑!

Double the sales meetings = double the revenue AND fun 

I’ve shared a lot thus far about Calendly, but it’s not just because I think it’s a cool platform – it’s because of the results their scheduling automation is enabling their customers to have!

Take CallRail for example, a company with a hybrid product led and sales led growth motion. Note: I’m choosing CallRail in particular because I recently worked at a product led growth (PLG) company. 

Before I get into how CallRail used Calendly to 2x their sales conversions while also netting huge cost and time savings benefits, let me share a quick note on how not sexy exhausting product led sales can be.

In a successful product led sales motion, you’ll have thousands of people come to your website and of those thousands web visitors, you’ll see hundreds of them sign up for the free version of your product. 

As your free trial sign ups start taking actions on your platform, there will be some backend system capturing how the product is being used. That product usage data will then be written back into a CRM of some sort. 

From there, sales reps will review product usage data points for each free trial to see which leads to prioritize. After that, they’ll use a combination of product usage data and prospect information craft relevant messaging that will resonate with their prospects. 

Even with all the work sales reps put in, they’ll still miss out on converting more free trials to qualified pipeline because of the manual lift it takes to follow up with free trial leads.

tl;dr It’s a wildly cumbersome process that is prone to all types of opportunities being missed. And we haven’t even talked about the challenge of trying to coordinate calendars yet. 😩

Back to what I was saying about CallRail though…

CallRail’s product led growth process wasn’t much different than what I’ve described – a high volume of trial leads, inefficient ways to engage them, and missed opportunities galore. Something had to change. 

Working with Calendly, CallRail set out to meet the following objectives:

  • Increase meeting production with quality trial leads
  • Accelerate their sales process
  • Eliminate scheduling friction (duh, it’s Calendly we’re talking about)

You didn’t think I was going to stop at the 2x increase in sales conversions did you?

Calendly worked wonders for CallRail’s ability to meet their objectives! The results speak for themselves:

  • Increase meeting production by getting quality leads scheduled with their sales team as soon as possible – the combination of Calendly’s Round Robin and automated meeting reminders work to make sure scheduled meetings turn into meetings completed 😉
  • Accelerate their sales process by using Calendly as the email CTA – 🎉Calendly gets bonus points here for enabling companies to bring on the right internal resource at the right time to keep a deal moving forward!
  • Eliminate scheduling friction by including different event types based on lead source – a 10-minute meeting for automated, outbound campaigns and a 30-minute meeting designed to convert free trials to paid users

🥳Calendly also netted CallRail some major cost and time savings – like $150K and 3,267 hours, respectively.

It’s more than what you thought

I started off today’s note with what used to be my favorite piece of advice to share. My go-to now?

Remove the word ‘just’ from your sales vocabulary. Whatever you’re offering isn’t ‘just’ a software. Whatever your title is, you don’t need to put ‘just’ at the front of it (I’m talking to you, SDRs). 

And Calendly isn’t ‘just’ some scheduling link to avoid emailing back and forth about availability. 

It’s so much more than sales folks have been giving it credit for.