avatarAldric Chen


My CRO’s Face Twisted When a Gen Z Called Him an ‘Outdated Salesy’. I Almost Died.

I’m befuddled. Really. I won’t do that. I won’t.

Interviewing fresh blood has been fun, tiring, and intriguing. Do you feel the same? Photo by The Jopwell Collection on Unsplash

For me, I am done with interviewing people.

The formality-driven final round is next.

This is the round when interviewees have everything to lose and nearly nothing to gain. We are ready to make them an offer. That is if candidates maintain their good game.

That is a big if, by the way.

I am due to meet Jacob this afternoon. This is my CRO’s formality round, and a senior manager must be present for an objective, alternative professional opinion.

The truth is — I offered none of that.

Here’s why.

There Were Sharp Opinions from the Get-Go

I ought to mention this.

We are ready to offer Jacob an experienced-level role in consulting sales. He has 3 years of experience in sales. We honor that.

Jacob was on time and appropriately dressed in business attire. There were no Snoopy ties or tattered jeans.

I like that.

Jacob carried himself professionally. He maintained eye contact, stacked his hands on his crossed knees, and gave straight answers.

20 minutes in, and I thought this guy nailed it.

I could tell from my CRO’s face that he likes this new guy.

That is… until this question.

“How and in what ways can you bring our sales organization to the next level? How can we, with you in the team, achieve a 15% growth in annual revenue?”

It was a standard, boring question.

The answer, however, wasn’t.

“I think how you run sales is outdated. The company is still playing margins. We must stop that. We must do social media, create personal brands, and spend big on website SEO. Meeting clients is so passe.”

I almost choked on my coffee.

Fortunately, I managed to prevent any drips of black from landing on my white shirt.

I put my cup down, checked my top, and then turned to my boss. His face was coated in steel black.

I thought he would ask Jacob to get lost. Politely, of course.

But he didn’t. He is in a good mood this morning.

He played along.

“Winnie, Do You Have 15 Minutes? Can You Come to Change Room?”

‘Change’ is the name of the room we are hosting Jacob.

Winnie is our Marketing Director. She knows the ins and outs of our marketing engine. She is a hard worker. I respect her for that.

My boss shares my sentiments.

“Sure thing. I am grabbing a cup of coffee. Give me 2 minutes and I’ll be there.”

The call ended with no fluff, zero objections, or the classic I’m busy pushback.

Winnie talks shop and stays there.

2 minutes later, Winnie entered the room and sat on my boss’s right. I was on his left.

The interview resumed.

The CRO repeated Jacob’s question.

Winnie listened and nodded while allowing the cup to gradually cover her face in half. The coffee must be good. She finished it in one go.

“I got it, Number 2. Let me reply. Nice to meet you, Jacob. Thank you for asking.”

Winnie elaborated on how the company’s website has been optimized for SEO and Google ad words, and the digital spending is 5% more than our competitors.

She also mentioned how our people — sales and non-sales — grew their social media presence from 0 to 200,000 followers in 3 years.

The real problem, however, is the following.

  • Digital presence works for sales, but it is a slow grind. It takes time for results to show. And people need to be egged on to put in the effort.
  • Face time matters. Customers hate patronizing emails with call-to-action and Calendly icons. They want to be attended to. Sales folks must invest with their legs.

I can see why my boss places his trust in Winnie. She makes sense. And she speaks with a big picture. Her observations were on point.

The CRO smiled.

I sensed relief.

But this is far from over. Winnie said her piece. She hasn’t asked any questions yet.

And she did.

It was an 800-pound counter punch.

“Thanks for asking these questions, Jacob. May I ask what the success rate was in your previous company, converting sales from personal branding or social media? Maybe I can learn from you.”


At that instant, our heads turned, and 3 pairs of eyes matched his. It was an unspoken, well-coordinated, ape-like reflex.

Jacob did not expect this. He looked down and at his hands.

We were expecting him to say something concrete.

He didn’t.

“Going digital is the right thing to do. I hate meeting clients. It’s tiring. I may get screamed at. I prefer to deal with my laptop. I posted a question on Quora to confirm my thinking. Everyone online supports going online.”

Dead silence.

That last sentence kept ringing in my head.

“Everyone online supports going online.”

I mean, duh?

I don’t get his point.

Perhaps Winnie did.

But she was visibly unimpressed.

“Thank you for your feedback, Jacob. Number 2, I take my leave. Got a meeting to attend, and I am running late.”

The CRO said his thanks.

Winnie exited swiftly. She has always been a woman of purpose.

At this point, I wondered whether Jacob would still be on our offer list. I had doubts. The CRO was in deep thought. I know he was.

He was spinning his pen.

“Jacob, thank you for coming. I need to reconsider this offer. You may be a good fit under Winnie and not with sales. I will think about this and have HR get back to you.”

I agree with my boss’s judgment.

Although… I am not too sure whether Winnie will be pleased [or pissed].

The Close

I was ready to make my way out after Jacob’s departure.

My boss stopped me.

He wanted a quick 10-minute flyby on the candidate pool for the sales team. He was worried that we were not getting quality sales folks.

I shrugged my shoulders and said this.

“I don’t know. A candidate came in tattered jeans and a Snoopy tie yesterday. The younger folks seemed to think the sales world operates on laptops speaking to laptops.”

I heard a loud sigh.

I guess the next round of the hiring cycle will commence earlier than planned. James, the HR director, will not like this. We rejected far too many candidates for no-experience and low-experience roles.

And on our part — I think we must reflect and adjust.

We might be blinded by our own life experiences. We did not grow up with smartphones and laptops.

We [probably] need to transport our existing expectations to mature hires and lower the bar for no-experience hires.

Maybe that is the way? Maybe.

I have no idea.

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Oh, oh, you can buy me a cup of black too! Thank you!

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