3 steps for effective Calendly conversations (2022)
I am personally getting close to nailing the art of having effective and purposeful Calendly conversations with strangers — after having 50 of these with founders, mentors, advisors and VCs.
But I wasn’t always like this. I started off as someone who’d be extremely nervous with basic conversations. I would beat around the bush, not get to the point and just waste everyone’s time. Being bad at something however, doesn’t automatically excuse you from being unskilled at it forever.
Every skillset, more or less, can be improved upon over time. And with having video calls and audio calls with strangers on the internet, it’s an easy skill you can work on from your bedroom! Just make sure you blur out the background please.
I’ve prepared an audio version of this article if you’re interested. You can hear my sweet voice here (audio version). If you’re more of a reader, let’s dig in!
Step 1: Prepare, do your homework.
Time needed: 20 mins
Especially if you’re meeting someone new, look through your blogs and social media to understand (a) what they like / dislike (b) what matters very much to them (c)the topics they care deeply about. You might not think this is important but the truth is a lot of people don’t do this ahead of time and end up asking basic, obvious questions on the calls about the other person.
This works against you because a few minutes into the call, they’ll already think you are incompetent and didn’t take a minute to read up on them. Funny enough, if you know more about them than they do about you, generally, they will get more curious about you on the call. Funny how things work.
Pro tip: Reading into a person’s background lets you understand their personality and will enable you to drive the conversation towards an end-goal / objective more easily. E.g., extroverts may want to share their day’s activities so the conversation might be a little-hearted. Conditions do apply.
Step 2: Set the stage.
Time needed: 30 seconds.
Take the first 20–30 seconds of the call to let the person know what the main objectives of the call are. This helps everyone on the call feel at ease because sometimes (surprise!) people can forget why they’re on the call, where it’s headed, etc. People have a lot going on with their lives. Everyone gets busy. Don’t take it too personally!
Here are some samples you can modify and use:
Formal: “Thank you everyone for joining! To start us off, I wanted to make sure we’re on the same page and discuss the agenda we have for today which is to (a) xxx and (b) xxx. Is there anything that I missed? Does this sound sufficient for the time we have today.”
Informal: “Hey, awesome. Now that we’re all here, I just wanted to make sure we have our ducks in a row for what we’ll talk about today. There’s xxx and xxx. And also, the xxx. Does that sound good? Anything else you want to cover?”
Ideally, the agenda / objectives will be mentioned very clearly in the meeting invite details. When filling in the invite, avoid generic wording like “synergy”. Make it crystal clear why you’re meeting them or what the expectation of the call would be from each or all parties, etc.
Step 3: Be respectful of their time.
Time needed: N/A
If it’s 25 mins into a 30-min call, and you know the conversation will go overtime, just let the person know you’re closing in on the 30-min mark — and ask if they can stick around for 5 more mins. Don’t keep extending obviously. Stop at 35!
This shows that you care about their time and speaks to your character. 9/10 times unless it’s a very structured conversation or a short-lived one, calls will go over the expected duration. It happens. We’re not superhuman and it’s okay.
It’s also totally acceptable to say, “Hey we’re 2 mins from the 30min mark. Let’s close off early now, and I’ll email you the rest of our bullet points.” People love those who respect their time. Do that and you’ll keep having people give you more and more of it!
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I am confident these three beginner tips will help you get started on having better Calendly conversations (audio / video chats) online. Remember, no one is the best from Day 1. You need to train, try, fail, fail, fail, try and train to become the best! :)
Objective of your calls: If you are having conversations with potential business mentors, Sparrow is obviously where you want to be! But if you decide to find a startup advisor elsewhere, this guide we wrote might be useful. Wherever you go, we wish you the best! :)
If you’d like to reach me, I’m on Twitter and I’m the founder of Sparrow. Always down to help!