How I use Calendly in venture capital

My calendar shows me that the work of an investor involves lots of conversations.

Every week is packed from 8 am to 6 pm with conversation. Time is precious and how it is allocated is key to success.

Calendly gets the job done.

Calendly is an app that allows easy scheduling of meetings without the back and forth of emails. I can create ‘Events’ configured to match my availability and then create workflows around them so that everyone gets the best experience.

Here is how I use it to manage the chaos.

The velocity of discussion planning

Setting up a meeting can take a long time. It is tough when there is minimal time on both sides. It is also easy to procrastinate because it is hard. When procrastination sets in, the demands on time start to pile up.

When a meeting request comes in, I make the following decision:

  • Should I take this meeting at all? With limited time, I need to prioritise my effectiveness. It is often better for the person requesting the time to get a quick email response with the assistance they need rather than delaying their next step for weeks when the calendar opens up. In this case, I have a Superhuman snippet that helps me decline and prompts me to think of other ways to help.
  • If a meeting is the best way, I will send a calendly link.

Is using Calendly rude?

Some people are offended by receiving a Calendly link. It feels impersonal. Indeed, it is possible to send a link rudely. I like to treat everyone like the most important person I can think of when I send it. At a minimum, I package up the link with something like this:

‘Here is a link to my calendar to make it easier to find a time that works for you.’

My Meeting Templates

The standard external meeting

I have a standard 60-minute meeting that I send to most people. I tried 30-minute sessions for a while and found them to be utterly useless for both sides, and by the end of each day, I was ragged. I was busy but got nothing done.

I only allocate part of my day for this event type because I need time for internal work.

I add a question to the booking form “What do you want to get out of this meeting?”

Pitch Meetings

I have a particular version of the 60-minute event type for first pitches. It is similar to the standard meeting, but it has a workflow to improve the experience for the guest.

It sends an email with notes on making the most out of the 60 minutes, helping the founder to line up their pitch to what we are after at the firm. It also sends a follow-up email so that I can get feedback on the session.

Knowing I am going to get feedback keeps me on my game.

The ‘important’ meeting

Sometimes I need to squeeze in meetings late in the evening, early in the morning or during my internally allocated time. I have a special link for that which I use for special occasions.

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