Habits of a CEO

The next morning arrived like a summons. Isabelle Dela Cruz stood at her bus stop with a black coffee in hand and a notebook tucked beneath her arm. Her shoes pinched slightly, but she didn’t mind. It was day two at Villareal Holdings, and she had a mission—learn every habit Damian Villareal had and keep pace with the rhythm of his world.

If she couldn’t anticipate his needs, she wouldn’t survive this place.

By 7:35 AM, she was already in the office pantry pouring fresh coffee into Damian’s preferred matte black travel mug. She had memorized it the day before—double espresso, one sugar, no cream. She placed the mug on a tray alongside the first printed copy of the day’s agenda and a small, untouched bottle of water.

Ana Romero glanced over with a raised brow but said nothing. Isabelle took that as a minor victory. A nod from Ana, even if silent, was as good as a bronze star.

By 8:00 AM sharp, she walked into Damian’s office—his door always left slightly ajar until the first meeting. He sat behind his monolithic desk, eyes already on his screen. She placed the tray gently at the corner of his desk.

“Your schedule, sir. Today’s briefing memo is on top.”

He glanced at the tray and gave a single nod without looking at her. It wasn’t thanks. But it wasn’t dismissal either. She quietly retreated.

Back at her own desk, Isabelle pulled out her notebook and jotted down timestamps. When he checked his phone. When he stood. When he left his office without a word. By the end of the morning, she had a detailed log of his patterns: what time he returned emails, how he liked his folders organized, which executive he responded to the fastest (CFO Clara Yeng), and what tone he used depending on whether a meeting went well or badly.

The man was a machine. But machines could be learned.

She studied his behavior like a language. It wasn’t just about learning protocols—it was about decoding him. And with every passing hour, she refined her instincts. She started predicting his movements, preparing things a step before they were requested. Water on his desk just before his 11 AM meeting. A fresh printout of notes for his legal consults. A backup USB in his drawer just in case.

By Wednesday, Isabelle could tell by the way he tapped his pen on the table whether he was irritated (sharper, faster) or merely thinking (long pauses). She reorganized the draft folder once again, placing active projects on a new shared dashboard he could review in real-time.

When he noticed it, he didn’t say a word. But the next morning, she saw that he had edited the tags himself. A silent form of collaboration. And from Damian Villareal, silence was rarely neutral—it was often tacit approval.

That same afternoon, Isabelle shadowed Ana during a budget logistics prep for an off-site meeting. Ana didn't offer much conversation, but Isabelle was keen enough to learn from her posture, her expressions, her brief side glances. Working with Damian, Ana had developed a sixth sense. Isabelle wanted that sense too.

She began studying old emails Damian had replied to—comparing tone, urgency, and sentence length. In meetings, she watched how he responded to interruptions versus proposals. It was all a delicate algorithm she was determined to crack.

On Thursday, he handed her a manila folder without comment. She opened it. Inside was a list of client accounts with his handwritten notes in the margins. The handwriting was rushed but precise, the ink a dark blue she realized matched the exact shade of his tie that day. He was consistent, even in that.

She stayed past 8 PM that night, coding the client notes into a color-coded table, complete with flags for pending updates. When she left the folder back on his desk, she included a single yellow Post-it:

Let me know if this view works better. — I.D.

The next morning, the Post-it was gone, but the table had been printed and annotated in pen. Some of her headers had been underlined. One column had a checkmark. Small signs—but clear.

Progress.

Friday brought with it chaos.

The copy machine on the executive floor malfunctioned two hours before a client pitch, shredding the only hard copies of Damian’s presentation. When Isabelle found out, she didn’t wait for Ana’s orders. She pulled up the files, reformatted the slides herself based on Damian’s preferences, and printed them from the legal department three floors down.

She sprinted back, hair falling loose from its bun, breathless, but the fresh copies were in Damian’s hands fifteen minutes before the client arrived.

“Where did these come from?” Ana asked, eyebrow arched.

“Legal floor.” Isabelle straightened. “They owed me a favor.”

Damian gave a single nod as he flipped through the pages.

Later that day, Marco passed by her desk and dropped a wrapped energy bar beside her keyboard.

“From the CEO’s personal stash. You’re making an impression.”

She laughed softly. “Is that a good thing?”

“It means he’s paying attention. Which is rare.”

That night, Isabelle walked home under dim streetlights with aching feet but a strange sense of contentment blooming in her chest. This job was more than she expected—more brutal, more consuming—but also more rewarding in the quiet victories.

By the end of week two, Isabelle no longer relied on the handbook. She knew how he liked his emails structured—bullets, no fluff. She knew he never ate lunch on Thursdays, only drank black tea. That he rotated three pens throughout the week. That he avoided the 11th floor entirely and never scheduled meetings before 9:00 AM, but always stayed until 8:00 PM.

She began using the silent rhythm of his habits to build her work schedule. Tasks that would take most assistants an hour, she completed in thirty minutes, anticipating the next instruction before it came.

She even began to understand the subtle tension in the office. How Damian’s mood could shift the energy of the entire floor. She’d hear whispers of staff adjusting their plans based on whether his office door was left open or shut with force.

Late one evening, as she was about to leave, she heard his voice again.

“Ms. Dela Cruz.”

She paused in the hallway.

“Yes, sir?”

He didn’t look up from his monitor. “The numbers you included in the Paragon file were correct. Well done.”

A beat. Then she smiled. It wasn’t quite praise. But it was something.

And for now, that was enough.

She turned and walked toward the elevator, the weight of exhaustion heavy—but the satisfaction heavier.

Every day, she was learning him. Every day, he was starting to see her.

Even in silence, a bond was forming. Quiet. Powerful. Inevitable.

This wasn’t just survival anymore.

It was transformation.

And Isabelle Dela Cruz was only getting started.

Somewhere between his coffee preferences and his client memos, she found herself awakening to an unexpected hunger—not just for success, but for something intangible. A connection. A foothold in this glass-and-steel world where she was more than just a secretary.

Maybe even someone Damian Villareal couldn’t ignore.

And in that, there was power.

Real, palpable power.

The kind that only came when you stopped surviving—and began to thrive.