Have the rise of techno-assistants unwittingly turned us all into self-centered douchebags?

Like many, as a solo consultant I don’t have the luxury of any administrative support staff. This has forced me to find ways to maximize my time and create efficiency strategies to keep me track with how I spend my time. Important to note at this point in this piece: I am a really annoying techno nerd. I use a lot of beta platforms and frequently call the developers / CTOs to share my experience and offer ideas and report bugs. I love software - even though I cannot write a single string of code. 

Ok- so back to my situation as a solo-preneur. Time management is a challenge. Ok, ok - so I’m not unique. We all know that even the simplest of tasks can quickly become time consuming as more and more complexity is heaped into the system. I started getting myself into calendar traffic jams a few years ago - and began exploring scheduling apps to help resolve it. Calendly, ScheduleOnce, x.ai, etc. The list goes on. This is a growing category and there's a reason.

While using these platforms can be extremely helpful, I can understand how being on the receiving end of one of these scheduling apps or bot assistants can be very off-putting for many - and may promote a perception of the user as a lame geek who hides behind screens and uses tech as an isolation strategy. Not to mention it can also come off as simply rude. Being confronted with a bot assistant can be the equivalent of “talk to the hand”. For sure the optics on these tools can be challenging. No one wants to occur douchey and all self-important but at the same time these tools are incredibly efficient at managing what is in reality a frustrating process. 

While it does seem like it should be easy for two people to simply set a meeting, in actuality it has become a great deal more complicated than that. I’ve done the math on this. Setting a meeting with someone - which occurs predominantly over email - is a simple exchange roughly about 40% of the time. The other 60% is more typically a back and forth series of notes about which date and which time works and what number to call and who’s zoom or slack or meet or teams or blue jeans or ass hat account should be used. It’s really become a mess. 

The new scheduling platforms offer a very simple and unified way of handling what has unfortunately become an overly complicated exercise. And that’s just between two people. Add just one more person to the mix and you’ve got an exponentially more complicated shit storm on your plate. It’s crazy. So I find these scheduling platforms to be helpful and they solve a real new world challenge. That being said - the point about the optics and perception that these tools generate is very real and valid. Used incorrectly, tools like these are highly impersonal and can inadvertently result in creating negative perceptions and turning people off. That’s also very real. So, I’ve worked out some strategies to manage / mitigate the rude-factor of these platforms. Here’s what I have employed to make the use of these bots a bit more digestible for my clients and prospects:

1. HOW we do things is sometimes more important than WHAT we do. 

If I am scheduling a meeting with someone via email, I am very deliberate about being upfront and human about this. For example:  

“Great, Steve, I’d love to spend some time discussing this with you. I have a few openings this week to talk. Would you be ok if we use my scheduling link below to find us some time? I know these can occur as a bit impersonal but I find them useful to arrive at the best mutual time in the most efficient manner.”  

Even this small acknowledgement removes the majority of the nose holding that can ensue from these tools. Add a little humanity to the mix and miracles happen (this a general philosophy that we should all heed).

2. Everything is not a nail. Use common sense. 

One of the main rookie mistakes that newbie assistant bot users make is to over-use them - or use them when its not appropriate. Here’s what I mean:

If you are on a call or an email exchange and the other party offers: “Great! Are you free Friday at noon?” - and you are - DON’T send them a schedule bot to set that up. That’s a tone deaf way to respond to anyone. In this case, just send them an invite for Friday at noon. I know this seems blatantly obvious but you would be shocked at how many people who use schedule bots seem obsessed with finding any excuse to use them in ANY situation. 

However, if, like in many cases, you get a: “I'm not in front of my calendar right now- I'll look and get back to you with some times that work for me.” You know this can be the beginning of a shit show. In this case, I counter: “Not a worry. Why don’t I just send you a scheduling link and you can plug in whatever time works best for you?” I’ve never had a negative reaction to this maneuver.

3. Stealth is good. Let the respondent make a choice.

One thing that I find works really well is simply leaving a scheduling link in my signature. It looks like this:

Let's set a time to chat

Let's connect on LinkedIn

I get about 4 -5 errant invites from prospects and contacts per month from this signature alone - without me requesting a meeting. Allowing my network to choose this option is best because I am not dropping an app-bomb on them. 

4. Phone call Poker: Another weird thing that's developed:

Another weird cross-streaming conundrum is the “who calls who” moment in a meeting set up. For some weird reason, when two people agree to take a phone meeting, an existential non-spoken mexican-stand off occurs when deciding who calls who. Now, this should be easy right? If I ask for a meeting, I should make the phone call, no? If someone asks me for a meeting, THEY should make the phone call, yes? But there seems to be this silent haughty ‘my crotch is larger than your crotch’ moment that occurs sometimes when both parties agree to the meeting equally. So, it's a weird one. 

Here’s what I’ve done to resolve this: 

I use a bridge number that we BOTH have to dial into (I prefer Uberconference). So it evens the playing field and negates the potential ego battle. If asked why, my response is that: 1) it's really secure 2) I use it to record and log important calls (via an integration with an AI audio transcription platform - more on that later). 3) It has no pass code so it looks and feels like a normal NY 917 number.  Another nifty little feature of Uberconference is that it allows you to choose your own on-hold music. I've got a Zeppelin tune on mine (Good Times, Bad Times).

For those interested, here’s a look at my current solo consultancy tech stack:

• Woven calendar (integrates calendar, invite sharing, linking, event polling and analytics all into one) 
• Zoom
• Meet (trying it out - sucks so far, frankly)
• Otter.ai (Transcribes the audio all of my phone calls, meetings and video calls - for notes and content development) Super cool, integrates with Zoom, Slack, Google, etc. 
• Uberconference (my conference bridge - slick, no code needed, integrates with everything)
• Freshbooks (easy to use invoicing platform, good set of features and integrations) 
• Dropbox (storage, retrieval and sharing)
• Loom (records my screen activity for demos and sharing)
• Slack (mostly for a few clients and to engage with some great slack communities)
• Skitch (easiest free screen grab app - allows markup and integrated image sharing)
• 1Password (decent password management tool - considering a move to Dashlane)
• Monday (project management) 

Thanks for reading and genuinely sorry for being a douche.  

Let's set a time to chat

Let's connect on LinkedIn

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