Sales teams know the pain: you’re chasing deals, but scheduling a call turns into a mess of emails, double bookings, and lost momentum. Your prospect goes dark. The deal slows down—or worse, disappears. If you’re tired of losing hours (and deals) to calendar ping-pong, this guide is for you.
Here’s how to cut the back-and-forth and speed up your sales cycle by automating meeting scheduling using Pick. No fluff, just what actually works.
Why Scheduling Drags Down Sales (and Why Automation Helps)
Let’s be honest: scheduling is boring, repetitive, and it kills deals. Every extra email is a chance for a prospect to vanish or get distracted. Here’s the real cost:
- Slower cycles: More time between replies means slower deals.
- Drop-off risk: Prospects ghost after scheduling gets annoying.
- Wasted energy: Sales reps lose focus chasing calendars, not closing.
Calendly, Outlook links, and other tools exist, sure. But if you want something frictionless—especially if you’re booking across busy teams or need flexibility—Pick is worth a look.
Step 1: Get Your Pick Account Set Up
First, sign up for Pick. (If you’re not already using it, just head to their site and sign up—it’s quick.)
Real talk: Don’t overthink this. The free version is fine for most individual users. If your team books a lot, the paid plan adds group scheduling and integrations. But get started before you worry about features.
Setup checklist:
- Connect your main work calendar (Google, Outlook, etc.)
- Set your working hours and preferred meeting length.
- Sync any secondary calendars if you use them (personal, side projects—whatever keeps you from double-booking).
Pro tip: Set your default meeting location (Zoom/Teams/phone/etc.) now, so you’re not fiddling with it later.
Step 2: Build Your Meeting Templates
Templates are where Pick starts to save you real time. Instead of sending a one-size-fits-all booking link, you can set up different templates for different types of meetings—discovery calls, demos, follow-ups, etc.
What to include in a template:
- Duration: 15, 30, 60 minutes—keep it tight for first calls.
- Buffer time: Add space before and after so you’re not rushed.
- Meeting location: Auto-add your video link or dial-in.
- Questions: Ask anything you need upfront (e.g., “What do you hope to cover?”). But keep it brief—nobody likes a homework assignment.
Why bother? - You can send the right link for the right context (no more “Let me know what works for you” emails). - You can control your time. Want to keep demos out of your Friday afternoons? Easy.
Step 3: Share Links That Actually Get Used
Here’s where most people mess up: they send links that feel impersonal or even rude (“Here’s my link, book yourself in”). That rubs some prospects the wrong way.
How to do it better:
- Use a short, friendly intro: “Happy to make this easy—here’s my calendar. If you don’t see a good time, let me know what works for you.”
- For high-value deals, offer a couple of handpicked slots and the link. “Would any of these times work? Or you can grab anything that fits here: [Pick link]”
Don’t:
- Don’t bury the link under a wall of text.
- Don’t send the same generic link for every type of meeting.
Pro tip: Save your best-performing templates as email snippets in your sales tool or inbox.
Step 4: Use Group Scheduling (If You Actually Need It)
If you’re selling to teams, or need to wrangle multiple calendars, Pick’s group scheduling can cut a ton of hassle. It checks everyone’s availability and suggests times that work for all.
When to use it:
- You’ve got more than two people on the call (AE + SE + prospect, for example).
- You’re tired of “Does Tuesday at 2pm work for everyone?” email chains.
How to make it less painful:
- Add internal teammates’ calendars to Pick (with permission).
- For prospects, Pick will poll their availability via email—just make sure you explain what’s happening, so nobody thinks it’s spammy.
What doesn’t work:
- Don’t try to force everyone to create a Pick account. It’ll slow things down and nobody needs another login.
Step 5: Integrate with Your Sales Stack (But Don’t Go Overboard)
Pick can plug into your CRM, video conferencing, and email. This can save even more time, but only if you set it up right.
Worth doing:
- Connect your video tool (Zoom, Teams, etc.) so links are auto-generated.
- Sync with your CRM (like Salesforce or HubSpot) so meetings get logged automatically.
Probably not worth it (at least at first):
- Overcomplicating with every integration under the sun. Start simple, then add as you go.
- Custom API stuff, unless you have a clear problem to solve.
Heads up:
Integrations sometimes break. Test before you trust your pipeline to them.
Step 6: Fix the Follow-Up (and Avoid No-Shows)
Automation’s great, but people still forget meetings. Use Pick’s reminders and follow-ups, but don’t count on them to do all the work.
What works:
- Set automatic email reminders for both you and the prospect.
- Share an agenda or key points in the invite, so everyone shows up prepared.
- If it’s a big deal, send a quick “Looking forward to our chat tomorrow” email yourself. Bots are fine, but a human touch still matters.
What to ignore: - Over-customizing reminders. Most people just want one or two, not a barrage.
Step 7: Measure, Tweak, Repeat
You won’t get everything perfect on the first try. The point is to spend less time scheduling, not obsess over settings.
How to keep it simple:
- Check your calendar a couple times a month. Are you seeing fewer scheduling emails? Are meetings happening faster?
- Ask prospects if your process was easy. If you’re losing people after sending the link, tweak your templates or communication.
- Don’t chase every new feature. Stick with what actually saves time and helps you close.
Honest Pros, Cons, and What to Ignore
What works:
- You’ll book meetings faster—period. That alone can help you close more deals.
- Less back-and-forth means less risk of losing prospects to “calendar fatigue.”
- Group scheduling, when you need it, is a lifesaver.
What doesn’t:
- Some prospects still hate links. You’ll always need a backup plan.
- Over-automating removes the human touch. Don’t let tools replace real follow-up.
What to ignore:
- Fancy analytics dashboards, unless you’re running a massive team.
- Chasing the perfect integration setup. Good enough is good enough.
Keep It Simple—And Iterate
Automating your meeting scheduling isn’t magic, but it kills a real bottleneck. Start small—set up Pick, get your main templates working, and use them for your next five deals. See what breaks, fix it, and don’t add more complexity than you need.
The faster you get meetings booked, the faster you can move deals forward. Let the tool handle the boring stuff—so you can focus on selling.