I am fully prepared to take some heat for this article, as there are many financial advisors who tout Calendly as the most innovative tool they’ve added to their tech stack in several years, but as a recipient of many Calendly links and inbound meeting requests, I’m here to declare that human error is ruining the user experience.  The technology tool can work, but the vast majority of users are not taking the time to properly learn the system and make it an efficient process for their clients.  It seems that when it comes to Calendly technology, advisors have completely forgotten their mantra of “putting clients’ needs ahead of our own” – while this technology drives efficiencies for the advisor, it makes their clients’ lives worse, as outlined in my list of complaints below.

Complaint #1 – It Can Come Off as Rude

Several times per month, someone reaches out to me on an unsolicited basis and asks if I could spare some time to speak with them and provide some guidance and/or explore ways in which PFI Advisors could possibly market their product or service.  They promise that it won’t take too much of my time, they explain that it would be a huge help to them and if there is anything they could do to help me in return, they’d be happy to reciprocate.  I love growing my network, so after spending a few minutes researching the person and the company, I almost always agree to a call.  Once I let them know that I’m willing to take a call, however, all of the deference and politeness disappears and I usually receive a curt, “Here is my calendar – please find a time that works for both of us.” 

When I click on their Calendly link, more often than not, the first available timeslot is 3 or 4 weeks out and I’m always left thinking, “Gee, I guess they didn’t really need to speak with me that bad!”  The communication style from their first outreach to their second is markedly different and always leaves me with a bad taste in my mouth. I cannot help but wonder, “Do advisors treat their prospective clients this way??”  This isn’t a limitation or flaw of the technology tool itself, it’s the chosen communication style of the individual using the technology that is off-putting.  A few people do it right and reply with something along the lines of, “That’s great – thank you!  Please provide some days and times that work for you, and I’ll make sure I accommodate your schedule, or, if you prefer, you can book time directly on my calendar here,” and they provide a link.  With that second response, both communications match the same tone and I’m much more excited to speak with the person.

Complaint #2 – When the Meeting is Scheduled, the Title is Vague or Incorrect

As stated above, when booking an appointment on someone’s calendar who has reached out to me requesting a meeting, their first available time is often many weeks in the future.  By the time the meeting rolls around, I’ve often forgotten who the meeting is with and what the purpose is.  This is perhaps my biggest complaint with how people use Calendly – because they use the technology tool for a number of different types of meetings, they use very generic descriptions like, “Intro Meeting” or “John’s Zoom” – when I see that on my calendar weeks later, I have no idea what the content of that meeting will be or worse, who I am meeting.  I’m left scrambling through my deleted and sent emails to figure out the who and why minutes before the call.  Had they booked the meeting themselves on the calendar, it would undoubtedly say something like, “John Smith and Matt Sonnen Discuss XYZ Advisors and PFI Advisors Collaboration.”  Some meeting descriptions are even more off base and will say things like, “Portfolio Review” (I’m not a client, so this clearly is incorrect!) or “Product Demo” when they are asking me marketing advice or even career advice – the topic of our meeting has nothing to do with a product demo.  Again, the technology is working as intended, but the way it’s typically configured, the focus is not on the user or client experience, but solely on making the advisor’s life easier.

Complaint #3 – I’m Often Stood Up

In the scenario described above, someone is reaching out to me, telling me that I can help them, and explaining how excited they are to spend time with me.  After I book time on their calendar via the Calendly link, when the day and time of our meeting arrives, I’m often left sitting alone in the virtual meeting or abandoned in the waiting room or, most frustrating, the person arrives late and flustered and angrily says, “I have a client meeting right now, why are you here?” 

“Umm…I’m here because you reached out to me and asked me to book a time that was convenient for you – this was booked through your Calendly app.”

“Oh.  My settings must be wrong…I don’t have time right now.  I’ll send you another link,” and then they abruptly end the meeting. 

This is not an isolated incident – it has happened enough for me to confidently declare it’s a pervasive issue when booking time on someone’s calendar through the app.  And the irony never evades me – they expect me to go through this process AGAIN and feel good about it!  I’m always skeptical that the problem isn’t the settings inside the application as the person stated – but rather it’s because the person didn’t take any time to book the meeting themselves (and because they reached out to me four weeks ago!), making it less personal and therefore easier for them to blow me off and not truly value the time on my calendar.

One problem that truly is the result of poor settings inside the application is the fact that when the meeting is booked, Calendly often generates both a Zoom link and a Google Meet link (or Microsoft Teams, etc.).  When the time of the meeting comes up, I wind up sitting in an empty Zoom room for 10 minutes and the other person is sitting alone in the Google or Microsoft room.  And just like in my previous example, when they do finally meet me in the proper virtual room, they are angry with me – “You are in the wrong room!”

“I clicked the first link that appeared in the calendar invite.  How would I have known that you intended for me to click the second link buried underneath the Zoom link???”

Again, this is someone who reached out to me, begging for time on my calendar, and now they are angry with me.  And yes, I’m always left thinking, “Do they treat their prospective clients this way???”

There are true efficiencies to be had with Calendly, no doubt.  But I don’t think humans are ready for it.  The above scenarios have played out far too many times for me to continue to declare these snafus as isolated incidents.  I assume the creators of the technology intended it to improve the lives of both the user and the recipient, but I don’t think they anticipated human nature and the fact that the majority of its users would not take the time to properly learn the nuances of the software and ensure recipients of their calendar requests would not be massively inconvenienced by the experience interacting with the person and the product.  I just don’t think the human race is ready for it!

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