Posted on by Kris
Relationships Can’t Be Automated



It’s not uncommon to hear people go gaga over the latest software or sing the praises of the hottest new app. This is nothing new, of course. When I was working at my first job in downtown Chicago, I remember people talking excitedly on the Metra about the release of Windows 95 (codename: Chicago). You couldn’t go anywhere without hearing someone talking about all the new bells and whistles Windows 95 was going to have. I wondered: why was everyone so excited about a computer system update? I just didn’t get it. Or maybe I didn’t see what the big deal was because I have always been a Mac girl.


A recent example of “software over-excitement” was a sales person I knew who was drooling over a new email marketing program. He was excited about all of the features it offered in lead generation tracking, integration, and management.


In this case, this person was excited about the software’s ability to automate an email “drip campaign” where he could set up a series of introductory emails that could be personalized with a new lead’s contact information. Then, in theory, every time a new prospect was brought in, he simply had to add them into the system, and the process would run itself.


About a year later, I saw this person again and asked how the drip campaign was coming along. He kind of avoided answering the question and we moved onto another topic. But then I realized: he hadn’t launched it yet. He was still working to perfect the campaign. After a year.


The problem here is that sales is a process that can’t be automated. You can – and should – track leads, touches, calls, emails, or any contact you have with your prospects. Any person in business would be foolish not to. But expecting a software program to take over the sales process and do it for you is just unreasonable. Maybe that’s why he was having such a hard time with figuring out the messaging: because you simply cannot automate human interaction.


When we were in a growth phase a few years ago, I hired an excellent seasoned account manager with years of agency experience who recommended a specific accounting platform to better track our billing and invoicing. This program was geared for creative agencies like ours and promised to work wonders. It would track every employee’s working minute and calculate their billable hours, track all project purchases and expenses, see where we could improve, and make us more profitable. I assessed the program and what it could do for us, weighed the cost and learning curve against the long-term benefits, and gave the purchase my blessing.


The time it took to transfer all of our accounts over to the new platform was no small task. Even more time-consuming was the training our staff went through to install the program, enter and code their time properly, and learn how to track their hours differently.


After we downsized again a few years later, I went back to the previous system I had been using because that just worked better for me. Sure, the software had been excellent, but I didn’t need all the extra stuff. One could look back and say the switch to this software program was a major waste of time and money. And I know I looked at it that way for a while. But after I got a little perspective behind me, I began to see it differently.


The accounting software was powerful, but the one thing it couldn’t track was: my time. Sure, it had fields where I could log my hours. But – what about all the phone calls and meetings and business lunches? What about all the conferences and networking and follow-up?


What about the ideas I’m always jotting down in the car on the way to pick up my kids from something, or the revelations I have on my daily walks? What about when I’m in church and something speaks to me? Am I tracking my time then?


As a business owner, I am always working, 24/7. My brain literally does not stop running. When you’re a creative person, the ideas just keep flowing. And most entrepreneurs and sales people – at least the really excellent ones I know – are super creative. They just automatically know how to make those connections from one person to another, to see a problem and find a solution. Their minds are constantly working to put the pieces of the puzzle together – usually, without realizing it. That’s what creativity is all about. Making connections that others can’t see. And everywhere I go, I find that the most successful people share this trait, across all walks of life.


When I looked at the time tracking software a little more deeply, I realized it wasn’t just my time that couldn’t be tracked. It was my value. I realized that all of the hard knocks of rejection and failure and setbacks we experience over the years really hurt at the time, but without them – we can’t grow.


When we rely too heavily on software and systems to do the work of people, we put our focus on the wrong things. Whether it’s Windows 95 or the latest CRM software – when you take people out of the equation, then you’re just left with – numbers. In the quest for the “results” that so many of these applications promise to deliver, we can too easily get caught up in flow charts and reports and presentations and layers of meetings and management – and forget the toll that all this wasted time takes on people’s energy.


A great sales person – and a great business owner – is someone who knows how to cultivate lasting relationships. And there isn’t a software program in the world that can automate that process.


I’m curious to know: when have you seen people go crazy over the latest tech trend? I would love to hear your stories, so please email me at – I’d love to connect!


This article first appeared in the Winter 2019 edition of Enterprising Women Magazine. Please click the logo to go to Enterprising Women Magazine:








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