The Uncanny Valley of Email Automation

Trust is built over repeated interactions between people. If your business requires long term relationships then you have to make sure that investments in automation are not deployed in a way that undercut your ability to have real conversations. Unfortunately, some uses of email automation tools are pushing sales conversations into the “Uncanny Valley” because they strive to simulate–but miss–a genuine personalized touch.

Experiencing the Uncanny Valley of Email Automation

Sometimes when I sign up for a trial of a new service I start to get a stream of emails that are written like horoscopes: they seem like they are just for me until I read them a little more closely and realize they are mass e-mailed. In one situation about four months ago I signed up for a service and replied to the first “personalized email” with some detailed questions and started an email exchange. But at the same time I continued to get a stream of personalized “on-boarding” emails that made no reference to the ongoing conversation and in some cases had been obsoleted by the “real” email exchange. In particular this one came in after I had already exchanged email with Brian of FlinstoneYourBusiness (all names changed) on the first lesson:

To: skmurphy@skmurphy.com
Hey Sean Murphy,

A few days ago, you requested a free lesson from my course, Flintstoning Your Business. Just checking in to make sure you were able to access it.

Can I answer any questions? Just hit reply.
Brian (@FlintstoneYourBusiness)

I had a few seconds of thinking to myself, that’s odd, didn’t I already have an email conversation with this guy about his course? Then I read the “just hit reply’ which is a funny way to end a actual personal e-mail and I realized that it was one of a series of scheduled follow up campaign emails triggered by my registration. So I wrote back:

To: Brian@FlintstoneYourBusiness.com
Brian, I was able to access it and we exchanged email about it. I think your automated email campaign is pushing you into the “uncanny valley” where you are sending what appear to be personalized messaged but in fact they are a pre-programmed campaign that is sent regardless of other communication.

Regards
Sean Murphy

Full points for actually sending it from a real address not a “no reply” one but I think it would have had the same effect (but a different affect) if it had not been sent under the pretense of a personal E-mail. Brian’s reply indicated this was not the first time a genuine email conversation had been interrupted by a drip irritation campaign.

Hey Sean,
Ya, sorry for the automation. Of course, I do read and respond to every reply though. And I found lots of folks find it useful as a way to start a mini Q&A with me, which I enjoy :)
Brian (@FlintstoneYourBusiness)

I think the risks with this approach are that his genuine emails may be ignored because they are categorized as more auto-generated content. Or that a campaign e-mail interrupts a real conversation and stalls or diverts it. This may not matter as much for an entrepreneur who is playing a numbers game where the customer may purchase a $9 e-book or even a $19/month subscription but Brian is selling a $400 course and personalized coaching at $300/hour. If prospects are confused as to whether it’s a personal reply or an email chatterbot it undercuts his brand.

The stakes are even higher if you are selling to businesses where the opportunity value is $10,000 or $25,000 or $100,000. There are not as many prospects, you are competing against other folks who are at the top of their game, and a prospect’s first reply to you may come when they are already halfway through their evaluation–thanks to all that good content on your website and third parties writing about you–and they are looking to narrow the evaluation list.

Marketing is a Broadcast, Sales is a Conversation

I think there is absolutely a role for automation and a team approach to marketing and sales. In a small team the founder in charge of sales does not have to do everything by hand or face to face–the same for enterprise sales people–but to me there is a clear line between what can be automated and what can’t. Marketing is a broadcast, sales is a conversation. Once you have had a conversation with a prospect who may be in an active evaluation you personally have to maintain the thread of the conversation until you get to a decision. There is still a role for “nurturing” content but I think it’s best used sparingly and should be clearly written as if it were a newsletter or a standard communication, not as a horoscope designed to sound personal when it’s not.

When we help clients chase active prospects we rely on tools like Salesforce or Pipedrive or–in the early going–just an Excel spreadsheet. The latter surprises a number of early stage teams but I see too many entrepreneurial engineers focus on automating their sales process before they have debugged it. In the beginning when you only have a handful of real leads the effort to automate can get in the way having real conversations and reflecting upon their implications.

Personal Email Is Critical to Keeping The Sales Conversation Going

When you are reading this blog post, even if it was delivered as an email to your inbox, you don’t believe that I wrote it for you personally. If you read a newsletter you know that it was not written for you personally. Personal messages come from people you know and normally reference either directly or indirectly some prior shared experiences or context.

When I send a follow up email after I meet someone at an event where they may have met many other people at the same time I always try and add some specific references to the conversation’s time and location as well as one or more things that we discussed that may help them remember the conversation and remember me.

BeamWise Experience at Photonics West 2015

We recently attended Photonics West 2015 with the BeamWise team and sent two kinds of email: a generic “thanks for stopping by our booth, here are links to demos and more information” to about 100 people whose contact information we collected; a personalized email to about 20 folks we had detailed conversations with and exchanged business cards. In the first case it was clear it was a “mass email” and in the second case we provided details from the conversation designed to jog their memory.

Recent Experience with TouchingBase

Until recently I have not had a good system for the personalized nurturing. I define that as when the next conversation you should have is in more than two weeks but less than two months: the prospect expressed some interest but it was not immediate or clear. You don’t want to put them on a 3 month newsletter follow up cycle but you don’t want to push them into the “hot” list where you are focused on execution.

For the last few months I have been using TouchingBase.io for these conversations. I met Matt McCormick, the founder, at a Bootstrapper Breakfast last year and when he described his product I had this flash of recognition: this is something I should try. I did and have been very satisfied even if most of what it did was allow me to change my behavior and do a better job of managing leads in this grey zone between “hot” and “long term nurture.” I was interviewed about how I use it at “I had been looking for a simple system to nurture warm leads” but the key advantages it offers me for my workflow are:

It works inside GMAIL: I can tag an email when I send it for follow up and it will create a new draft if I have not gotten a reply in the timeframe I have specified.
I can see the nurture list at any time, so on slow days I still see progress.
It allows me to make a commitment to myself when to follow up as I send the e-mail. If I don’t get a reply in the timeframe there is no need to second guess myself.
It facilitates writing a short personalized follow up Email by starting a very basic draft.

There is a role for automation tools like iContact and MailChimp and SurveyMonkey as well pipeline management tool. But I think TouchingBase.io‘s model of facilitating a personalized email is one to consider adding to your mix

Auditing Your Email

Hashim Warren left a thought provoking comment:

The bigger problem with marketing automation is there are a billion user scenarios that you simply can’t predict. You can’t trouble shoot a problem context because most people won’t alert the sales guy to the problem like you did

When I used to use Eudora it had a flame warning that would check the content of an email for a controlled vocabulary of the swear words and insults. Handy for a sanity check on late night e-mails when “Something is wrong on the Internet!.” It may make sense to bcc a canary address that collects all of the sent e-mail for review.

The Uncanny Valley of Twitter Automation

There may be an opportunity for an independent twitter monitor since that stream is easier to monitor and a lot of automation is being applied both to generating tweets and re-distributing content in tweets. The monitor might be a mix of automated review and a personalized analysis based on branding goals and need to stay out of the Uncanny Valley.