Calendly: wonderfully effective or just plain rude?

The response to a recent post on Linkedin about the use of Calendly (a diary management app) was significantly more heated than I had expected. Is it the best and most effective way to manage our time, or will clients see it as just plain rude? Some really great thoughts to consider below (plus a video of me chatting about a pre loved greenhouse – you won’t want to miss that).

I explored the use of automated diary management and found that half of people are fully behind it, but a third of people still have reservations about the tech or simply the lack of manners they perceive of in its use. The conclusion is that if the tech is well used and the benefits communicated clearly, the concerns of the laggards can be addressed and the tech is here to stay.

I’m a big fan of process. Which makes it easy for me to be a big fan of automation. Using technology to automate processes or parts of processes seems to be logical and obvious to me. And many people agree with me. I’ll be exploring automation and sharing my findings with you across the next few months, but I wanted to share something I have observed pretty close to the start of my journey: the biggest challenge to automation is where it involves people.

I guess that shouldn’t be a surprise. After all, connecting Calendly (automated diary management) to Hubspot (automated CRM) via Zapier (linking technology) isn’t going to offend any of the servers the pieces of software sit on. But sending someone a link to my Calendly account and saying “help yourself to any date from my diary” is like chucking petrol on a bonfire for some. So I set out to explore this reaction in more detail.

I’m sure you’re aware of Calendly, the diary management software. Effectively you connect it to your calendar (Outlook in my case) and you can then make that calendar, or parts of it, available for others to chose a convenient time slot for a meeting.

I use it for general meeting arrangements (my whole calendar is accessible to those with the Calendly link) and I also have a separate Calendly which allows agency leaders to book a free surgery on Wednesday mornings should they fancy a chat. In that case, it just shows the free surgery slots and nothing else.

My view on Calendly? The basic functionality is amazing (and no, I’m not important enouigh to be paid to say that). It allows people who want to meet with me access to all of my available time to choose one that suits them most. It couldn’t be simpler or more open. The surgery calendar is even smarter. Not only does it allow people I haven’t met yet to book a slot with me (via a link on my LinkedIn page to a dedicated surgery booking form), it takes their details and automatically populates my Hubspot with their name, email address and the fact that they came via the surgery link. It seem obvious to me that this kind of process automation is a must for time starved small businesses.

And we all know what a huge time drain diary management can be. Last week I introduced two agency owners, who I really like and deeply respect, who might well benefit from some joint activity. I did the intro by email and stepped away, but they kept me on “cc”. Their emails went backwards and forwards with lists of dates and times they could and couldn’t do. It was apparent that each time they did this they were checking their calendars, writing dates and time options into the email and then replying. They eventually agreed on a date, by which time it was no longer available for one of the party, so they started again. At this point I asked to be removed from cc.

What is more interesting to me is that both of these smart, knowledgable and curious leaders had responded to a survey I created on LinkedIn asking people about their views on automated diary management. They had both ticked the it’s “impersonal &/or a bit rude” box.

The technology exists to have reduced their correspondence to one email and would have been so simple. But they both feel that it’s an intrusive and potentially rude way to arrange a meeting. And before you say it, you could argue that this to-ing and fro-ing of emails allowed them time to connect and begin the process of getting to know each other. You wouldn’t say that if you saw how evidently, but politely, frustrated they both became. There are better ways to become more engaged prior to a first meeting, but that’ll be an essay for another day.

They are not alone in their views about automated diary management? A third of people who responded (32%) ticked the “impersonal &/or a bit rude” box. Mind you, half believe it to be a superb/efficient solution, with one in five (18%) straddling the fence.

Those who see the benefits talk about the ease of scheduling a meeting, the convenience of avoiding protracted email exchanges and conflicted diaries, the generosity of making your entire calendar available to people and the message it sends about your willingness to embrace new technologies. Of course the invitation needs to be presented properly – but if it is, a Calendly link can only be seen as a very open and generous offer of access to your diary.

Having read the replies, I think I know what is happening. The feelings of the one in three who are resisting this change seem to be forming an opinion based on their experience on the receiving end of a poor application of the technology or poor communication of the purpose. And perhaps a little misunderstanding of how to use the technology to your advantage.

Dan Coleman sees it quite clearly. He says “You get an email saying ‘Hey I think you could be doing what you are doing better. Book a call in my calendly so I can sell you some horseshit’. These are a whole stack of rude”. That’s a case of blaming the bullet not the person holding the gun. Dave Hodson is more concerned about proliferation of apps. As it happens, in this case, Calendly integrates entirely with Outlook, Gmail and so on and you’re not aware of using the software at all.

Will Hill, founder of Charity Nest, is a fan of autmation but suspect he knows why people resist. “I believe our egos can get in the way of what is actually a good solution. We’re used to booking time with someone who is “superior” in one sense or another, so if someone we believe to be “inferior” to us ask’s to book their time it can damage our ego”. He may have a point. As Anders Hjorth implied, it’s just like saying “book it with my secretary, I’m too important for this stuff (but implying you aren’t)”.

Nick Suckley, a very experienced agency leader, worries about people trampling around in his calendar willy nilly. I agree that it does take a bit of a change in behaviour to make sure that you allocate time in your calendar for things like lunch, getting to and from meetings, having time to get away from your desk, picking the kids up an so on. But there are some smart settings in these technologies that allow you to be quite subtle about what people can and can’t see and can and can’t help themselves to in your calendar.

I can see everyone’s point of view, but as I said, if it’s used well, the tech is understood, the benefits communicated clearly automation of this type will only become more prevalent.

I’d be happy to set up a workshop for anyone who feels that a simple lack of understanding of the tech’s capabilities is stopping them use this awesome time saver. Just drop me an email or maybe I can send you a link to my Calendly ;).




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If you have something on your mind, a challenge you’re wrestling with or just want an alternative point of view, I’d be very happy to lend an ear and maybe help you start to unpick the issues.