A Gen X Client I Secured Annoys My Younger Colleague. I Try [Really] Not to Judge.
Is the problem communication or technology? Beats me.

Alex hates every 3rd Thursday of the month.
“Sigh. I hate meeting Gin. She makes me do irrelevant things, and I cannot say no.”
By her — Alex was referring to Gin.
I have no issues with Gin. Of course, I am coming from an account management angle. Gin renews her software subscription contract with me annually, with routine upsizes. She is a good client.
However… this 58-year-old client routinely frustrates her IT team and service providers.
Like Alex.
Beyond Frustration
Alex is my up-and-coming team member.
He is known to be patient. Very few clients push him over the psychological cliff. Gin is a prominent one. It further irritates Alex that Gin is our diamond client.
He knows the stake.
And that is why he is suffering inside.
“You know what happened last week? She asked me to help her trash the bin. I was shocked! No way I am doing it! But what she meant was clearing her email bin. I mean, she doesn’t know how to do that?”
It does surprise me.
I am not here to judge, to unearth the why, and to discover the mechanics behind the scenes. Alex is my team member. He supports me for post-sale work.
I make it a point to listen to him.
- He does not have issues with work tasks, per se.
- He has challenges coping with tech laggards.
Alex is not expressing himself in a mean way. I used to think he was, but I was profoundly mistaken. This young man grew up with the Internet and social media. The iPhone walked into his life during his teens.
Contrast that to Gin.
She [still] uses a Blackberry, gets her work done on a CPU-operated desktop when everyone else in her company is now on laptops and uses LAN ports because she has trouble connecting to WiFi.
I have seen it for myself. Hence, I empathize with Alex.
He shared that Gin blew up on him because the software was no longer working. Alex got befuddled. How would it be when it is on-cloud, and everyone else [sitting just outside] has no problem assessing it?
Being the typical problem-solving-default-mode Alex — He flipped into solver mode.
He checked with the others outside, tested the connectivity, checked Amazon Web Services, and contacted the IT team for infrastructure support, checking their firewall settings.
It took him 90 minutes. Gin grumbled at him in the background all this while.
Imagine that.
After all that Wild Goose Chase, Alex isolated the problem to a user issue. He [absolutely] hates this. Why? Because it involved dealing with people.
Alex returned to the room and took a quick look. He noticed the issue.
He asked Gin for permission to touch her desktop. She agreed. He then typed in the correct web address and pressed the enter button. The log-in page popped up.
“It’s here, Gin. It will be good for you to bookmark this page.”
Alex staked his father’s reputation when he recounted how he said that with a smile of sincerity.
Haha, I accepted that.
But what happened next shocked him.
Gin did not bookmark the page. She stared at the screen, read the web address out [loud], and wrote every single letter, symbol, and whatnot on a random Post-it note she stuck on the wall beside her.
She confused Alex.
He asked Gin why not bookmark the page. Gin exploded at him [Alex’s recount, not mine].
“Stop telling me all these! I need to focus on my work! All these technological stuff are distractions!”
Alex had a rude shock. He stood there like a frozen turkey and couldn’t understand what happened. I suspect his patience battery was near depletion. He mustered a fake smile and left.
I applauded him for not blowing it.
Gin’s Struggle with Technology Is Real
“It’s my fear of my lifetime.”
She said this to me when we were lunching.
It was time for our quarterly business review. Being one of our diamond clients, I meet her every 3 months for a pulse check. Of course, generating an upsize sales contract value never left the back of my head.
It’s business.
But we rarely spoke about business.
She needed time and space to air her troubles. I gave her that.
“I have many tech wizards in my team. They talk about Tinder, Insta, open-source, and building an online business scalable on the web by 1-person. I cannot understand that. I struggle with Google Sheets.”
Can you imagine her daily frustrations at work? In the beginning, I cannot. Sharepoint and Google Sheets are straightforward to me.
Not so for her.
Gin keeps her ignorance to herself because she hates to be labeled as a dinosaur. I can understand. No one likes that.
“I get angry with myself when I cannot find the trash bin on my email account. The IT guy and your Alex mentioned that it is that rubbish bin icon. Is it? That icon did not look like the real one beside me.”
I was quiet.
I wanted to appreciate the depth of her struggle as a tech laggard. These were simple functions. How would she ever take the next step to learn that next thing when every software update comes with a bundle of new features?
I listened to her as she spoke.
There was fear, ignorance, indignance, and then, utter annoyance.
“I thought I could compete with the younger ones on experience. It is a losing game. They can outcompete me with technology. Luckily for me, my boss is a paper and pen guy. If he is into tech… I am done.”
In truth, I ran out of words. I am, after all, not at 58. I cannot blindly imagine the challenges one 58-year-old has in the workplace.
That is not my point of interest, either.
I worry for myself.
Will technology overshadow my relevance, credentials, and experience in the workplace? My initial answer was no. But I forgot. I am in technology.
Gin is not that lucky.
This is business to me. Technology innovation(s) such as Cloud, software integrations, subscriptions-as-a-service, and administrator outsourcing — I must understand it. That is how I earn my keep.
To Gin, technology is a tool. It should complement her work. She never expected that the tool would evolve beyond incomprehension.
The Digital Divide is real.
Both Gin and Alex reminded me of that.
The Close
Alex never failed to lament about Gin.
“You are not the one working with her directly, Aldric. You don’t know how it feels.”
I sighed…
… While silently acknowledging that this young man might be right.
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